Caterina Fake — Lessons from Flickr, Kickstarter, Etsy, and Much More (#360)


Credit: Richard Morgenstein

“I really am a big believer in people’s creativity flourishing when they come at things from a different direction and see things in a different way.” — Caterina Fake

Caterina Fake (@caterina) is a long-time Silicon Valley pioneer. She is the Cofounder of Yes VC, a pre-seed and seed stage fund investing in ideas that elevate our collective humanity. Previously, she worked at Founder Collective as a Founder Partner, served as Chair of Etsy, and was the co-founder of Flickr.

At Flickr, Caterina and her team introduced many of the innovations — newsfeeds, hashtags, “followers,” “likes” — that have become commonplace online. Caterina went on to found several more startups (FinderyHunch) and became an active investor, advisor and board member, helping to build companies like Etsy and Kickstarter from their beginnings. (Other investments include Stack OverflowCloudera, and Blue Bottle Coffee.) Caterina is an early creator of online communities and a long time advocate of the responsibility of entrepreneurs for the outcomes of their technologies.

Caterina sits on the board of Public Goods, the Sundance Institute, and McSweeney’s. She was given the Silicon Valley Visionaries award in 2018 and has received honorary doctorates from both the New School and the Rhode Island School of Design (RISD).

Caterina is also the host of the new podcast Should This Exist?which asks the question, “What is technology doing to our humanity?” Should This Exist? can be listened to on Apple Podcasts, at or anywhere podcasts are found.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform.

#360: Caterina Fake — Lessons from Flickr, Kickstarter, Etsy, and Much More

Want to hear an episode featuring another early Silicon Valley startup legend? — Listen to this episode featuring investor, Masters of Scale host, and LinkedIn co-founder Reid Hoffman, which features the 10 commandments of startup success. (Stream below or right-click here to download):

#248: The 10 Commandments of Startup Success with Reid Hoffman

This podcast is brought to you by Athletic GreensI get asked all the time, “If you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. As a listener of The Tim Ferriss Show, you’ll get a free 20-count travel pack (valued at $79) with your first order at

This podcast is also brought to you by Uber. Uber makes getting around town easier than ever before, and now Uber is introducing Uber Rewards, a new rewards program that helps keep modern life going. With Uber Rewards, you can earn points on Rides and Uber Eats and unlock rewards such as Uber Cash for your next Uber ride or your next Uber Eats order. You can unlock new benefits at every membership level, such as flexible cancellations with Gold, price protection with Platinum, complimentary surprise upgrades with Diamond, and more. For terms and to learn more about all the ways you can earn Uber Rewards, go to

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Read More

3 Comments / Leave a comment or question

The Tim Ferriss Show Transcripts: Tobi Lütke (#359)

Leave a comment

Please enjoy this transcript of my interview with Tobi Lütke (@tobi), founder and Chief Executive Officer of Shopify. Tobi was named The Globe and Mail‘s 2014 CEO of the Year; has served as Chair of the Digital Industries Table, an advisory board commissioned by the federal government to provide recommendations on how to turn Canada into a digital leader; and is an active advocate for computer literacy and education, serving as a board member of Canada Learning Code, an organization working to give all Canadians access to digital skills. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform. 


Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.


You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.


No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on or (obviously) license photos of Tim Ferriss from Getty Images, etc.

Tim Ferriss: Hello boys and girls, ladies and germs. This is Tim Ferriss, and welcome to another episode of the Tim Ferriss Show where it is my job each and every episode to deconstruct a world class performer from any number of different domains, business, sports, entertainment, military, and so on. And today’s guest, who will perhaps debate that he himself is world class – but I will not allow it – is Tobi Lütke, who is the founder and chief executive officer of Shopify – the CEO, that is, of Shopify. In 2004, Tobi began building software to launch an onboard snowboard store called Snowdevil. It quickly became obvious that the software was more valuable than the snowboards, so Tobi and his founding team launched the Shopify platform in 2006. He has served as CEO since 2008 at the company headquarters in the metropolitan epicenter of tech, Ottawa, Canada. It’s a fantastic place.

I’ve spent time there. BeaverTails, also incredible. Tobi is an active advocate for computer literacy and education and serves as a board member of the Canada Learning Code, CLC, an organization working to give all Canadians access to digital skills. In 2014, Tobi was named The Globe and Mail’s CEO of the Year. He served as chair of the Digital Industry’s Table, an advisory board commissioned by the federal government to provide recommendations on how to turn Canada into a digital leader. And that report was published, that is of the Table, in September 2018. Tobi, welcome to the show.

Tobi Lütke: Thanks so much for having me.

Tim Ferriss: I feel like this is a long time coming. We go way, way back. And we’ll get to that. But I thought we could start with your penchant for related optimization. So I want to do a quick fact check here. So this is something I came across in The New York Times. It doesn’t surprise me, but here’s how it goes. “I also have a weird obsession with optimizing things.” This is supposedly a quote of yours. “Even when I was walking to elementary school, I counted the number of steps on different routes so I could figure out which one was shortest.” And I’ll just finish this up. I’ll just connect some things. “If I have to do something once, that’s fine. If I have to do it twice, I’m kind of annoyed. And if I have to do it three times, I’m going to try to automate it.” Did you count steps?

Tobi Lütke: I did. That sounds ridiculous, doesn’t it? It’s one of those situations where I think I was together with my mom and my sister. And my sister as complaining about me trying to optimize something. I think we were talking about going for a walk. And I’m like, “Well, you know, if the place we’re starting from is the same as the destination, why don’t we just not go?” And my mom merely said, “Do you realize you did this from when you were like four?” And she told me the story. And it kind of, unfortunately, tells people way too much about me. So I don’t know why this made it into The New York Times. I’m actually kind of unhappy about this right now, but here we are.

Tim Ferriss: And here we are. And the optimization or the looking for efficiency, is that something that either of your parents has? Or did that seem to kind of come out of left field?

Tobi Lütke: I don’t know. It’s probably one of those unexplained kinds of quirks, which, after probably many, many years where it’s annoying everyone around me, suddenly, it starts becoming useful because, especially as a programmer, it’s been wonderful. I love these old machines. I can understand every chip that’s in the machine. You can kind of figure out what’s what. Trying to make a video game in the ‘90s was really, really hard. And so those are the kinds of things which really, really attracted me.

Tim Ferriss: And just to give people a snapshot of where things are now, and we’re going to certainly continue with this retrospective rewinding the clock, but how big is Shopify at the moment? What are some of the numbers?

Tobi Lütke: So as you said, Shopify started in 2004. We released it in 2006, which, again, that’s almost 100 internet years ago. It’s been a long time. And the company now is about the company. There are about 4,500 people who work at Shopify. We have offices largely across Canada but also in Berlin and Australia and so on and all sorts of other places. And what else is good for size wise? We have about – I don’t know what the newest official number is. Let’s call it more than 700,000 customers all around the world, 175 countries and so on.

Tim Ferriss: So it’s become this, by almost any metric, fantastic success. I was mentioning when we were having lunch before this, that I was unpacking some boxes that I had not yet unpacked from my move from San Francisco to Austin. And I found the coin from the initial public offering. And it really made me smile because I remember when we first met, Shopify had, what would you say, 15 people?

Tobi Lütke: 15 people.

Tim Ferriss: And was that 2008 or 2009?

Tobi Lütke: It was 2008, I think.

Tim Ferriss: It was 2008. And could you tell what you remember of that first meeting? Where did we first meet?

Tobi Lütke: We met at a conference called Rubi-Con. It may have been RailsConf. That sounds right. Ruby on Rails being the technology Shopify has been programmed in. And you were invited as a keynote speaker. I think you did an interview with David.

Tim Ferriss: That’s right. David Hannermeyer Hansson.

Tobi Lütke: Exactly. So I think we talked in the green room. It’s like, “Hey, I love everything about your book. But the worst part about it is you keep talking about using your Yahoo Stores for your supplement business. And you really should have used Shopify. What can I do to convince you of” – I wasn’t that direct. I was probably really shy.

Tim Ferriss: But the timing was perfect also because I was in the process of doing the final editing for the revised edition of The 4-Hour Workweek. And I had been polling my readers through social media and the blog and so on, which, at that time, the blog already had millions of readers, and asking for suggestions for updates for the tools and resources. And Shopify was the most consistent recommendation for the e-commerce platform. And then, I go to this conference. We meet in the speakers’ room, effectively. And you have let’s say 15 or so employees. And that was the beginning of our exchanges and then, collaboration, which we’ll get into. But, on one hand, it seems like a previous lifetime. And on another hand, it just doesn’t seem that long ago.

Tobi Lütke: It doesn’t, does it?

Tim Ferriss: And I have to say, for people who perhaps wonder this, does money change people, I have to say it’s been so – I didn’t expect you to change, and you didn’t. And it’s really refreshing. And I don’t know if I’ve said this publicly, but Shopify is one of those companies where everyone I’ve ever been involved with has been just such a genuinely good person. It’s an example of when the good guys have won, in a way. And it just makes me so happy that you guys have had the outcomes that you’ve had.

Tobi Lütke: Thank you so much for that, Tim.

Tim Ferriss: Yeah. I just want to start there. It gives me so much joy to think about. And let’s get back to your odd behavior as a kid. So this is from a separate piece, and this isn’t going to be all quotes. But some of these are just so fantastic, I can’t not mention it. This is from Globe and Mail. And this, I think, speaks to a superpower of yours that may have caused problems in the beginning. And I recall reading a quote, and I’m going to butcher it. But Francis Ford Coppola, the director, incredible, legendary filmmaker had said, “You receive lifetime achievement awards for the things that would have gotten you fired in the beginning.”

Tobi Lütke: That’s fantastic.

Tim Ferriss: Yeah. So here’s the quote. And this is the writer. “From an early age, Lütke had what he calls ‘authority problems.’ In school in Koblenz, Germany, he preferred to deconstruct the questions teachers gave him rather than deliver the expected answers.” And I was like, yeah, that sounds right. “He took shortcuts, determining the minimum number of hours he needed to spend in a particular class and still pass, so that he could spend most of his time with his computer.” One of the patterns that I have observed with you over the years that I think is so so valuable and so simultaneously important, but undervalued or underdiscussed, is not just asking the question in front of you, but dissecting it to determine if it’s the right question.

So could you elaborate a bit on that or think of any examples that could serve as a launching off point or even maybe start with why you do this?

Tobi Lütke: Yeah. Well, this is already going to interesting places, isn’t it?

Tim Ferriss: Yeah.

Tobi Lütke: We have talked about my authority problem and my obsession with optimization, so where do we go from here? Here’s what the authority problem thing has morphed into, and I think this is exactly the sort of pivot point from which it went from problematic to very useful. And that is I have a serious problem just of accepting autotoxy, like, “Here’s how things are done.” That doesn’t grab me in any particular way. And so what I’ve determined for myself is I really want to understand the situation and the various pressures acting on the situation that I might get myself into. So you were taking us back with the little coin that you found, which is one of those artifacts the New York Stock Exchange gives you when you take a company public. And so we got to do this together.

Before that date, when you actually rang the bell, at least traditionally, companies like Spotify and Slack now were doing the direct listing, which I think is really, really healthy for that particular industry. But before that, you worked with bankers, you build with prospectors, and then, you go on a road show and all of these kinds of things. It’s been a grueling – talk about I don’t want to do a thing two or three times. I had to give the same presentation 103 times in eight days. There’s a complete –

Tim Ferriss: Tobi’s version of hell.

Tobi Lütke: It was my version of hell, which is funny because my business partner, Harley, is like the opposite of me and loved it. It’s good to have these people around who can –

Tim Ferriss: Side note, Harley, probably the person I’ve heard most described as a force of nature. That phrase applied to Harley.

Tobi Lütke: Yes. Exactly, which I’m decidedly not. So Harley loved it. I wanted to automate it all the way through. But I’m taking us back there because I think it’s a good example of this kind of thinking. One thing I did very early in the process of actually taking the company public was to not just understand how could Shopify become a good, public company, but there was this sort of obvious agency problem that exists on the investment banker side. And so I spent a good couple of months talking to people, figuring out what kinds of things happen in the performance review of investment bankers. How do they make their money? How do they make their bonuses? How do they string together a career? What’s good, what’s bad? If they get a lot of these kinds of fees, is that good for them, or is that neutral?

So I would like to come to a conclusion, and often this is the same conclusion: that autotoxy would have just sent me to myself because I want to say, “Okay, I’m going to do these following things because I, from the first principle, argued that this is the right thing to do.” And I think this, more often than not, leads to very interesting insights where you can say, “Because I understand what’s at play here, I can disagree with someone’s suggestion. And I can maybe improve something slightly.” And I think, in an interesting way, Shopify is a very long exercise in doing this over and over and over again, rather than saying, “Well, the internet needs online stores.” They are super important. Online retail is one of the biggest entrepreneurial opportunities of our lifetime. It’s a $1.9 trillion industry now. It’s going to be $4 trillion soon.

Online stores need to be something that people can create. Cool. But do people really care about online stores? They care about selling. They care about becoming successful entrepreneurs. They care about reaching for independence and the success of that, which pretty quickly send us into the direction saying, “Okay, they do the online store thing. But that’s actually a bit of a soft bed that actually supports people in the activity of reaching for independence.” And because of this, it became something else. And success came through that.

Tim Ferriss: This also in a way connects some dots from earlier today, when we were chatting about a mutual friend, Seth Godin.

Tobi Lütke: Yeah.

Tim Ferriss: And Seth and I, not too long ago, had this conversation where he gave the example, which was borrowed from an example that he read, but he elaborated on it, which was: No one wants a quarter inch drill bit, they want a quarter inch hole. And then, it’s like, no, but they don’t really want a quarter inch hole, they want a shelf. And they don’t really want a shelf, they want a place to put their books, and so on and so forth, so that you don’t sort of mistake the current characteristics of a temporary solution as the ultimate objective.

Tobi Lütke: Because the world has sorted itself into solutions based on the world that’s long gone in a way. Just looking back at my industry, why was there an online store industry and a point of sale system industry and all of these eBay power seller tools? Each of those instances, someone has a product and wants to sell it through whatever channel. Do you want to go to three, four, five different vendors to get the software to participate in all of these channels? No. You just want to do it, right? And so I think it’s really worth going through life and just saying, “Hold on a second. What are people actually trying to accomplish? What is the actual problem here?” I think the most impressive story along those lines that I’ve ever come across is, are you familiar with Malcolm McLean’s story around the invention of the shipping container?

Tim Ferriss: I’m not, but I’ve had a book about shipping containers recommended to me multiple times.

Tobi Lütke: Yeah, The Box probably.

Tim Ferriss: The Box?

Tobi Lütke: Yeah.

Tim Ferriss: What was the person’s name you said?

Tobi Lütke: Well, his name was Malcolm McLean. He’s one of us entrepreneurs who would absolutely be on your podcast if he would be alive right now because he spent the first money out of college on buying a truck. He started a trucking company and tried to get things shipped across the country or even to Europe and realized we can make the most efficient trucking system, or the train guys have the most efficient trains, and the boat guys have ships all over the world. But getting something through multiple stations is impossible. You have to unload everything. So he ended up just buying a bunch of tankers from the US Navy, which had surplus tankers at the end of World War II and just came up with this idea of putting a shipping container together that you can put things in the factory in Maine and then ship them all the way to Berlin.

And the moment he did that, the cost of sending a unit of goods went from, I think, $6 to $0.16.

Tim Ferriss: That’s incredible.

Tobi Lütke: We all live in Malcolm’s world because the shipping container has been hugely influential in history. It’s like a lot of people talk about free trade agreements and globalization. In reality, globalization happens the moment a shipping container opens in a country. And it’s a fascinating, rather underexposed story. But what’s so cool about this is the reason why he put this off is because, again, the Vanderbilts and the train guys really loved the trains. And the boat guys loved the boats. And he was the only person who just cared about moving things. He wanted to solve the problem of moving things in the world and then, you come to better solutions. We need more of that kind of thing.

Tim Ferriss: Yeah. The versatility, I don’t want to get too taken off track, but the shipping container – when I was – the brilliance of the modular design and the ability to take a single container and move it across different means of transport is an endlessly fascinating topic. And a lot of folks also don’t realize the sort of genius of the design of shipping containers and the considerations of the dimensions and the ability to cool or control temperature. And then, the entire aftermarket use of shipping containers also, just how I came into it. I kind of backed into it looking at different types of design and construction. That book was called The Box?

Tobi Lütke: Yes.

Tim Ferriss: The Box. So since we’re talking about it, we might as well just hit on something I was going to ask about anyway, which is books. So you’re, I would say, a veracious but very selective consumer of information. And there’s a lot of garbage out there. You mentioned The Box. There’s another book, and I think it might have been in Harley’s office where I first saw it at Shopify, but High Output Management by Andy Grove.

Tobi Lütke: That’s one of the best books ever.

Tim Ferriss: One of the best books ever. And then another one that I have listed here is Drive by Daniel Pink. I’m not sure if you want to comment on that. But could you mention a few books that you have found particularly helpful? And maybe start with High Output Management and why that is a good book.

Tobi Lütke: So I’ll take you back to the early days. I started at Shopify as “Hey, I only want to do the technology. I’m a programmer by trade, so this is my world.” And I wanted to treat the business as a black box for the first couple of years. And then, for various reasons, I was sort of thrust into also having to take over the business side of Shopify. Around that time, actually, we met. And I did a poll with people I knew for two books to read because I wanted –

Tim Ferriss: So business folks?

Tobi Lütke: Exactly. From this point, I was knee deep in Martin Fowler and Kent Beck and all of these kinds of luminaries of the programming world, but I had no idea about business. And so the two books I read, which is funny because it tells you how good that selection process was because I still think probably they would rank in the top five books I’ve ever read, and I had a completely wrong view about how good business books were after I read some, were High Output Management by Andy Grove and Influence by Cialdini. So they were the two first books to read.

Tim Ferriss: You got off to a good start.

Tobi Lütke: Yeah. So Andy’s book is unapologetically almost a how to manual, but kind of deconstructs the world of business into first principles. It’s like, “Here’s what matters. Here’s how to think about it. No one needs a degree. There’s a little bit of circumstantial contextual understanding that you just have to have.” But basically, at the end of the day, making business is an engineering exercise, which is brilliant for me because that actually made the whole thing about becoming CEO significantly less scary to me because engineering I understand. And then, Influence was just the most mind-bending book you can imagine, because it essentially taught you always humans are flawed and influential and how, yes, computers are predictable. And you can deal with it.

But once you make things for people, you need to go into storytelling – and framing matters – which were also news to me, frankly. I spent my teens with computers, not with people. My wife would dine out on this topic and just probably make fun of me for hours, but she always says I’m an immigrant to the human condition. So it was to send me off to a good start. I just want to say though, I’m a voracious reader. I’m dyslexic. I actually read very slowly. I have sort of overcome dyslexia, but I read books very slowly. It’s actually an advantage, frankly. I have a very high recollection. But because of this, I have to be very selective on the books I read. I’m not one of those 100 books a year kind of people.

Tim Ferriss: Yeah. How do you choose books now? Or maybe as an example, The Box, why did that come on your radar? How did that make the cut?

Tobi Lütke: The Box came because I usually have a topic and then, just dive. I dive into it. In this case, I was like, “Hey, I’m running Shopify. Shopify causes tens of billions of dollars of commerce activity. And most of this is going to go through a logistics network that I don’t understand. And I feel my job as a CEO is to have the most full stack understanding of every component that’s at all related, which is, frankly, given that we are working here in world trade is almost the entire human condition.” So it’s an endless source of interesting deep dives into topics. But in this case, it was more about the logistics world. It’s a fascinating world because it’s been built for millennia. The Silk Road still has an impact on the way the economy works today. And stitching these things together is absolutely fascinating.

But just even in the sort of first, “Let me start digging,” it became pretty clear that there was a history before the shipping container and history after the shipping container. And in these situations, there’s a specific date where everything changes, like The Industrial Revolution or another example of that. What I tend to like doing is I like to find the players, the people who have a lot of input on this kind of thing or at least who have the front row seat and then read their biographies, because they don’t tend to try to sell you anything other than that this person played an important role. But they tend to be the most credible witnesses to the actual outside events, without so much bias towards convincing you that it was good or bad. And so in this particular case, it was very easy. There was, actually, a perfectly good book about exactly the guy who came up with it.

And so it was the obvious choice.

Tim Ferriss: Before we get to subjects and more books, because this may bridge over to something that I did not know, I feel like I should have known this, and it makes perfect sense, but I did not know this. So this is, I suppose, one of your problem domains. We can discuss what that means. When you became CEO, I have a question about that also, but this is a quote from a media piece. And I could try to paraphrase it, but it would take a lot longer. So here’s the piece. “As part of his self-directed crash course, he decided to fly to Silicon Valley.” Now I’m going to pause here for a second because people listening might think, of course you go to Silicon Valley to learn from fantastic entrepreneurs and so on. But it takes a different turn here, which I think is really indicative of how you’re thinking, how you apply very structured thinking to things.

Back to the piece. “He set up meetings with venture capitalists and listened to their questions about Shopify’s attrition rates and conversion rates and ‘funnel’ (the various means by which a company attracts the attention, and secures the commitment, of new customers).” That’s a long way to say that. “He had no idea what they were talking about, but he wrote down the terms. Then he went back to the hostel he was staying in,” that also tells you something, “and looked everything up on Wikipedia. He would read up on how to calculate contribution margin ratio (the amount by which sales exceed variable production costs), then go to Shopify’s database to get the numbers. ‘Oh,’ he’d think, ‘that’s an interesting way to look at the business.’ Then, at the next meeting, he was able to answer one more question.”

This is a really clever way to go about getting up to –

Tobi Lütke: Thank you. I think it’s about time.

Tim Ferriss: You’re learning by observing the questions and then defining the terms.

Tobi Lütke: See, this is why I love podcasts. My favorite thing in the world – books definitely rank up there, but there’s one thing that is better, which is being a fly on the wall and two experts talk amongst each other, which is one of those situations where it was almost impossible to line up as an outsider. And now, suddenly, it’s completely democratized for a wonderful invention of podcasting. But back then, and before that, I sometimes managed to do it via finding a chat room or forum where experts talked amongst each other. It’s something I was always seeking, in this case. So when I was trying to learn about some technology like some esoteric 3D rendering algorithms that I found interesting, I used to try to find where people talked about optimizing these things.

And then I just don’t understand anything that they’re talking about. But then, I chip away at it, and I would come into the knowledge. And so I tried to replicate this. And talking to venture capitalists ended up being a way I figured out how to potentially do it because, again, I had no background in business. I had no idea how this all worked. And I had to do it fast because, in 2008, Shopify wasn’t doing well. It was very, very tough to keep the company alive.

Tim Ferriss: This is maybe a good opportunity to explain to people why you took over as CEO, just these circumstances.

Tobi Lütke: The circumstance was simple and probably fairly common. I had a co-founder for Snowdevil, which was the snowboard store. And I did the technology, and he ran the store and did a million other things like finding us an office at some point, and so on. But as the company pivoted much more to being a software company and started growing and acquiring more and more people, at some point, it was just a different situation. And so he sort of came to me and decided he wanted to transition out. and that was very surprising because, again, I really wanted to treat the business as a black box. I was a programmer. We don’t like business.

Tim Ferriss: Yeah. I was going to say treating it as a black box is a very diplomatic way to say it as a programmer.

Tobi Lütke: Yeah. I just didn’t want to become the Pointy-Haired Boss in the Dilbert comic! So this was the situation that just arose. And I actually looked for a CEO for a long time. I met with a lot of people who came recommended as potential CEO replacements. And it was one of my early investors, actually my only investor, frankly, who at some point took me aside and said, “Tobi, you will never find anyone who will care about Shopify as much as you do. And so you should just give this a go.” And that was pretty scary advice. But I liked the challenge. Why do we entrepreneurs do this thing? Why do we even build companies? It’s such a silly idea, right? Think about how we rationalize this. This is not my quote. But someone said “You spend 100 hours a week avoiding working 40 hours a week for someone else.”

Tim Ferriss: Right.

Tobi Lütke: It kind of makes no sense, right? Especially tech, there’s such a minor chance of actually getting any kind of returns on it. So you don’t do this for – I can only speak for myself. I certainly did not do this for monetary reasons. The reason why I did it was because I thought it sounded amazing not having to answer to anyone – back to authority problems. And I wanted to make my own technology decisions and these kinds of things. And I wanted to see what I could do. I wanted to challenge myself. And I said, “This is the right time in my life.” I was 24 when I started. “This is the right time in my life to give this a go. I will learn a ton. There is no way this could be a failure on a personal level other than in the way that maybe people lose money.” But failure was a very real thing, but I knew I would learn a lot.

And so I reconnected with [? 36:05] and said, “There’s another challenge to become the business side of the business as well. And I’m going to learn a lot again.” And so I traveled to Silicon Valley. It’s funny because I found this hostel close to Sand Hill Road where all of the VCs were back then. And I bought a bike on Craigslist and just biked to all of these things. If you look at Sand Hill Road, it’s not made for bikes.

Tim Ferriss: It’s not made for bikes.

Tobi Lütke: And biking interviews like gleaming palaces of capitalism.

Tim Ferriss: I just have to imagine they’re like, “Yeah, some guy is coming in from Ottawa, Canada. Ottawa, Canada?” And they’re like, “Wait, is that him on the bike?”

Tobi Lütke: This is exactly the situation. You’re just adding to the picture that’s perfectly accurate. And so I talked with them. I learned a lot. I thought they found that somehow I was endearing, in some way, because I actually did keep in contact with a lot of them. They didn’t actually run me out of the offices, which also speaks to Silicon Valley. It’s an amazing place where you can take meetings with people who will give you their time and advice. And I puzzled it out, I figured it out. It turns out I needed to learn a lot about certain terms and so on.

Tim Ferriss: You figured it out.

Tobi Lütke: I figured it out.

Tim Ferriss: First, an observation, which is how much fun it was for me and also instructive to meet you when I met you. That is quite a transitionary period in which to meet Tobi. So it’s been really, really fantastic to watch as things have evolved over time. That said, part of what makes it interesting is the good decisions but also the challenges and maybe some of the bad decisions. Can you talk to, in any order you like, some of the good decisions that you made and some of the bad decisions that you made, after taking on the role of CEO?

Tobi Lütke: Yeah. It would be good to have some sort of obvious examples here. But almost every good decision starts somehow bad first. We’ve made almost every mistake in the book. But we also are the kind of company that wants to in a way. It’s been so important to me to build a company that is unafraid of experimentation and where failure – within Shopify, I think we succeeded in this. We eliminated the talk of the term failure. We call it the successful discovery of something that did not work because I think it really changes people’s disposition to it. So what did we do wrong?

Tim Ferriss: I was just going to say, I don’t want to interrupt your answer, but I think that what you just said could also take us in a pretty interesting direction if you want to buy some time to think about the failures.

Tobi Lütke: Let me buy some time.

Tim Ferriss: Or not the failures, “failures” in quotation marks. So there are a number of things that seem paradoxical that I don’t think are paradoxical in practice. Maybe they are, but I want you to comment on them. And I just have to find the right quote here. Well, I’ll give you the first part. So the first part is a quote of yours, I believe. “‘Your work here needs to make an impact like a crater.’ So it’s not like just good work, it’s not excellence; it’s like massive, cosmic impact. It needs to be visible from outer space.” And so people are encouraged to take risks. Now, at the same time, another quote here. Toby Shannan, right? So you know what’s coming.

This is on receiving feedback from Tobi. “Be prepared to be crushed,” says Shopify’s vice president of revenue, Toby Shannan. “‘If you can’t be crushed, you don’t make it on the executive team. You need thick skin. It’s not that Tobi shouts or treats people meanly. He’s simply direct, unfiltered. When he looks at the fruits of someone’s labor, he says what he thinks, even if what he thinks is: ‘This is shit.’” Okay.  So how do you combine these two things successfully? One of the things I love about you is that you don’t get the sugar coated, kid glove version of Tobi’s thought. You get Tobi’s thought. So how do you encourage risks when the feedback you receive at the end might be, “That was total shit. You can do better?”

Tobi Lütke: No, I want to register that that quote came up in 2015. And since then, I have learned that I should translate something like “This is shit” into “Is this really the best way we can do this?” But it’s the same thing in a different form, really. Wikipedia, right? I hope I get the name right. There’s a specific editor from the early days of Wikipedia who, I think, was called [Lee Daniel Crocker]. And he declared something like Crocker’s Rules, which said that he wanted everyone to edit his pages just to make them better. And he didn’t want people to apologize for it or try to politically give him credit or something. He said, “I’m going to take 100 percent responsibility for my own mental state. You cannot make me unhappy by just giving me feedback in some way. So just give me raw feedback without all of the shit sandwich around it.”

And I love that. I would like to run my team on Crocker’s Rules because I think there’s so much time spent. First, you have to talk about the weather.

Tim Ferriss: And then you have to say, “Nice sweater. That’s a really nice sweater.”

Tobi Lütke: Exactly. So you have to find something and then ideally, address some very productive character traits, then talk about the thing you want to talk about. And then figure out some way, afterwards, talking about something highly positive again. That’s the sort of standard formula. And I can do it, but I don’t think that the highest performing teams in the world should spend time doing this to each other. I think there’s a level of progression that comes if you’re part of one of the teams. Again, we are one of the bigger technology companies in the world. Certainly, we’re the fastest growing SaaS company on the market. And so I don’t want to compare it too much to sports because sports is sports. But this is like a big game. We need to be very good at what we’re doing, otherwise, we cannot build Shopify.

And so I think these things are in the way. So yes, I want people to be impactful. Again, if a hard object collides with a soft object, suddenly, there’s no crater to prove it. And so I want people to take their mental state in their own hands and just say, “I’m going to learn how to be intrinsically reminded that I’m good at what I’m doing and not have to rely on other people constantly telling me.”

Tim Ferriss: Does Shopify have any type of training or resources or cultural rules that are explicit that help to facilitate that type of awareness? Because there are people who meditate for 10 years with that objective and never quite get there. And you can already find the people. You can go out and hire Jocko Willink to run your HR Department. I’m kidding. And he would give them all a copy of Extreme Ownership and be like, “Here we go.” But then, there are people who come in who might be exceptional performers but very sensitive in some way. I run into that quite a bit.

Tobi Lütke: Yeah.

Tim Ferriss: What do you do in a situation like that? Or what are the things that you do or that Shopify does to help people take that ownership of their internal state? Because it is hugely important.

Tobi Lütke: Yeah. It’s hugely important. So one thing that’s so neat about Shopify, let’s get a little bit back to this Ottawa, Canada thing. Clearly, as you said, this is off the beaten track of the startup world. It ended up being a phenomenally good place to build a world class company, but for reasons that were also not clear to me when I started there. A couple of things that happen when you’re not in Silicon Valley, when you’re not in – let’s call it a primary company creation city. Tenure gets longer. If I hire someone through this very intricate hiring process that we have, there’s sort of an understanding that the chance of us still working together in 10 years is actually really high. It’s a commitment from both sides. And the company needs to be worth working for for 10 years.

That’s what I work on day in and day out. Because of that, we can have a very different relationship than in a place where the expected tenure is 18 months. And in an 18 month place, I really have to kind of access every good idea and productive power of an engineer. So immediately, they need to be productive.

Tim Ferriss: And they need to be really pampered, in some cases.

Tobi Lütke: To even keep them for over 18 months because –

Tim Ferriss: That’s right. Via Facebook, Google, and then, name five other companies who are all pitching the same employees at those five companies via headhunters.

Tobi Lütke: Yeah. And so in a place like this, it ends up, for better or for worse, in a world where people don’t actually go have careers at companies anymore because the way to have a career is actually jumping between companies. So your new position is always slightly higher. And so our cities aren’t like that. We assume that we have these long tenured relationships, and therefore Shopify can invest in people who are part of Shopify in a completely different way. So we probably hired all business coaches in Canada and then beyond, at this point, to be full time employees of Shopify because we’re investing so much in the people. We hire people on future high potential and then try to get them there as fast as possible because that actually works for us. It works for people, and it works for Shopify fantastically well.

And so we have a lot of these opportunities because of that to make some slight edits to the normal psyche. So feedback is a gift. It’s not just a simple sentence, but it really is not the way most people think about feedback.

Tim Ferriss: Feedback is a gift.

Tobi Lütke: Feedback is a gift because it is. It clearly is. It’s not meant to hurt. It’s meant to move things forward, to demystify something for you. I want frank feedback from everyone, and I get it. Although funny enough, you might not have thought about this, I tend to get it from the Germans at Shopify more frequently than anyone else. So there might be a cultural component here, too. But yeah. Did you say call it crusher of egos or get your ego crushed? That sounds so dramatic.

Tim Ferriss: Yes, be prepared to be crushed. If you can’t be crushed, you don’t make it on the executive team.

Tobi Lütke: I would say that might be a little –

Tim Ferriss: Or learn how not to feel crushed.

Tobi Lütke: Yes. So this is the executive team that is directly my team and the people who I have the highest requirements of and we have worked together for the longest. So I don’t think it’s like this everywhere in Shopify.

Tim Ferriss: So are there particular books, particular types of training, exercises that are used within Shopify to help people take ownership of their internal state or to view feedback as a gift that people listening might be able to use or explore and think about, in some way?

Tobi Lütke: Different companies have different sort of personality traits, testing kind of things that they like. Shopify is very partial to a system called Enneagram.

Tim Ferriss: Enneagram? I just had my first Enneagram typing last week.

Tobi Lütke: And you are an eight?

Tim Ferriss: I appear to be a loyal skeptic six.

Tobi Lütke: Oh, wow. Interesting. There you go.

Tim Ferriss: Yeah, we could get into it. This is all new to me. This is all new to me.

Tobi Lütke: It’s very interesting. But Enneagram, it has worked very, very well for us. In our internal system, you can actually see the Enneagram with everyone else.

Tim Ferriss: Really?

Tobi Lütke: And it tells you what nuances, what means for how to work together, for instance. So that’s one. But the other thing, I think, why personality tests are interesting is it doesn’t even matter which one it is. After you kind of do one, it already kind of teaches you like, “Hey, wait a second. The way I’m wired is different from the people around me.” And I think this is so fruitful of a discovery, especially early in your career because, again, a lot of the people we hire, the average age at Shopify is 29, I think. So we get to people very early in their career because the thing that we want to accomplish, and this is really the goal of all of the internal programs, is we want to take people from a – find out what kind of areas they have a fixed mindset on, and try to get people to acquire a growth mindset.

Think of their intelligence as something that can be trained. Think of their skill as a program and not as something static. And when someone comes and tells you there’s something you could have done better, that’s not someone finding out that you’re not as good as you thought. That’s actually a teacher appearing. And once people acquire this growth mindset on at least a number of different traits, usually, they make it very, very far, and they can have these 10 years of a career in 1 year on the work clock. And it’s a wonderful kind of thing when it happens.

Tim Ferriss: How would you suggest that people acquire a growth mindset? Because there are books – I haven’t read Angela Duckworth’s book, Grit. It’s been recommended a number of times. But there are a number of books that talk about the importance of fostering growth versus fixed mindset in child rearing. And you shouldn’t say, “You’re so smart.” You should say, “You worked really hard and did a good job,” and so forth because, inevitably, if they have what’s perceived to be a failure or make mistakes, it’s then not indicative of them being stupid but rather something related to effort and/or chance that they can play a part in resolving or improving.

But if we’re talking about – let’s just say there are any number of people certainly listening to the podcast like, “I’m sure I have a fixed mindset somewhere. But I don’t know if it’s a blind spot. I don’t know how I would spot it. And then, how do I fix it? What would your thoughts be?

Tobi Lütke: I think that it’s a really, really good question. I wish I had a better answer. I do find that Carol Dweck’s original book called Mindset is probably still the best.

Tim Ferriss: That’s D-W-E-C-K, right?

Tobi Lütke: Yeah.

Tim Ferriss: We were talking about Josh Waitzkin during lunch, also a book that he’s quite a fan of.

Tobi Lütke: Yeah. I’m a big fan of the book. It talks you through the theory. And what I’ve observed is even with a very, very high super successful executives who come to Shopify and have worked at Shopify for a very long time, they end up reading the book. And they say, “You know what? I was actually fixed mindset on all of these three things. And it’s like it really irks me now.” It’s just really funny how it wakes you up to this reality that we kind of all have that. It’s not something you can completely overcome. But it’s something that just having the awareness is really powerful. And also, if you have to have reports in a company, even if that book does nothing for you, it will allow you to be a much better lead to most people because it’s just priming you to detect fixed mindset talk in other people. And pointing it out is hugely beneficial.

Tim Ferriss: So I want to note an observation that may or may not be true. But it seems to me that the discussion of fixed and growth mindset pairs quite well with Enneagram also. Enneagram, by the way, I was introduced to by Drew of Dropbox. And I was always skeptical, and I still am somewhat skeptical of certain aspects of Enneagram, which I think actually means nine pointed. So there are nine different types. Then there’s a lot of discussion through different books and experts about Enneagram. But like you said in your commentary about Enneagram, it’s not necessarily the specifics of the business acceptable horoscope that you get. It’s the fact that you begin to look at relating to other people and your own weaknesses and/or fixed mindsets differently. And so I found it very useful.

My girlfriend did her typing. And I’m going to have all of my employees do their typing also just so they think with awareness about interactions through that lens, even if the exact content may be 50 percent hand waving, if that makes sense.

Tobi Lütke: Yeah. Here’s why all of these things matter. I don’t particularly believe in Hell. But I like this definition I’ve heard. Hell is meeting the best version that you could have become of your life. And so I think that one of the really, really fun things about an experience like an entrepreneur journey like with a company, the careers we have, the books we read, if they end up being pointed in a direction that allows us to minimize the difference between that person we will meet and the person we are, at that point in time, I think that’s time well spent. And there are some key events in one’s life that have to go through it. At some point, hopefully, you realize that the people around you are very different. You have some unexplained traits in you, which some of them becoming big strengths and some of them are weaknesses.

And you double down on your strengths, and you try to work around your weaknesses. And by the way, later in life, it might actually flip which one is which, which gets really weird. But that’s another one of those kinds of things. The sort of awakening to a growth mindset is another one of those life events, I think. And so these events matter because what you’re building, eventually, is like some kind of path that allows you to wake up smarter every day. And if you get there, really, really powerful things happen. Suddenly, jumping into a completely new job that you have no qualifications for doesn’t sound scary anymore. It probably still does a little bit. But the challenge and the thrill of this sounds real. “I could fail; I have to grow to make this work” actually becomes hugely motivating.

And I think that one of the most amazing things that anyone can go through and can do in their lives is a variation on the theme of going on a journey, doing hard things surrounded by friends. Company building is one of those things. Often travel is another one, sports are really good at these kinds of things. I would love Jocko’s opinion on if war is like that.

Tim Ferriss: I think he would definitely say that.

Tobi Lütke: So variations on this theme is what you want to prepare for.

Tim Ferriss: I want to come back to something you mentioned earlier that I think is very, very relevant here. So I’m going to try to tie a few different things together. You talked about taking risks and looking for opportunities for massive impact. You also talked about how you have looked at certain opportunities or transitions as opportunities for learning and that you’ve made a lot of mistakes. But it seems to me that you’ve, in some ways, optimized for learning. And I just want to highlight for folks listening, and also just to remind myself, that this is something that comes up quite frequently with people who seem to just step up to bat and hit home run after home run. If you really dig under the hood, that’s not necessarily the case.

But, for instance, people who are in any number of different fields, whether it’s Scott Adams and Dilbert or some of the investors I deeply respect Marc Andreessen, who has been on the podcast. They talk about rather than trying to be the top one percent in the NBA, which is very hard to do and very attribute dependent, you could be top 10 percent or even top 25 percent in things that are rarely combined. It could be computer science and law. It could be Warren Buffett and value investing and public speaking. He says the best investment he ever made was in a Dale Carnegie public speaking course because it magnifies everything else that you do. And so there’s the combining of skill sets that are rarely combined. And, as Scott has also written about quite extensively and I agree with, and I’m paraphrasing here, so I might be mixing and matching a little.

But if you optimize for learning new skills and developing new relationships that transcend any one given project, it’s really difficult to fail completely. And so you end up accumulating these skills and relationships that then, help for you to combine these different disciplines in unique ways. So that I just want to mention because it’s tempting and debilitating to think that you have to be the absolute best top one percent in X. And when you really look at people, whether it’s all of the various billionaires on magazine covers or what have you, that’s not necessarily the case.

Tobi Lütke: No. So I could not agree more with you. And it’s interesting because I almost have two phases to my life, in this regard, because I really was trying to become, I don’t know, I don’t know if I was trying to become the best programmer in the world. But I certainly was making a bid for it. My life completely revolved around writing code, understanding more of it, and just being very, very good at it. I was going for mastery anyway. And then this situation that happened there, again, I had to pause and have to go into business. And I ended up really, really liking so many aspects of it. I really pivoted from someone who was going to try to get – I would like to understand 100 percent of a field to I want to, as quickly as possible, understand 80 percent of every field. And I like it way better on this side.

And I’m eternally thankful for having realized this, at some point, because it actually doesn’t take that long. You wrote an entire book on this. I’m, obviously not trying to convince you on this, but it doesn’t take long to understand the first 80 percent of any number of fields, right? But of course, you can’t understand 80 percent of every field. There are too many. So you’ll follow your interests pretty automatically. And when you find out exactly what you just said, and this is something that’s worth looking into the Shopify universe. The people who are really successful are the people who usually have some multiple skill sets and combine them into some kind of new product. It’s like sort of an obvious example is boosted, boards. It’s electrical engineers who also like skateboarding, and it’s combining those two things by putting a battery into the skateboards.

And so it’s really, really hard to be the best in the world at a single discipline. But as soon as you start overlaying three different interests, you make Pokémon inspired jewelry or something, you can make the best Pokémon inspired jewelry in the world pretty quickly.

Tim Ferriss: The speed with which you came up with that makes me think that that’s a store on Shopify somewhere.

Tobi Lütke: Absolutely. Yes.

Tim Ferriss: You’re in a great position to see hundreds of thousands of these examples.

Tobi Lütke: We see millions of success stories and attempts at success stories. This is, honestly, the most interesting part of Shopify is really that we see this. Let’s actually zoom out for a second here on my entrepreneurship topic because it’s really dear to me. But it’s also at a stage where a lot of people don’t really quite appreciate it. Entrepreneurship is in big crisis right now. It’s a complete counternarrative to what most people think. But right now, new company information is at the lowest point it’s ever been. Gen X has started a lot fewer companies than its parents. And millennials are lower yet. So it’s the least entrepreneurial generation so far. And all numbers are down.

Tim Ferriss: Is that measured by LLC formation, entity formation?

Tobi Lütke: Just general companies of all classes in the United States over time. Once you look at the graphs, they are looking like they tanked, especially since 2005/2006. So the very beginning of the financial crisis, it suddenly fell off a cliff. So why is that?

Tim Ferriss: Tell me, Tobi. I don’t know.

Tobi Lütke: Well, I wish I knew. It’s like I know some contributing factors. One thing is we just don’t need too many copies of everything anymore. Back in the day, you probably lived in a smaller community, you visited a big one, you saw here’s a certain kind of hardware store, some kind of business you’ve never seen before. You’d say, “Hey, I might be able to do that back at home.” And that’s a new company. Now, everything is franchised and centralized. And it’s a lot harder to do these kinds of businesses. But the same thing is going on on the internet as well. The internet is, as much as it can be a democratizing force, it really benefits centralization. We have one social network. It’s one search engine and so on. So it’s just harder to start businesses. And you kind of have to clock in the top percentile of a field or at least an intersection of multiple fields to even partake in entrepreneurship.

And I think that’s not good. If you would give me like there are two versions of a world, choose one. One in which entrepreneurship is common and easy and straightforward and one where it isn’t, who takes the one where it isn’t easy, right?

Tim Ferriss: So how would you make it easier, whether in the US and maybe not Canada specifically – could be – but is there anything that you would do to increase the number of entrepreneurs? And why is that important? Is it important?

Tobi Lütke: Yeah. That’s a good question, which I think should be studied. One thing, if you look at this completely from an economics perspective, if you think that we need to provide employment to people, a couple of mega companies are not going to employ everyone. I think everyone understands this. We need millions of 10, 20 people companies, SMBs where almost everyone is employed by small businesses if you look at the actual numbers. So with small business going away, that’s definitely a force in the opposite direction. So how would you do it? One thing that’s actually a real problem in the United States, but it’s actually a problem everywhere, is licensing. It’s a crazy situation that I can get a laptop and start $15 billion Shopify and need to ask no one. But if I want to become a hairdresser, I need to get a license for it, right?

And I need to go invest quotas in many places, and you can’t because of all of these reasons. So that’s kind of one of the things that probably people have to have a look at. But the other one is just friction. How difficult is it? How many things do you have to understand to start an online business? You built a supplement business back in the day.

Tim Ferriss: Yeah.

Tobi Lütke: What were all of the things you had to learn?

Tim Ferriss: Well, even before that, when I was taking a stab at a few businesses, all of which self-immolated. But just setting up a merchant account, I remember, back in the day, was a complex and hugely involved task.

Tobi Lütke: I had to post a $30,000 bond to get a merchant account when I started Snowdevil. That was all of the capital I had.

Tim Ferriss: It’s wild.

Tobi Lütke: But both kinds of points of friction are everywhere. I don’t want to make this [inaudible] [01:08:08], but Shopify is not the solution to this problem because it’s a much more global and bigger problem. But the retail world is one of the most accessible parts of entrepreneurship. And that’s really all Shopify is. Try to take the learning curve of partaking in entrepreneurship, building online businesses, and make it as flat as possible so as many people can succeed. That’s what we’ve been working on for the last 14 years now.

Tim Ferriss: I think this might be a good place to chat about the Build a Business competition.

Tobi Lütke: Oh, yes.

Tim Ferriss: The Build a Business competition, we’ve been talking about just smoothing the path or removing impediments to entrepreneurship. But you also have incentives. And incentives are also important. What is the Build a Business competition?

Tobi Lütke: Let’s go back to where it comes from because it’s so relevant to the two of us. Well, certainly to me. I don’t know if it’s relevant to you.

Tim Ferriss: To me, too.

Tobi Lütke: You were involved. So this was 2009. At this point, Shopify was completely running on fumes. All sorts of things didn’t work. Like you asked me earlier, the things that didn’t work – the company kind of didn’t work. I had the numbers, and people were selling things, and it was valuable to them. But there was no real business being built around it. And it kind of all just didn’t function. My father-in-law was gracious enough to give me a check every week for the running payroll at that stage. And he said he would do that for some time. And by the end of it, we kind of had to figure out what we had to do. At this point, we were talking. And the reason why, again, we see the world in a similar way; you wrote The 4-Hour Workweek. But what I tried to meet in this focus [1:10:07] like what you were talking about: just building a business and then actually doing other things, like I was seeing people doing this on Shopify.

But I was like, “This is an underexplored form of what you can do online. People should know about this, that this is what some people do, and we should obviously tell people that that’s what we will do on Shopify, and Shopify is good for this kind of thing.” So we had this conversation. I was at my college. I was actually on a boat when we had this conversation. And we were like. “How can we overcome this built-in fear of failure that everyone is running around with?” So many people come to me, come to you and say, “One day, I’m going to start my own business.” It’s like, “Okay, what about today? What’s wrong with today?” And there were all of these kinds of reasons. And I think our working theory was: we need to test this by really incentivizing people, to which I said, “We should give away a MacBook Pro or something.”

And then you did what you always did in our phone calls. It’s like, “Tobi, first of all, that’s way too nerdy, and only you care about MacBook Pros. And second, if you want anyone to notice, you need to go like 100x that in terms of prices,” or something like this, which is probably easier to say on your side.

Tim Ferriss: I also remember exactly where I was. I was in Glen Park walking down – I think it was Diamond Street past Ocean Tide. I remember the exact block I was on when we were having this conversation. Yeah.

Tobi Lütke: It’s funny. Sometimes, these things are just branded in your mind because I think we both realized we were egging each other on to make something big. And what we ended up doing was saying, “You’re going to take the last $100,000 in the bank and just put it up as a competition. And whoever is going to build the biggest business starting now in the next six months is going to just get the check.” Which at this point, I said, “This is either going to work, and then we’ll make the money during the competition to then give to people, or the company is bankrupt anyway, in which case I’ll deal with that in some other way.” But we did. And I think, through some contact of you, you introduced me to Lora. The New York Times ended up talking about it because it was surprising.

It was a tiny start up in Canada putting up something that’s beyond every business plan competition in terms of prize money. It was a pretty stunning amount.

Tim Ferriss: Yeah, the biggest ever.

Tobi Lütke: It was a huge success. You were super confident that it would be a big success from the beginning. I thank you for this because I was like oh, my God.

Tim Ferriss: And it’s been really awesome to watch also year after year as it has grown and evolved. So you could give some examples, but from the beginning, which we’re not entirely sure – on some level, we know where the $100,000 is going to come from. But this is an existential bet, in a way. But like you said, it’s like there are other inherent issues that, if we don’t do it, it’s not clear what the picture is going to look like. And then you flash forward, and you’re doing these Build a Business competitions. And it’s like a high end reality show, in the sense that you have the mansion from The Great Gatsby with DiCaprio. And other people are flying all over the world. And you have Tony Robbins coming in to mentor the finalists and so on.

Tobi Lütke: Yeah. We took everyone to his place in Fiji, right.

Tim Ferriss: Yeah. It’s been so much fun to watch. You guys have done a fantastic job of executing. And it’s ended up coming full circle also as I’m considering, with the audience that I have, what could I do potentially competition wise? You guys have taken the ball, run with it, and have done this so many years now. I’m like, “Hey, which lawyers did you guys use?” It turns out, by the way, anyone who is thinking about doing something like this, you have the prize money, but then you have the putting together of a competition of this complexity, which is no joke.

Tobi Lütke: No joke. Every state, even every province in Canada, has completely different laws for this. Everyone will come and ask, “Hey, is this a game of chance here or is this a game of skill?” Which is actually an interesting question because the intellectual answer is chance. I would try to never get confused about this. Shopify is enormously successful, but it’s like 99 percent chance. You can’t predict all of these kinds of things which happened to transpire, which led to success. But, of course, when you’re talking to the lawyers, it’s a game of skill, absolutely, 100 percent skill. And so we launched this in 2010. And we had an amazing winner at the end with DODOcase. It was so cool.

Tim Ferriss: Yeah. Can you tell people a little bit about that?

Tobi Lütke: Yeah. Patrick and Craig, two brilliant entrepreneurs from San Francisco who – I think this was around the launch of iPad. And so they realized these iPads need cases just like the phones. And so they got together with some traditional bookbinders and made some Moleskine looking, beautiful – it was really just wood and whatever Moleskine is, a case for iPads. And I think they gave fliers to everyone waiting in line at the Apple Store before iPad got launched. So people wrote about it. And they were one of the competitors in the competition and won it. And a fantastic story. There’s a later picture of President Obama with his DODOcase, which, of course, they used very successfully in every one of their marketing campaigns.

And I think, actually, this goes back to the thing that really excites me about the effects that come from all of these kinds of things. Not only was this an entrepreneur success story for them, and they got $100,000 check in the end. They also quadrupled or even beyond the number of professional bookbinders in the San Francisco Bay region again. This was an area which had a lot of bookbinding talent when that was an industry. And that’s not an industry anymore because it’s just not done manually anymore. But they got people out of retirement to come back making these iPad cases. And the industry exists. And I think these are just the stories which I find so so great.

Tim Ferriss: So let’s talk about it. We don’t have to get into all of the specifics of a ton of them. But I was very curious, from the first competition, to see what can people do. What can people actually do?

Tobi Lütke: In six months, right? It was six to eight months. It’s nothing.

Tim Ferriss: But some of these people are creating multimillion dollar businesses from ground zero. And it’s been really inspiring to watch and inspiring not just because of the size but also the variety. That having been said, one of the things I look forward to every year, when you guys are running the Build a Business competitions, is what patterns will emerge because you begin to spot, and this is much like I feel like with my audience from The 4-Hour Workweek or the podcast, but just the millions of entrepreneurs who allow me to pattern recognize because I just have the 30,000 foot view on my audience, show me things that are coming. It’s like William Gibson in Neuromancer said, “The future is already here, it’s just not evenly distributed.” So you see these patterns that are sort of this smoke signal in the distance.

And then, five years later, it’s everywhere. And with Shopify, for instance, I remember the first year that a number of the category winners – because there are different categories, so it’s not all or nothing, at this point in the competition. There are different, what would you call it, industries or product categories?

Tobi Lütke: Yeah.

Tim Ferriss: Which gives more people a chance to win. And it’s like wow, okay, I’m making this number up, but it’s like three out of the six used Kickstarter. That’s interesting. And looking at the different tools and different approaches, different tactics and strategies that seem to be used with great efficacy each year are also something that I have really looked forward to.

Tobi Lütke: And this goes beyond the tools into the approach, I think. And this is actually where I feel like I learned the most from the entrepreneurs because these are really the best who are coming. Actually, we had first time entrepreneurs win categories. But they always had some kind of fantastic insight that they’re kind of adding to this exploration of how to build companies in this digital age. So even the Kickstarter folks, the question I always had is like, “Was Kickstarter itself valuable, or was it that they had to put a certain video on the website where the founders the company had to explain why this product needed to exist? Why does not every product in the world have an inventor declare why they felt this thing needed to be created? Why can it only get there from the people who happened to go on Kickstarter?”

And most of them ended up figuring out approaches, which are really about storytelling. What’s the story? The DODOcase story is a story of the revitalization of a craft, which people connected with. The beautiful object that came out of it was completely imbued by this story. And when I was walking around with my DODOcase, someone would talk about it. I would talk about how this was handmade by real bookbinders because I owned part of that story. And that’s really a great thing. The really great thing is that the things that are powerful and work have actually not changed in the internet age. Our ancestors were once storytellers at least for people who listened most to the stories. This is how language developed. We’re storytelling creatures. And it just is rediscovering this medium after medium is something that is really fascinating.

Tim Ferriss: And if you’ve looked back to the two books you’ve mentioned, if you’re looking at Influence or you’re looking at Andy Grove’s book, also not a snapshot in time dependent on the technology of right now. These are principles. And I’ve often thought about Kickstarter also and other platforms like it as a talent assessment for some of the basic competencies that one will need in the company they would then subsequently build. If you cannot sell your product in a video and then marshal resources and try to garner PR, however, you take your approach to raise a potentially nominal sum of money for a first manufacturing run, how can you ever have the confidence then that you would be able to proceed and build something large over an extended period of time? It’s an audition, in a sense.

And so then, it brings up all sorts of other questions. Just getting back to one of the first things I asked you about, questioning the question. Is it a survivorship bias? Is it that there are more people attempting things and, therefore, they can kind of stress test and then run with the things that work, and that is why you have this higher percentage appearing in, say, a Shopify Build a Business competition? In any case, it’s been such a fun ride. And thanks for having me as part of it.

Tobi Lütke: Well, you kind of started it. You shouldn’t downplay your input on the whole thing.

Tim Ferriss: Yeah. And I wanted to also, before I forget, and since I think other people listening might find it of interest, mention a book that’s kind of going to segue over to something that may or may not bear fruit, we’ll see, but the book that I would recommend – bear with me, guys. This is going to get very Tim Ferriss ADHD for a second. But you mentioned dyslexia. Do you not have any issues with real time review of code as you’re writing it?

Tobi Lütke: No.

Tim Ferriss: Okay. That’s interesting.

Tobi Lütke: None.

Tim Ferriss: Okay. That’s for another time. Neurologically and optically, that’s very interesting to me.

Tobi Lütke: It’s a fascinating question, but no, I don’t.

Tim Ferriss: Okay. I had that come to mind because I’m going to recommend a book. But it’s a short book by a reasonably recently deceased Jesuit priest who was also trained as a therapist named Anthony de Mello. The book is called Awareness. And the subtitle is The Perils and Opportunities of Reality. But it’s a collection of effectively transcribed talks that were given by Anthony. It was recommended by a guest on this podcast, Peter Mallouk, who is in finance. And I decided to pick it up because he said, every time he reads it, and he re-reads it more than any other book, it gives him an extended sense of peace. And I was like, that is not the phrase or explanation that I would expect.

Tobi Lütke: It’s a hell of a way to sell a book.

Tim Ferriss: Yeah. And I picked it up. Awareness: The Perils and Opportunities of Reality, I think, you might just find strikes a chord. It’s a very easy read. And for me, it did give me this extended afterglow effect of inner peace for two weeks. And I decided that I’m probably going to re-read it less than a month after having finished it. And it has proven very valuable for me, even though I do have a meditation practice, to reinforce through the prefrontal cortex the value of owning your internal state and be choosing to be or develop the responsiveness as opposed to reactivity. And this, on a macro level, makes me think of comfort, discomfort, and how humans relate to that.

Something that came up in doing research for this was the concept of – and then, I may be barking up the wrong tree here, but we’ll see where it goes, the next box and what the box is. Not in the shipping container sense. Could you talk about what I’m referring to?

Tobi Lütke: Yeah. It’s a term from a talk I gave. I was invited to a local event, and they needed me to do a keynote. And I don’t tend to do these kinds of things a lot. But they just asked me to share something. And so I said, “Well, personal growth is something that I’m thinking a lot about and feel like I was going through.” So I decided to just explain it the way I see it without really going deep into what I was thinking about it. And so this is what I explained. When you’re back in high school, I remember being back in high school, and I remember that there were cool kids and uncool kids. And we probably were two different sides of that divide. I was with the uncool kids.

Tim Ferriss: I was the Dungeons & Dragons nerd kid camp. So I actually got my ass kicked up until about sixth grade, and then, a growth spurt, and then I was just an angry, rageful vigilante. But up until sixth grade, I was definitely in the nerd camp.

Tobi Lütke: So and, again, I don’t know why we keep talking about me as a kid because it’s not that interesting, but it seems to keep coming up. This is already going to tell you way too much about me as a kid. At some point, I decided I want to analyze why some kids are cool and why I’m not. And what I came back with was the cool kids all had Air Jordans. So I wanted them, too. And, of course, at some point, I got them, and it totally didn’t make a difference. But the reason why this is valuable is that high school is a universe. It’s kind of a box. And it’s hard to get in it because it feels very uncomfortable. You don’t understand it. You don’t understand the social network or inferences. And then you’re trying to make sense of it in your own way, and it actually becomes reasonably comfortable after you sort of explain it to yourself.

Now, it’s a small box, narrow. And probably your understanding of it is wrong. Clearly, mine was about how I could join the cool kids. At some point, hopefully, what happens is you find a crack somewhere in the narrow box you’re in, and you go into the outer box where this box you just came from is like a tiny parcel in the corner. It’s a much bigger place. It may be college or work life. But, again, it feels super uncomfortable. You arrive in that new box not understanding physics, not understanding the situation, what’s expected of you. It’s all ambiguous. You have to reinvent – even the things you figured out before are no longer true. And you notice this at sort of an internal level. And the trick is to, at some point, figure it all out. And then comes the dangerous part because it’s now comfortable again.

And so what you have to do is you have to go and find the crack and go into the next box around this where, suddenly, all of your college life and all of these kinds of things just are a small box in the corner somewhere. And, suddenly, your world is much bigger, and you need to learn more and understand more and so on. I find I’ve met, luckily, at various times in my life, these people who clearly occupy the much larger box. And they just sort of bend down to me to talk to me because they could just somehow – like you said this one thing, and what they said back to you was so clearly right, but you could never have understood yourself based on this vantage point you had. And they were usually the way that you entered into a larger box and so on.

Tim Ferriss: Can you think of any, or are you willing to give any, examples of an exchange like that?

Tobi Lütke: Yeah. It’s a recurring thing. It still happens to me to this day. The specific case I was thinking of, back in the day, I left school after tenth grade. I started my apprenticeship as a computer programmer, which is the thing you can do in Germany. And I spent a good deal of time on computers and understood them. I could do programming and so on. But there was a guy by the name of Jürgen Saar, who was sort of my designated mentor in this apprenticeship program. And he was one of those people who I could ask any question, and you could write down what he said back. Everything came back fully formed.

Tim Ferriss: Sam Harris type.

Tobi Lütke: Exactly. And but also, he was just an incredible mentor to me because he created almost these scenarios for me. He would do quote reviews and so on. But also, he would sign us up to drive to some customer, which he and I were writing some software for. And then, he would just find an excuse for not being able to do and just let me go myself. And I was like 17 or 18 years old. I just got my driver’s license.

Tim Ferriss: I’m just trying to imagine having spent a lot of time with you.

Tobi Lütke: I had to get 400 D mark, which was before euros, which was like 200 euros, to buy a suit from the company. I did not have that money. Going to a customer and selling software.

Tim Ferriss: Now why did he do that?

Tobi Lütke: Because he thought I could do it. And that was just it. It’s like he did think that I would probably not fail and that I was good enough also for him. And he also knew the customer well so he can pull a stunt like this, and they would find it’s funny. So there was very little personal risk for him. And then, you do this, and I learned a lot. And, of course, it totally didn’t work, and I had to use some satellite uplink to get the new version. But I came back and said, “Hey, in this sort of bird view box thing I was in just yesterday, it’s implausible that I would have succeeded doing this thing that I just did yesterday. So therefore, I think I’m in a comfortable new box right now. And I have to relook at everything I know and recategorize everything.” And Jürgen kind of just figured out how to get me through a couple of those. And so I don’t know if it’s a good metaphor for growth.

But it’s one that just sort of came to my mind the first time I was supposed to explain this to people. And what I like about it is that it affirms the thing that makes it hard to grow because it is the dangerous part of when you feel comfortable in the box you’re in. And every one of us has, at the family reunion, the one uncle who decided to not traverse into further boxes way too early. The had the entire world figured out, and everything makes sense to them. And, of course, everyone else looks at it and says, oh, my God, what are they talking about, right?

Tim Ferriss: So I have a few questions about that. Comfort zones are a topic of great interest to me. But also, it comes back to awareness as well. For instance, do you know what box you are currently in and the next box you want to go to? Or is it not possible, until you have someone bend down and kind of poke you in the forehead?

Tobi Lütke: I don’t think you can. I know I’m always in a box. Personally, I think I have figured out the box I’m in. And I’m currently not seeing the exit, which makes me uneasy.

Tim Ferriss: I’m sorry, say that one more time. One more time.

Tobi Lütke: I would say that I understand the box I’m in, and I haven’t found the exit. And the funny thing is I’ve done this so many times that I’m actually really uncomfortable being comfortable. I really dislike not understanding where that comes from. So I’m a seeker right now.

Tim Ferriss: Are you comfortable sharing what the box is that you’re in that you don’t know the exit from?

Tobi Lütke: It’s nothing terribly profound. It’s like it’s my life. I understand how to be a public company CEO. It’s just a crazy sentence that [inaudible 01:34:53] we would never have met and me uttering. But I understand the systems of Wall Street. And I understand the company that I’ve built. I understand how to be the best leader I can be for the company. I’ve made a lot of progress in my personal life. I started working out and just have a meditation practice, all of these kinds of good things that you have been recommending forever and I finally came around to. So that’s good, but it’s comfortable, in a way. I’m seeking right now. I’m trying to poke at this. I am trying new things to figure out how to break out of it.

Tim Ferriss: How do you choose those things? How do you choose the things that might be the right stress test to find that crack?

Tobi Lütke: Books are generally good. Like, far afield books are useful. I’m really interested in just psychology right now because there are a lot of more interesting topics than people think. But I’m also challenging myself. I’m in a driver development program for motor racing, which is super fun.

Tim Ferriss: That sounds amazing.

Tobi Lütke: Talk about getting in a car not thinking about anything for two hours or three hours.

Tim Ferriss: Yeah. You’re highly incentivized not to think about other things.

Tobi Lütke: Exactly, because there are real repercussions. This is not like the successful discovery of something, but it did not work. This was a wall. So, like doing things that are just different from anything else. Imparting things from other people’s boxes who are presumably in bigger boxes is a way of doing it.

Tim Ferriss: Now I would also love your help to clarify something, not so much for me because I think I know the answer, but maybe for people listening. And that’s a distinction. I know, as I’m sure you know, many, many people who think that more money, more X, more Y will make them happy or content or at peace. And they never reach that moving goal post. And you and I also, I’m sure, have come across – it’s more common in Silicon Valley than Ottawa perhaps – but people who have tens of millions, hundreds of millions of dollars and are absolutely miserable. And is the feeling very uncomfortable with comfort a symptom of lack of contentment? Or is it something else, if that makes sense? In my time with you, you don’t strike me as – like you are not one of those miserable people.

I’ve seen you with your family. I’ve seen you with your friends. You surround yourself with good people. I wouldn’t be like, “Oh, no, no, Tobi is an unhappy guy, and he’s not going to be happy because it’s just chasing this ever growing number,” which is definitely what you’re chasing. And I can say that for sure. But is there an aspect of it that makes it hard for you appreciate where you are currently? Or is it different?

Tobi Lütke: I think it is. You are right. I’m the most fortunate person on the planet, I sometimes think. I have an incredible family of three boys, a wonderful marriage. I’m on one of those journeys at an incredible scale surrounded by friends. So I have a lot of things going for me. But I certainly have my demons, too. I’m pretty serious that I’m going for a minimal distance from the person I’m meeting at the end of life to the person I become. I set very high requirements for me partly because I know that I was the bottleneck of Shopify for a couple of years around that 2008/2009 time period. I was holding us back. And a lot of my family and friends were dependent on this thing working out for obvious reasons. And so I just really don’t want to get in this situation again.

I need to challenge myself intrinsically to be ahead, to understand what comes next, for better or for worse. If you’re running a company, and you have a product type CEO, you have to have a pretty good crystal ball about the future and where things are going. And that doesn’t need to be always right, but it certainly should be more right than it isn’t because building software takes a while. And if you’re building against it now, it’s going to be old in two years when it’s done. And so you need to build against the state of the world in 2021/2022 and so on. I’m chasing becoming the best version of myself. And a lot of good comes from that. But it can also be stressful.

Tim Ferriss: What do you think caused you to be the bottleneck? Can you define what that means to have been the bottleneck? And why do you think that happened? Was it because you didn’t know how to hire, you weren’t willing to hire because you, for whatever reason, weren’t expanding your skill set fast enough? What did it mean to be the bottleneck? And looking backwards, how do you do the forensic analysis?

Tobi Lütke: I just did not make decisions that I had to quick enough. There was this whole thing about, “Is Shopify a lifestyle business or a growth company?” I struggled with this so much. And it seems silly now because, obviously, we can all look at the result of it becoming a growth company at some point. But it was really unclear to me. And so I ran it cash based looking at bank accounts and making decisions based on “Hey, I need this amount of money in the bank before I can put $5,000 in cool adverts and so on.” And I just made a lot of decisions way too slow because I just didn’t feel comfortable understanding the implications of them. And so I didn’t know I was doing this, but I did. And I’m really unhappy that I did.

I think I unintentionally slowed down the growth of the company for a period of time so that I could stay on top of it. And only realized this after I finally made the call to just say, “Let’s get some venture capital.” And once we had extra money and could spend it on all of these marketing campaigns, which we never did, it’s like every single one we tried worked. And the company just took off to a degree that is almost comical. The VCs are still talking about those times as something they’ve never seen before. I got my Series B, I think, six or seven months after the Series A. And they wired the money before we even started talking about it. It’s like, “You need more money. You didn’t raise enough money because the numbers were so good.” And so I just held back, and I don’t want to do this again.

Tim Ferriss: Yeah. So just for people listening, they’re going to think, “Wait a second, Ferriss, don’t gloss over that!” So everything worked. Why did everything work? Was it because you were bootstrapped? And I’m not trying to answer the question for you. But was it because you were bootstrapped and, therefore, all of the focus was on the product for an extended period of time? Was it because of something else? Was it because you had a lot of interaction with your customers and, therefore, knew how to position things so that when you turned them into more expensive campaigns, you had already honed the material? Why did things work?

Tobi Lütke: Yeah.  A little bit of all of those things. Shopify, when it came out in 2006, was a brilliant solution to the problem of “I need to start an online snowboarding store.” That’s it. Unless you happen to also want to make a snowboarding store, it was no good. But I was in customer support on top of everything else. And here’s the kind of interaction that happened all of the time. It’s like someone would send me an email saying, “I cannot imagine you’re calling yourself an e-commerce system and you don’t even have this feature.” And I’m on the other side of this email, and I’m starting to try to write an essay about what went wrong, and it’s clearly not coming together, which then means I spend the entire night – I implement the feature. I deploy it in the morning, and I reply from the email actually, “What are you talking about? It’s right here.”

So that on top of also having been a merchant and really understanding – I was and I still am in absolute love with this particular problem in the same degree McLean was in love with shipping things. For this type of business, this retail product based business, I just want to give people a chance to reach for independence and start something that’s meaningful and turns them into an entrepreneur because I remember what it felt like when I did it. And so to spend years just chipping away at this problem, making it better and better, making Shopify better, it really came together around 2008/2009. And then, the financial crisis kind of just happened. And we thought we were dead. But, suddenly, at this point, it was actually quite good, at this point. And it was also really cheap compared to everything else. So people started to –

Tim Ferriss: The service itself, Shopify was cheaper.

Tobi Lütke: It was $29. We had people converting from a $900,000 a year bill to a $59 a month plan, which, of course, tells you exactly how good I was at business at this time. But for us, it was a point of pride. We loved this. And so we invested everything in our product. There were 20 years in our mind of the roadmap, which we couldn’t get to because it was a tiny team. And so again, in this timeframe, the software was really good. But then the people who used it loved it, but it was hard to get the word out. And so to test anything, everything, I had $5,000 additional reoccurring a month, I had to make a decision: “Am I going to hire this one person, which is going to be really good for our product, or am I going to spend this as a test in some kind of marketing capacity?”

And so what I ended up doing, finally, and it was the right thing to do, is I got the top five ideas for marketing. I saved up the $25,000 so I could divvy that out amongst those ideas. And I said, “Let’s try all of them. Because if one of them really accelerates our growth, then we are actually a growth company, and we should get venture capital.”

Tim Ferriss: And we should know sooner rather than later.

Tobi Lütke: And we should have done it sooner.

Tim Ferriss: No, no, I’m saying you do all five at once as opposed to sequentially, because then you get the feedback sooner.

Tobi Lütke: Exactly. Because, otherwise, we don’t know. It’s already changed too much. This was still not very scientific, but it was better to do it at the same time because they are different ideas. It’s like radio and adverts in this way and other campaigns in this way. And all five worked. It was stunning, honestly. They all worked, and every single one clocked in better than what we expected a highly successful campaign should return, at which point, I took this as an Excel spreadsheet to the venture capitalist and said, “Here’s a formula. I need to fund this formula.” This changed the conversation quite a bit.

Tim Ferriss: They’re like, “Tobi, I remember when you came here on a bike.”

Tobi Lütke: Exactly.

Tim Ferriss: Oh, my God.

Tobi Lütke: First come with a bike, then, I come with a formula.

Tim Ferriss: As you said earlier, there’s a lot of chance involved with a lot of this stuff. And I wish I could give credit to the writer who came up with this term, and I’m blanking. You may know who this is. But they talk about a luck surface area and increasing your luck surface area so that chance has a higher likelihood of sticking. I know there’s a lot of confusion in that sense. But the importance of that hands on, those customer calls, is sort of hard to overstate. And I know some companies that require all of their executive hires to do a period of customer support.

Tobi Lütke: Same with us.

Tim Ferriss: Same with you guys, all on the front lines.

Tobi Lütke: And I still take customer calls. I do it periodically. I work with customer support. And I have my own account there. I take some tickets, and I take the phone. I go visit customers all of the time. This is actually the distance to front line becoming bigger has probably killed more companies from probably many other forces that people would immediately think about when talking about disruption.

Tim Ferriss: Yeah. I love it. Tobi, I’ll ask just a few more questions, and then we’ll wrap. We have some dinner and maybe some wine or something else to have later. But you mentioned the crystal ball and the importance of looking into the future, particularly with the types of products you’re developing and the technology that you work with, to go back to my notes. Here we go. “John Phillips considers it his job to go to Lütke’s office once in a while and get him to clear everything off this desk. As CEO, he feels he shouldn’t have any actual work to do.” We’ll kind of gloss over that part. “‘He has guys to do that. And if he meddles in it, he’ll cause a problem.’” That is pretty funny. But you have to be looking ahead.

So this would be a super fantasy of mine. Is it literally clearing stuff off of your desk? What does John or other people do to help get you out of the stuff you shouldn’t have your hands in?

Tobi Lütke: Yeah. This has been such a journey. I want to say I like the really high level strategic things. And I like the absolute tiny, minute details.

Tim Ferriss: Then you are also in the customer ticket.

Tobi Lütke: Right. The thing that I optimize away is everything in between those two.

Tim Ferriss: Oh, right.

Tobi Lütke: And so that helps a lot because, again, these tickets matter. I think John has been such a massive help. He’s the same person I mentioned earlier who came to me and said, “Tobi, you’ll never find someone who is going to care as much about Shopify as you do.” Which encouraged me to take the CEO role. So he was there at many important parts of the Shopify journey and was full of good advice. And so he had me build out this practice over time to just hire great people for everything in the middle and allow me to think about the sort of long term, big picture kind of things. And but I really, really, really do like pulling my chair, in some part, with engineers working on some important performance detail and so on. But that teaches me something about the company.

And it also allows me to access the latent pieces of mastery that I once built, which is actually – you were talking about happiness and contentment. Tapping into some kind of mastery, you just can’t spend all of your time just working on things which are going to finish two or three years up from now. The feedback loop’s too long. It doesn’t nourish you in the way that just doing something that’s fun to do now. That’s a really important component. But lastly, on this crystal ball, here’s the way I think about it. First of all, the future is not predictable. The future is a random walk and depends on macro economical events and climate change and a million other things. You can’t actually know the future. But there are two things you can do. One is really important, which is just draw the trend lines forward like a minor version of what Ray Kurzweil would do.

In 2009, we knew that almost all traffic to Shopify would be coming from mobile phones by just looking at data and connecting two points and drawing it forward. It was kind of predictable. Computers getting faster, AI classes being around, and all of these kinds of things, we should add those into our calendar to say by then, they probably are very important. And we should be aware of them. So that’s one component. The other, much more interesting component is you need to be a credible witness to reality. And you have to have a model of what – this is currently January 2019. Almost no one in the world knows what January 2019 actually looks like because of exactly the William Gibson quote you just talked about.

“The future is already there, it’s just not evenly distributed yet.” It used to be that you could go to Silicon Valley, and what you would see around you observing the things around you would be potentially 95 percent accurate rendition of the most up to date current version of the particular time you were in. So if you were an entrepreneur in Silicon Valley, and you looked around, and you just said, “I’m seeing what people did when cars just appeared by pushing a button on my magical piece of glass of in my pocket.” I’m going to try to disrupt the laundry industry. I’m going to do it in that way. You just, by osmosis, kind of are aware of what’s possible. Now, it’s much harder. China is a much bigger component, for instance. A lot of innovation is coming from China.

And a lot of people have not realized that China is completely flipped on its head, in terms of it’s not copying ideas from the west. It’s actually delivering ideas. These fully automated supermarkets that people are talking about and coming to various cities are all over China.

Tim Ferriss: Yeah. The way they use facial recognition to gamify citizen behavior, in certain cities, and WeChat. It’s incredible.

Tobi Lütke: I want to steer away from sort of a moral and political side of China. But I think just looking at it through just what is life like in China, it’s appreciatively more futuristic than it is anywhere else by just we are in a post-credit card world for which we pay on all of these kinds of things. It unlocks completely new business models for them. So it’s worth our understanding. But there are other things. Who actually, in the business world, understands the video game industry? It’s the biggest industry no one cares about.

Tim Ferriss: Yeah. I remember one time – I don’t want to interrupt, but I will since I’ve apparently had too much caffeine. I know very little about video games. But I remember I was looking at it because you see it all of the time, if you go to Rotten Tomatoes, you see the box office earnings of the biggest movies in the world, at least domestically. And then I saw some of the numbers for video game releases. And it was a multiple of the entire total of the list.

Tobi Lütke: Yeah. The video game industry is a good deal larger than television, music, and Hollywood combined.

Tim Ferriss: It’s incredible.

Tobi Lütke: Right? But it’s also one of the most competitive environments ever. It essentially is a massive industry on the Hollywood model that a hit is everything that everyone aims at. One hit clears the money from the industry. And so what these guys have found out in the video game industry about just human psyche is just fascinating and hugely futuristic compared to what these sort of business people figured out. And so what I’m getting at is you do the trend line thing and nothing at the table sticks. And people just need to do a good job of doing that. But that’s also not that hard. And then you have to look around the planet and just say, “Where are the competitive fields? What tools have the winners figured out in them? How can I impart this back into the rest of the world?”

And I think through the intersection of those two disciplines, you can actually get a crystal ball and make assumptions on the future that start becoming reasonably precise so that they are better than not having them as guiding posts for making product decisions and so on.

Tim Ferriss: Tobi, the Oracle of Ottawa.

Tobi Lütke: That sounds so wrong, in a way.

Tim Ferriss: You should have just said that because now, I’m going to make it my job to make that your next headline.

Tobi Lütke: That’s my fate now.

Tim Ferriss: So let’s wrap up with a couple of questions that I like to ask and listeners seem to enjoy. I’ll just go for some of the hard ones. If you had a billboard, metaphorically speaking, a message, a quote, a question, a word – he lifted his glasses and is scratching his eyes as I’m asking this. That’s his sign of –

Tobi Lütke: I know you ask this question. Why was I not –

Tim Ferriss: That’s his sign of approval. What might you put on it? It can’t be an advertisement.

Tobi Lütke: I’m going to stay on topic. “Entrepreneurship is precious and needs to be celebrated” is what I would put on the billboard.

Tim Ferriss: Besides the books that you’ve mentioned, are there any other books that you would put – one that comes to mind is most frequently gifted or recommended? It doesn’t have to be one book. It could be whatever comes to mind.

Tobi Lütke: The most frequently gifted book is The Elements of Style because I like good writing.

Tim Ferriss: Now is that a passive aggressive thing to employees?

Tobi Lütke: People hate getting that book. But I think I might have 50 copies in my office. It happens frequently.

Tim Ferriss: “John, by the way, great use on the semicolon, however, here’s a gift.”

Tobi Lütke: Yeah. It’s more like, “Hey, I like the content of the memo, but I don’t think you’ve written a non-passive sentence in a year. So I think you need to” –

Tim Ferriss: Not to stereotype it, but it’s like the most German thing I’ve ever heard. We have to talk about your passive voice.

Tobi Lütke: Exactly. A book I love giving to people, I try to, of course, aim at the right moment, is A Guide to the Good Life is one of the best books I’ve ever read.

Tim Ferriss: That’s the introduction to Stoicism, William Irvine?

Tobi Lütke: Yeah, exactly. I think that’s the best gateway to walk into this world.

Tim Ferriss: That is a great book.

Tobi Lütke: Did you read The Courage to be Disliked?

Tim Ferriss: No, but I love the title.

Tobi Lütke: It is probably the best book I’ve read in the last couple of years.

Tim Ferriss: Wow.

Tobi Lütke: It’s an introduction to Adlerian psychology, which is sort of anti-Freud. They were two factions in the Vienna –

Tim Ferriss: What was the name?

Tobi Lütke: It’s called The Courage to be Disliked.

Tim Ferriss: But the psychologist?

Tobi Lütke: I think Alfred Adler is the name. And absolutely fantastic. Clearly a student of Stoicism, but I think he took it further. His concept of the separation of tasks is probably – maybe that would be another thing I would put on a billboard. But I think it requires a little bit of context and explanation.

Tim Ferriss: What is the separation of tasks?

Tobi Lütke: It is the basic idea of “It’s not your task to be liked. It’s your task to be likable, and it’s someone else’s task to like you or not. It’s up to them.” The biggest wedge between your psychology and someone else’s that could ever be driven into it. And I think, potentially, a more tangible way of getting people into this mindset than I think the stoics who came at it from a very high mindedness. It all makes sense. But I think what Adler does really well is he developed tangible tools to facilitate a lot of those kinds of outcomes with stoic but a sort of reasoning about it. So a fascinating book.

Tim Ferriss: The Courage to be Disliked. That is one of the better titles I’ve heard in a very, very long time.

Tobi Lütke: Agreed.

Tim Ferriss: Do you have any parting requests, asks for the audience, last comments for now that you would like to make? Anything you’d like to ask them to do, suggest that they might check out, or anything at all that you’d like to say?

Tobi Lütke: Yeah. The broad question, again, we didn’t really get into this too much. I sort of alluded to it probably enough. I’m a huge fan of people just going for it, reaching for independence, building businesses. I think it’s worthwhile for especially your listenership to sort of understand that there’s no law of the universe that makes entrepreneurship stick around. It actually happens because governments and various people made very deliberate choices to facilitate it. We do see friction massively increases the participation in entrepreneurship. This is not a plug for Shopify. Shopify is a player in the space. But actually, we need more companies to figure out ways to reduce the friction of entrepreneurship across the entire spectrum of how people engage in entrepreneurship because, I think, if you don’t, this is going to end up being a serious economical issue, eventually.

Because, by the time people figure out why is employment going away, why small business employment is down, it’s actually because small businesses are going down. There are, potentially, so many systemic effects in play that it’s going to be hard to undo a lot of the damage. And so I think it’s an underappreciated area of entrepreneurship. It is entirely possible to build a company that’s highly valuable by focusing on this. You don’t have to go up market like the way everyone tells you to, specifically, investor types. And Shopify proves another way if you’re looking for a kind of blue print. And so I would love for more people to think about this.

Tim Ferriss: When you’re going into your oracle toolkit with the crystal ball and surveying the global landscape, are there any particular countries or cities that you think are worth examining or modeling that do a good job? I don’t know if Singapore would be an example.

Tobi Lütke: Yeah. It’s sort of Singapore, but also Stockholm is another one. What’s going on in Berlin is really interesting. But also, Shenzhen. I think visiting Shenzhen would be highly, highly –

Tim Ferriss: And that’s S-H-E-N-Z-H-E-N?

Tobi Lütke: Yeah, I think so. It’s exactly the kind of thing I have trouble with with dyslexia.

Tim Ferriss: Chinese is pretty hard for everyone who is not Chinese.

Tobi Lütke: But just because you go in the world’s biggest electronic markets, and you realize, “Hey, if I wake up early enough and make my goal ‘I’m going to build my own cell phone,’ I can be done by the end of the day by just getting components in this place.” And these buildings just don’t exist anywhere else in the world. And that kind of everything is possible attitude is also shared by everyone there. And it’s a really fascinating place. It’s really interesting. So I think that’s a place which figured it out.

Tim Ferriss: Yeah. That has sort of a silver lining on what could be a very large, systemic problem is that there are exemplars out there. There are cases to study. Tobi, this is so fun. I’m really glad that we ended up having the opportunity to cross paths yet again and sit down. Of course, people can find out more about Shopify at On Twitter, they can say hello to you @Tobi. And then, Twitter, Instagram, LinkedIn, of course, Shopify is on all of these platforms. And I’ll link to everything in the show notes. I also have a Reddit link here. And maybe you can explain what that is. There’s a shake of the head.

Tobi Lütke: I don’t know how it made it there. I thought I was anonymous on Reddit. This is no good.

Tim Ferriss: Okay. So that is not to be mentioned. The name that shall not be spoken. And I’ll link to everything we discussed, the books, and so on, the principles, philosophers, psychologists in the show notes as per usual. You can just search Shopify or Tobi, T-O-B-I, and everything will pop right up. Tobi, thank you so much.

Tobi Lütke: This was fun.

Tim Ferriss: Yeah. A really good time. I’ve always enjoyed spending time with you. You started off very humble and understated. You remain very humble and understated, which I think is a real testament to you. And I think it is true that companies tend to develop a culture around the personality and attributes of their leaders. And you’ve assembled a fantastic team and built a wonderful company that’s doing a lot of good.

Tobi Lütke: Thank you so much, Tim. And, again, kudos to you, too. Actually, thank you to you, too. You were a big inspiration along the way, a massive help. Thanks for making yourself available, when we needed you. And it was incredibly gratifying to spend that really fun day at the New York Stock Exchange ringing that bell, being there together. Again, it’s all about being on a journey surrounded by friends. So thank you so much for being a friend to a company.

Tim Ferriss: Oh, my pleasure. And what an honor to have been in the right place at the right time, RailsConf.

Tobi Lütke: Who knew?

Tim Ferriss: It is really important to have companions on the path. Many adventures ahead. And to everybody listening, thank you for tuning in. And try to figure out which box you’re in. And check out some of the resources in the show notes. Thanks for listening.

No Comments / Leave a comment or question

Tobi Lütke — From Snowboard Shop to Billion-Dollar Company (#359)


“Feedback is a gift.” — Tobi Lütke

Tobi Lütke (@tobi) is the founder and Chief Executive Officer of Shopify. In 2004, Tobi began building software to launch an online snowboard store called Snowdevil. It quickly became obvious that the software was more valuable than the snowboards, so Tobi and his founding team launched the Shopify platform in 2006. He has served as CEO since 2008 at the company’s headquarters in Ottawa, Canada.

Tobi is an active advocate for computer literacy and education, and serves as a board member of Canada Learning Code, an organization working to give all Canadians access to digital skills. In 2014, Tobi was named The Globe and Mail‘s CEO of the Year. He served as Chair of the Digital Industries Table, an advisory board commissioned by the federal government to provide recommendations on how to turn Canada into a digital leader.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

Want to hear the story of a go-getter who launched his now seven-figure business on Shopify? — Listen to my conversation with SpyGuy’s Allen Walton in which he describes how he made the switch from overworked and under-appreciated employee to entrepreneur (stream below or right-click here to download):

#351: Real 4-Hour Workweek Case Studies — Allen Walton and SpyGuy, The Path to Seven Figures

This podcast is brought to you by Peloton, which has become a staple of my daily routine. I picked up this bike after seeing the success of my friend Kevin Rose, and I’ve been enjoying it more than I ever imagined. Peloton is an indoor cycling bike that brings live studio classes right to your home. No worrying about fitting classes into your busy schedule or making it to a studio with a crazy commute.

New classes are added every day, and this includes options led by elite NYC instructors in your own living room. You can even live stream studio classes taught by the world’s best instructors, or find your favorite class on demand.

Peloton is offering listeners to this show a special offer. Visit and enter the code TIM at checkout to receive $100 off accessories with your Peloton bike purchase. This is a great way to get in your workouts, or an incredible gift. Again, that’s and enter the code TIM.

This episode is also brought to you by LegalZoom. I’ve used this service for many of my businesses, as have quite a few of the icons on this podcast — such as Automattic CEO Matt Mullenweg of WordPress fame.

LegalZoom is a reliable resource that more than a million people have already trusted for everything from setting up wills, proper trademark searches, forming LLCs, setting up non-profits, or finding simple cease-and-desist letter templates.

LegalZoom is not a law firm, but it does have a network of independent attorneys available in most states who can give you advice on the best way to get started, provide contract reviews, and otherwise help you run your business with complete transparency and up-front pricing. Check out and enter promo code TIM at checkout today for special savings and see how the fine folks there can make life easier for you and your business.

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Read More

18 Comments / Leave a comment or question

The Tim Ferriss Show Transcripts: Ken Block (#358)

Leave a comment

Please enjoy this transcript of my interview with Ken Block (@kblock43 on IG and TW), a co-founder of DC Shoes and a professional rally driver with the Hoonigan Racing Division. His rally career began in 2005 when he won Rookie of the Year in the Rally America Championship and has continued with an accumulated five X Games medals and global fame through his wildly successful viral series of Gymkhana videos. His latest project is The Gymkhana Files, which takes viewers behind the scenes of GYMKHANA TEN: The Ultimate Tire Slaying Tour, a video that, as of this writing, just went up and already has nearly 20M views. It’s all complete insanity. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, or on your favorite podcast platform.

#358: Ken Block — The Story of DC Shoes, Rally Car Racing, and 500+ Million Views (#358)


Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.


You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.


No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on or (obviously) license photos of Tim Ferriss from Getty Images, etc.

Tim Ferriss: Ken, welcome to the show.

Ken Block: Well, thanks for having me on. I really appreciate it.

Tim Ferriss: Where are we sitting right now?

Ken Block: We are sitting in the Hoonigan Racing Headquarters in Park City, Utah.

Tim Ferriss: And we are inside of a shipping container.

Ken Block: Yes, we’re – a very expensive shipping container.

Tim Ferriss: Very expensive shipping container.

Ken Block: But, yeah, I have about 40 shipping containers that are cut up, that make up my offices and shop here in Park City.

Tim Ferriss: And you were explaining this to me a bit earlier, before we started recording, but what is the practicality of having these shipping containers that are bolted to the floor?

Ken Block: Well, in my earlier life, I was one of the founders of DC Shoes, and we grew from a very small brand to a very big brand. And over that course of growing, we moved probably five different offices, and therefore building all new drywall walls all over the place and all that, and it cost a lot of money. So when I built the race team offices here, I decided I wanted to build something that – we have a recycling message with using things like used skateboards as tile and used shipping containers for offices – that sort of thing. But also, if I have to move, you can actually pick up these entire offices and easily move them somewhere else on a shipping truck.

Tim Ferriss: So if you need to upsize, or downsize, or anything in between size, you have everything here that you can pack up.

Ken Block: Yep. Absolutely. And it actually ended up making a very cool looking office, too. We had a lot of fun being creative with this office and doing something unique and different, but also, to me, it’s something that’s on the leading edge of what I hope people do in the future with empty warehouse spaces like this and building offices.

Tim Ferriss: It’s a beautiful –

Ken Block: A lot of drywall gets wasted out there as people change buildings and change businesses.

Tim Ferriss: It’s a beautiful space, and all put up – and certainly, there’s no shortage of footage of this space online – but I’ll put up a bunch in the show notes as well. You’ve had a number of different careers, and it makes me think of Bruce Wayne in some respects. So you’ve had – you’ve lived many lives in one life. This is not going to be chronological, but first, Hoonigan. Where does that name come from?

Ken Block: Well, the word hoon is basically similar to our laws here in America of reckless driving. So if someone were to say, “Oh, you were hooning,” in Australia, that would mean you were out doing something reckless with a car. But once that term made it over to America, it became a term of endearment like, “Oh, you’re out having fun with a car. Great.” Whereas, if you are reckless driving here, it would be like, “Oh, you’re going to get a ticket.”

So a couple journalists here in America started calling me King of the Hoons because I was a racecar driver who was out having fun with my cars. Also, around that time is when I started making the Gymkhana videos. So that was really the epitome of technical driving but having fun with the car because it was a racecar that I wasn’t racing, which is just something unique and a bit different in the world of motorsports.

So that word hoon then became something that we started using more and more. And then, we started to develop the brand of Hoonigan – the idea of it – and I came up with the term Hoonigan. And it just stuck for us and ended up being great for the brand. And now, we’ve continued to grow and grow. I think we’re in our seventh or eighth year with the brand.

Tim Ferriss: And you have a track record as a very successful entrepreneur, which we’re certainly going to dig into. You also are very adept with media, and marketing, and branding. And you mentioned Gymkhana. For those people who have not seen it – we’re going to talk about that in just a minute, but the video series Gymkhana has around, or maybe more than, what, half a billion views now collectively?

Ken Block: Yeah, the main videos themselves have almost half a billion. And there’s a bunch of ancillary videos around that also, and we keep tabs on all of them. And we just totaled up the other day. It’s over 600 million views on all of that stuff all together. So quite insane. Not something I really ever expected to happen, but it’s been very cool to be a part of this visual digital revolution that is how the Internet has evolved over time.

Tim Ferriss: And then you have your competitive career, right? And then you have your competitive career. And for some people listening, they may think, “Well, much like other sports” – or, even as we were discussing before we started recording, say motocross – you must’ve started when you were, what, four, five, or six years old?

Ken Block: Started what? I started skateboarding at that age.

Tim Ferriss: The rally car racing.

Ken Block: No, unfortunately, I started rally car racing when I was 37 – very, very old in the world of motorsports. So I grew up in Long Beach, California, skateboarding and riding BMX bikes as a kid, and then moved down to North San Diego. My parents decided they wanted to own an avocado grove, so they moved me down to the countryside of North San Diego and I continued skateboarding, but then started riding dirt bikes. So I raced amateur dirt bikes when I was in my teenage years, but didn’t actually start racing cars until I was 37. Although I’d been a fan of rallies since I was very young, I was never a fan of American motorsports for some reason.

My brother had drag raced and all the – I knew all that stuff existed, but as a kid I was most interested in Formula One, but really rally, like cars that slid and jumped and raced in the snow and then through Africa. It’s just something that I related to much more than a car that just went straight or went in a circle. I – no disrespect to those sports. It just wasn’t interesting to me. And I think that’s also why I loved dirt bikes so much as a teenager, was the creativity of it – of jumping, of sliding, of racing around a track that had all these obstacles. And really, rally racing was that, but with a car. And so I just genuinely loved it from since I was quite young. But I never had an opportunity to do anything with it, or even knew it existed in the States until I was around 36 or 37.

Tim Ferriss: Now, was that – was your first exposure, in terms of training, at Team O’Neil, or was it somewhere else?

Ken Block: Yeah, my first rally car driving lesson was at Team O’Neil in New Hampshire. It all roots back to Travis Pastrana. So at the time, I was the Chief Brand Officer of DC Shoes, and Travis Pastrana was one of our moto athletes. And Travis, in 2004, did a couple rallies. And that just woke me up to the fac that rally even existed in the States, and that I could potentially go do it.

And so Travis’ agent Steve Astephen was a good friend of mine. And I called Steve and I said, “Hey, I want to go do that, what Travis is doing. How do I do that?” So Steve connected me with the team. The team said, “Yeah, come out. We’ll take you to a great rally school,” which ended up being Team O’Neil. They put me through a four-day course and I was hooked. I couldn’t have enjoyed myself more. I felt like I had a little bit of natural talent for it. I could throw the thing around exactly how I wanted and I was pretty quick. But no clue as to where that would go. I was just was like, “Hey, I really like this. This is fun. I need to do this more.”

Tim Ferriss: So I knew for the first time about your time in New Hampshire with Team O’Neil because I spent a week there for a TV show – short-lived, but still entertaining – called The Tim Ferriss Experiment. I went there to train and compete against a friend of mine. And, much like your wall on the other side of where we’re sitting, with all of the damaged and destroyed pieces of various vehicles, there is some shrapnel from some of your cars up there in New Hampshire. And I found it be such – I do not have, I don’t think, any preternatural super skill related to rally, but training with pendulum turns, and finish flicks, and all of that was so endlessly interesting. And –

Ken Block: Well, and it’s genuinely fun. It’s –

Tim Ferriss: It’s so much fun.

Ken Block: – a fun way to drive a car.

Tim Ferriss: It’s so much fun.

Ken Block: It really is.

Tim Ferriss: And the science – there’s so much science behind it. You have people who have done it from a very, very young age. I mean, there’s certainly a number of countries that seem to produce a lot of champions. How, at 36/37, did you think about tackling this seriously?

Ken Block: Well, at the beginning, it was just a hobby. The first year, I went out and funded my own racing. I was just as amateur as an amateur gets. First year out, just learning the ropes – I had a good team behind me. I had a great co-driver Alex that helped a lot. But in the beginning, it was just like, “Okay, let me figure this out. Let me throw everything into it if I’m really into this.” And I really did try and learn as much as I possibly could. And luckily for me, I was already in very good shape at 37 years old because I loved riding dirt bikes. And, with DC, we sponsored guys like Ricky Carmichael, and Jeff Emig, Ryan Hughes, Jeremy McGrath – some of the best guys in the world. So I got to go ride with them.

So I wanted to be in shape to go do that stuff. And being around guys like that – and Danny Way, and Travis Rice, and Andy Irons – these guys that were the top of the field in all their areas, I got to see how champions trained. I saw how they ate. I saw what it took to be a champion. So I knew how to train and how to mentally get myself there and do those things. So I was able to take all of that and apply it to myself, to develop my own talent to go do something that I loved to do.

So 2005 was the first year I raced, and I was able to get fourth overall in the National Championship – and actually beat Travis that year. So from there, I was like, “Holy shit, this is fun. And I’ve got some natural talent for it. I’m just going to put as much effort as I can into doing it and try and see where it goes.” I had no idea where it would go. But it ended up going a lot further than I ever expected, and it’s been a completely wild ride.

But I really give a lot of credit back to, not only the experiences that I had with DC, of trying to be successful and figuring out what it takes to be successful, but also understanding the mental and physical sides of studying and watching these friends of mine that were champions, and what it took for them to do what they needed to do.

Tim Ferriss: And we’re going to visit DC very shortly. But since we’re on topic, does anything come to mind that differentiates some of the guys you just mentioned – I mean, those are big names, very competitively successful. What did you see that made them different? Or what – any behaviors, any beliefs, any practices? Was there anything in particular that comes to mind, or anything that comes to mind?

Ken Block: Well, the funny thing about all those guys is they all have different stories. There is no magic formula. There is no perfect human that then has the perfect formula. Everyone’s different. What worked for Ricky Carmichael would not work for Andy Irons – that sort of thing. But what you do see with a lot of those guys, that you see with any top athlete, is the drive and determination. There are guys out there that aren’t the most talented, but they’re willing to outwork everyone. And that’s where I was. I was an older guy – 37/38 – and I was competing against 20-year-olds. And I was like, “Well, I’m just going to be smarter. I’m going to train smarter. I’m going to prepare smarter. I’m going to do everything – I’m going to find every trick in the book that I can to maximize the opportunity.”

And I think that’s really a lot of what it takes in the end, with a lot of athletes. There are a lot of outliers out there, the Ricky Carmichael’s of the world, that just – he’s the greatest of all time for certain reasons that no one else can match. But other than that, there are a lot of other people out there that it’s a matter of mastering the game, always being a student of the game, and finding every little moment where you can find some sort of advantage. And that means you have to live it. You have to live it day in and day out. You cannot be a champion of a sport, generally, without that study, without the living, breathing, existing in that form of sport day in and day out. So I think that’s the main thing that I’ve seen as a constant, is that dedication to the craft.

Tim Ferriss: What were some of the tricks or approaches you found worked for you? And I’m just thinking, moments before we started this, you had your breakfast/lunch – which was a cup of coffee with some protein in it – some plant protein plus MCT oil. And you commented that it makes it a lot easier to train if you’ve, say, consumed something like that rather than having a very heavy meal. So that just jumped to mind as, not necessarily an example from a long time ago, but a habit that might aid in training for any number of things. So are there any other things that you decided as a 37-year-old? You’re like, “Okay, the 20-year-olds are doing A, B, and C. If I do that, I’m not going to be able to match what they’re doing,” or any other tricks of the trade that you ended up adopting for yourself?

Ken Block: Well, I think that, with any sport, it’s about being smart about what makes you successful in it. For example, I race cars. I don’t have to be a shredded, strong individual to do that. I have power steering and a foot pedal.

Tim Ferriss: Right.

Ken Block: So it’s more about reaction time. It’s more about quickness. It’s about mental quickness. It’s about what it takes to have these moments where, “Hey, at 3:00 in the afternoon tomorrow, I need to be at the highest cognitive recognition level that I can possibly be. So what does it take to get me there?” Is it supplements? Is it training? Is it a particular exercise that I do before I get in the car? So a lot of it, to me, is the experiment. It’s working with the right people that help you with different training exercises. And a lot of it is just trial and error, and figuring out what works and what doesn’t work. And when something – when a mistake does happen, trying to figure out what caused that mistake, and then how do I correct it and make myself better for the next time.

Tim Ferriss: What were some of the things you’ve found to work? I know you’ve been a long-term – it seems like – trainee with kickboxing and have worked with some fantastic athletes. Do you have a particular – you mentioned exercise before getting into the car. Do you have a particular exercise, or any exercise, that you do?

Ken Block: Well, I grew up in North San Diego. Do you know who Paul Chek is?

Tim Ferriss: I do. Yes.

Ken Block: Yes. So Paul Chek – I’ve worked with many Paul Chek trainers. I’ve worked with Paul Chek himself. And so I grew up in my training world around people that really worked with those sorts of ball exercises and balanced exercises – all that sort of stuff – to really mimic more real-world balance needs as opposed to just grabbing a barbell and doing curls. So all that training, to me, helped a lot. But then, upping the level of that, I worked with a couple of trainers that would help me with mental skills along with those physical skills.

So with rally, you’re having to hear notes. So you drive down a road that’s, say, 10 miles road – twisty, winding, going through forests. You’re going 90 miles an hour sideways next to trees. And while you’re doing that, you’re hearing notes that’s telling you what’s coming up next. And it’s – and they’re triggers. They’re not like, “Hey, by the way, there’s a left coming up that’s really dangerous.” No. It’s, “Left five. Keep in. Caution.” And those have to be triggers in your mind that you automatically react upon and drive as quickly through every situation as possible.

So we would actually do that stuff in the gym, where I would actually be training, doing a particular exercise, and my trainer would have me looking or listening to things and then having to react to that with certain triggers that I would then react with. And it was all brain-type exercises. On top of that, even bouncing balls off a wall and having to react – with my eyes closed, open them, and react and catch a ball. It was all about being able to see peripherally, see directly in front of me, see short distance, see long distance – all that sort of thing. So it was a lot more – really, these little things that are harder to train with your brain that would potentially make you quicker.

Because with rally, we’re battling for seconds over each stage. With rallycross, you’re battling for tenths of a second each lap. And if you can do that quicker than your competition because of how you’re trained, then that’s one way to be faster.

Tim Ferriss: So you’re a student of success. And maybe we could rewind the clock a little bit and get back to DC. Now, I was doing, as I always do, homework for this conversation. And it seems like DC was certainly not your first business. And maybe you could tell us a bit about how you got into entrepreneurship. Because I’m reading – I have Eightball Clothing, Blunt Magazine, Droors Clothing. How did entrepreneurship enter your life? How did you end up in business?

Ken Block: Well, the funny thing about that is, I didn’t necessarily intend to be an entrepreneur in the beginning, but it just kind of seemed like the only avenue – not the only avenue. It seemed like the avenue that I was left with, with the things that I loved to do and my interests. So the funny thing is, I started off in high school studying architecture. I wanted to be an architect. I did all sorts of drafting through high school and then, when I got out of high school, I went straight to a computer aided drafting school and did that for a year. And then, I got into the business and I hated it. I loved it as an art, and I loved it as a study, but actually the business of it, I just didn’t like. So I –

Tim Ferriss: What didn’t you like about it?

Ken Block: I guess, because it – I enjoy the art of architecture. But the only people that get to do the art of architecture are the people at the top.

Tim Ferriss: Right.

Ken Block: And it takes either a ton of money or 30-40 years of climbing to the top. And I just saw that – once I realized, being in the business, what it took. And I just said, “Yeah, that isn’t for me.” So being a skateboarder and a snowboarder, I wanted to do that stuff more. So I actually quit working for this architecture firm and ended up moving to Breckenridge, Colorado for two years and being a snowboard bum. I was actually friends with a bunch of pro snowboarders, and I looked up to those guys and wanted to be them. But in the end, I just knew I didn’t have the talent. I just didn’t have the skillset that they had, and I saw that.

So I moved back to California and went back to college and started studying screen printing, graphic design, graphic layout – all that sort of stuff. And I just really enjoyed it, and I thought, “I could” – because of my interest in skateboarding and snowboarding, I started designing some shop t-shirts for one of the shops that I was friends with out in Colorado. And I thought, “Oh, this would be great, if I could actually be a part of this industry I love.”

And in the meantime, at the same schools, Palomar College in Vista, California, I met Damon Way, who’s the older brother of legendary skateboarder Danny Way. Damon and I hit it off and we both had interest in trying to be in the industry of skateboarding and snowboarding, and we had this real mutual interest in that. I was more of the graphics business type guy, and he was more of the clothing designer type guy. So we just merged our talents and started working together, and started very small with Eightball and Droors. And eventually, I did a magazine called Blunt as part of this whole company. And we sold a company called Type-A Snowboards, which were some friends of ours and we owned part of that.

And eventually, we started DC. We were lucky, with DC, that we got all this experience of a couple of years floundering around with these other clothing companies and a magazine. But we learned a lot, so that by the time we got to making DC – which was ’94/’95 – we were able to make this startup work very well very quickly. So we already had the infrastructure of buildings, and artists, and salespeople, and warehouse all of that, so that when DC got plugged into that it took off. But we were able to manage it and make it work. If we hadn’t had all of that other stuff and experience and all that, we wouldn’t have had all that.

Now one thing that I did forget to mention in all that, though, is business is not easy to start. And I come from a family – my dad had his own business and he was fairly successful with it. And my parents, by the time that I was a teenager, had a decent amount of money. I wouldn’t say they were overly rich, but they were – they had enough money to by 16 acres of avocados and a house in Valley Center. So as I was growing up, I wanted certain things. There were kids in my high school that drove BMWs. I’m like, “I want that,” and my dad just laughed. He’s like, “No way am I buying you that. You are going to earn everything that you get.”

So I grew up with that mentality, that whatever I did, my parents were not going to give me anything. They were going to help me, but they were going to make me work for it. So that’s something that I really, genuinely appreciate, and something I’m going to pass on to my own kids, that life isn’t easy. You’ve got to figure certain things out, and you’ve got to make it work. It takes hard work to be successful. I’ve seen a lot of people who’ve had stuff given to them and they’ve floundered with it. And I think that experience really is the best lesson.

And so when I was starting our business, I went to my parents and said, “Hey, I need some money.” And my mom said, “Well, I’m not sure that your dad will do that, but let’s try.” She said, “Write a business plan. If you want $10,000, prove to us what you’re going to do with that $10,000 and how you’re going to pay us back.” And I said, “Okay.” So I bought books and figured out how to make a business plan, wrote that business plan, and I got $10,000 out of my parents to help start the business.

Tim Ferriss: That was DC? Or that was –

Ken Block: That was actually for Eightball and Droors. And Damon came in with some money, and we were equal partners in the beginning. But really, it was from my parents. And my parents – however you like to say it – ethics – business/family ethics – that basically set me in motion of how to learn business, how to start a business, how to pay back a loan – all that stuff. Because I was a 19- or 20-year-old kid who was just trying to better himself, and they helped me set the path to do what I did. That’s something that I genuinely appreciate. Any time anybody asks me – from, “How do I start this business,” or, “How do I get sponsored,” the easiest lesson is, if you don’t know business, and you don’t know what marketing budgets are, and you don’t know advertising or sales – you have to understand that stuff and understand a business plan to go anywhere.

And there are so many basics of life that, if you understand how products get made and how companies profit and what it takes to spend advertising dollars – there is so much in life that you’ll understand just by knowing those basics.

Tim Ferriss: And you have such a keen eye. You’ve studied architecture. I’ve watched a lot of what you’ve done over the years, and I just want to underscore – maybe using different words – the value of someone who has artistic ability in learning the business side is not sullying your hands with some crass aspect of the world necessarily, but enabling yourself to further the art and what you want to do in the world, right? And it’s a real liability not to have that. And what’s struck me also is that you have these seemingly disparate lives that you’ve led, and success in these different realms, but they’ve also built on one another, in the sense that you sponsored athletes and now you are a sponsored athlete.

And you know how to do – you know which athletes you sponsored did a great job, versus did a mediocre job, versus did a do-not-pass job. And so you’re able to fulfill that role really, really effectively for the companies that you work with, right – like the Fords, and the Monsters – whoever it might be. And you have an operational awareness that enables you to them pursue the craft that you want to pursue. Let me ask you about – we’re going to talk about good decisions, and resources that helped you, and so on and so forth. But do any mistakes –

Ken Block: Before you go on, though, let’s talk about that real quick.

Tim Ferriss: Yeah.

Ken Block: That was one of the things that, when I trans – the transition for me from going from Chief Brand Officer at DC to racecar driver was actually a real – it was a bit difficult for me at first. And mainly because, as Chief Brand Officer at DC, I actually liked to be in the background. Damon and I didn’t really like us getting press for DC. We liked the athletes to be the people that stood out front and represented the brand. So as I became a racecar driver I was like, “Oh, crap. Now I’ve got to put my face out there and I’ve got to be the voice. And I have to show a different attitude and a different” – not necessarily different, but I had to be worried about what I said, and how I said it, and how I presented myself, which I just didn’t have to worry about before that.

So that transition was a bit tough. But once I got into it, I basically said, “Okay, I know what bothered me,” or I saw the good and bad of all these athletes that I worked with for 15 years before this. So how can I take all those experiences – what I liked and disliked about what all these different people did – and make myself the best of what I can make myself. And I’ll tell you a really stupid example. We had guys that we would send out to a shop to do an autograph signing, and there would be 1,000 kids lined up waiting for these guys to sign autographs. And some of them, instead of being engaged with these fans, they’d be looking at their phone, or turning around and smoking a cigarette around kids, and stuff like that. And it just – they didn’t have the right understanding of what they were there to do.

And to me, that’s a real simple example that, when I go to an autograph signing, we try to make the best poster. I try to be as engaged as possible, always trying to make the fan as happy as possible. They’re there for me, and I’m there representing all these different brands and maybe the shop that I’m there for – those sorts of things. So it’s understanding the whole situation because of where I came from before, which has then made me such a great ambassador for all these brands, and hopefully a very good and engaged athlete for these fans that follow me.

So it’s been a very fun process to go from that guy behind the scenes that kind of understands it all – because I wrote the contracts, I made the ads, I directed the social media, we made commercials, I made skate videos – to now being the guy on the other side and delivering what the sponsors needed. And there were certain guys that actually pissed me off over the years that I saw so much potential for, and just watched them fail because they didn’t understand – that I said, “I’m going to prove – whether these guys ever see this or not – what is potential if you just understand the process.”

And that’s actually been very fun over the years, maximizing the potential of social media, really maximizing the potential of YouTube, and delivering what the fans what. Because, at the end of the day, this is all a business. I love to race cars at the end of the day, but without the sponsors, without the series that are out there, without all the fans, there’s a whole culture here that all interacts and goes together. But if you don’t do it right, you can’t be as successful as the potential is there to be.

Tim Ferriss: And did you – even when we were walking around this building earlier, you were mentioning learning from every success, learning from every failure. You had your informal business school, so to speak, in the form of starting these businesses before DC. What were some of the mistakes that you made in some of those earlier ventures, where you’re like, “Okay. Now that we’re doing DC, we are not going to do these following things. We are not going to make these following mistakes.” It just brings to mind – one for me, for instance, is in one of the first companies I started, I became really interested in radio advertising. But I knew nothing about it. And so I bought remnant space – I thought I was so smart because there was this huge discount on space for drive time. And I was like, “Oh, my god. Drive time. Perfect. I found a needle in a haystack.”

And then, all of my ads were run at 4:45 a.m. because it was defined in the contract, drive time was 4:30-9:30. So I just lost it all, right? So I learned a lot of lessons in that one. But do any particular mistakes or failures come to mind, that have informed what you did with DC in any way?

Ken Block: Well, I think that all marketing and advertising – a lot of people don’t realize – they’re like, “Oh, we have $100,000 to spend. Sweet.” Well, you need to turn that $100,000 into, say, $1 million worth of business. So it’s about targeting and having the right message to reach the consumer that’s actually going to guy the product. And that can be very difficult, and there can be very many opinions with that. And even in a company, you can have 10 different opinions on that, even have some personal agendas thrown in. And so it can be very difficult. And a lot of it is a learning lesson, and you’ve got to look at everything else that’s out there, and what your competition’s doing, and try and do it better.

But it’s a difficult process, and it’s one that you really have to work at and think through. I’ve had so much random stuff – like your example right there. I had one of our athletes who was like, “I want a bus. I’m going to build a bus. It’s going to be $300,000. I need $300,000 out of you. And we’ll put a big logo on it. Everybody on the freeway’s going to see it.” And I’m like, “I don’t care about everybody on the freeway. Those aren’t my consumers. If we’re going to spend $300,000, we need to spend that targeted specifically on who we think is going to buy our product.”

Tim Ferriss: For DC, who was that? Who was your archetype of your customer? Who was your customer in the early days?

Ken Block: Well, DC – I mean, we were mainly selling to skate shops in the beginning. So you’re talking teenage kids, mostly boys, that were going in and buying the shoes to skateboard in. So back in those days – mid-’90s – we had all the skateboard magazines, because that’s when magazines still existed and were big. So we had at least one to two ads a month that were making to drop in all those magazines. And then, you add various video projects and there was 411 Magazine, the video magazine. And then, on top of that, you sponsored – we sponsored maybe 10-12 skateboarders that were the top guys of the industry, that fit our brand.

And so you have all sorts of different genres of types of skateboarders out there, same as basketball. There are guys that like high-top shoes, guys that like low-top shoes – there’s guys – so you have different athletes that represent different things like that. So we spent all our marketing dollars to attract those teenage kids to come into the skate shops and buy. And over time, as the brand grew, and we did more and more sales, we expanded to more mall stores. And so that kid isn’t affected as much by the pro skateboarder and the skateboard magazine.

So then we started working with artists like Mike Shinoda from Linkin Park. And we had a Mike customer signature shoe and did stuff like that. Eventually, we worked with artists like KAWS and people like that. So as we branched out into more of youth culture, as opposed to only skateboarding, we found our unique marketing angles to do that, and do it in fun and innovative ways. We grew the brand – I think at its peak, in 2007-2008 or something, was around $550 million. So it really grew to be quite a big brand and was actually on target – there was a plan at one time, with a guy that was running our company – Nick – to be a $1 billion brand. Unfortunately, it never made it there because of some problems that Quiksilver was having when they bought us in 2004. But it was incredible to take a brand from nothing to over $500 million in sales a year.

Tim Ferriss: It’s a huge accomplishment. What does DC stand for?

Ken Block: DC actually stands for Droors Clothing. Almost every word or variation of the word in the English language is trademarked in some way or another. So as we were trying to work on names for the brand, we had all sorts of names that we submitted. Everything was taken.

DC was actually – I had made DC logos for Droors, because of Droors Clothing. It’s just an abbreviation – something you could make a simple logo and put on a sleeve. And so I knew that I could make logos and art for that. So we submitted that and it came back that, yeah, that was possible to do. So the crazy thing about trademarks, though, is even when you trademark something for one category, it doesn’t mean that it’s good for another category. So eventually we made snowboards. But the logo that we have looks kind of like Chanel, and Chanel actually has that trademarked for snowboards. So that’s why you never see our logo done the way it is on shoes on a snowboard. Really random bit of side legal information there. But –

Tim Ferriss: Yeah, if –

Ken Block: – that’s the sort of thing you deal with with a company.

Tim Ferriss: Oh, for sure. And just a side note for people, because I run into this a lot with people who are starting businesses. Intellectual property is really, really nuanced. And having a trademark, or having a patent, does not protect you. It just gives you the right to sue someone who infringes, right? This is just really important.

Ken Block: Oh, yeah. The actual expense spent over years protecting our trademark around the world is millions and millions of dollars.

Tim Ferriss: Yeah.

Ken Block: And it’s just a fact of business. And it’s an ugly world. It’s not any fun. And I’ve been in various parts of the world, and shown up and found bootleg versions of our shoes. And not even good bootleg versions. They came straight from our factories, too, where they were like, “Oh, we have too many of these soles and too many of these uppers. We’ll just put them together and sell them out the back door.” It’s really unfortunate, but that is the world we live in, unfortunately.

Tim Ferriss: It’s part of the ride.

Ken Block: Yeah.

Tim Ferriss: You mentioned a book when we were walking around that beautifully colored table tennis – what would you call it, platform – over there. When did that – so Dale Carnegie. Just to kick off a conversation on maybe resources and other things that have helped you in your entrepreneurial journey – so what was the book and when did it appear?

Ken Block: Well, the simple background of that is, I was a young 20-something and all of a sudden I have a business and I have to manage it. And I have no management experience. I didn’t go to work in some other company and rise up through management and learn management skills. I went straight from junior college to having my own business. And our business opportunity was growing every year. It was successful every year. And it was successful because my business part Damon and I worked very hard. But we were working on our talents. And after a while, those talents were starting to run out.

We were successful, but for us to continue to grow we needed smarter people than us around us. And that meant that we needed to hire them, we needed to manage them, and no matter what, in every company, you have ups and downs of dealing with people and success based on the people you surround yourself with. And so I needed to grow as a person in that position and I knew that management was really one of the keys. So the first actual book that I picked up to learn communication skills and management skills was How to Win Friends and Influence People by Dale Carnegie. And I don’t know – how old is that book now?

Tim Ferriss: It’s – I would say it’s at least 40, probably 50 or 60 years old. It’s –

Ken Block: I think it’s older than that.

Tim Ferriss: It’s got to be.

Ken Block: I think it might’ve been written in the ’20s. [Ed. Note: 1936]

Tim Ferriss: Maybe even like 80! Yeah, it’s a fantastic book. Parts of it are a little dated and kind of make you chuckle or cringe depending, but –

Ken Block: Yeah.

Tim Ferriss: – great book.

Ken Block: Yeah. But I think that book – I think there are a lot of good lessons in it. And I like the attitude, even the title How to Win Friends and Influence People. And that actually fits very well with how I like to manage, how I like to work with people. And a lot of it is about working as a collective and getting people on a team to accomplish something as opposed to just being a director and barking orders. So I’ve always enjoyed the collaborative effort of working in a company that, “Hey, we’re trying to get this done. We’re trying to finish this campaign” – whatever it is. And everybody knows and understands the goals, and we’ve set a bar. We’ve set this bar high. How do we all get there?

And that book was really one of the first books that really helped me achieve my management style and what’s helped me really be successful. There are plenty of other books, like The Habits of Millionaires [Ed. Notes: The 7 Habits of Highly Effective People] and all that sort of stuff – those books, too. But I think that book really was part of what shaped me as a businessperson and a director.

Tim Ferriss: If we look at the – let’s just say the apparel business. I’ve spent a good amount of time around, say, Daymond John at FUBU – which stands for “for us, by us,” by the way, for people who don’t know that – or Marc Ecko in the early days. And it’s a tough – or it can be a really tough business, right, where people are relatively undifferentiated and it’s – and they’re, in some cases, depending on the scale obviously – it’s an appealing business for a lot of people to go into.

So what were some of the key decisions, or approaches you took, that were different enough that led to this year-on-year growth? Was it innovation on how you approached the stores? Was it something very unusual about your marketing? Obviously you did a lot with product innovation also, but what were the ingredients, right? Because there were a lot of players – potentially a lot of players in that world.

Ken Block: Well, I – that’s a tough question.

Tim Ferriss: Yeah.

Ken Block: But when I look back on it, one thing that always – that Damon and I always thought about was really – the easiest thing is saying, “Set the bar very high.” And when you say that, you’re like, “Okay, well how does that apply? Does that mean you make a really nice t-shirt?” Well, no. I mean, that’s part of it. But a lot of it has to do with like – okay, if we’re going to go do marketing, how do we do it unique and different? How do we be creative? The thing about the world today is it’s easy to make a t-shirt. But how do you get someone to buy it? Why is Supreme more desirable than say something else? Just for a random example, even throwing Reebok or something else like that – the kid’s definitely going to take the Supreme shirt over the Reebok shirt.

So – but that is because of a brand essence. You’ve sold someone a story. You’ve sold someone an image. And to do that, and to do it at a very high level, is very difficult. It takes years of development, and really having that bar set so high, and judging everything against that bar so that you end up with marketing projects that are huge, and different, and really capture people’s attention. Or you have products that lead in the industry. Or that you have athletes that really stand out and stand right along with you with their huge accomplishments, and represent your brand with them at the same time.

So it’s all of those things in one that create this brand essence for everyone from big companies like Nike and Apple down to small brands, even like us with Hoonigan. So if you can capture the interest of the consumer with the right story that touches the right nerves in each of these markets, then you can really set yourself apart and then drive that consumer to buy the product. Because at the end of the day, a t-shirt – pretty easy to make.

Tim Ferriss: Yeah.

Ken Block: Even nowadays, a pair of shoes – pretty easy to make. Lots of competitors out there. So how do you grab the attention of that consumer and say, “Buy ours instead of theirs.”

Tim Ferriss: Can you think of a particular campaign or a particular athlete that was just the Willy Wonka Golden Ticket, where you guys were really going to ace the – or one that completely face-planted, where you were like, “Okay, this is the reason why this didn’t work?”

Ken Block: Well, back in the day, when we started Droors, we were a couple industry guys – me and Damon – that – we didn’t have the experience of a lot of the other companies that we were competing against had. But we just had a vision. We had an idea of what we wanted to do and we came up with some very innovative marketing concepts, not only for Droors, but in the DC. But the first thing that really started us off in Droors was just coming up with really fun and unique, kind of twisted, ideas. And Rob Dyrdek, who is now a fairly big MTV star – he was one of our skateboarders back then. One of our first ads that really stood out in the magazines was literally just – I poured blue paint over his head and he was smoking a cigarette. And we just had these really obscure photos of just his head with blue paint being poured over it.

We were selling clothing. There was no clothing in the ad. But this was the early ’90s and we were just trying to be a bit outlandish and different than what everybody else was doing in the magazine world at that time – in the skateboard world, I should say. And it was much more of sort of a fuck you fashion style attitude. And it just really worked. And we played on that idea of just being rebellious through the years. And it’s fun because skateboarders are generally like that. So it was fun really playing into that over the years.

DC, as we were growing it, got a bit more professional. The style of DC was a bit more of a slick style skateboard shoe, more performance. So we played into that over the years and had some funny taglines and made creative but slick ads. But in the end, one of the biggest things that we ever did was build a giant ramp – what’s called the mega ramp – for Danny Way to do basically giant skateboarding tricks that had never been done at this scale. And that was around 2003-2004. And that had really made us and him stand out in a way that really – we were seeing skateboarding go to a whole new level, to the point where X Games adopted that ramp and put it in the X Games. And I think the mega ramp style is still in the X Games today.

But all initiated from Danny thinking in an innovative and different way, and then us funding it and creating a video part all around this. And that was just the type of stuff that we did to set DC far apart from all of our competition.

Tim Ferriss: Was there anything with pricing or distribution? You were mentioning the contracts with the athletes – that comes to mind that, outside of product and marketing, you guys did differently? We’re going to come back to video for sure because that seems to be a very native medium for you.

Ken Block: Yeah.

Tim Ferriss: So we’ll come back to that.

Ken Block: On the business side, like I said earlier, Damon and I were smart about realizing we weren’t the smartest guys in the room, and to hire those people and then, manage the expectations of what we were trying to do and grow the business. And –

Tim Ferriss: How did you find those people?

Ken Block: How did we find them? Some of them were friends. Some of them were friends of friends. The guy that ran our business for a while was actually the father of someone I went to high school with. And then, as we grew bigger and bigger, we used headhunters to go out and steal people from Nike for sales and stuff like that. That’s just the reality of big business is, if you’re trying to go a certain place, like with sales, you need to hire the guys that do that for someone else. And we would hire – find and hire the right people and we were able to grow it quite well over the years.

But that’s the tough part about business. I was a marketing guy. I was very good at design. I had some design experience from doing architecture in high school. I ended up basically designing the first 15 models of our shoes – with some of the pro athletes, but I did the drawings. I flew to Korea. I immersed myself in the business, said, “This is what I have to do to succeed,” and did it. But that doesn’t mean I’m a good salesperson, doesn’t mean I’m a good accountant, and you just have to hire the right people and be able to manage them. If they can’t perform, the management side of you has to fire them and move on and hire someone better.

To me, that’s a big part of success, is understanding your strengths and weaknesses and hiring the people to really help make a business successful – that you can’t do everything yourself. There is no way, at least in my mind – there’s no way that you can be a brand director along with an incredible accountant and an amazing salesperson. But you just have to have the wherewithal to understand what those jobs – what it takes to succeed in those jobs and then hire the right people to do it. So that’s one thing I’ve really learned – probably in a big way – over all of this, is that it really takes a big community of smart people to make something successful, but at the top you still need to be able to set that bar and manage that bar to get something where you intend it to be.

Tim Ferriss: Did you guys – up until the acquisition by Quiksilver, did you self-fund or did you bring in financing for the business along the way?

Ken Block: No, we self-funded. We had our names on very large lines of credit, which I genuinely hated – which was one of the reasons why we eventually sold. The liability of that if there was a down year or the economy crashed or something, the business would’ve gone away quite quickly. Because we didn’t have – we were not cash heavy. We were definitely very debt heavy. But that’s what we needed to grow and how we did grow. And it made for a very successful company, but also that can make things volatile in the long run. And that’s why we saw a purchase with someone like Quiksilver as a very good route to a good end for us, and it worked out really quite well.

Tim Ferriss: So video. I promised to get back to video. Let’s talk about Gymkhana Five specifically. As someone who – because that was the first Gymkhana video I saw. I was in – I lived in San Francisco for almost 20 years before moving, and I would imagine – a way to describe it, for people who haven’t seen it – everybody should see it, by the way. Last time I checked it had – I’m sure it’ll be past 100 million by the time most people hear this, but 99 million or so views – at least one version of it on YouTube – so quite a few people have seen this.

And it is really mind boggling to watch this video. Maybe you can describe it for people, but also, I hope, in describing it for people, explain how it seems – at least, from the editing – that you basically shut down San Francisco to do this. Because you don’t see a soul on the streets. So what is Gymkhana Five? Maybe that’s a way of explaining what Gymkhana is. And everybody should absolutely go check this and all of the other Gymkhana videos out. But almost 100 million views. What is Gymkhana?

Ken Block: I love how you just jumped past four very viral videos to the fifth one.

Tim Ferriss: Oh. Well, I jumped to number five because all of the tech nerds, who are my friends, live in San Francisco and they were just like, “What in the fuck is this?”

Ken Block: Yeah, well the funny thing about that is, Gymkhana Five is my favorite video. We started making these videos – the first one, it took us two days to produce, so it was a very small team. And it was the first time that we really had a video. Because we’d made several recap videos of me and Travis racing. I’d done some stuff with Nitro Circus. I’d done a 170-foot jump on a dirt bike track with my rally car for a program called Stunt Junkies that got 10 million views.

But Gymkhana – the first Gymkhana video that we did, it’s called Gymkhana Testing and Practice. It was the first real viral video. It got 10 million views in a couple of weeks and then just kept going. It was actually – this was before YouTube was really popular. So I had a video player on my Ken Block website and it got 10 million views there alone. And finally, I was paying for this –

Tim Ferriss: I was going to say that –

Ken Block: I was paying for this website to host this and it was costing a lot of money. I’m like, “Shit, we’ve got to put this on YouTube. This is just costing me too much money.” So that’s how long ago this was. It was over 10 years ago that we started doing this. And it’s weird to me that – you think about this today, that YouTube wasn’t the video standard that it is now. People were still putting videos all over the place. Because YouTube today is just the standard. Everyone puts stuff there, from The Daily Show to the YouTube community that – some of them have subscribers in the millions.

So anyway, we created this video and it was really fashioned after skateboarding. So a skateboarding video part – a guy will go out and say – he’ll skateboard and try and capture certain tricks on film for a year. And he’ll go to a certain handrail and he’ll try 30 times, and slam 29 times, roll away on the 30th time, and they make sure they get all the best angles of it. And they’ll take 20 of these tricks and put them together to make a video part. And it’s just the best of what this person can do. And this is done a lot in skateboarding, snowboarding, surfing, motocross – they make these videos that are then sold to the consumers.

So basically I created that same thing, but with a car. So I went and did a certain number of tricks and slides and around different obstacles at an airport called El Toro in Irvine. And that’s what the first Gymkhana video was. And I thought it was really cool. It wasn’t about trying to do something in one try. It was about trying something 10 times to get the perfect shots to make it look really good and tell the story of driving around this airport – and put it all together as a course.

And when we first put it out, I was like, “Oh, I really like this video. It showcases what I want to watch – what me and my friends want to watch.” And when we put that out, it turned out that a lot of other people like to watch it too. And that video really took off. And so my sponsor said, “Hey, when are you going to do that again? We really liked that exposure.” And so DC paid for me to do the second one, and the third one, and the fourth one, and then the fifth one being San Francisco.

Now the second, third, and fourth ones all are a very similar filming concept, but we just found different locations. The second one was on some piers in Long Beach. The third one was a really unique old race course in France that has these banked walls that go up to 51 degrees. Gymkhana Four was on one of the studio lots up in Hollywood. So you’ve got Jaws, and you’ve got The War of the Worlds, and all of these different sets that I was driving through that made it a really unique thing.

But these were all closed sets – private airfield, and private racetrack, and that sort of thing. And for Gymkhana Three, we’d actually gone to San Francisco – not San Francisco. Detroit – and scouted Detroit. And then when we went to go get the permits to film there, the city was like, “We don’t like certain locations you’ve picked.” And we were like, “Well, why?” To us, everybody knows Detroit as a part of the Rust Belt. It’s an industrial city that isn’t so industrial anymore and has a lot of urban decay. And we liked the urban decay. We had some new stuff in there too, but a lot of Detroit, to us, was very cool urban decay. And I wanted to drive in and through a lot of that.

And they just didn’t like that. They wanted to veto – even on set, they could say, “No, we don’t like what you’re filming,” and veto us. So there was no way we could put up all this money to go film at a location where they’re going to randomly veto us in the middle of shooting. So we never ended up doing Detroit. We just thought, “Oh, that’s going to be too difficult.”

So anyway, getting to Gymkhana Five, we went and scouted an area outside of San Francisco that’s an old military base where they use to build a lot of bombs and warships and that sort of thing – right on the water. And it cool but it didn’t have enough creative driving situations to make a whole video. So we went and looked at it and were disappointed, and we’re driving back into town to go to the airport. And the scout that was with us had just scouted San Francisco for, I think, Iron Man 3. So he’s a very high-level scout that does Hollywood type stuff. And he’s like, “Hey, do you want to go check out these spots in San Francisco?” We just laughed like, “San Francisco’s never going to let us do this in their city.”

It had nothing to do against San Francisco, it was more of the idea of – we’re hooning with cars. We’re having fun with cars. I’m doing giant slides and donuts with a car. There’s no way a city’s going to let us do that. But also, we just didn’t understand the movie world as well back then. And so the scout was like, “No, no. We can do whatever we want. We get a permit, we have that street to do whatever we want.” And so he took us to a couple of locations and we were blown away. We were like, “Really? We can use these locations?”

And so he had some good stuff. But we said, “Hey, we need a jump,” we need this and that. “We need a real twisty street. We need something down by the water.” And so he came back to us a month later and said, “Hey, I have all that stuff. You ready to go look again?” So we went back to San Francisco and looked at everything he brought us. And we said, “Wow, we have enough here to make an amazing video. We still need a few little things, but we have enough here.” And then, in that process too, the city came back and said, “Hey, do you want the bridge?” They offered us –

Tim Ferriss: That’s absolutely nuts.

Ken Block: – the Bay Bridge.

Tim Ferriss: How do you get the Bay Bridge? How do you clear the Bay Bridge?

Ken Block: I would’ve never even thought that would be possible. But that’s the thing that’s interesting about all this. As we went through this process, you learn, “Oh, a city like San Francisco, where a lot of TV shows are shot, a lot of movies are shot, a lot of commercials are shot – there’s a very good film department there.” The police force are very adept to understanding what the needs are for these movies and things. And they understand what you need to do to do this. So they offered us the bridge and we were like, “I would’ve never thought we’re going to shut down the Bay Bridge and use the Bay Bridge.”

But they were like, “Oh, yeah. We do that Sunday morning. We block them over by – between Oakland – they start – they get on the bridge over by Oakland. And then, as they get towards the island” – I don’t remember –

Tim Ferriss: Treasure Island?

Ken Block: Yeah, I think it’s Treasure Island.

Ken Block: And they start slowing everybody down. And when they have everybody start to slow down, the traffic then empties out ahead of them, and then we get on at Treasure Island, or whatever that’s called, and then go out and do what we need to do – where the traffic’s still stopped before the island. We have 10-15 minutes to do what we need to do and then we move on and the cops just let the traffic go. So really, they’re only stopped for 10-15 minutes. And we did that, I think, four times? So it messes up some traffic, but for a short amount of time on a Sunday morning, which is the least amount of traffic on that bridge.

So it’s all about just really smart usage of public streets. And I would’ve never understood all that unless we’d actually done that project. Now we’ve shut down the busiest road in Dubai – the main strip through Dubai – that had only been shut down once before for George W. Bush, Sr. So he was the only one that they had ever shut it down for before that. So it’s been wild to go on this ride of, “Oh, they’ll never let us do that,” to shutting down some of the biggest cities in the world to do some of this stuff.

Tim Ferriss: It’s really astonishing. I mean, I never would’ve thought it possible.

Ken Block: Yeah.

Tim Ferriss: And is it a function of, let’s say, the scouting ace that you had, or someone else putting together a pitch for the city like, “This is what we’re planning. This is why it’s going to bring a lot of tourism?” Or is really just the infrastructure’s set up, we are going to film, this is how much – what is the retail price point for this? What’s the rate card for shutting down these streets?

Ken Block: Well, I think that the exposure is a good thing. They do look at that. San Francisco looked at it and said, “Okay, yeah. That’s good. This is a viral series that could potentially give San Francisco more exposure.” But at the end of the day, I just think it’s money.

Tim Ferriss: Yeah.

Ken Block: You’re paying the film commission, the city, the government to go do this. And the city’s getting paid, the police department’s getting paid. It’s a commerce system. And so – and there are a lot of jobs around that that are being produced, too – everything from our crew, to the guys that – there are certain streets that they don’t want marks on. So we’re having to pay local guys to come in to clean up marks.

Tim Ferriss: Right.

Ken Block: So it really is a wild process.

Tim Ferriss: No shortage of marks –

Ken Block: Yeah.

Tim Ferriss: – in that video.

Ken Block: Yeah. And if you look back at that video, it’s – San Francisco, to me, is one of the most unique driving cities in the world. And not only does it have some amazing driving situations, like Russian Hill, some of the twisty streets, all the elevation changes, and all of that – but it’s also been immortalized by movies like Bullitt.

Tim Ferriss: You – for sure.

Ken Block: Bullitt wasn’t filmed in Akron, Ohio. It was San Francisco – jumping down those crazy streets and the bridges and everything. And that’s what makes it so legendary in its essence as San Francisco, as a unique place for cars. So when I – we got the permission to do that, oh man. It was really quite an honor and very cool, to me, that we were going to San Francisco to make this video. And I’ll tell you that I’m very lucky. I have an incredibly great crew around me of smart, very innovative and creative guys. And that’s what helps me make these things, too. When you watch that video, there are a ton of things in there that I do with the car, but I can’t do that without the great race team behind me and the great creative team behind me, too. It’s a very big collaborative effort for us to do these things.

And not only that, even my experience and connections in the industry. We have Travis Pastrana in there doing a wheelie that’s part of one of the elements of the movie. And that’s a part of the system and everything that’s built into what we do with – my agent is Travis’ agent and Travis is a long-time friend of mine. So it’s such a great mix of friendships, creativity, and hardworking people that make this happen.

Tim Ferriss: If you’re comfortable talking about it – because, certainly, it’s a burning question in my mind, putting aside the – separating out the production cost – put the production cost on one side, meaning all the cameras and all the crew for the actual filming, what does it – we don’t have to make it specific to San Francisco. But to shut down areas like that in San Francisco, what is the range in cost to doing something like that? Do you have any idea?

Ken Block: Well, the funny answer to that question is I ignore budgets. I get to focus on the creative stuff. And that is the honest truth. I only deal with budgets when there seem to be overages – and most of those times are caused by me. I’m like, “Yes, I’d – we can use the Hollywood sign but it’s going to cost another day? Yeah, let’s really do that.” But luckily, for what I’ve been doing, there’s been a lot of success with this. And DC funded the first five videos, and I didn’t have to deal with any of the budgets for that. There’s always a marketing director that figured that into his budget and we did five years’ worth of those videos with them.

And since then, my agent and Hoonigan have dealt with working with companies like Forza, and Ford, and Toyota to fund all these projects. There’s a cost to doing it. And the more creative you are, and the more extravagant you are, the more the cost is. But luckily, we’ve had a great set of sponsors that really understand and see the value in this and have really let us go wild and get these things done. The sky is not the limit. There are some very distinct budget restrictions. But these have been big budget things. There are movies that have sold in Hollywood that have smaller budgets than what we work with.

But it’s very cool to do this process. And the creativity that goes into it all through the process of production and everything, it is on some of the highest level there is that – with people that we work with in Hollywood. And it’s really cool to be able to do that and have directors like Neill Blomkamp email me and be like, “Dude, I want to direct one of your videos.” And I’m like, “I loved District 9. Yes, how can we get you involved?” But it’s just been a really fun, wild ride and a really fun extension of, not only my creativity as a marketing person, but also the creativity I’d love to do with the racecar itself.

Tim Ferriss: And at the same time, when we were having – well, I guess, meandering around the kitchen earlier, you have somewhere between 4.5-5 million followers on Instagram. And you were mentioning how – we were discussing the affordability of the gear that I’m recording this podcast on right now. You were saying that some of the most popular pics and so on that you’ve put up have, in some cases, just been from an iPhone, right? Or something like that. What, in your mind, for people who may not have a high budget and have seen footage that seems to also do well – for instance, where even recently, in British Columbia, where you were snowboarding and had Roman candles as you were going down through powder – what advice would you give to people who are hoping to create videos that get attention?

Ken Block: That’s a tough question. But it –

Tim Ferriss: I love tough questions.

Ken Block: Well, it’s a tough question, I feel like, in general – in marketing, in society, in whatever. Because today, like we were saying – t-shirts. Yeah, it’s easy to purchase a t-shirt. But how do you build a brand essence? It’s the same with a lot of equipment nowadays. It used to be so hard for – to get a really good photograph. Well, nowadays, I can get a really good photograph with my phone. So it’s not about, necessarily, the equipment nowadays. It’s about the content. And I think that’s really what made us successful back in the day, was hiring the right photographers, artists, videographers, and all that stuff, to produce the right content for all of our marketing – especially for DC. It’s a –

Tim Ferriss: And you were some of the first guys to take high quality black-and-white shots of athletes – and not just black-and-white, of course. But it seems like – is that accurate, that you guys were – at least, that’s what I’d read, that you were some of the first people to really place and emphasis on that.

Ken Block: Yeah, I mean, there were all sorts of different campaigns that we did – various different things in black-and-white. But, for us, a lot of it was connecting with the consumer in a different way, and in a way that they wanted information. And when I say that, I mean – even when you watch a simple video, you can capture something on an iPhone that, as long as you capture the right essence of something that connects, that’s way more important than hiring a guy that can hold a RED camera; that may make it prettier, but it just costs you $10,000 instead of pulling out – something out of your pocket.

So for me, it’s always about the storytelling. It’s always about connecting the content with what the consumer wants to see. And I think we’re lucky on my side that the guys behind me enjoy – we all enjoy the same stuff. So we want to produce the content that we want to watch, if that makes sense.

Tim Ferriss: It makes total sense, yeah.

Ken Block: And I think that that’s why you see our stuff so passionately done, because we genuinely love this stuff. But back to that storytelling thing, it was funny when we started – just a random example that pops into my head. We started making ads and doing a lot of marketing with motocross guys back in the late ’90s with DC. We sponsored Jeff Emig, and Ryan Hughes, and Ricky Carmichael. And when we went into the magazines, we looked at everything and the motocross photographers shot really tight because the dirt bike sponsors wanted them – they wanted to show their logos on the bike. And the bike manufacturers, they wanted the consumer to see their bike up close.

So you just have all these photos of a guy in the air and no reference to the ground and that sort of thing. Well, we did the opposite. We hired skateboard photographers to go shoot these dirt bike guys, and they would shoot long lens and really show how big these guys were jumping. And then, we’d buy a spread ad and run it in black-and-white. And Ricky’d be way up in the sky, and you’d see the real distance – 100 feet – that he’s jumping. And it would look dramatically different than everything else in the magazine. But that’s how we stood out. And the consumers love it, because they’re like, “Hey, you’re showing the sport that we love in a more dramatic and beautiful way.”

And so we really had a huge success from those campaigns – like in motocross – because we were just standing out and doing it different, but once again delivering to the consumer what they wanted to see, and doing it in a fun and unique way. So – and we carried that everywhere, including – random example – the director of photography that I use, for like Gymkhana Ten – he’s a snowboarder. He doesn’t know anything about cars. But he has a certain eye. His name’s Pierre Wikberg. I’ve known him, I don’t know, almost 20 years. He used to have a company called Robot Food. And they made snowboard films.

And we hired him to make two films – Mountain Lab and Mountain Lab 1.5 – about our research and development facility that was my home here in Park City. But they were some of the most fun and creative movies because Pierre has such an eye for not only filming and making things look fun, but then editing together with the right music, and the right story, and the right feel. So it’s guys like him that help make our stuff look and feel a certain way, and that’s what continues to make our stuff successful, because we keep attracting and bringing in these guys and managing all of the content – and the look, the right way – that we know is going to hopefully be successful. And according to three weeks of Gymkhana Ten being out there and 11 million views so far, apparently it’s still successful. So we’re pretty stoked about that.

Tim Ferriss: So many different directions we could go – so many different questions I want to ask. But let me ask you about something – it might seem mundane, but I think it’ll apply to a lot of people who are listening in some capacity. And not just because they’d be involved with athletes, but I’d love to talk about the right way – or the smart way – to sponsor athletes. Because you have agreements with athletes, and hopefully there will be lessons people can pull from this related to not just the specifics of sponsoring an athlete, but just thinking about deals and contracts, right?

We were chatting about negotiation a little bit earlier, but we won’t get into that. We’ll save that for another time. What did you learn – or what were some of the key takeaways that, if you were – let’s say one of your kids starts a company and they’re going to be sponsoring athletes, what would you – are there any particular red flags or warnings that you’d say, “We tried this in the early days. It was a complete disaster. Make sure you do not do this. Make sure you have this kind of clause.” Is there anything – the macro or the micro – that comes to mind about — given your experience, which is vast – how to do it the right way? Sponsoring athletes.

Ken Block: That is a very vague and difficult  question. It all depends on what your ultimate goal is. Is it just a logo exposure? Is it trying to move a particular product? Is it using the athlete for an advertising campaign? Because all of those situations equal different types of contracts, different types of pay levels – everything.

Tim Ferriss: So just to – maybe I’ll try to clarify. So the reason I ask is I’ve seen companies do really well sponsoring athletes. I’ve also seen companies now – I’ll – what does sponsoring mean. In this case, it could be a supplement. It could be an apparel brand. They want someone to wear their stuff, be featured in advertisements, be willing to be quoted as a testimonial – a lot of people starting out don’t even know what the options are, right? They just want someone famous or well respected to wear their stuff, eat their stuff – whatever it might be. I’ve seen people also go under because they’ve overpaid or not thought through the contracts. So I’m trying to wade into this as someone who actually does not know a lot about it. But it seems to be an integral piece of launching a lot of different businesses.

Ken Block: Yeah. Like I said, it’s – there are so many scenarios and so many options there, that it really all depends. If you’re just trying to get someone to wear a pair of shoes to go do something, from skateboarding to basketball, well there’s a certain value there. If you’re trying to put a logo on a video that’s going to get a million views, well that’s a whole different value. And in my case, there are companies like Monster that, all they want is a big logo on the side of the car. They see the amount of exposure that I can get, and they put a certain value on that.

So it’s a really difficult one. I’m amazed at the expertise and the understanding of value that, say, someone like my agent has. Because he has so many companies come to him – from Ford to CBMD – that say, “Hey, we want this.” And he’s able to say, “Oh, well, the basic running value of that, industry standard, is this.” And so that’s where I see agents as a real important value to this process of making sure that the company’s getting their value and that the athlete’s getting their value out of it also.

So it really is a difficult process. I actually don’t deal with any of the companies that I work with really anymore on the negotiating side. My agent does all of it because I don’t understand what Nike is paying a similar person as me somewhere else. He would understand that and understand the value of and then how they’re using them. That’s something that – it’s a crazy world out there. But that is marketing and advertising, though. And there are very particular values that people pay, and certain athletes are quite different.

And even as you change countries – my agent represents a basketball player that actually does a lot of marketing in China. And there’s a whole different set of values as to how he does that, and how much time that takes, and what that value and commitment is. And – yeah. So the question you’re asking is –

Tim Ferriss: It’s a tough –

Ken Block: – not a simple –

Tim Ferriss: No, it’s not simple.

Ken Block: – if you ask me how much that logo is worth on my car sitting over there, I can give you a rough idea. But what a skateboard company pays to put a logo on someone’s t-shirt nowadays, it really is something that is quite a difficult answer to answer without an agent.

Tim Ferriss: Yeah. Yeah. This particular – which is why I bring it up. Because there’s a lot of information out there, but it can be somewhat opaque and confusing at first. So if you want to figure out what books are selling for, there’s a site called Publishers Marketplace and you can buy a subscription. And you can see the rough range of advances that are being paid for different books. So it’s a great source of information, even though most people aren’t familiar with it. Or IMDbPro – although, that’s not necessarily going to get into all the dollar figures, but it gives you a level of granularity, right?

The agent piece is tricky because – I mean, I have agents. But it’s – for someone who’s just getting on their feet and trying to learn, they may not have access to an agent. But I suppose they might have access to a lawyer, if they’re not hiring them for a specific contract, just to walk them through the specific deal templates. Because I know that, when I’ve done deals, you may – you don’t get what you deserve. You get what you negotiate, which is why it’s so helpful to have an agent do it on your behalf. But you might – that sponsor might want category exclusivity, right? And you may certainly not want category exclusivity.

And then, you have duration, right? You might have – if they want social support, you’re going to want it to be really well defined and capped. They might not want it to be well defined, because then it allows them to ask for more. So it’s one of those black boxes. Is your agent from one of the big, three-letter acronym – like WME or ECA? One of those guys? Or UTA?

Ken Block: Yes, WMG.

Tim Ferriss: Yeah. It’s interesting to me precisely because it is so difficult, right, if you’re just getting started, to try to figure it out.

Ken Block: Yeah, but I would say, if you’re a very small startup without much budget and you’re – you don’t really know where you’re going, that can be very difficult. But if you are a bigger company that has money, that understands the business and what they’re trying to do, it makes a lot more sense. An agency like WMG, that represents me, they also help companies with marketing, with actually making videos, commercials, social media posts, all that stuff. So they’re actually a full-service agency.

Because, back in the day, you would have your ad agency over here on the left and you’d have your agents over here on the right. And nowadays, that stuff’s getting much more all-in-one. Because an agency like WMG, and my agent Steve – somebody can call and say, “This is what we want to accomplish. These are the people we want to connect with.” And not only can the agent determine what athlete is right for what they’re trying to achieve, they can then help them write the campaign and actually get the connections directly with those consumers – not only with the company’s social media, but with the athlete’s social media. Because we’re able to target things through Facebook and Instagram, and obviously make the right messaging with the videos, photos, or whatever to really reach what someone’s trying to market towards.

So it – that’s why I say it’s a very difficult question. It is genuinely different when you talk about a really small company – someone with – very inexperienced and very little money, compared to if a bigger company says, “Hey, we want to grow into this category. How can we do that? How can we hire the right athlete?” That’s where an agency like WMG can really help maximize that in a much bigger way nowadays. And most all of them are doing that. A lot of these agencies have really realized, “Hey, we need to be full service.” This is a big world now and social media has made things much more dynamic than in the past.

Because when I started DC, it was like, “Oh, we need to make one skateboard ad a month. We need one message.” Shit, nowadays you need eight mini messages just for Instagram. So the world has gotten so much more direct, so much more – I would say, complicated. And complicated in a way that your brand messaging and your voice needs to be very thought through, very well put together, and done multiple times a day, which is much more difficult than when I started.

Tim Ferriss: Yeah, for sure. And just to put a button in this topic, I would just say for folks, also, if you can’t get an agent, don’t want to get an agent because you don’t necessarily want to get married and then figure out the specifics – for something like this, with, say, endorsement contracts and so on, you can find entertainment attorneys, and they’ll be more than happy to take your money for – to give you a 101 education. It will not be cheap. It’ll cost you a few thousand dollars, and you’ll get a pretty good baseline on – ask for a template agreement. If you just pay them for a template agreement, given whatever your basic parameters are, you can actually learn a lot from that.

Now you are 50-51 at the moment?

Ken Block: 51.

Tim Ferriss: You are still very physically active. Are there any – what does your training look like on a weekly basis, or on a daily basis? What does that look like?

Ken Block: I hate the gym, but I realize it’s a tool that I have to use. So I’m in the gym three or four times a week doing stuff like – I did an hour of kickboxing today with a very good trainer. I also have a regular physical strength trainer. I have some tears in my left shoulder, so I’m actually using a very good trainer right now that specializes in shoulder rehabilitation. So he’s actually been able to take me from not being able to do a push-up for two years to actually functioning, really, quite normally.

So I spend probably about four hours a week in the gym doing everything from high output intervals to basic weight training. And, on top of that, I try and get out and do as much physical outside activity as I possibly can – from snowboarding with my kids to downhill mountain biking. I hike a lot with my dogs in the winter. I basically live right next to the Park City Mountain, so I hike up into the mountains and snowboard back down. I just love the cardio of it, and it’s a great way to get my dogs out and get them exercised. And I take my snowboard, because it’s extra weight on me – and then, instead of walking back down in the snow, which is just not fun at all to me, and there’s no physical benefit to walking down, I can snowboard back down and be at my house in five minutes.

So it’s stuff like that that I really enjoy getting outdoors and doing. But the one thing that I really enjoy about the outdoor stuff is keeping me sharp mentally. Downhill mountain biking, the quickness and reaction that you need on that stuff – and the potential risk through injury and/or death – really keeps you sharp. So I enjoy getting out and doing that stuff as much as possible. But at the end of the day, for what I need, the reaction stuff, kickboxing – really being physical in that sort of way is what I think helps benefit me the most when I get in the racecar and go race. So I really enjoy those things that really keep me mentally sharp and hopefully keep me young.

Tim Ferriss: You’ve definitely had no shortage of injuries, right? I mean, you’ve had your fair share. Was – oh, I was going to ask you about the jump and the vertebrae. We’ll table that for now. Is there anything you’ve stopped doing, where – certain types of exercise or certain types of driving – where you’ve taken it off the table for yourself as you’ve gotten older?

Ken Block: Two things – I don’t ride dirt bikes anymore. It’s so easy to get hurt on a dirt bike. I love dirt bike riding, and it’s just – unfortunately, it’s called hurt bike for a reason. Or the other thing is, with age comes the cage.

Tim Ferriss: Oh, god.

Ken Block: But I absolutely love it, but the risk – I used to ride a lot of tracks. I love track riding and big jumps and that sort of thing, but I’ve also been injured many times from it. So I’ve quit doing that just because of the risk. If I can’t show up to one of the events that I’m paid to go race or go do demos at or whatever because I hurt myself on the dirt bike, well that’s just dumb. So I don’t do that anymore.

And the other thing is, because of the physical side of it, is – I used to do – I used to go out and run with my dogs. I used to play racquetball. But my right ankle has gotten so damaged from skateboarding and snowboarding over the years – there’s a lot of calcium buildup. They actually call it arthritis, but that just sounds like a very old-person term to me. But it’s actually from just all of the impacts of skateboarding and snowboarding, and then actually rolling my ankle from skateboarding – that there’s just a bunch of calcium built up around the joint itself.

So I went to a doctor in San Diego that’s worked on a bunch of different skateboarders and snowboarders. He’s a very good doctor. And he’s like, “Ah, I could fix that for you. It’ll be six months of pain and rehabilitation.” He’s like, “Do you make money playing racquetball?” And I’m like, “Nope.” He’s like, “Then just quit doing that.” So I had to quit playing racquetball. And not – I like racquetball, but I liked the mental and physical challenge of it, because you’re having to predict where the ball’s going. You’ve having to turn and rotate, move, react – I really loved that training to make me quick, to be in the car. And I just had to give it up.

Tim Ferriss: Have you had to modify how you do your kickboxing training because of the ankle or other injuries?

Ken Block: No, because the – just doing pad work and little bit of sparring, it isn’t that bad. Even I was – I did a bunch of kicks this morning, and it hurts the top of my foot. But that’s only because I didn’t place my foot where I should’ve on the pad. That’s my own mistake. But other than that, it doesn’t really bother me whatsoever. And even – because I do need some wrist strength and forearm strength, I actually work with a lighter glove. It’s not a real MMA glove. It has padded fingers and all of that, but it’s a very – it’s a much lighter glove. And I don’t actually wrap my wrists. So it actually keeps my wrists and my forearms actually very strong. So I don’t have a – I’ve broken both my wrists before. But my wrists are –

Tim Ferriss: But not kickboxing.

Ken Block: Not kick – no, dirt bike. Dirt bike and snowboarding. But they seem very strong now and just this process of not wrapping and doing this pad work keeps them even stronger.

Tim Ferriss: We’re going to wrap up in just a little bit, but – so to speak – but I wanted to ask you – and I ask a lot of my guests this because it’s – there are people who listen to these podcasts or see your accomplishments and feel very intimidated and think that it’s always been home runs, one after the other. To humanize things a bit, is – could you talk about maybe a tough time that you’ve experienced, or a time of self-doubt – whether it’s with DC or otherwise – just a specific situation or period of time that you could tell us about?

Ken Block: I would say, one part of time with DC growing was – when you reach a certain level and things start to flatten out. And there was a point in time with DC that the guy running the business side of the company was doing things – what we eventually found out wasn’t exactly the most approved way by the IRS. And then, he wasn’t treating the IRS officials very well. And at the same time, we’re struggling as a company. It really was a hard lesson for us to learn of what it really takes to run a company through the tough times.

And those are the times that you learn the most from. The easy times, when things are all up and up, and you can’t do anything wrong, you actually don’t learn that much from those times. It’s when you have your failures, that certain products just aren’t working, or maybe the market you’re in turns left and you’re still going right, or the business practices that you have going on behind the scenes that you think are all on the up-and-up – maybe people aren’t doing things exactly what – to the directives that you think they are. And those are the times that you make the adjustments, that you really dig down and learn what you need to learn to direct the company the way that you need to.

And those times are some of the most uncomfortable that I’ve ever had – sitting in a room full of attorneys and suits, and I’m sitting there in a pair of DC skate shoes and a t-shirt and having to make these decisions that are way – to me, would’ve been way beyond my experience level. But I dug down and we researched, we read, we worked hard to find the knowledge that we needed to succeed. And those were the times that we learned ourselves the most from. And I know – I’m sorry those aren’t very specific, but I – for a company like they – what we had, there were plenty of times that we hired athletes and they didn’t work out, or we made a particular shoe and the consumer just didn’t want that.

But at those times, too, you’re not relying on one. You have 50 products. One may fail. Okay, we still have these others succeeding. Or we have 15 athletes – we hire a new one. Oh, he didn’t work out. Damn it, we tried. We really liked this guy but he just didn’t perform. We’ve got to move on. And that’s just the way it is. But those are little lessons. The bigger lessons really are the larger business things that – for me, as a marketing guy, we really did try to hire much smarter people than us in those areas. But when it came down to it, we still had to make the decisions. We still had to say, “No, this is the right way to go. We’ve got to let this guy go. He doesn’t get what we’re trying to do.”

Or there were other people that just didn’t have the same integrity that we did, and weren’t acting in the same light that we were, and didn’t represent us the right way. Okay. You’ve got to go, too. And those are hard decisions. And when – I mean, shit, I’ve made a lot of those decisions when I was in my late 20s and early 30s. That’s when I still drank a lot. It’s just a different mentality than I have today. But it was a great learning experience and I came out better at the other end.

Tim Ferriss: So you no longer drink?

Ken Block: No, I still drink. Just not at that same level. I don’t quite have the same – how would you say – stamina to wake up the next morning and do things at the same level every day. It just affects me more nowadays.

Tim Ferriss: So I’ll ask some – a couple of light questions. Favorite drink. So what is your favorite drink?

Ken Block: Wow. Favorite alcoholic drink?

Tim Ferriss: Favorite alcoholic drink.

Ken Block: My favorite alcoholic drink – I have two of them right now. In the summer, it’s called The Long Drink. It’s the official drink of Finland.

Tim Ferriss: Okay.

Ken Block: It’s just something that they made for when they held the Olympics in Finland a long time ago. They were like, “We need an official drink.” It’s gin and grapefruit juice and it comes in a can. It’s amazing. It’s an amazing summer drink.

Tim Ferriss: Sounds great.

Ken Block: But then, year around, I actually really like a good sipping tequila, like Clase Azul or something like that – just over some ice. Just amazing.

Tim Ferriss: Do you have a default breakfast these days, or a favorite breakfast?

Ken Block: I find that I actually work the best, and work out the best, in the morning. But I hate spending the time to make breakfast and/or digest that breakfast. I want caffeine in me as fast as possible, and I want to be able to work as much as possible in the morning, and work out. So I found that just drinking coffee and eating a light breakfast worked really well. But nowadays, I drink, basically, a Bulletproof Coffee – coffee with butter and MCT oil in it. But Onnit makes a very good mix that goes into it, with flax seed, chia seed – that sort of thing – called –

Tim Ferriss: Yeah, hemp protein.

Ken Block: Yeah, called Vitality Mix. And so I drink that ever morning and that lasts me until 11:00-12:00 every day. And I get a great workout in, and I get a lot of work done. And that, to me, is one of those little life hacks that people have come up with that – it’s not – it’s an unusual thing. But, man, if you can get on it, it really works.

Tim Ferriss: Do you have any wind down or pre-bed rituals, anything you do to start shutting down before you go to sleep?

Ken Block: Oh, wow. That’s a tough one. Try not to look at social media for about a half hour before. As I get older – the messed-up thing about getting older is it seems like sleep gets harder – it just really – my mom’s 85 and it’s really hard for her to sleep. So I feel like the actual best sleep ritual is actually working out really hard during the day in some form or another.

Tim Ferriss: Definitely.

Ken Block: Your body actually physically feeling tired going to sleep, and then getting a good recovery by a very good deep sleep, is really key to me. But as far as really winding down, I mean, I have three semi-young kids. My oldest is 12, so we spend every night doing something with the kids and then putting them to bed. And then, my wife and I hang out doing whatever – drink a glass of wine, hopefully not too late, and have a mellow evening and go to bed. So it’s not anything specific besides try not to look at electronics too late at night.

Tim Ferriss: And get the exercise. That’s a huge component.

Ken Block: Yeah, it amazes me how many people don’t realize that, if you’re going to be a successful, functioning human that you’ve got to eat well, you’ve got to take care of yourself, you’ve got to be in good physical condition. Your mental abilities actually coincide with your physical abilities.

Tim Ferriss: Yeah.

Ken Block: And if you put crap into yourself, you’re going to get a crap output. And so I’m a firm believer in good exercise. There’s a – you’ve got to take care of yourself really well physically to really expect a high output mentally.

Tim Ferriss: Yeah. You’ve got to protect the asset. Last one or two questions here – if you could put a message, or a quote, or a word – noncommercial – on – this is a metaphorical question – on a billboard that millions or billions of people would see, is there anything that comes to mind? Any type of message – question –

Ken Block: Don’t be an asshole.

Tim Ferriss: That’s acceptable. That’s perfectly acceptable.

Ken Block: Well, the funny thing is, I say that because I feel like social media is just – and the Internet’s made it so that you’re not talking to people anymore. It’s so easy to be rude. And that’s one thing I really impart in my kids. You’ve got to look at people in their face and make a statement. You greet someone, you look them in the eye. You cheers them, you don’t look away when your glass is hitting the other glass. You look them in the eye. And I just feel like the human nature of us as beings on this earth, we’ve got to treat everybody in a good and fair way. And that – if we all did that, I think the planet would be a lot better.

So that’s a very basic thing. But on top of that, though, I think we’re here – we’re not here for a long time, but let’s have a good time. Let’s be innovative. Let’s be creative. Let’s have fun. There’s a lot of shit out there in the world that we’ve got to deal with, but let’s do things in a better way. Let’s do things in a fun and creative way. Why not? Why be stuck with the mundane and be set with the bullshit. I want to be creative. I want to be fun. I want to do things the best way I possibly can, and I want to be proud of whatever I do.

Tim Ferriss: Yeah.

Ken Block: Everything in life – if it comes to – from the simplest thing to the biggest thing, I want to be proud of what it is and stake my claim, “That’s mine and that’s how I do it.”

Tim Ferriss: Hear, hear.

Ken Block: Did that –

Tim Ferriss: That answers it.

Ken Block: Shit, that was a long billboard.

Tim Ferriss: No, that’s – you could have a sequence. You could have a sequence of billboards. But don’t be an asshole, I think, gets us – checks a lot of boxes. Well, Ken, I really appreciate you taking the time today. This was really fun. It was also fun to be in your backyard and playing in the snow for a few days before getting a chance to sit down together. Is there anything in particular you’d like people to check out? Certainly, they can say hello on Instagram, @kblock43; also @kblock43 on Twitter; Facebook, Ken Block Racing; Are there any particular things that you’re creating, working on, or have created that you’d like people to take a look at?

Ken Block: Well, Gymkhana Ten – the tenth installment of this video series, just came out recently. It’s on YouTube. And The Gymkhana Files, which is the documentary series that Amazon had us create around what I do with making these Gymkhana videos and racing and all that stuff. That’s on Amazon Prime right now. Both of them are very good. We’ve made a documentary about me and what I do, but I think it’s very cool. The documentary genre out there has become very popular. It’s something I really enjoy. So for us to make one was really cool and fun. And it’s a bit different than what else you see out there because we’re showing people what we do, how we do it – to make these viral videos that have become a big part of everybody’s life nowadays.

And we’ve really pulled back the curtain to show what it takes to do this stuff. And that was a lot of fun to do. But different than a lot of other documentary series. At the end, you actually get a prize. You actually get to see the end result of what we did. Unlike The Clinton Affair documentary, you know what the end result is. It’s a cool way that they actually told that documentary and I really enjoyed it. But at the end, yeah he gets impeached – but then he doesn’t get impeached. He did a bunch of bad stuff. We all know about it. It was a cool story. But our documentary series actually was a cool twist on all of that. At the end, you actually get to see what we spent two years making, which I think was really cool and innovative on Amazon’s part, to hire us to do all this.

And it was fun for us to take this experience of making these viral videos and then tell that whole story and show how it all comes to life. So yeah. If – whoever’s listening to this, go check Gymkhana Ten and The Gymkhana Files and all of that’s produced by our small company called Hoonigan that you can find easily online. And, if you’re into cars, they make all sorts of crazy and different content that covers various car builds around the world, and doing funny stuff with cars, and doing very serious things with cars. So it’s a great and fun brand that we have, and it’s been growing a lot because we’ve been able to do very creative and fun projects.

Tim Ferriss: Well, we could talk – I’m sure we could talk for many more hours. We didn’t get a chance to talk about jamon iberico, or Nobu, or the UFC, Jim in Vegas – but we can do that another time. So folks, I will also link to everything we’ve talked about, including the videos that Ken just mentioned in the show notes, as per usual. So you can find all those links at Just search Ken’s name and it’ll pop right up. Ken, thanks again for taking the time.

Ken Block: Yeah, thank you. I really enjoyed actually talking about this stuff, and especially in a format where hopefully people will listen and actually take some of the lessons and knowledge that I have, and hopefully apply it to their own experiences, and hopefully better themselves.

Tim Ferriss: Yeah. Well, I’ve been very impressed over the years watching your longevity, and also how you folded one project into the next, and how the relationships and skills you’ve built from one thing have transferred then into other projects in seemingly distinct worlds. It’s been really fun and instructive, just to watch from afar. So it’s nice to actually be sitting in here having a conversation.

Ken Block: Well, thank you very much for having me.

Tim Ferriss: All right, guys. Until next time, thanks for listening.

No Comments / Leave a comment or question

Ken Block — The Art of Marketing with a DC Shoes and Gymkhana Legend (500M+ views) (#358)


Credits: Hoonigan Racing Division

“In life — from the simplest thing to the biggest thing — I want to be proud of what it is and stake my claim: ‘That’s mine and that’s how I do it.'” — Ken Block

Ken Block (@kblock43 on IG and TW) is a co-founder of DC Shoes and a professional rally driver with the Hoonigan Racing Division.

His rally career began in 2005, and he won Rookie of the Year that season in the Rally America Championship. Ken has accumulated five X Games medals and achieved global fame through his wildly successful viral series of Gymkhana videos. Gymkhana videos (including all associated edits) have racked up more than 500 million views, landing the franchise in Ad Age’s top-10 viral video charts.

In January 2010, Block formed the Monster World Rally Team (later renamed to Hoonigan Racing Division) and signed with Ford to pursue his dreams of racing in the World Rally Championship and in doing so, became one of only four Americans to ever score points in the WRC.

His latest project is The Gymkhana Files, which takes viewers behind the scenes of GYMKHANA TEN: The Ultimate Tire Slaying Tour, a video that, as of this writing, just went up and already has nearly 20M views. It’s all complete insanity.

Please enjoy this interview with Ken Block!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#358: Ken Block — The Story of DC Shoes, Rally Car Racing, and 500+ Million Views

Want to hear an interview with another entrepreneur who loves to race? — Listen to this interview with David “DHH” Heinemeier Hansson in which DHH shares his thoughts on the power of being outspoken, running a profitable business without venture capital, Stoic philosophy, and much more! (Stream below or right-click here to download.):

#195: David Heinemeier Hansson: The Power of Being Outspoken

This episode is brought to you by LinkedIn Marketing Solutions, the go-to tool for B2B marketers and advertisers who want to drive brand awareness, generate leads, or build long-term relationships that result in real business impact.

With a community of more than 575 million professionals, LinkedIn is gigantic, but it can be hyper-specific. You have access to a diverse group of people all searching for things they need to grow professionally, and four out of five users are decision-makers at their companies — so you can build relationships that really matter and drive your business objectives forward. LinkedIn has the marketing tools to help you target your customers with precision, right down to job title, company name, industry, etc. Why spray and pray with your marketing dollars when you can be surgical? To redeem your free $100 LinkedIn ad credit and launch your first campaign, go to!

This podcast is also brought to you by Athletic Greens. I get asked all the time, “If you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. As a listener of The Tim Ferriss Show, you’ll get a free 20-count travel pack (valued at $79) with your first order at

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Read More

13 Comments / Leave a comment or question

The Tim Ferriss Show Transcripts: Susan Cain (#357)

1 Comment

Please enjoy this transcript of my interview with Susan Cain (@susancain), Chief Revolutionary of Quiet Revolution and author of the bestsellers Quiet Power: The Secret Strengths of Introverts and Quiet: The Power of Introverts in A World That Can’t Stop Talking. Her writing has appeared in the The New York Times, The Atlantic, The Wall Street Journal, and many other publications, and her record-smashing TED talk has been viewed more than 20 million times and was named by Bill Gates as one of his all-time favorite talks. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, or on your favorite podcast platform. 

#357: Susan Cain — How to Overcome Fear and Embrace Creativity


Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.


You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g., The New York Times, LA Times, The Guardian), on your personal website, in a non-commercial article or blog post (e.g., Medium), and/or on a personal social media account for non-commercial purposes, provided that you include attribution to “The Tim Ferriss Show” and link back to the URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.


No one is authorized to copy any portion of the podcast content or use Tim Ferriss’ name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another’s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from the media room on or (obviously) license photos of Tim Ferriss from Getty Images, etc.

Tim Ferriss: Susan, welcome to the show.

Susan Cain: Thank you so much for having me.

Tim Ferriss: I have been looking forward to having you on the show for some time. And we have a lot of terrain to possibly cover. So we may end up having a part two and three. But I don’t want to get ahead of myself. I thought that we could look at public speaking just for a second because many people will associate you with this blockbuster megahit of a TED Talk. And rumor has it that you – straight in the delivery room from the get-go – were a natural-born killer on stage. Is this true? Were you born a spectacular public speaker?

Susan Cain: Oh, my gosh. Okay. Well, everybody listening, you can’t see Tim right now. But he has a very devilish smile on his face because, of course, the answer is the complete opposite. So I had a lifelong – well, dating back to middle school, I know exactly when it started. I had an almost lifelong fear of public speaking. And a lot of people say they’re afraid of public speaking, and they’re telling the truth. But they didn’t have a fear the way I had a fear of it. It was so extreme.

Tim Ferriss: What was the triggering event?

Susan Cain: Oh, okay. The triggering event was I had recently switched to a new middle school. And I was in an English literature class. And I probably appeared to the teacher in that class to be not a shy person at all because I love English, so I was always participating. Anyway, she called me up to the front of the room. We were doing Macbeth. And she called me up with a friend of mine. And she said, “Okay. You’re going to play Lady Macbeth. And your friend Rob is going to play Macbeth. And just improvise this scene.” And for me, as a shy person in a new school, this was total kryptonite. And I couldn’t say anything. I just completely blanked out and just stood there dumbly at the front of the class and finally just had to sit back down red-faced, not having said a word. And –

Tim Ferriss: That sounds terrible. It’s making my palms sweat just listening to it.

Susan Cain: Yeah. And I know this now, now that I’ve studied all this stuff, that if you have an experience like that, it gets encoded into your amygdala which is the part of your brain that registers all your fears. And then the amygdala, for the rest of your life, is doing its job by saying, “Oh, I’m going to steer you clear of any situation ever approximating anything like that literature class ever again.” So after that, any time I had to give a speech – and I did it. I used to be a lawyer on Wall Street and stuff. Any time I would do it, I would just suffer my way through. And I would always lose five pounds because I couldn’t eat before, like for a week before. So then I started writing this book, Quiet, after I had left law. And I really, really, really cared about it. It was my dream come true to be a writer. And I cared so much about the ideas in the book. And I didn’t want my fear to stand in my way. And I was giving this TED Talk. So I had to overcome it.

Tim Ferriss: How did the –

Susan Cain: So –

Tim Ferriss: Sorry to interrupt. But now that I’ve had a cappuccino, as long-time listeners know, I tend to jump a lot. How did the opportunity for the TED Talk come about?

Susan Cain: So I had a friend who worked at TED. Told him about the book. And he passed on the idea to the curators at the time. And I think that they understood that most of the TED audience is really introverted. And so they knew that it would relate with their audience. And I think that that was probably why they invited me in. And I’ll come back to how I overcame my fear in a minute. But I will tell you they turned out to be so accurate that after I gave the talk, I came down off the stage, and I was absolutely mobbed for the whole rest of the week by every single other audience member who were all coming to tell me, “That’s my story too. And I’m going around pretending to be this very confident, extroverted person. And that’s not really who I am.”

Tim Ferriss: Amazing. Present company included.

Susan Cain: Is that right?

Tim Ferriss: Oh, yeah. Absolutely. I will steer us back. And you will also bring us back to what we were just talking about. But last night at a group dinner which I helped organize, keep in mind, at a wonderful restaurant here in New York City called ilili – it’s a Lebanese place – I had to take four or five bathroom breaks, which were not to use the bathroom. That is what I do at any dinner of more than one or two people. I have to exit not just the conversations but the environment to just recharge my batteries and gather my bearings for a few minutes –

Susan Cain: And is it –

Tim Ferriss: – and then go back on.

Susan Cain: It’s like you’re feeling a kind of overstimulation in a setting?

Tim Ferriss: Overstimulation.

Susan Cain: Yeah. That’s so interesting because I’ve heard you talk before about moving to Austin and having these group dinners. And I thought, “Oh, that’s so interesting that that’s what Tim wants to do,” because I would never choose to socialize that way. I always love to socialize one on one, almost the way we’re doing right now, sitting here just talking.

Tim Ferriss: There’s a kind of boiling point for me in terms of size. Four to six I can handle. It depends for me also on the environment I think more so than the number of people. So when I do these group dinners, I will generally host them at home or have them at one of my friend’s homes, not in a popular restaurant like I did last night. So y –

Susan Cain: I’m just going to say what’s interesting about that is how strategic you are about it. And I really notice this with people. So we were just talking about TED. I was just talking to Chris Anderson who runs TED about this whole phenomenon. And he describes himself as an introvert too. And he said he loves group dinners if there’s a specific topic that everybody is gathered there to discuss, and he knows it’s going to be something really substantive. Then he’s in his comfort zone. But if it’s just this amorphous socializing, he wants to leave.

Tim Ferriss: So just on the tactical, practical side, I also tend to very frequently cook the meal for the group so that I have a task while people are arriving and talking. Also deliberate because I’m often inviting people who don’t know one another. So I want them to have a chance to chat without having me as a mutual crutch if that makes sense. But in any case, we talked about that for a long time.

Susan Cain: Yeah. No, and that’s a really common strategy. I hear that from many people, wanting to have the task.

Tim Ferriss: I can play extrovert. I’m good at playing extrovert. But up until sixth grade, I wouldn’t even go out to recess. I would sit on a step and read, usually books about sharks and fish because I wanted to be a marine biologist. But I wouldn’t even go out to recess. So a lot of what you talk about and have written about certainly strikes a chord.

Susan Cain: Now I feel like I want to ask you so many questions about this.

Tim Ferriss: Well, sure.

Susan Cain: I think I’m really curious if we could go back and talk to sixth grade you right this minute, would sixth grade you have any idea that you would have the life path that yours has taken that’s so public?

Tim Ferriss: Absolutely not. No. Definitely not. What happened in sixth grade also – just for people who might be wondering, “Well, what happened in sixth grade if it’s up until sixth grade?” What happened in sixth grade – or I should say more accurately, the summer of fifth grade – is that I had a huge growth spurt. And I had been bullied really badly. I was born prematurely and very small. And I was bullied really, really badly up until the end of fifth grade. Then I left to a summer camp and gained about 30 pounds of muscle and grew four to five inches over the summer, came back, and then –

Susan Cain: It’s like a Captain America narrative.

Tim Ferriss: Yeah, exactly. And then the bullies who had been accustomed to bullying me tried their usual playbook. And I just went on this vigilante spree, like the Punisher. And that changed the social dynamics. So I was able to actually go outside and do things that I wanted to do at recess from that point on. So it didn’t mean that I socialized a lot more. But it has more mobility. So that was what happened. But like you – and this is part of the reason why I wanted to start with this question about overcoming a fear of public speaking – is that’s when the people see the finished product, it’s easy to assume that it comes from an attribute as opposed to a skill. And in fact, a lot of what appears to be natural appears only to be natural because it started off very, very unnatural and someone has worked at chipping away at it over time.

Susan Cain: I think that’s true. I think almost all – so often, when you see someone who’s really good at almost anything, it’s because they actually started out exactly the opposite. And then they cared so much about fixing that problem. But in terms of how I overcame that fear – I have this kind of evangelical desire to share it because it was so extreme. I feel like if I could do it, then I know anyone can overcome any fear. So first of all, I spent years sitting in therapists’ offices cozily discussing, “Well, what might be the sources of this fear? And what do I trace it back to?” and like that. And that does no good at all.

I’m actually a big believer in therapy. But not for this type of issue. So what really does it if you’re afraid of something is you have to expose yourself very slowly to the thing that you fear in really manageable doses. So you can’t start off by giving the TED Talk. So in my case, I signed up for this seminar in – it was a seminar for people with public speaking anxiety. It was here in New York. And you’d get there. And on the very first day, all you had to do was stand up, say your name, sit back down, declare victory. You’re finished. And that’s it.

Tim Ferriss: What was the organization?

Susan Cain: Oh, gosh.

Tim Ferriss: Was it Toastmasters? Or something else?

Susan Cain: No. And I’m a big fan of Toastmasters. But this was almost more remedial than Toastmasters.

Tim Ferriss: Toastmasters light.

Susan Cain: Yeah. This was pre-Toastmasters. So the guy’s name – he’s amazing. His name is Charles diCagno. And you can find his organization. It’s And I think it’s spelled with three Es.

Tim Ferriss: Perfect. And I’ll put a link in the show notes for people as well.

Susan Cain: Yeah, because I really recommend him. And so you’d come back the next week. And maybe you’d stand up. And he’d do these things like he’d have people stand on either side of you, so you didn’t feel all alone up there on stage.

Tim Ferriss: That’s brilliant.

Susan Cain: Yeah. And then the audience would ask you questions like, “Where are you from?” and, “Where’d you go to college?” So really easy stuff. You answer the questions, and you’re done. And if you do that little by little by little, you actually really can overcome it. It’s crazy but true. But I will say, having said all this, still, there’s something about a TED Talk that’s on some whole crazy other realm of public speaking nerves.

Tim Ferriss: Yeah. Even if the setting is exactly the same, there is a performance anxiety associated with that three-letter acronym for sure.

Susan Cain: Yeah. We were talking about this before we started taping that so many of the speakers are really practiced on stage. And yet, you see them minutes before they go out, and they’re sweating bullets. And they’re all losing it.

Tim Ferriss: Yeah. We were chatting for a second about – and Chris Anderson can certainly correct me. I’m blanking on the exact term. But there’s some space right next to the stage behind the curtain called the Zen Room or the Relaxation Cube. There’s some very pleasant sounding name for this space. And it’s intended to be the next-up batting cage for the two or three speakers to come. And I remember it was probably 15 or 20 minutes before I was supposed to go live – or no. It couldn’t have been that. It was probably an hour before. And I really didn’t want to be around a lot of people. And in the Green Room, there were all sorts of staff and lots of people milling around and working on production. And I thought to myself, “I need to go to the Zen Room.” We’ll just call it the Zen Room.

And so I walk out to the Zen Room. And I won’t mention names, but there were three killers. These are consummate professionals who have done this type of thing thousands of times, people I look up to and would love to someday have a coffee with. And they are freaking the fuck out. And I was like, “Not helping. Not helping. I need to leave the Zen Room right now.” So yes. It’s a different beast. So how do you go from talking about your favorite color on stage with two people next to you to TED then?

Susan Cain: Right. Okay. So I graduated from that to Toastmasters, which I also completely recommend. And should I describe what that is?

Tim Ferriss: Yes, please.

Susan Cain: Yeah. Okay. So Toastmasters. It’s a worldwide organization. You can absolutely find one near you because they’re everywhere. And it’s basically this not-for-profit thing where you sign up for a group that meets near you. And once every two weeks you get together, and you practice public speaking together. And they have this ritualized way of doing it.

And some of the time, you’re practicing speaking off the top of your head. And sometimes, it’s a prepared speech. And it’s just giving you that exposure therapy of putting you in the beast of the thing that most frightens you. You have to show up every two weeks and do it. So I did that. But then the next stage after that – and it was my husband’s idea – was I hired a coach for the full week before the TED Talk, this really amazing guy named Jim Fyfe, who I also completely recommend. And since then, he has coached many other TED speakers. So I worked with him morning until night for a full week before the talk.

Tim Ferriss: Good for you.

Susan Cain: Yeah. And he –

Tim Ferriss: What did the working with him look like?

Susan Cain: Okay. So he did a really brilliant thing. He was very psychologically attuned. And I said to him, “I’m really comfortable, in general, talking to people one on one and cozily sitting on a couch and talking about life. I love that.” For me, at that point though, getting up on a stage and holding forth was the hard thing. So he said, “Okay. Let’s practice your talk sitting on the couch. And just talk to me about it. And we did that for two days. And it was only after that that we just moved to the stage and started getting into the theatrics of it. That kind of transition was so helpful.

Tim Ferriss: I just want to note that this is – I spend so much time with and I’m so obsessed with good teachers, good coaches. This is very common where they will effectively say, “Let’s start from where you are right now.” And they will always return if they sense any type of overwhelm or fear to bring you back to a point of familiarity or comfort and then edge into the next concentric circle of what is your limit of comfort.

Susan Cain: Yeah. And I think they also have to show a lot of non-judgment because I had some dark moments during that week. For me, this was the abyss. And I was just hanging out in the abyss for a week. And so he saw me. I had only just met him. And he saw me not in the most flattering circumstances, and yet I didn’t feel embarrassed by that. There was something about him –

Tim Ferriss: Did he do anything, in the beginning, to assess you or establish a baseline? Or was it more of an interview that he used like an intake? Do you remember what was –

Susan Cain: It wasn’t really formal like that. He’s such a human guy. It was just like we were just talking.

Tim Ferriss: Disguised as intake. Smart. Smart fellow.

Susan Cain: Yeah. So the amazing thing to me now is I now super ironically have a career as a public speaker. I travel the world going and giving talks to all different companies and conferences all over the place.

Tim Ferriss: Go ahead.

Susan Cain: I asked you, “Well, if we could tell sixth grade Tim where he would be, what would he say?” And I say that to myself too. If you could have even told me eight years ago that this would be my life, I would have been so shocked by it. And now, I’ve come to like it.

Tim Ferriss: Did you have any particular pregame ritual or anything that you did in the hours leading up to your talk that helped or that you didn’t do?

Susan Cain: I have things now. Back then, I just suffered.

Tim Ferriss: What do you have now?

Susan Cain: Now, have a few things. I do deep breathing just like everyone else. I’m sure you’ve heard that a million times. But it’s got to be real deep breathing where you really feel your belly and your diaphragm filling up. But for me, what I also do is I usually think to myself – and I do this especially when I’m speaking to an audience that I find more intimidating like a group of finance people at an investment bank or something – I will say to myself, “There, I am sure, is one person in this audience who has a child who is shy or introverted. And if that child has a better life because of one tidbit that that person hears today, then it’s all good.” And that pulls me out of myself instantly.

Tim Ferriss: Yeah. It gives you also a hurdle that you can clear for winning the presentation, so to speak, in that sense.

Susan Cain: Yeah. Right. It’s a manageable goal. But I think it feels deeper than that to me. It feels also like – I think when people get nervous about speaking, obviously, they’re really nervous about being judged. But this completely shifts the energy where it’s not any longer about how anybody judges me. It’s about “Can I help that kid out there?”

Tim Ferriss: And I want to say also that part of the reason I am more than happy, actually excited to spend so much time talking about this is that it is not specific to public speaking. This just happens to be a very common fear and perceived weakness of many, many, many people. Also, as a side note, what Warren Buffett says is his greatest ever investment. Put more specifically, a Dale Carnegie course that he took in public speaking because it magnified his ability to do almost everything else, to communicate effectively both in spoken word but also in the written word in some respects.

Susan Cain: Yeah. Oh, go ahead.

Tim Ferriss: I was just going to say that I’ve never – I don’t think I’ve ever spoken about this. But I also did Toastmasters. And if you have trouble finding it, oftentimes, there are large companies that will have within their HQ or any large location, their own Toastmasters group. And that’s actually how I found it in San Jose, initially. It was at Adobe. So I would go in. And I would do this Toastmasters. And your description of having this very logical progression of small wins layered upon small winds getting up on stage and then getting off stage. Getting up on stage, having two people next to you and answering a few questions and getting off stage – is so incredibly effective. And I’m laughing right now because I remember when I was preparing for my first presentation at South by Southwest – so this is a very large festival and conference in Austin, Texas.

And the timing was 2007. It’s about, I want to say, a month, month and a half before my book is going to come out, my first book which I’m very nervous about. There had been no speaking slots. But I had pitched Hugh Forrest at the time, who I had been introduced to, that I would take anything available. “Corner of a room, hallway, if there were any cancellations, I would really appreciate the opportunity to speak at the event.” And lo and behold, there was a last-minute cancelation. Not by a keynote speaker but by a sponsor who was going to have a stage to pitch their products from in this makeshift café.

And I was like, “I’m in. I’m in.” But I was so incredibly nervous about this that in the beginning, in particular, I was – and this is true today – too nervous to practice my rough, rough draft of the presentation in front of people.

Susan Cain: Yeah. I get this.

Tim Ferriss: And so what I did – I was staying at a guest bedroom at a friend’s house. He had three chihuahuas. And I went outside. I was playing with the chihuahuas. And they followed me into the garage. I practiced in the garage. I didn’t even want to practice in the house where my friend’s wife was. And I gave my presentation. I felt reasonably confident about the content. But I wasn’t comfortable with any of the performance aspects of trying to keep attention. So I gave my draft of this talk over and over again until I could get the dogs to sit and stare at me, somewhat bewildered, but to hold their attention. And that was the litmus test for me to graduate to giving a rough draft in front of humans. For those people out there who are wondering whether this all comes naturally to me, it does not at all.

Susan Cain: Have you talked about that before? Or is this the first time you are doing that?

Tim Ferriss: I don’t think I’ve talked about that. Certainly, I don’t think I’ve talked about it on the podcast. And for the TED Talk also, something I did – which I did not do for the South by talk, which I thought really made a difference – was I practiced giving the talk in front of small groups of strangers once I had a reasonably polished version. And I asked friends of mine who worked at larger companies who had teams during lunch hour if there happened to be an empty conference room, could they invite people to hear a rough draft of a TED Talk. And then I would ask them for feedback. And usually, there was enough time that I could give it two or three times. So I could actually incorporate their feedback, give another version. Once I had given the second version, there were a lot more people in the room who were willing to be critical. The first round, you get one or two.

Susan Cain: Yes. That’s so true.

Tim Ferriss: This is just something I’ve thought about a lot because I’ve been so nervous about public speaking for so long. And it, by the way, doesn’t really go away. At least for me, I still have those nerves. But with TED, very specifically, I assumed – and this came from sports, but I had never applied it – that I was going to be – my heart rate was probably going to be 30 beats per minute higher than normal and that it was not just important for me to practice the content, but to practice under the physiological stress that I would probably experience when trying to deliver the content. So I would do a bunch of pushups in another room and drink two double espressos and wait for it to hit and then go in and give my dress rehearsal to see if I could handle that stimulation.

Susan Cain: That was so, so smart. And listening to that story is reminding me of this crucial step that I left out and, in a lot of ways, a mistake that I made which is – I told you I worked with that guy, Jim, for a week who was amazing. And I thought I was pretty well ready at that point. So I talked to my friend Adam Grant, who’s a very dear friend –

Tim Ferriss: Very good speaker too.

Susan Cain: – and a really good speaker and who also started out as a very nervous and, by his description, a terrible public speaker. He says he used to get terrible reviews from his students. And he just worked and worked and worked at it. And now, he’s the most popular professor at Wharton. Okay. So I was talking to Adam about all this. And so he said – so I’m leaving for TED on Sunday morning to fly out to California which is where it was at that time. And he says, “Oh, I’m going to pull together a group of friends. And you can practice your talk in front of them.” And so this is Friday night. And I’m leaving Sunday morning. And so I show up at this apartment full of Adam and his friends.

And I think that I’m pretty well done with the talk. And this is the first time that I’m giving it in front of any kind of group because I didn’t have the foresight of what you just described. And not only was I so nervous, but I realized from the feedback that a lot of the content was all wrong. And it’s Friday night. And I’m leaving the day after the next day. So I went home, and I just spent the whole entire night rewriting the whole final third of the talk. And then I’m on the plane going out to TED trying to memorize the new talk. So I don’t recommend that kind of approach.

Tim Ferriss: You need to get real people in front of you. This is just like entrepreneurship, and people try to get the product perfect before exposing it to any prospective clients. You really need to get into the messy reality of what a live audience or a real customer looks like. And the same was true for me. I made a lot of changes in the last few days which I thought were just going to be fine tuning.

Susan Cain: Right. And then you end up –

Tim Ferriss: And I was like. Oh, actually, I really need to – I need to completely change 30 percent of this. And I was very, very nervous before the TED Talk. And I came off stage, and I did not think that I – I didn’t think that I blew it. But I didn’t think that I did a great job. I came off stage thinking that there were definitely bits and pieces I could have done better. But it worked out. Seems to have worked out.

Susan Cain: Okay. Wait. But I want to come back to one thing that you said and for the benefit of people who are listening now. So you said that you still are really nervous when you give a talk. But are you really as nervous as you used to be? Because I really want people to understand that you can get to a point – you might still have butterflies. It’s not like the nerves completely disappear. But they get to – in my experience, and from all the literature that I’ve studied on this, they really do get to a point where you can manage them. And the difference between manageable and non-manageable is gigantic in terms of its effect on your life and your career and everything. So I just want to make sure that people know that.

Tim Ferriss: Yeah. I can clarify. So it depends a lot on the event. So if we’re going to do a Q&A and it’s a friend of mine interviewing me on stage, that’s not, from my perspective, really public speaking. It is. But at this point, I could do that with zero preparation. If it’s anything resembling a keynote, if it is Tim on stage talking to an audience, and they expect something that has been well-rehearsed, my physiological response is still very strong. I get really sweaty hands. I pace. I have very minimal contact with anyone beforehand. But let me mention a few things. Number one, both Mike Tyson and Dean Martin used to vomit before nearly every performance.

But the way that they psychologically contended with that evolved over time. Well, since I mentioned Mike Tyson, Cus D’Amato, who was the trainer who really, in a lot of respects I think – boxing scholars or boxing fans would agree – made Tyson into what Tyson was at his prime as an athlete used to say something along the following, that the hero and the coward feel the same thing. It’s how they respond that’s different.

Susan Cain: Yes. Oh, I so believe that.

Tim Ferriss: Yeah. And there is no courage without the presence of fear. And for me, I have come to see those physiological symptoms that used to make me panic, that used to make me feel like I was doing something wrong, that used to make me feel like I was unprepared as simple precursors to a performance. So the way that I frame them for myself is completely different. And I’ve learned to view it as this energetic asset that I can use. And that has made all the difference. And it has decreased in some circumstances. But certainly, before TED, I had given hundreds of different presentations. And it was like I was getting on stage for the first time. In part, also, for people who don’t know, they are very – as they should be – strict about many things at TED, including running over.

Susan Cain: Oh, yes. Yeah. I was very nervous about that.

Tim Ferriss: If you’re running over – and I want to say – and this is exactly what they should say. But in effect, they say, “If you run over by – you should not run over, number one. Do not run over. If you run over, if you get to the point where you’re 30 seconds over, we will come up and remove you from stage.” And while I’m preparing and while I’m rehearsing, one of the things that made me most stressed out is that my finish times were really variable. And I would say 30-40 percent of the time, I ran over. Then other times, I would run two minutes under but miss something really, really important because I was rushing. And I was like, “Good God. This is just a crapshoot. I am at the craps table with my timing.” And that really was a concern for me. So that was another element that made TED unique for me was that degree of cutoff.

Susan Cain: Yeah. I felt that way too. And I did end up going over by over a minute.

Tim Ferriss: Oh, good for you.

Susan Cain: And there it is.

Tim Ferriss: And they were just like, “We cannot stop this performance.”

Susan Cain: Oh, I don’t know about that. But I want to say also, for anybody who is listening and who is right now in the grip of this kind of fear and isn’t sure whether they can really get past it, also, what is waiting for you on the other side of it is so gigantic because there’s something weird about public speaking where it has such disproportionate value to, in a way, what you’re investing in it. You’re going up on stage for 18 minutes or 40 minutes or whatever, or maybe within your own workplace, even giving a two-minute talk, suddenly, everybody is regarding you as a leader and as someone who they can turn to in a new way from if you hadn’t been willing to put yourself forward in that way.

Tim Ferriss: Definitely. There’s public speaking as the force multiplier for the value of your other skills which is absolutely true. And then public speaking, in a way, is also a wonderful diagnostic tool. And what I mean by that is I remember talking to a friend of mine who – he’s a wealth manager for a lot of muckety-mucks who you would recognize. And he said, “I know them generally better than therapists they’ve been seeing for a decade within the first few hours because money brings up everything. Talking about money brings up the full spectrum of someone’s insecurities, fears, desires, neuroses. Sex, also true. And public speaking, I think, if it makes you remotely nervous when you start to learn public speaking – at least for me – brings up all your stuff.

So if you were simply interested in personal growth, it brings to the surface many different pieces of your personality and psyche that you can then work on in a way that transfers to other areas. So that, to me, was my experience and I find really interesting. It’s like, “Okay. Well, maybe you don’t have to play hide and go seek with talk therapy for 20 years to find all of the bits and pieces when, rather than following these different gingerbread trails, you can use certain fearful circumstances to just bring it all right – or a lot of it to the surface.” That was my experience. I’m not saying it’s true for everybody. But it was one of those things like talking about money, talking about sex, or public speaking. It’s like, “Okay. Now we just bring everything to the forefront.” So for me, that was also – even if I had not had any interest in getting on stage and giving presentations, it would have been valuable in and of itself.

Susan Cain: Yeah. No. That makes complete sense.

Tim Ferriss: Are there other things that you’re fearful of or have been afraid of that you’ve overcome?

Susan Cain: No. That was really the big one for me. We were talking about this. Before, I guess, my bugaboo, in general, is that I just tend to be a worrier. So I don’t know. Other than the experiences I had with public speaking, it’s not like I have full-on panic or anything like that. It’s more like it’s a very familiar companion for me. So I’ve had to just come up with various hacks around it.

Tim Ferriss: What are some of your hacks.

Susan Cain: Gosh, there are so many. Okay. Wait. So this is going to get us into another big topic. But why not?

Tim Ferriss: Why not?

Susan Cain: So for example, when I stopped practicing corporate law, and I decided that I wanted to be writer, I told myself that it’s really hard to make a living as a writer. And I said, “Okay. The goal is to publish something by the time you’re 75.” And at the time, I was 33, at the time that I said that. And I did that instinctively because I was always doing these hacks of just wanting to completely take the pressure off of something that I otherwise loved so deeply. And I just knew that if I turned this thing that I deeply loved into a source of, “This has to be the place where I make my living. This has to be the place where I derive some kind of professional stature,” it was going to soak a lot of the joy out of it. And so that’s the kind of hack that I just naturally do.

Tim Ferriss: On a very related note, could you give us a little bit of context around the leaving law, like why you left law? And then you decide you want to be a writer. And you alluded to it, but does that mean that suddenly, your rent is dependent on writing?

Susan Cain: Right. Okay. So I had wanted to be a writer from the time I was four. And then, for a whole bunch of reasons, and like so many people, I graduated coll – well, I took some creative writing classes in college. And I decided, “I’m not actually that good at this. And I need to make a living.” And I also had a desire I think to show myself that I could be out there as an alpha person out in the world of finance or something. So I went to law school. And I practiced Wall Street law for almost a decade. And during that time that I was practicing law, it was so all-consuming that I completely forgot about the fact that I had wanted to be a writer. It wasn’t like I was walking around conscious of this broken dream or something. I’d completely forgotten. And in the first few years of practicing law, I really loved it. It was just this crazy adventure that I was on. And as the years went by, it started to get really tough for me.

I’m not a very natural lawyer in a million different ways. But I was on this partner track. And I was committed to it. And then came the day. And I think I may have told you about this in an earlier correspondence. But then came the day when a senior partner in my firm walked in and said – I was supposed to be up for partner that year. And he said, “Well, we’re not going to be putting you up.” And the funny thing is, to this day, I don’t really know if he meant we’re not putting you up ever for partner or just not anytime soon. I don’t really know what he meant. All I knew was, number one, I burst into tears. And number two, here was my get-out-of-jail-free card.

So three hours later, I had left the firm. I was gone. I took a leave of absence. And I just started bicycling around Central Park. I didn’t know what I was going to do next. But as soon as that space opened up that I now had free time for the first time in 10 years, I started writing. And I had no idea that was going to happen. It was almost like in a movie.

Tim Ferriss: That’s cool. Yeah. It’s just been waiting for you.

Susan Cain: Yeah, literally. I remember that night, curled up in my sofa in my apartment. And I had just started writing on my laptop. And then a week later, I signed up for a class in creative nonfiction at NYU. And I just had this complete feeling of certainty that this was what I wanted to be doing and zero expectation that I would make a living out of it. And this is a really important thing I think. I think if you have that kind of a creative dream and a creative love, you have to do everything you can not to spoil it with the pressures of paying the rent and all those other things, or the pressures of needing to derive professional status from it. So I set up a little side business teaching people negotiation skills. And that was how I was paying the rent. But the thing I was really doing in my heart was this beloved hobby of writing.

Tim Ferriss: This is super, super, super, super, super important. I think it’s true in creative fields – which is pretty much every field, but just for the sake of illustration, writing, music, etc., also, in entrepreneurship – you hear these stories of desperation where necessity is the mother of invention and bada-bing, bada-boom. Magic wand. And then there’s a billion-dollar company. Or there’s J.K. Rowling or whatever it is. But those are, in my experience, the outliers. They make for great cover stories in magazines. But the fact of the matter is that from what I’ve seen certainly, with guests on this podcast is that – for instance, Soman Chainani, who has a number of mega-successful novels.

But he had an SAT prep counseling service that he offered well past the point that his first book was successful because he wanted to always feel like he had a safety net so that the writing would not be tainted or even subconsciously influenced to match the market or whatever the lens might become by this pressure. And that is something that, whenever possible, has come up as a really valuable – I suppose, on one hand, financial survival mechanism but even more so as psychological freeing device.

Susan Cain: Yeah. And I think we’re so addicted to having a really glamorous narrative for things. And the glamorous narrative is you had so much courage. You took the risk. You were dependent on this company or this book or whatever. And if it didn’t work, it was going to be a disaster, but you were the one who beat the odds. We love that narrative. And for most people, that’s a really bankrupt narrative. And there’s a deeper glamor, actually, in the kind of story that you just told because the glamor comes from you’re doing everything that you can to deeply protect the thing that you love most.

Tim Ferriss: Definitely. Now, the book, itself – people may not know the backstory. I’m sure a lot of people don’t. How long did it take to get that book done?

Susan Cain: Okay. So I’m laughing because it took a really, really long time, especially by Tim Ferriss standards. I listen to you and I look at your life trajectory. I’m like, “How does he do that?”

Tim Ferriss: Lots of cheating the format is the short answer. But I won’t take us off track.

Susan Cain: So yeah. From start to finish, it was about seven years. And I will say, in my defense, that during those seven years, I also had two children and was raising them. So that was part of it. But I also just think I’m a slow writer. I like to really, really think about everything super deeply. And what I think people might not know – I had a deadline, as all writers do. And I turned in some sort of draft upon my deadline coming due, after 18 months or two years. And my editor basically read it and said, “This is terrible.” And she said, “Go back and completely throw that out. Start from scratch and take all the time that you need.”

And you might think that when that happened that I would have been really bummed. But I was actually elated because I knew that it was terrible. And I knew that I needed much more time. And I had no idea what I was doing. I had never written anything before. I was just really happy to have that time. And it’s actually really unusual. They had given me a big advance for the book. And usually, they want their advance back. And they’re not willing to delay like that. So that was huge.

Tim Ferriss: A very understanding editor.

Susan Cain: Yeah. She’s brilliant. And I’m working with her again on my next book.

Tim Ferriss: Yeah. It’s also smart in the sense that – a mediocre book is more of a liability than no book at all for everyone involved.

Susan Cain: For everyone involved. Yeah. And because I have this philosophy about writing – that it’s the deep love that has to be protected at all costs – because of that, I don’t care how much time it takes. I’m just interested in doing it as well as I can.

Tim Ferriss: What does your writing process at this point look like? So you had your experience with that book. And now, when you are writing, do you have a daily process? Does it go through phases of research period, then organizing, then putting all of that into prose through synthesis? What are your writing routines? Or how do you think about writing these days?

Susan Cain: So for me, I take whatever thesis I’m working with. And then I spend a year or two just walking around the world looking at everything through the lens of that thesis. So it used to be introverts. And now, I’m on to a new topic. And I’m taking crazy notes through that period. So every conversation that I have, every book I read, it’s all going in.

Tim Ferriss: How do you take and organize your notes? Do you do it notebooks? Do you do it digitally? I know this is nerdy. But I’m –

Susan Cain: No. It’s not nerdy at all.

Tim Ferriss:  – into it because a lot of writers do it differently.

Susan Cain: The reason I’m laughing is I’m thinking when you hear my answer, you’re going to know that I need a consultation with you for the next book because I don’t do it in a super systemic way. Basically, all those conversations, all those ideas and notes and thoughts I’m having, I stick them all into one Word document. And then I go – and that document becomes about seven- or eight-hundred pages by the time I’m done. And then I go through that document. And I’m tagging as I go along. And then I’m separating everything out by topic. So I end up with eight or nine loose-leaf binders that are organized by topic. But in each of those binders, it’s just –

Tim Ferriss: One big Word document.

Susan Cain: – one big mass of notes. And then I think about where do I want everything. And also, whenever I have an idea – whenever I’m emotionally moved by one of the ideas that I’m taking notes on, I try to write out the riff around that idea right then and there because you don’t know if that emotion is going to come back. So you have to capture it when it happens.

Tim Ferriss: I think that’s a perfectly fine system. So you –

Susan Cain: I just feel like technology must have come up with something better. I do it in Microsoft Word.

Tim Ferriss: There are probably better tools available. But I would say also that a lot of people confuse new tools for better content. It’s very easy, at least – I’ll speak for myself for a second. When I’m writing, I have to disallow myself from thinking about, say, marketing because marketing is fun and exciting and –

Susan Cain: To you.

Tim Ferriss: – easy for me because I had insomnia as a kid and watched too many infomercials or something. In any case, that take – it’s a way to procrastinate doing the harder piece, which is the actual research and digging and prose. That’s the hard part for me. Always has been. But it’s the most important part. And I think similarly, a lot of folks can become consumed by upgrading their tools, multiplying their tools versus just the words. You got to put the words in. And I have some questions about this Word doc, though. So when you’re going through and adding things to the Word doc, and you come in, and you’re tagging things so you can separate them – and you mentioned binders.

So you’re printing this stuff out and then separating them. Does that mean that when you put in a new note in the Word doc, you go to a new page if it’s tagged differently, so you can separate them more easily later – does that make sense? – as opposed to each time you add a note, then hit return twice and then add a new note? If they’re tagged differently, it would seem like you would have to cut up the page into multiple pieces. So do you start a new page – are there any particular ways that you tag? For instance, would it be a chapter name? Or would it be a theme? What would a tag look like? A lot of questions.

Susan Cain: Yeah. It would just be a topic or a theme. So every time I’m adding a new note, if I know that it relates to something I’ve already done, then I’ll search for the thing I’ve already done so I can add it to that section to make it easier later. But sometimes I don’t, or I can’t think of it. And then I’ll just add it to the end of the document.

Tim Ferriss: Control F, right? Word. And then good to go.

Susan Cain: Yeah.

Tim Ferriss: Yeah. Simple works. Robert Rodriguez, the filmmaker, keeps a journal. Puts it in almost every day at midnight. And it’s Word docs. It works.

Susan Cain: Yeah. I will say I tried – for this next book, I spent a few days reading the instructions for Scrivener, one of these programs. And I just ended up thinking, “This isn’t for me. It looks great, but –”

Tim Ferriss: Scrivener. Well, some other time, we can sit down. That is one tool that if you set it up really simply and you don’t use 98 percent of the features, I find really useful just because you can create a view by which you see all of your separate documents. Or actually, I should say rather, you see your tentative table of contents on the left side in a vertical pane. And then you can look at what you’re – on the right-hand side, then I would have it set up so that I have two split windows. So the left-hand side, you see your table of contents. And then there’s research. And you have whatever research you want.

That way, you can be working on a document in the upper right-hand pane while you have your research that you’re working off of in the bottom right. And if you decide to move docs around to see how it affects flow, it’s just drag and drop. It’s actually quite wonderful. They did have some issues with footnotes. Or maybe I was just too technically incompetent at one point when you then had to export when the publisher insists on, say, Word which maybe that’ll change at some point. But I’m getting a little geeked out. But I’ve used Scrivener for almost all of my books. There may be one exception. I think 4-Hour Chef, because of how visually intensive it was was done outside of that. And in terms of routine or ritual, you spend a year gathering these notes. So then you have –

Susan Cain: Yeah. A year. Maybe more.

Tim Ferriss: Yeah, or more. So you have 700 to 800 pages. That’s a big Word doc. And then what happens?

Susan Cain: Yeah. So then I spend the time sorting them out. So I get to the point where I’ve got my eight or nine loose-leaf binders that are more or less organized by what the chapters are going to be. And then comes the time to write, during which, I’m still doing more research. But I’m starting to write. For me, the writing, the sitting down with my laptop and thinking about it all, that’s – I want to say it’s my happy place. But that’s not really the best description. It feels like it’s this place that I go deep in my mind. And I really love being there.

And it’s like no matter what happens to be going on in my outside life, I always have those few hours a day where I’m going to a café or a library or whatever, and I’m sitting with my laptop and my cappuccino, and I’m just doing it. I’m stressing the emotional aspect because that’s so huge for me. And I feel like I trained myself to associate writing with all of these pleasures of sitting around in cafés and things like that.

Tim Ferriss: Do you have a consistent time when you sit down with your cappuccino and do this? Are you a morning writer? Or are you just catch-as-catch-can writer? Are you an evening writer? You also have kids. You have other obligations. So when do you tend to do your writing or do your best writing? You can answer it however you like.

Susan Cain: Well, there’s what I do, and there’s what would be ideal. But as you say, I have kids. So my routine is that I drop my kids off at school. That’s at around 8:00. Then I go and I either play tennis or do yoga every day. And then after that, I do my writing. And that’s a pretty good time for me. But –

Tim Ferriss: What time of day would that typically end up being?

Susan Cain: Oh, yeah. That probably ends up being around 10:00 or so that I’m starting. But if I had no other obligations, the best times of day would be more like either 7:00 in the morning and also super late at night. So two time periods that I have no access to for this stage of life.

Tim Ferriss: And you start writing – this is really interesting to me. Hopefully, interesting to other people. So you start let’s say around 10:00. Do you break for lunch? Do you skip lunch? Do you have a standard type of lunch that you would have? And the reason I ask is that I think part of the reason so many writers seem to work between the hours of – just make this up, but 10:00 p.m. and 7:30 a.m., and they tend to either be night owls, like me, or early risers is that there are fewer distractions. And they can get a relatively uninterrupted block of three to five hours. But if you’re starting at 10:00, then most people would have lunch scheduled shortly thereafter, like two hours later.

So do you break for lunch? Do you have something really small? How do you handle that? Because for me, just speaking personally, I might have time – of course I have time for a five-minute phone call. But if I do a five-minute phone call about something very mechanical or mundane like calendaring stuff or whatever, and I’m juggling 15 pieces that were on paper in my head, I have to start over a lot of times. I drop all those balls I’m juggling because of the task switchings. So I’d love to hear – not that that’s true for everybody. But it’s true for me. So what does your schedule look like then once you sit down?

Susan Cain: I’ll just go until I realize that I’m not concentrating well anymore. And very often, it happens after two or three hours. And I just have to take a break. I have a lot of discipline if my brain would cooperate. So I would happily sit there for seven hours until my kids come home from school. But at a certain point, I’ll notice that it’s just not coming anymore. And so then I’ll take a break and I’ll eat or something like that. But I would say – I think you were mentioning, “Well, people might work at night because it’s when you get uninterrupted time.”

And I think that that’s one factor. But I also think the reason that those hours tend to be so good – so nighttime is when your cortisol levels are really low which, of course, is your stress hormone. And so I notice this in myself all the time, that the ideas that I come up with late at night are different from the daytime ideas because they’re completely unfettered by any stress. And so I’ll just – I don’t know. I just make different kinds of associative leaps. And there’s a softness and an ease in my thinking and my feeling about the ideas. So I think that’s one advantage of late night writing. And then in the morning, you’ve got the high cortisol. But you also have this acute attention.

Tim Ferriss: I can totally see that. I can definitely see that. I also find that writing late at night – if I’m writing at 2:00 in the morning, it’s very hard for me – I want to say it was Ayn Rand who wrote a – she had a book about the craft of nonfiction. And there was some – it wasn’t a metaphor. I think it was a real-world example. But in effect, she’s saying many writers will do almost anything to not write. And there’s this story about the white tennis shoes, like, “I have to clean my white tennis shoes before I’m going to write because I’m going to go out and da-da-da.” And when it’s 2:00 or 3:00 in the morning, “I have to check email to make sure X,” is just not a viable excuse. So it also just removes a lot of bullshit distraction that I would impose on myself to avoid doing what it is that I find hard.

Susan Cain: Oh, my God. I so relate to this. So when I was writing Quiet, I suddenly developed this idea that I had to learn everything in the world about digital photography. And I was reading all these books about it and the rule of thirds and all this stuff. And I have never had any interest in photography before or since. It was just these two weeks of mania where I didn’t want to have to be looking at that manuscript over there.

Tim Ferriss: Are there any particular – you are a student of the craft, right? You’ve taken creative nonfiction courses. Are there any particular books or resources or writers who have had a significant impact on how you view or practice writing?

Susan Cain: Oh, gosh. I’m sure the answer is yes.

Tim Ferriss: And I can try to buy some time too if helpful. Draft No. 4 by John McPhee I think is really – I was very fortunate to spend time with him when I was an undergrad in college because he was teaching a seminar. But the structure –

Susan Cain: Yeah, at Preston. That’s where I took my creative writing classes.

Tim Ferriss: Right. Yeah. Thinking about structure in the way that – a few things about structure saved me because I thrive with some type of predetermined blueprint for structure. It’s very hard for me to just freehand, flow of consciousness let things take some emergent form. It’s very hard. I do know friends who do that really, really well. That terrifies me. So I need the scaffolding. Bird by Bird by Anne Lamott –

Susan Cain: Oh, I love that book. Such a good book.

Tim Ferriss: Bird by Bird, for people who don’t know the book – I will say just before getting into a short description – has saved at least a half a dozen friends of mine from the precipice, meaning they were at the point of throwing in the towel and just quitting their books. And they were all writers in this case. But they were at the point where they were like, “I’m done. I can’t do this. It’s too stressful. I don’t like this. I don’t want to do this. It’s going to be terrible.” And they were going to, in some cases, return their advances and just walk. And I want to say at least half of them read this book, went on to finish their books. And their books went on to become New York Times Best Sellers. So talk about an important window for making a decision. And the gist of the book – the title, I should say, comes first from – I think it was her brother, Anne’s brother. Anne Lamott is a writer.

And her brother had this experience where he’d had something like an entire semester in – I’m making this up. But let’s just call it fourth grade to prepare for this end of semester project. And he was supposed to put together a term paper on birds or something like that. And it was the night before. He hadn’t done any preparation. And this poor kid – who, granted, kinda deserves it because he didn’t do any prep – but nonetheless, is having this nervous breakdown at the kitchen table with 15 books about birds. And he just is paralyzed. And I want to say it was Anne’s dad who came over and put an arm on his shoulder and said, “Just take it bird by bird, buddy. Bird by bird.” Something like that.

And it’s a psychological life raft, break glass in case of emergency kit for writers who are just hitting that point like maybe you did with the photography where you’re just like, “I want to do anything other than look at that screen or that page. I can’t handle it, and I don’t know what to do.” So for that reason – not necessarily for the nuts and bolts of the writing process itself but for the psychological component. It’s like if you were a top athletic coach, and you had your sport-specific technical coach, and then you had a mental toughness coach who also doubled as a shrink, the mental toughness coach who doubles as a shrink is the Bird by Bird.

Susan Cain: Yeah. And I’m remembering she also talks about shitty first drafts. And just those three words are incredibly helpful because when you’re looking at your draft – and it is always really shitty at the beginning. And so just knowing, “Okay. That’s what it’s supposed to be.” The other thing that’s been really helpful to me – so I told you I started taking that creative nonfiction class at NYU. All of us who took that class got along really well. So we formed a writers group after the class was officially done. And we stayed together for years. And we would meet once every week, every two weeks and read each other’s stuff. And especially at that stage, that really, really helped, getting the feedback but also having the camaraderie and support system. And in fact –

Tim Ferriss: Not feeling totally isolated. Yeah.

Susan Cain: Not feeling isolated. And I actually met my literary agent from one of the people who was in that group who was a publishing lawyer. And I said, “I have this idea for this book about introverts,” which at the time, to me, seemed like the most idiosyncratic project on earth. But she said, “When you’re ready, I know the right agent for that.” And that’s a really serendipitous thing because – wait. I want to share this. When I put together the proposal for the book that became Quiet, I sent it out to that agent who she recommended and to four other super amazing agents, two of whom I had connections to.

And every single one of the other ones passed. And some of them said, “I really like the writing. But I think this topic is not commercial enough. And I just don’t think it’ll sell. So could you come back with a different topic?” And the guy who became my agent instantly saw what the potential was going to be. And we’ve been together ever since. And I feel like I owe him everything. And I love him. And his name is Richard Pine if you are out there looking for an agent. And I think about this story all the time not only because of book writing but because all these people, these other agents, these are experts. And these are the culturally anointed gatekeepers. And they know what they’re doing. And yet, they didn’t see this one particular thing. And I think that that happens all the time.

Tim Ferriss: Totally. No, I’m glad you shared that. And I had a very similar experience. I reached out to – I want to say it was four agents who were introduced by a very successful author who I had met something like seven years earlier by volunteering at a nonprofit, which is a great way to meet people above your paygrade, as a side note, just filling water glasses for panelists. Works really well. And so I had the right introduction, the writing. I didn’t think my writing was Tolstoy or anything. But it was passable. And complete rejection from three of the four.

Susan Cain: Wow. This was The 4-Hour Workweek?

Tim Ferriss: The 4-Hour Workweek. Two of them were pretty heavy-handed about it. One of the third – I remember her name. Jillian Manus. A very good agent. And she passed. But she gave me a lot of really helpful feedback. And she didn’t say, “This won’t work.” She just said, “I don’t think this is the right fit for me.”

Susan Cain: Right. And that one, fair enough.

Tim Ferriss: Which is totally fair. “But here’s a bunch of advice.” And one of the pieces of advice she gave me, actually – wow. I haven’t thought about this in forever – was, “Think of each –” I was intimidated by the prospect of writing a book. I’d never written a book before. She said, “Treat each chapter like a feature magazine article. Beginning, middle, and end. Self-sufficient. Each chapter can live on its own.” And I’ve followed that advice ever since with nonfiction which makes it easier to write also because if you get stuck somewhere, it’s not like you have to cross that bridge to get to a chapter that sequentially, should show up three chapters later. You can treat it in a modular way. If you get really bogged down, you can skip, which also, in some cases like the rest of my books, leads to a book that can be read non-sequentially.

So three out of four turned it down. Finally signed with my current agent, Stephen Hanselman, who I still work with to this day, similarly. And he had just become an agent. He had just become an agent. But part of what attracted me to him was that he had a long career as a very successful editor and also is just an eclectic guy, went to divinity school, plays in a jazz band. Really my kind of person. And then we went out to sell it. And I think it was – I always forget if it’s 26 or 27. But nonetheless, it was something like 27 – somewhere between 26 and 28 publishers turned it down.

Susan Cain: Really? Wow.

Tim Ferriss: Yes. But you only need one. That’s the thing. It’s not about how many people don’t get it; it’s about having the right person or people who do get it, which is so clear with your book. You don’t need all the people in the world to think it’s a good idea. You don’t need half the people in the world to think it’s a good idea. You need the people who it resonates with to have it resonate. That’s it. And it does not need to be millions of people. It could be. But it doesn’t have to be. I have a note down also to just – and we don’t have to necessarily spend a ton of time on this. But just to clarify the – talk about introversion versus shyness. And I came across this when I was doing a bit of homework which is people think of, say, Bill Gates as maybe one example of someone who could be useful in distinguishing between the two. But could you clarify what an introvert is and how you define introvert and how it might differ from –

Susan Cain: From somebody who’s shy?

Tim Ferriss: Right.

Susan Cain: Yeah. So introversion is really about the preference for lower stimulation environments. And you can trace it to our neurobiology. Introverts have nervous systems that react more to all the incoming stimuli, and so that means that we’re at our most alive and happiest and switched on when things are a little more chill around us – which is probably why when you’re in those group dinners, you’re going to the restroom every so often because your nervous system wants to tone it down. And extroverts have the opposite situation and the opposite liability because, for an extrovert, you’ve got a nervous system that’s reacting less to stimulation. And that means when you’re in an environment that you find too quiet, you start to get really listless and checked out. So that’s the liability there.

And I always feel like my work has to do with both introversion and shyness, by the way. But shyness is much more about the fear of social judgment. So you’ll know if you’re a shy person because when you encounter someone who has a neutral expression on their face, you will have a tendency to read disapproval in there and to react really strongly to the disapproval. You feel really unhorsed by it. And it can take different forms. So it could be a fear of public speaking. Or it could be a job interview or any kind of situation where you feel you might be evaluated.

So in reality, lots of introverts do tend to be shy and vice versa but not necessarily at all. I don’t know Bill Gates personally. But my guess is that he’s an introvert but not especially shy. And then somebody like an Eileen Fisher who – she’s got this wonderful – and I think it’s been decades now – super successful fashion brand. She describes herself as a shy extrovert. So she really wants to be around people all the time. She wants to be connecting all the time. You talk to her. She’s constantly setting up this workshop and that program. And you look at her life, and she’s always surrounded by lots of people and things going on. But she’s often feeling intense discomfort and needing to work through that.

Tim Ferriss: Wild. Yeah. I would certainly describe myself as an introvert. And I never knew quite how to frame it until coming across your definition of preferring lower stimulation or environments with fewer stimuli because I’ve, ever since I was a little kid, been very sensitive. My sight is very sensitive. My hearing is very sensitive. But I’m not shy in the sense that I want to engage and ask questions and interact. But if the volume is turned up too much or there are too many speakers metaphorically or physically, I have a lot of difficulty parsing it all.

Susan Cain: But you don’t have – shyness would be like – before you go into those group dinners, are you feeling a kind of social anxiety?

Tim Ferriss: No.

Susan Cain: Right. That’s the difference. Yeah.

Tim Ferriss: There are so many questions that I want to explore. Because we have maybe 10 or 15 minutes more, let’s ask a few of the questions that I always like to ask. Are there any books that you have given the most to others as a gift or any books you’ve gifted often to other people?

Susan Cain: I think that the book I’ve probably, for the last few years, been giving out the most is Waking Up by Sam Harris.

Tim Ferriss: Yeah. It’s a fantastic book.

Susan Cain: It’s such a fantastic book. And it was really, for me, completely lifechanging I think for probably the reasons it is for many people which is I hadn’t really known much about meditation before reading it. I think by my nature, I’m a cross between a skeptic and a mystic or something. And the skeptical side of me – and it’s a pretty deep skeptical side. It really needed somebody like Sam, who’s such an extreme skeptic and then who, very conveniently, spent like 28 years of his life or something investigating all these different spiritual tools and then reporting back on them. For me, that was a narrator I felt I could really rely on.

Tim Ferriss: Yeah. It’s a fantastic book. Just because I think you’ll – we were talking a bit about Sam before we started recording because we were both fanboying and fangirling about his mediation app and a handful of other things. But I haven’t told you – and I don’t know if I’ve even mentioned this publicly, but here we go. So the first time I met Sam – this relates to TED. Went to TED for the first time as an attendee which, by the way, was too much stimulation. So I never went back. But I went to TED for the first time as an attendee. And I was invited to one of these group dinners. And so I go out to this group dinner. And we’re eating dinner. And off to the side on a separate table, there’s this tray of brownies. And I love brownies. It’s one of my weaknesses. It is an Achilles’ heel. And I have zero portion control. And these brownies are large brownies. And I sneak over in between courses.

And I’m like, “I’m going to skip one of the later courses and just substitute the brownies because I love brownies.” And so I eat two of these brownies. And about 20 minutes later, the host, who I shall not name, comes up to me and goes, “Tim, did you eat any of the brownies?” I go, “Yeah. I had two of them.” And he goes, “Okay. Everything’s going to be fine.” And I’m like, “Wait. What? Everything is going to be fine? What the hell are you talking about?” They were heavily dosed pot brownies. And I am not a habitual pot user.

And so I suddenly, in the middle of dinner, just get hit by this tsunami of cannabis. And you combine that with my discomfort with high stimulation environments, and I’m like, “I need to get the hell out of here.” So I excuse myself to go to the restroom. And by this point, I’m already a huge fan of Sam but have never had any contact with him. So I run off to the bathroom to escape. And I open the door. And literally, at the sink, run straight into Sam Harris in the men’s room. And I’m like, “Sam Harris. Hi!” off my rocker. And that was my first intera – and he looks at me. He’s like, “Hi,” kinda sideways because I’m just beyond reality at that point. And that was my first meeting with Sam.

Susan Cain: That’s hilarious. And did you tell him your brownie story?

Tim Ferriss: I did. I did tell him, which he appreciated because he does have some history with –

Susan Cain: Yes, he does.

Tim Ferriss: – altered states.

Susan Cain: But yeah. No. I found that book and the subsequent meditation app and all of it incredibly helpful and fantastic. The one piece of it that I’m trying to explore separately because I feel like he looks at much less is the whole tradition of loving-kindness meditation, all the meditations around that. So that’s really, really of interest to me. And so I’m charting a different course there. And I’ll tell you, even just last night, I was interviewing on stage this guy, Haemin Sunim. I don’t know if you’ve heard of him.

Tim Ferriss: I don’t know.

Susan Cain: But he’s a really renowned Zen Buddhist monk from Korea. And his books are all number-one bestsellers in Korea and lots of other countries. But here, he’s less well known. But anyway, he has a new book out. So I was doing this interview. And we’re up on stage. So you can see the audience. And it happens to be a pretty formal audience. So before we start, the audience is sitting there, still, in their seats. And then he opens by doing a loving-kindness meditation. And it was so amazing to see the transformation on their faces. And he did this for maybe one or two or three minutes. It wasn’t long. And suddenly, they’re totally smiling. And they’re open. And they’re happy.

Tim Ferriss: It’s remarkable. Yeah.

Susan Cain: It’s remarkable. And I think it’s so weird and dispiriting how in the mainstream media and in corporate life – it’s great that there’s been this incredible embrace of mindfulness meditation. But I think there’s a kind of allergy towards going too much in the loving-kindness direction. And I spoke to Sharon Salzberg about this, who’s one of the great teachers. And she said that people have this sense that it must be phony, that you couldn’t possibly actually have those feelings. And so it gives them a creepy feeling to do it. But I feel like that all needs to get completely rethought.

Tim Ferriss: Loving-kindness, the label, I think smells of hand-wavy, hippie associations. And therefore, people veer away from it. Or if they have a sensitivity to that stuff, which I do and have for a very long time –

Susan Cain: But so did mindfulness for many years.

Tim Ferriss: Absolutely.

Susan Cain: And that’s been recast successfully.

Tim Ferriss: But I mention that as a contrast to my then subsequent experience with loving-kindness meditation, also called Metta, M-E-T-T-A meditation, which I was introduced to – not first by Jack Kornfield, although I did spend some time with him, who’s of the same cohort of Sharon Salzberg. They’re close friends. And Sharon’s been on the podcast – but Meng. Chade-Meng Tan of Google, actually, who started this class within Google called – I think it’s Search Within Yourself. And it was a course that included many tools including mindfulness. And he has a book called Joy on Demand, which is fantastic. I thought it was a fantastic title. I was like, “I could use joy on demand. Let’s take a look at this.” And there’s a very short part in that book which I ended up excerpting for, I want to say Tools of Titans about loving-kindness meditation.

And he tells the story of this woman who, as an experiment, guided or suggested by Meng, did a one-minute loving-kindness meditation on the hour every hour for one work day. And she would pick people who were walking out of the office or so on. And she came back. And she said, “That is the best day I’ve had at work in seven years.” And I think part of that is, at least for me, that I am a very – historically, have been very trapped in my head. I’m very prefrontal. And I come from a family of worriers, people who are –

Susan Cain: Warrior or worrier?

Tim Ferriss: Ah, worriers.

Susan Cain: With an O?

Tim Ferriss: Not the battleaxe type, but the Larry David type.

Susan Cain: Yeah. I come from one of those too.

Tim Ferriss: Right. And when you are consumed with worry or anxiety – and this is not my description, but it’s been described to me as being trapped in the future. Depression is being trapped in the past. And anxiety or worrying is being trapped in the future. At least for me, it’s a focus on the self. It’s like, “Me, me, me.” It’s all things that might happen to me, things that I should do.

And the loving-kindness meditation, which can be so short and have an impact gets you – unlike most types of mindfulness practice that are popular or becoming popular in the west, it gets you out of yourself. And I recall when I was writing Tools of Titans, I decided to take Meng’s advice. And I did loving-kindness for literally two or three minutes every night. I was at this hotel. And they had a dry sauna. And I’d go into the dry sauna really late because I was doing my writing really late and just do two to three minutes of thinking about a friend and wishing them happiness and seeing them smiling and giving them a hug and having them smile back at me and wishing me the same. And it was transformative with regards to my mood. It was really just incredible. Low dose. Really, really low dose.

Susan Cain: And I’m curious. You mentioned that you were meditating on loving-kindness to your friend. Did you also start with the traditional practice of wishing it to yourself? Or is that less comfortable for you?

Tim Ferriss: This is a great question. So I did not – it did not even occur to me to do this until years later when I went to my first seven-day – it might have been 10-day. Seven-day? No. It was a 10-day silent meditation retreat at Spirit Rock. And Jack Kornfield was there. And I went in – they check in with you to make sure you’re not having a total psychotic break for a few minutes every other day. And I had this meeting with Jack and one of his co-teachers for the event. And we were talking about loving-kindness. And as I was leaving, the woman with Jack said, “Just out of curiosity, have you been doing any loving-kindness for yourself?” I don’t know how to describe this in a way that doesn’t make me look like an ass. But it just struck me as such a silly question. I was like, “No. Of course I haven’t been doing it for myself.” And then I realized how much that probably explained a lot of my problems. And she goes, “Yeah. You might want to try that. Why don’t you experiment with that?” And I remember Jack later saying, “If –” and I’m paraphrasing but, “If your compassion doesn’t include yourself, then it’s incomplete. And that has become –

Susan Cain: Yeah. And you can’t really give it to other people in a complete way through –

Tim Ferriss: Right. So that has become probably – I’m so glad you asked that – one of the biggest changes in my – and I could call it a mindfulness practice but my way of relating to the world and thinking about helping others has been actually taking time to show or think on self-compassion, specifically for the self at a handful of younger ages which I do at mealtimes. And I might talk about that more at some point. But that’s –

Susan Cain: Oh, I think you should.

Tim Ferriss: – become really – it’s become a very, very, very, very important ritual for me.

Susan Cain: But I don’t think you’re alone. Sharon Salzberg mentioned to me that many people have trouble – the traditional progression of the practice would be start with yourself and then move progressively outward to other people in your life. And she said many people have trouble beginning with themselves. And so I was really struck because last night, this monk, Haemin Sunim, who I love began in his meditation by directing it to ourselves. And I asked him about that afterward. And he seemed puzzled by the question which made me wonder if this is a uniquely American problem. I don’t know.

Tim Ferriss: It reminds me of this story I heard of this – I don’t know what it was. Nepalese or Bhutanese monk who came to the US. And he was in a car on the way to some event. And there were these – this was in the US. And there were these people jogging on the side of the street to get in shape. But they looked like they were dying. They looked like they were running from hyenas. And he was just like, “Are they okay? What’s wrong with them?” It was so foreign. My goodness. So we have just a few minutes. Let me ask you the billboard question. So if you could put a message on a billboard – and this is metaphorically speaking – to get a message, a quote, a question, anything non-commercial out to millions or billions of people, what might you put on that billboard?

Susan Cain: I think I’d probably put this one aphorism that I’ve loved since high school I think, which is, “Only connect,” by E.M. Forster.

Tim Ferriss: Only connect.

Susan Cain: Only connect. Yeah. At the end of the day, that’s all that really matters.

Tim Ferriss: What does that mean to you?

Susan Cain: It just means connecting on some really deep level with the people around you. And that might sound like an ironic aphorism for someone who wrote a book about introversion, but to me, those are not contradictory things at all. And so for me, connection, it can happen in person, for sure. But it could also happen just by listening to music that’s really touching you, and you feel completely connected to this musician who may not even be alive anymore or a writer who might not be alive anymore. But they’re expressing something deep and unchanging about what it’s like to be human. So I think there’s nothing more important than that.

Tim Ferriss: Only connect.

Susan Cain: Only connect. Yeah.

Tim Ferriss: Is there anything you’ve done that has helped you to more deeply or frequently experience those moments or any advice you might have for people who want to cultivate that?

Susan Cain: So aside from meditation, which I am a huge proponent of – but I think you really do have to pay attention to what works for you. And it really is so different for everybody. So for me, I love to have deep, one-on-one conversations. It happens through music. It happens through literature. And that’s how it happens. But I think it really is a different answer for everyone.

Tim Ferriss: For each person.

Susan Cain: And I’ll tell you – this is maybe a different topic, but the whole idea for my next book came out of one of these kinds of experiences, which is I have always had a love of bittersweet and minor key music. And the book’s not about music, but I’m going to tell you this story anyway. Okay. So when I was in law school, I was listening to music like that in my dorm. And a friend came by. And he was a funny, wise guy. And he said, “Why are you listening to this music to commit suicide to?” And I thought it was funny, and I laughed. But I thought about it for decades afterward. I was thinking, “Well, why is it – first of all, what is it about our culture that makes this music so suspect that you make that kind of joke? And also, what is it about the music itself that, for me, is not suicide inducing at all?”

It’s the opposite. I feel when I hear music like that, completely connected to everything because it’s like the composer is expressing some really deep truth about what it is to be human. So I’ve thought about this for decades. And the place that I’m going with this next book is that I think that tuning into the sorrows of the world actually is a kind of secret superpower that we’re not really allowed to access very often because, of course, we live in this culture that tells you, “Don’t go there. And always wear the smiley face,” and so on. But if I can say, look at somebody like you. Even before you started being really open and upfront about some of the demons that you’ve struggled with – which, by the way, all the honor to you for doing that. It’s amazingly brave and generous. But even before you did it and if you had never done it, I don’t think you would have been touching all those people the way you have all these years if it weren’t for those sorrows.

Tim Ferriss: I agree.

Susan Cain: Yeah. So it’s all about that.

Tim Ferriss: Well, I’m excited to read your next book. I think that’s a really, really, really, really important topic. That is really important. Well, we’ll have to do round two in that case.

Susan Cain: I would love that. That would be awesome. I just have to write a little faster.

Tim Ferriss: I will happily wait for your best work. So no need to rush. Well, Susan, this has been such a joy. And I’m sure people can hear it. But just to maybe underscore the point, you’re a very present person when you’re speaking with someone else.

Susan Cain: Oh, thank you. So are you.

Tim Ferriss: And I can feel that in the room. And so you’re walking the talk, which is always refreshing and not always the case. So thank you for taking the time today.

Susan Cain: Thank you so much. I really enjoyed it. It’s great to hang out.

Tim Ferriss: And I will link to everything in the show notes for folks including the name of the Korean monk that I couldn’t spell to save my life at the moment. But we will have links to everything at And you can just search Susan, and it’ll pop right up. People can find you online, presumably. Where are the best places to say hello, learn more about what you’re up to?

Susan Cain: Well, best thing is to sign up for my newsletter which you can get to if you go to which is for Quiet Revolution. So you’ll find it right there in the homepage. There’s a signup form. And there’s a newsletter that goes out every week. So that’s the absolute best. And then I’m also super active on LinkedIn and on Facebook.

Tim Ferriss: Great. And is that simply Susan Cain? Because I think Facebook – correct me if I’m wrong – I think is Author Susan Cain.

Susan Cain: Oh, gosh. Thank you for saying that. Yeah. So on Facebook, it’s Author Susan Cain. And on LinkedIn, I actually don’t remember. But it’s part of the LinkedIn Influencer – if you put in LinkedIn Influencer and my name, you’ll get there.

Tim Ferriss: It’ll pop right up. And then Twitter maybe less active?

Susan Cain: Yeah. I am on Twitter. A little less active.

Tim Ferriss: But @SusanCain.

Susan Cain: @SusanCain. Yup.

Tim Ferriss: And can’t wait to see the next book and continue to follow your work. Thank you for doing it.

Susan Cain: Thank you so much. I will say the same to you. What is the next book?

Tim Ferriss: What is the next book? Well, based on an episode that came out a few days ago, I think it’s going to be this book that I have been waiting to give myself permission to write which is about – it’ll be a close cousin to what you are thinking a lot about right now. It’ll be how to pay attention to these psycho-emotional undercurrents and components of life very closely and how to use tools, both on the beaten path and very, very, very off the beaten path for finding resolution for problems or challenges or insecurities or trauma that are at least in current conventional practice considered very difficult to treat or untreatable. So that would be, as far as I can tell – and I’ve been gathering notes for about five years now. That would be the thrust of it.

Susan Cain: That’s going to be your most important book.

Tim Ferriss: I hope so.

Susan Cain: What’s your timetable?

Tim Ferriss: What’s my timetable? Who was it? I think this is something I Heard on a TV set once. They didn’t want people to rush, but it was – the gist was people need to rush. But they didn’t want to say that and make you all panic. So they said, “We need everyone to move with purpose.” So I think my answer is move with purpose but not in haste because I want to treat it with the depth and thought that it deserves. So I don’t want to rush. I will probably write it without signing, before selling anything or signing any contracts. I’ll probably –

Susan Cain: Oh, you’ll write the whole thing first?

Tim Ferriss: I’ll probably do it on my own time.

Susan Cain: Oh, interesting. Okay.

Tim Ferriss: But it is a top if not the top priority.

Susan Cain: Wow. So are you working on it every day right now?

Tim Ferriss: I am in some fashion working on it every day. But it’s going to be a while before I get to the composition prose stage. But the vast majority of the work that I do on my books is the experimentation and the traveling for subjecting myself to all sorts of unusual things and the notetaking and the organizing of said notes. And I’m doing some piece of that almost every day.

Susan Cain: Wow. Oh, I’m so glad you’re doing this book. So if I can help – if you want an early reader or whatever, I would love to. It’s completely up my alley.

Tim Ferriss: Well, likewise. Likewise. This has been so much fun. And until next time. Thank you so much.

Susan Cain: Thank you so much.

Tim Ferriss: And to everybody listening, same. Until next time. Thank you for listening.

1 Comment / Leave a comment or question

Susan Cain — How to Overcome Fear and Embrace Creativity (#357)


Photo by Pasi Salminen

“So often, when you see someone who’s really good at almost anything, it’s because they actually started out exactly the opposite — and then they cared so much about fixing that problem.” — Susan Cain

Susan Cain (@susancain) is the author of the bestsellers Quiet Power: The Secret Strengths of Introverts and Quiet: The Power of Introverts in A World That Can’t Stop Talking, the latter of which has been translated into more than 40 languages. Quiet is in its seventh year on The New York Times Best Sellers list, and it was named the number one best book of the year by Fast Company magazine, which also named Susan one of its Most Creative People in Business.

She is the Chief Revolutionary of Quiet Revolution, and her writing has appeared in the The New York Times, The Atlantic, The Wall Street Journal, and many other publications. Her record-smashing TED talk has been viewed more than 20 million times and was named by Bill Gates as one of his all-time favorite talks.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, or on your favorite podcast platform.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#357: Susan Cain — How to Overcome Fear and Embrace Creativity

Want to hear more about loving-kindness and mindfulness meditation? — Listen to this episode with world-renowned meditation teacher Sharon Salzberg! (Stream below or right-click here to download):

#277: Sharon Salzberg, World-Renowned Meditation Teacher

This episode is brought to you by LinkedIn and its job recruitment platform, which offers a smarter system for the hiring process. If you’ve ever hired anyone (or attempted to), you know finding the right people can be difficult. If you don’t have a direct referral from someone you trust, you’re left to use job boards that don’t offer any real-world networking approach.

LinkedIn, as the world’s largest professional network and also used by more than 70 percent of the US workforce, has a built-in ecosystem that allows you to not only search for employees, but also interact with them, their connections, and their former employers and colleagues in a way that closely mimics real-life communication. Visit and get $50 off toward your first job post!

This podcast is also brought to you by Peloton, which has become a staple of my daily routine. I picked up this bike after seeing the success of my friend Kevin Rose, and I’ve been enjoying it more than I ever imagined. Peloton is an indoor cycling bike that brings live studio classes right to your home. No worrying about fitting classes into your busy schedule or making it to a studio with a crazy commute.

New classes are added every day, and this includes options led by elite NYC instructors in your own living room. You can even live stream studio classes taught by the world’s best instructors, or find your favorite class on demand.

Peloton is offering listeners to this show a special offer. Visit and enter the code TIM at checkout to receive $100 off accessories with your Peloton bike purchase. This is a great way to get in your workouts, or an incredible gift. Again, that’s and enter the code TIM.

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Read More

20 Comments / Leave a comment or question