“Trip of Compassion” — The Most Compelling Movie I’ve Seen In The Last Year


“I felt like I went through 15 years of psychological therapy in one night.” 
– Actual patient featured in “Trip of Compassion

This post is about the most compelling movie I’ve seen in the last year.

I first watched “Trip of Compassion” about six months ago, when I was sent a link to a private video. The film had been broadcast once on Israeli television, but it wasn’t distributed or available anywhere else. This documentary affected me so deeply (and immediately) that I flew to Tel Aviv, met the filmmakers, and offered to help launch the film digitally worldwide. Everything I am doing for this film is 100% pro bono, and all proceeds go to the filmmakers.

Why am I doing this, and why is this film so exciting to me?

Tens of millions of people worldwide suffer from post-traumatic stress disorder (PTSD). Millions more have suffered from emotional and physical abuse but never get diagnosed. I would put myself in the latter category for reasons I’ll explain another time.

Trip of Compassion” documents one unusual approach to healing trauma that might astonish you, an innovative treatment involving the psychoactive drug MDMA (commonly known as “ecstasy”). As you will see firsthand, if the therapy is well designed, true rebirth and transformation can happen in a matter of weeks and not years.

If you’ve ever felt held back, felt defective in some way, or felt that you’re not living up to your full potential, this film will give you hope.

This is also the first feature documentary to show actual therapy session footage (to our knowledge), to which the patients consented because of the incredible results they experienced.

Filmed at the Beer Yaakov Mental Health Center in Israel, “Trip of Compassion” provides a rare glimpse into a treatment process that can restore optimism and even the will to live.

Thank you for watching this film (just click here to stream) and, if you find it as powerful as I did, thank you for sharing it or this post.


In addition to helping launch this movie, I am supporting broader access to MDMA-assisted therapy in the USA and elsewhere by donating to MAPS.org, a non-profit dedicated to making this treatment available to those who need it (e.g., phase 3 trials, regulatory work, scholarships for low-income patients).

If you also decide that this work is important, please consider visiting MAPS.org to donate. NOTE: Be sure to specify the following in the donation form (there is a field for this, as they have many initiatives): “Funds are restricted to MDMA phase 3 trials.”


Thank you so much for reading this far. I couldn’t be more excited to share this film.

And remember as you watch: this is possible now. To quote William Gibson, “The future is already here — it’s just not very evenly distributed.”

Let’s help make this treatment more evenly distributed.

More to come,


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The Tim Ferriss Show Transcripts: Graham Duncan (#362)


Please enjoy this transcript of my interview with Graham Duncan (@GrahamDuncanNYC), the co-founder of East Rock Capital, a multi-family office investment firm that manages $2 billion for a small number of families and their charitable foundations. Graham graduated from Yale with a B.A. in ethics, politics, and economics. He is a member of the Council on Foreign Relations and serves as co-chair of the SOHN Conference Foundation, which funds pediatric cancer research. 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.

#362: Graham Duncan — Talent Is The Best Asset Class


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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 to deconstruct world-class  performers of all different types, whether they come from military, entertainment, sports, business. It’s a pretty wide spectrum. And today, my guest is Graham Duncan. You can find him at grahamduncan.blog, eastrockcap.com, and @GrahamDuncanNYC on Twitter. Graham is the co-founder of East Rock Capital, an investment firm that manages approximately $2 billion for a small number of families and their charitable foundations. Before starting East Rock 14 or so years ago, Graham worked at two other investment firms. He started his career by co-founding an independent Wall Street research firm. Graham graduated from Yale with a B.A. in ethics, politics, and economics.

That’s a lot of stuff. He is a member of the Council on Foreign Relations and serves as co-chair of the SOHN Conference Foundation, which funds pediatric cancer research. Josh Waitzkin, one of our very good mutual friends who will probably pop up here and there in this conversation – thought of most often as the basis for Searching for Bobby Fischer, although he would cringe to hear me limit it to that – calls Graham “the tip of the spear in the realms of talent tracking and judgment of human potential and high stakes mental arenas.” That is a very Josh sentence. And Graham, it is a real pleasure to be sitting here with you.

Graham Duncan: Thanks, man. Thanks for taking the time.

Tim Ferriss: And we’ve had many conversations. We haven’t caught up in a while. We’ve also had terrible food poisoning together, along with Josh. So I feel like we’ve seen each other in high stakes – maybe not mental – physical arenas. We, if I recall correctly, almost decapitated each other when learning to paddleboard with Josh at one point. And I am excited to chat for a lot of reasons. Number one, I always learn something when we sit down and talk.

And I don’t think of you first and foremost as an investor. You certainly do that very well. But I enjoy watching your thinking and listening to your thinking. So I think that for people who are in the audience and who might be wondering right off the bat, “How will this apply to me?” it is hopefully transferable to just about any domain. I think that clear thinking is really a lot of what we’ll be discussing. But for people who just heard this bio and are scratching their heads as to what you exactly do, how do you explain what you do?

Graham Duncan: Well, I try to find people who are better at doing a thing than I am at doing that thing. And I first came to this 20 years ago; I had just started a firm with a professor of mine at Yale, and we were running this independent research firm. And I’d hired a sales guy who – we’re two years in. And we’re in a group meeting. And he says to me at a certain point, “Graham, what the fuck do you do here?” And at that point, I had some real imposter syndrome going because I was hiring and firing 30 people much older, much more experienced than me. And so I sat there for 30 seconds because it’s like, “What the fuck do I do?” And I finally said to him, “Robert, when you first interviewed to come to our firm, you were applying to be an analyst, and I was interviewing you as an analyst. And I didn’t see your eyes light up when we talked about political analysis or economic analysis.

“But then you proceeded to stalk me for the following four weeks – you called me at home back then. You emailed me twice a day. And I had this moment of revelation: I was also interviewing salespeople. ‘Robert should be our salesperson.’ And you trusted me enough to come and try it. And now you’ve built our entire business. And I’m not a good analyst. I’m not a good salesperson.

“But I put you in that seat, and then we built this thing. I put you into this positive feedback loop that we are calling a business here. And that’s what I do.” And I feel like it’s – I wouldn’t pick that scale out of a lineup as my thing. It’s the cards I was dealt. It’s what I end up being compulsive about and interested in in this way. The world seems to like me doing it. But it’s an odd center of gravity. But today, I think about it as my mission in life is to get as many people as possible into positive feedback loops. And it’s a good skill to have because it’s right next to a weakness of mine, which is I’m kind of lazy.

Tim Ferriss: Maybe that’s why we get along so well.

Graham Duncan: So I like getting the design right up front so that I don’t have to – if I had to be talking to Robert once a week as a political analyst saying, “Look. Do this. Don’t do that,” that would have been – I don’t want to put something into somebody. I want to have them do the thing that they want to do anyway. And if you construct organizations and teams that way, you unlock a lot of stuff.

So today, I use that philosophy a lot because I act, in effect, as a general contractor for families to manage their wealth. In order to do that, my team and I meet over 1,000 teams a year to hire the best investment craftsmen of any given sub-strategy. And sometimes, those craftsmen, those investment managers who are trapped inside large organizations start their own firms on their own or with our help. And you unleash all this extra investment energy and genius that they weren’t accessing in their prior context. And we get to participate in that together with them. So it’s now been 20 years, but I feel like I’ve basically been playing different variations of the same game.

Tim Ferriss: And at that time, how old were you, roughly?

Graham Duncan: 24, call it.

Tim Ferriss: 24. So we’re going to talk, I’m sure, a lot about this. And I won’t make this just a list of Josh quotes, but I was texting with him. And he reiterated I think what you just said. And Josh, my apologies. I know we didn’t talk about me reading your texts upfront, but this is pretty safe. So “Core genius for Graham is talent hunting, finding funky A-plus –” so that funky word, at some point we’re going to talk about. “A-plus potential mental performers in the finance space.” And then he goes on. Now you have systems and frameworks that you use for this. At 24, though, I would be really curious to hear you try to describe what made you good at it then also if there’s anything that comes to mind. Are there things that you see that other people tend not to see? Or are there any types of questions that you ask yourself that even at that point, perhaps, you had picked up along the way? Is there anything that comes to mind?

Graham Duncan: Well, I think of it as having a certain taste in people. And I like taste because – and I think I had a certain taste back then. And it’s evolved, and I can articulate a little better than I could back then. But if you think of taste – I like taste over judgment because judgment implies there’s one answer, whereas taste is – you have a certain taste in podcast guests. There’s something similar to the group. And you could pick a Tim guest out of a lineup, in a way.

Tim Ferriss: Tall, dark, and handsome. Sorry.

Graham Duncan: Yeah. So taste. And so I’m trying to think. Back then, I think the imposter thing helped because I knew – I was trying to hire people who were better at doing a thing than I was at doing it. And I knew I couldn’t do it. And so I was forced to say, “Okay. What constitutes excellence in this thing?” And we had hired a bunch of – in that context, we’d hired a bunch of sales guys. And they actually didn’t like cold calling. And a lot of sales guys, understandably, don’t like the rejection of cold calling. And I’d found this one guy who, for whatever reason, thrives on it. A couple of years ago, I ran into somebody who was a prospective client of ours back then. And he said, “I still dream this guy Robert is trying to get me on the phone. And I wake up in cold sweats in the middle of the night.” We built our entire business on this guy. So I think it’s seeing – and I find myself curious about what makes people tick in this way that I don’t get tired of it.

Tim Ferriss: And how has that taste evolved to today? So if a component of that taste, or at least alerting your spider sense, is identifying certain outliers in preferences or behaviors back then, like Robert thriving on cold call rejection, what do your tastes look like today or more recently? Or what constitutes your taste when you are scouting for talent or evaluating talent in the world in which you now operate?

Graham Duncan: I read once that people are like musical instruments. And the range of notes they can play is dependent on the range of tensions that they’ve learned to hold. And I like that because it acknowledges that everybody – whatever they’re playing right now, there are actually other notes they can play in a different context. So as an example, the tension I’m focused on right now in the investment management world is I think there’s something really interesting about the tension between someone’s intensity and integrity. Or if you double-click on each of those, aggression and humility. And if you were to rank the – to try to use a concrete example, I’ve written an essay before about David Tepper. I don’t know David Tepper. He’s somewhat in the public domain. He’s on CNBC. He’s written some. And I think of David Tepper, in many ways, as the Platonic ideal of a good hedge fund manager and a good investor.

And one thing that he holds is – I think people who work for him – but I’ve interviewed people who worked for him. They experience him as that mix of super aggressive in taking a position in an equity or debt security from zero to 20 percent of the fund with no hesitation. If you were on the other side of a transaction with him, he’s not going to do something that you characterize – you would never say fraudulent. But he’s not going to be overly aggressive. He’s playing the game because he enjoys it. But he has an ethical core.

And I feel like that tension – at Goldman Sachs, they have this term, “Is someone commercial?” And I think of that – I love that word. And I think of commercial as people who give off this vibe of, “I’m going to create more value than I capture here,” versus somebody who’s more transactional is trying to capture all of the value. And people who are commercial, who balance that tension of aggression and integrity or aggression and humility, they tend to clump together. They like doing business with each other. And so you hit these pockets of people with that.

Tim Ferriss: How do you test for something like that or stress test it, in the sense that I would imagine many of the people, if not all of the people who make it to the point that they’re interacting with you or your team have already cleared a lot of hurdles? They’ve already checked a lot of boxes. And many of them will be good at selling themselves. And no one is going to volunteer that they lack integrity. “Well, there’s one thing. I’m very, very, very skilled and intelligent, deceptive artist!” Or whatever. So how do you try to evaluate that?

Graham Duncan: Well, one evolution of my process has been I just treat my interview as one perspective. And then people think of references as a thing you do after the fact. To me, it’s the whole thing, references and getting the sense of how someone’s interacting in a repeat iteration game in this thing we call financial markets. To me, there’s a – people generate trust. And it’s this intangible asset that’s around them. And the trust sits in the heads of everybody they’ve interacted with over time. And my job is to see how everybody else they’ve interacted with, their employees, their former bosses, their peers end up relating to them because of the body of work they’ve had in the past.

And so we did that dinner with Chris Fussell that time. I think Fussell and Stan McChrystal’s language around trying to assess someone’s credibility, and then based on that assessment, how much decision space to give them – to me, that’s so beautiful. And that’s exactly how I think about what I do. And they have this formula: credibility equals proven competence plus relationships plus integrity. And so what I’m trying to do when I’m trying to understand, for instance, someone’s integrity is understand how they behaved in prior moments of stress. So 2008 was an amazing – for anybody that’s still investing who was around in 2008, it’s a great moment to check in on how they behaved during that period because that was like an earthquake going off. And it tested every single possible human relationship. It tested when people were partners in investing, and they’re both portfolio managers.

A lot of people got divorced after that. Limited partners – the people who invest in hedge funds – and the general partners. It tested those relationships. It tested people’s relationships with the banks. So if they’ve been around a while, to me, an interesting question is, “What happened in ’08?” And I’m sure we’ll have additional crises soon that will, again, enable us to separate those who behave well from those who behave badly in those periods of stress. So it’s super reference focused. And then I have a series of questions I ask people that I feel like has high signal value. But again, I try to have a lot of humility and a light grip on my ability in a one-hour meeting to figure that out.

Tim Ferriss: What are some of the high-signal questions that you’ve filtered through over time and have found to be particularly useful? Do any come to mind? What types of questions come to mind?

Graham Duncan: Well, the main one that I think applies would be looking for an OB/GYN for your wife to have a kid or anything is you ask somebody, “If you were hiring somebody to do this, what criteria would you use to hire them?” because what it captures is their definition of success. And it also captures some nuance that you wouldn’t have even known to ask about. So when my wife and I were looking for an OB/GYN, this was my question. And one guy said, “Well, what you’re maximizing for is the downside. And if you have some sort of – if the baby is in distress, you need a good NICU. So my primary criteria –”

Tim Ferriss: Which is natal –

Graham Duncan: Intensive care unit. And the best NICUs are usually attached to teaching hospitals like Mount Sinai. So I would look for affiliation of that doctor with a good NICU. And then I would also – his second criteria was, “I would ask the nurses, because the nurses know who freaks out during tricky situations and who’s got ice in their veins and who makes good decisions, who treats people well in those settings.” And the good nurses want to work for the best doctors in that hospital setting. And I actually have this thought that the equivalent in financial markets is the traders. The traders are on the receiving end of a portfolio manager’s decisions. And they often have a very strong sense of who the good investors are. David Tepper’s trader I bet might – and again, I don’t know this.

But my hypothesis would be they’re in awe of David Tepper because they’re on the receiving end of when he’s buying when everybody else is freaking out. Now you have to be careful. And one of the arts of references I think is controlling for the context and the perspective of the reference giver. Traders like traders. So somebody who doesn’t trade a lot, they may not think as highly of this portfolio manager who’s really more of a buy and hold person and doesn’t give them any business and they think is kind of lazy. Well, okay. That could be true. But it also could be just they were on a super concentrated portfolio. They only buy one thing a year. So I really like, “What criteria would you use?” And the other great thing about the question is it improves your own criteria for the next interview.

Tim Ferriss: Yeah. That’s really, really fascinating. I was just chatting with a friend of mine, Tobi, who’s the CEO of Shopify. And the way he learned the business side is he went to Silicon Valley and met with – let’s just call it a dozen venture capitalists as an engineer. And each meeting, he would pick up new questions, new terminology, be able to answer one more question. And it just improved his ability to vet not only venture capitalists but also to learn the lingo and the terminology. Question related to the references themselves.

So, most folks out there, if they think of references, whether they have provided references, been references, or they’re trying to hire is you ask the person you are interviewing or will be interviewing for their references. They give references who they expect to give praise. And then you get in contact with those people. So there’s a piece of which questions to ask. And then there’s the piece – there are many others – of which people to talk to. What does your process look like for determining who to talk to as references?

Graham Duncan: So I actually think the candidate giving you references is – obviously, you want to find off-list references if you can. And one advantage of interviewing a ton of people in a given thing is, often you know people that they’ve worked with in other contexts that they didn’t give. But I actually find on-list references bizarrely high signal value because what happens is after 10 minutes on a reference, people run out of – nobody wants to lie.

Tim Ferriss: They run out of their script?

Graham Duncan: They run out of their script. And so one of my closest friendships in the business was when somebody who runs another family office was calling me on a reference on somebody. And my job – I went into that call thinking, “Okay. I like this guy. We don’t have money with him. I respect him. He stuck me on his reference list. Okay.” And the guy sat on me for an hour and would not allow me to basically give a positive endorsement without specifics, which I think of it as a net promoter score. So either at the beginning or the end of a reference, I’ll say, “Okay. What I hear you saying is you’re giving this guy a seven on the net promoter score. Is that right? Did I hear that correctly?” Or I’ll just ask it directly. “On one to 10, what’s your level of endorsement of this person?” If I was calling you on a reference on – let’s make up a fictional assistant that worked for you four years ago.

And I was debating hiring them. Well, first, we know each other. So I would do it in person. I would track you down and say, “Tim, so what’s the skinny?” But let’s say we don’t know each other that well, and I’m calling you on a phone. I would be trying to understand, “Okay. Are you still in touch with that assistant? What’s the social dynamic?” Or to make it safe for you, “Look, I’m calling 20 people. I am not passing any of that information back to the candidate unless you ask me to.” So you need to make it safe for them. But if at the end, I’ve got, in effect, an aggregate number of net promoter scores on a different person, you start to see patterns after reference number four. And then you know you can stop because you’re hearing the same thing over and over again.

Tim Ferriss: Yeah. I’m very primitive. Of course, you’ve done infinitely more hiring. But I remember this bit of advice that I was given by – I’m thinking about who it was. I’m blanking on who exactly it was. Kyle Maynard is who it was who’s a quadruple congenital amputee who’s climbed Kilimanjaro and was a star wrestler. Fascinating guy. He learned it I think from – it was from a very successful CEO. And it was, “Rank X – could be anything – from one to 10. But you can’t use a seven.” And I have used that in restaurants. I have used that for so many things. And it removes that safe, mild endorsement. When you are then speaking to these references who have been provided, are there any other approaches you use to ferret out weaknesses?

Graham Duncan: Well, one stance that I think is really important is that I’m not trying to catch somebody in any way. I’m just curious. And the references pick up on this vibe. And I want to help the candidate construct the best environment for them because there’s no “gotcha” to it. We’re all crazy. We all have lots of weaknesses. And so one thing I see other people in equivalent roles to me do is they have this “gotcha” –

Tim Ferriss: What was that?

Graham Duncan: One thing that I see other people who are in equivalent roles to me do is they have this “gotcha” thing, which I don’t agree with. So all I’m trying to do is help the person get in the best possible context for them. So I feel like that stance elicits a lot more because then you’re on the same side, particularly if you’re talking to a former boss. So I guess that’s how I think about it.

Tim Ferriss: Yeah. It’s the mindset with which you go into it and the tone that you transmit.

Graham Duncan: Yeah. One question I like to ask is, “If I were going to hire a partner for this person to complement their strengths and weaknesses, what would that person be good at?” because then, it’s like – and you gotta be careful. In the investment context, you want it to be another investing partner because – and then I actually use that. And then I can help – the extent it’s applicable, help that person try to make sure – because one misconception I feel like people have sometimes is that there are products. And in my opinion, in investment management, there are no products. There are only humans. And that’s why I’m so focused on the people side of it. And the only product is the mindset of the individual and the decisions they’re going to make prospectively from here.

So, if you were invested in a fund at Fidelity, and the portfolio manager leaves and there’s a new portfolio manager, from my perspective, that’s a completely new decision, whereas some people have a mentality of, “Oh, I’m looking to put out –” it starts with I think a dangerous mindset which is, “I need to put out some assets. And to do that, I’m going to invest in some products.” I think you don’t want to have the mindset of, “I need to put out assets.” You always want to feel comfortable holding cash. And there should be no pressure to put money to work. And then secondarily, to the extent you’re going – and in my world, we’re pretty indifferent on do we have people in-house or out in the field. Most of the time, external teams are the most commercial people want to run their own firms. And so we have a bias. We over time have constructed what I think of a team of teams. But it’s not a product of products. There is no –

Tim Ferriss: Yeah. That makes a lot of sense to me. And this may or may not be – I want to bring up a term that Josh suggested bringing up. And this may not be the right place. But that’s okay because this podcast is always all over the place, like Memento. He said, “Ask Graham about wild gardening.” Now, I’m going to laugh if this is actually, literally wild gardening, and it’s just a complete non-sequitur. But he put it in quotation marks.

Graham Duncan: So he calls me The Wild Gardener because I don’t like to force it. So there’s a great piece in The Atlantic Monthly from years ago where someone looking at the temperament of children divided them into orchids and dandelions. And it’s a little bit similar to the Susan Cain high sensitivity – there’s another thinker named Elaine Aron who has this concept of highly sensitive children, HSCs. And the idea is that if you get – orchids can be so beautiful. But they need just the right context. They need the right light, temperature.

And dandelions are just lower maintenance but maybe have less potenti – that’s not the right language. But the dandelions, you don’t have to worry about the context as much. And so I think of partly, what I do, back to the system design, is, “Okay. Let’s get everybody into a positive feedback loop doing what they’re actually – compulsive about –  what they actually can have a chance of being world-class at.” And I don’t like trying to stick a dandelion where it doesn’t want to be or an orchid where it doesn’t want to be. And I –

Tim Ferriss: So we’re talking about – we’re covering a lot that relates to talent selection and asking the right questions. We’re definitely going to spend some time on questions that you ask yourself as well, since that’s, in large part, what thinking is day to day. But I want to talk a bit about ambiguity, or cases that are not exceptionally clear. So if you talk to 20 references, and all 20 come back and say, “This person’s fantastic. Let me list the ways,” then that’s one thing. Or if they’re all negative. But no doubt you’ve had instances where you get negative feedback, or perhaps you have a lot of positive, but then one on a scale of one to 10 in severity is like a nine or 10 in severity, negative, how do you handle cases like that? How do you think through something that is not, at least at first glance, extremely obvious? Because a lot of life is like this. Or if there are any cases, any examples, not naming names but –

Graham Duncan: Yeah. I think it’s a matter of holding those contradictory perspectives as long as you need to to make sense of them. And so for me, people, my wife, my business partner can experience me as indecisive at times because I’m so tolerant of holding the ambiguity on somebody being really good at something because everyone’s genius is right next to their dysfunction, I think. And so until you’re clear on it, it can feel – and sometimes, you just don’t get clear in which case, there’s no need to do anything. But one central strategy I have of dealing with that is just spending more time with them. We got to know each other well on these intense surfing trips where we almost drowned. I almost beheaded you. And then we got food poisoning. And I like, in general –

Tim Ferriss: Welcome to Club Paradise. Yeah.

Graham Duncan: I like getting out of the conference room and not being pitched something across the table. And I like creating other contexts to interact with people. And if there’s ambiguity or ambivalence, we’ll look at investment with them. If you look at something that’s live with somebody, you learn so much about how they’re actually underwriting the mental models they’re using.

Tim Ferriss: What do you mean by underwriting it in this case?

Graham Duncan: So underwriting is a term used in the context of making an investment decision and are first in the body of work that an individual or a deal team has done to get comfortable advocating for an investment at a particular price. And so people will say, “Based on my underwriting, returns are attractive relative to the risk, in this case.”

And by saying, “My underwriting,” they’re putting their personal reputation behind the projections, and they’re taking ownership of the outcome of that analysis. So if we were looking at a real estate investment in Washington, D.C. in a potential hotel, we would – rather than investing in a fund, we would – if we’re getting a new partner – spend a lot of time on that, literally looking at that hotel investment and understanding how the sponsor is looking at the investment. And in that way, you get to know, “Oh, this is what they’re really focused on. This is what their strengths are. And maybe we should keep an eye out for these weaknesses,” or, “If we make the investment in a fund of theirs, this is something we keep an eye on.”

Tim Ferriss: And just for people who may not have put the pieces together – I want you to correct me here. But in effect, you have as clients your limited partners’ family offices. So these are wealthy families who want your help in then choosing different investment teams. And you are, in a way, I suppose, the team coach who is selecting the players.

Graham Duncan: Yeah. So we work with a handful of families who get to know us well and trust us to be their outsourced chief investment officer. They basically give us full investment discretion over their wealth outside of their personal property. And we manage that as one pool for them and diversify it across asset class – so we invest that pool in, say, a commercial real estate project in Seattle that we make with our real estate partners that are local there or in hedge fund partnerships run by the best teams we can find all over the world.

So if somebody’s got a fund, we’ll look at their fund. If they have an SPV, a special purpose vehicle where they’re investing in a publicly traded security or a private investment, we’ll look at that. If they want to start a fund, we’ll help them start a fund. If they don’t need our capital in a seed context but they just are looking for arms’ length normal, limited partners, we’ll do that. So we try to be as opportunistic and open-minded as possible about it.

Tim Ferriss: Are there any other patterns that you’ve spotted in the talent you end up selecting that does well? And the reason I ask is that from what I’ve observed – and this is not my world. But just hanging out on the sidelines, every once in a while, glancing over at my perception of what you do is that you’re picking folks, meaning investors, who are – they’re not Tepper, necessarily. They are rookie MVPs. Or maybe that’s not the right description. But you may not have a ton of data on these folks. Feel free to fact-correct any of that. So are there any other characteristics that seem to pop up more often than not in the people who end up doing well that you select?

Graham Duncan: Yeah. I’d say in addition to that aggression/humility tension, a second one I think about is originality and triage are these two – so we notice that the people who do best tend to have lots of ideas. There’s an academic named Dean Simonton who studied genius across field. And he observed that whether it was Bach or any given scientist that the sheer number of compositions that Bach had were 100 times more than average composers. And some of his lousy pieces of music were inferior to his peers at the time. But then he also ended up with some great pieces. So there’s something around just sheer quantity of ideas and original thinking that characterizes a lot of them.

Specifically, you’ll notice that in the language that people use. So I feel like in any field, I think, when you start to achieve mastery, often, people start creating their own language to capture the nuance that they’re seeing that makes them good at their thing. In investment management, Buffett is the Shakespeare of the industry. And everybody is living in his language and in his mental models to the point where it’s limiting. So I feel like a 25-year-old sometimes will be saying, “I’m sitting on cash just waiting for the fat pitch.” And I can’t tell whether he knows he’s quoting Buffett or not. And even if he’s doing it consciously, he’s living in this construct, which is a super useful construct. But if he proceeds to become the Tepper of his generation, he will generate his own language over the course of the subsequent 20 years.

And so when people use a lot of jargon and clichés and language that, at times, doesn’t feel like their own, to me, that’s a sign that maybe they’re a little bit earlier, and they could use another stage of apprenticeship. Or just that we would probably wait until a later stage. And then that second component, when people have lots of ideas, they’re usually not that good at killing them. So it’s a tension with this triage mentality of, “Look, I’m here to make money. I’m going to force rank – somebody’s going to die here. And I’m going to choose these – I’m going to save these four people and let this guy die.” It’s that triage, high-situational awareness. “Okay. I’m making life trade-offs here.” I think that’s a quality that really good portfolio managers have where they can force rank their portfolio, and they can kill their own ideas. So you see that often. And then just back to aggressiveness.

I was interviewing a guy. And he was talking about when he’s looking for – one question I like to ask people is, “If you were hiring an analyst, what criteria are you looking for in the analyst?” And people who’ve been managing money and managing people before begin to look for things in their analysts that make those analysts most valuable to them. And so there’s often signal in the way they answer that. And this guy said, “What I’m looking for is a trace of fear in myself that this guy is coming for me, that he will replace me.” And I think what he’s capturing is that level of intensity, that obsessiveness that you see in a minority, probably, in any field because of just how – they’ve found the game they want to play, and they bring an intensity and an obsessiveness to it that, over time, they’re just working so much harder. It’s like Wayne Gretzky finding hockey at age five.

He’s obsessed. And he’s just going over and over and over again. And there are people in the finance industry who are like that. They’re just obsessed with investing in this really distinctive way. Warren Buffett is, from a young age, obsessed. John Arnold, obsessed.

Tim Ferriss: You mentioned something I want to come back to for a second, which I may admit – I don’t think I’ll misrepresent it. I think I’ll probably get it. But you mentioned Buffett and the terminology and the language, the phrasing that he originates then popularizes and how people can parrot that, leading you to wonder whether they really understand what they’re speaking about or simply repeating something from someone who’s well regarded. And this makes me think of Richard Feynman and how his dad used to tell him that there’s a big difference – and I’m paraphrasing here – but between knowing the label, the word, or the phrase, and understanding what that label is intended to represent. And you can learn so much about not only others but yourself and your own thinking by looking at the language that you use.

And one of the questions I’ve wanted to ask you because it came up when you were in Tribe of Mentors was how you improve your own thinking. And something that stuck out to me – and I’m going to track it down here. This was in response to, “What is one of the best or the most worthwhile investments you’ve ever made?” And I’ll skip around here.

But the first line was, “I invested disproportionate amount of my income in paying for an ever-growing collection of trainers and coaches.” And you mention a handful. And one of them you said is “the most gifted listener I’ve ever encountered. She surfaces my hidden assumptions, the ones that hold me rather than me holding them, and teaches me to ask better and better questions.” How does – whether it’s this person specifically or others – help you to surface your hidden assumptions? This strikes me as so, so key to just about everything. And investing just happens to magnify the consequences in a very often obvious way of assumptions and faulty assumptions. But how would a coach help you to surface your hidden assumptions? Or how might they?

Graham Duncan: Well, this woman, Carolyn Coughlin, in particular, is within this Bob Kegan school of – he’s a professor at Harvard. And he has a theory about adult development, which is that the process of moving to adulthood is one of increasing your mental complexity and increasing the number of things that you used to be subject to, assumptions you had you couldn’t see, and making them object over time. So an example for many people would be if they grew up in a religious context, are they actively choosing their religious beliefs?

Or did they arrive at them because their parents and community – everyone was swimming in those beliefs together? And so what I feel like a really good coach can do is by listening to the way I’m making sense of something, can observe, “Oh, you’re actually assuming X. Your grip –” I think of it as grip. “Your grip on certain things is really tight.” And if a coach can find what you’re gripping really tightly, and you’re actually not – you can’t articulate the opposite of this belief you have, that might be a sign that you have identity or ego caught up in that thing.

Tim Ferriss: Can you think of an example?

Graham Duncan: So one assumption my business partner pointed out to me recently that I seem to have that I might be holding a little bit strongly is what he was calling Futurism, that I’m ready for things to be disrupted and paranoid about disruption in this way that he observed – I’ve got a little bit too tight of a grip around things. So when we’re investing in a hotel where there might be risks around climate change, I’m extra focused on the climate change. Or if we’re investing in a value investor who’s often going long things that Silicon Valley’s trying to disrupt, my partner’s observation is I will be extra focused on risks around that. And I think he’s totally right. Once he said that, it clicked. And I realized, “Okay. Now that doesn’t mean I drop it. It just means when it comes up, it’s more object to me that –” so yeah. That’s –

Tim Ferriss: And in a case like that, would you practice articulating the opposite, as you mentioned earlier? And as my mind is digesting this right now, I’m thinking of – you have read so many books. It just boggles the mind. And so you may be familiar with – it wouldn’t surprise me if you’re familiar with Byron Katie. But she has something called The Work, which I think is – you have to be careful with using it as your only hammer, because then you just start looking for nails everywhere. But part of that practice is taking this belief that is causing you – and I’m not saying this is an example here – but causing you some amount of discomfort or stress or anxiety and then going through the exercise of stating the exact opposite. So “My dad should be –” this is not a real example. I’m making it up. But, “My dad should be more attentive to my mom.”

And then you state it in a number of different ways, like, “My dad should be less attentive to my mom.” “My mom should be more attentive to my dad,” etc. And you have to, as part of the exercise, look for data points or even the smallest shred of evidence that you could put down if you were trying to make those arguments. And it helps to disentangle emotion and detachment from your initial statement. When your partner brings to light something that you might be gripping tightly like this, what are the next steps after that? Or is just the pointing out enough? It’s like looking at an optical illusion, and you’re like, “Oh, you see how if you look at it this way, it’s actually an old woman’s face instead of an hourglass,” and you can never again look at that and not see the old woman’s face.

Graham Duncan: Yeah. The Byron Katie – I’ve been to multiple workshops of her. I think she’s amazing.

Tim Ferriss: I knew it.

Graham Duncan: So across the street here, there’s a salad place, sweetgreen. And I was in there maybe three months ago, listening to Byron Katie’s new book, A Mind at Home with Itself. And Byron Katie and her husband, Stephen Mitchell, walk into the restaurant, order salads, and then proceed to sit right next to me. And it was the most unbelievable – I took a picture because I thought I might be tripping.

Tim Ferriss: So then you looked at your computer later, and no one was there.

Graham Duncan: And I will tell you they proceeded to have the most mindful meal I think I may have ever witnessed. There are some gurus who, out of context, you think are not walking their talk. In this particular case, I can affirm that she is like her stage presence to – you’ve seen her on stage?

Tim Ferriss: Yeah.

Graham Duncan: All the time. And so I find her credibility on that extra high. I think her thing of, “What’s the belief? Is it true? What’s the opposite of that? Can you absolutely know it’s true? How do you feel when you think that thing?” – I think it’s –

Tim Ferriss: Yeah. “What would you be without this belief?”

Graham Duncan: “Who would you be without –” I think it’s so powerful.

Tim Ferriss: Sorry to interrupt. But one thing that really caught me because I spent a little bit of time with her a number of months ago, and I can confirm what you just said. She is exactly what you would expect and hope her to be based on the books. The metaphysics can get pretty mind-bendy if you go in that direction. But the framing of using the word – we were talking about labels – belief, like, “What would you be without this belief as opposed to thought?” is also really key. It’s something you take. It’s a statement you take to be true. And it’s just framing it that way puts it under a different lens.

Graham Duncan: So to your question, I think I may have a little bit of ego identity around being unconventional or being into technology disruption and not thinking that the status quo is going to continue. And so what my business partner is pointing out is just watch that. And now that we have it on the table, when we’re evaluating an investment, it’s, “Oh.” I don’t want to be self-conscious about bringing up the paranoia, because I think it’s a useful lens to have. But being aware that I’m just a tiny bit subject to that is really useful.

Tim Ferriss: And if you’re looking at a team, whether that’s within these offices – we’re sitting in your offices right now – or could be any team, really. But specifically – just to keep us in your power zone – investing, when do you choose to – let me think about how to best phrase this – teach each individual person to offset biases like this versus hiring another person to provide a counterpoint? And the reason I ask is – and I’m getting way above my paygrade here.

But if you look at Buffett and Munger, and Buffett’s searching for bargains and wants to buy at a discount, and then Munger is – I’m going to get slaughtered on the internet, I’m sure – but is teaching him over time that there are cases where you can buy at market value or a fair price if the growth trajectory is really high. And they seem to complement each other very, very well. How do you think about each person developing the counterpoint or ability to look at the opposite versus hiring to end up at that optimal mixture?

Graham Duncan: Yeah. It’s back to grip. So if I’m evaluating a team, I’m trying to figure out – so sometimes I’ll hook up someone who is long Tesla with someone who is short Tesla. And when you’re witnessing that exchange, you can see whether the person who’s long Tesla and the person who’s short Tesla – are they actively seeking disconfirming evidence? Or is it an ideological thing? And Tesla’s a little bit of an extreme example because it’s very ideological on both sides. It’s not really a great example for that reason.

But you can see it because it’s more extreme. But right now, on Twitter, the shorts and Musk and the people who are long, they’re going back and forth. The vast majority of them are not actually looking to hold the other person’s perspective. In a team context, you can witness whether there is somebody who’s already there. In the hedge fund industry and the private equity industry, what’s cool is that the boundary of the firm is pretty fluid. So sometimes, a portfolio manager of one firm will have a close relationship with one to five other portfolio managers.

Tim Ferriss: Can you define here, just for folks – so PM, portfolio manager. Who is that person?

Graham Duncan: Portfolio manager. That’s the person who’s running the investment firm and who’s making the investment decisions and sizing the investments in that portfolio. It’s the main role.

Tim Ferriss: And inside a large firm, you might have multiple PMs, depending on –

Graham Duncan: Yes. I’m using it in – that’s a good catch. I meant more CIO. But if you had a –


Tim Ferriss: Chief investment officer.

Graham Duncan: Chief investment officer. Exactly. But a portfolio manager within a large shop, like Citadel, will have external relationships sometimes. And sometimes, those buy-side relationships will be testing each other’s thinking. And the equivalent of that Buffett-Munger thing often exists across firm, is my – so they don’t have to be within the boundary of the firm.

Tim Ferriss: So the looking for disconfirming evidence I want to stick with for a second. So this is something you see certainly in any good scientist. They’re not setting out to prove X. They are coming up with a hypothesis. And then hopefully, in as unbiased and objective a way possible – arguably not possible to be fully, fully objective – trying to then assess and actively look for disconfirming evidence, if it exists or if they can isolate it. How do you train – how could one train oneself to get better at doing that?

And it could be as seemingly indirect as you like. It would seem like one step would be developing what we talked about earlier, this ability to take whatever assumption or bias you have and then view it as an object, so that you’re aware of it. And some meditation can help with that. Doing something like Byron Katie can help with that. Are there other things, whether they’re precursors to looking for disconfirming evidence or that have it itself that help to cultivate?

Graham Duncan: Well, I think an underlying paranoia that you’re missing something is really useful. And the best portfolio managers have that. And maybe you dial that up by regularly reviewing all the mistakes you’ve made and thinking, “Okay. Some percentage of the time, I see things clearly. And some percentage of the time, I miss it.” One thing about financial markets in the publicly traded side is your hit rate is – a really good portfolio manager’s hit rate is 65 percent. That’s off the charts. And 55 percent will do just fine in a lot of cases, depending, particularly, on their slugging percentage, what percentage of – how do they size the winners versus the losers? You want to size the winners obviously bigger than the losers.

So, there’s something around how do you maintain paranoia and humility? I think one tricky thing in the hedge fund space is being on the record in any way in the form of writing letters or being on CNBC or being in the public domain, probably on the margin, makes it harder to drop it like a hot potato and go short. And to me, the most skilled portfolio managers have an identity not as, “I am smart, and therefore, I make money,” or, “I am good at financial stocks.” But the meta-identity is, “I’m a moneymaker. And if that involves right now – if in this era, in this moment in history, that’s going long Tesla, I’ll go long Tesla. If it’ll go short Tesla, I’ll go short Tesla.” But there’s no baggage – I remember walking into a guy who we have a ton of money with who I really, really respect. And he was short SolarCity.

And it was on the morning that Musk announced that Tesla was buying SolarCity. So it was a very painful morning for people who were short this stock. And I expected this guy to be moping around and super pissed at Musk. And he was laughing. He was enjoying the audacity that Mu – “He feels like he’s in this game. And I didn’t even – I knew it was a possibility. I didn’t think he was going to have the chutzpah to do that.” That mentality, that humor, that lightness, that, “Oh, got this one wrong. Onto the next one –” if that particular portfolio manager ever wrote about something in a letter – he doesn’t happen to. But if he did, I would have no qualms that the following month, he could easily be short the position he just – and so one nice thing about financial markets is that long/short thing, the ability to make money by going up and make money by going down.

Tim Ferriss: And change your position. This reminds me of something Josh decided some time ago which was that he wouldn’t – maybe this has changed, but I doubt it has changed given his current circumstances, which we won’t get into. But very unlikely. He’s giving many keynotes right now. He stopped giving keynotes because he felt like it would entrench his thinking and calcify his positions because he would be repeating these statements and concepts that he would then be less likely subconsciously or consciously to modify. This is something I ask everyone. And you’ve heard this before. But are there any particular books that you have gifted the most to other people? They don’t have to relate to what we’ve been discussing at all. But you are so widely read. Do any stand out as books that you’ve gifted or recommended often to other people?

Graham Duncan: Yeah. So in financial markets, I really like this somewhat obscure book called The Aspirational Investor by this guy, Ashvin Chhabra, who runs Jim Simons’ family office. Jim Simons started Renaissance Technologies, which is the dominant quant fund.

Tim Ferriss: Amazing story. We’re not going to get into it. But Renaissance is really fascinating. So please continue.

Graham Duncan: And one thing I like about Renaissance and Jim Simons, he has this line in a New Yorker profile of him that he thinks what he has is really good taste in interesting problems. And he uses the word taste. And it’s a similar – and this guy runs his family office. Used to run the endowment at the Institute for Advanced Study. And in the book, he identifies what he sees as the flaws in modern portfolio theory, which have totally dominated prevailing beliefs about investing for decades. And Ashvin suggested a totally different approach to portfolio construction based on how people actually behave and what they actually care about.

And so that’s a book I give out a lot. On the culture side, of somebody starting a firm – I’m looking over your shoulder because I’ve got a bunch of them on the bookshelf here. Tribal Leadership by Dave Logan. Dave Logan has looked at thousands of organizations and puts them into categories. And Phil Jackson, the former coach of the Chicago Bulls has observed that that framework that Logan discusses in Tribal Leadership is the best framework for understanding world-class teams that he’s come across. We can go into it if it’s of interest. Culture Code by Daniel Coyle I give people.

Tim Ferriss: What do you find of value in that book? This book has come up a lot on the podcast. I still have not read it. It’s come up in many different contexts. What is that book about?

Graham Duncan: Which? Culture Code?

Tim Ferriss: Sorry. The last one. Yeah. Culture Code.

Graham Duncan: Culture Code. He’s looking at a bunch of different cultures. Pixar, Navy SEALs. He’s got three others or something. And he’s looking for patterns among what makes people disproportionately effective as a culture. And I think he captures some of the nuance that if you’re trying to set up teams, it exposes you to that. He’d be a good guest on the podcast.

Tim Ferriss: Another book on my homework list. Check.

Graham Duncan: I also like The Tools. I give that out sometimes. That’s by Phil Stutz and Barry Michels. Have you ever heard of them?

Tim Ferriss: I have. Are they screenwriters? Worked in entertainment? Am I –


Graham Duncan: Yeah. They’re psychologists. And they’re in Hollywood. And they treat a lot of screenwriters. And New Yorker reporter Dana Goodyear did a profile of them that highlighted them. And then they wrote a book called The Tools. And they have a bunch of good hacks in there that I like.

Tim Ferriss: Some of the most – I won’t mention them by name. But a few of the documentary filmmakers who are on a very short list of documentary filmmakers who create massively commercially successful documentaries have recommended this book to me. That’s how it first came up on my radar.

Graham Duncan: Just as an example, it’s very apropos of Wim Hof. They have this whole analogy of saying this model of, “To get to what you want, you have to go through some pain –”

Tim Ferriss: So just pause. Could you describe for people who Wim Hof is if they haven’t – oh, boy. So Wim Hof first – I think his first podcast interview was on this podcast. Interesting guy. But who’s Wim Hof?

Graham Duncan: Wim Hof has developed a way of exposing himself to the cold and a methodology around exposing himself to the cold that he now teaches to millions of people thanks to you and Laird Hamilton and others highlighting him.

Tim Ferriss: The Iceman. Yes. A dubious honor, in some cases, because you do need to watch your fingers and toes. But he has a number of training approaches – although one sometimes wonders how much of what he can do is attribute versus training – but for cold exposure and also for breath holding. I don’t want to take us off the rails. But quick note on breath holding. Our mutual friend Josh almost died from a shallow water blackout in a pool here doing breath hold training. Never do it in water. There’s really no good reason.

Graham Duncan: No. So these guys have this metaphor of – they’re basically coaching you on your self-talk. And they say you should rub your hands together and say, “Bring it on,” when you’re anticipating doing something that is going to be painful. And they use the metaphor of going into the cold water at the beach and that regular embracing of discomfort is a skill that Waitzkin is also into and a theme of learning to – Waitzkin calls it the other side of pain.

But it’s getting used to exposing yourself to pain on a regular basis to a point where you don’t bounce off of it. Stutz and Michels observe that in their work with producers, agents, screenwriters, and etc., in Hollywood, that people were avoiding doing the thing they needed to do. They were bouncing off of it. And so if you can create a skill and a mechanism to make yourself go into it and get in that habit – and they’ve got six of them. And so I do this with my kids. We’ll literally rub our hands together and be thinking, “Okay. Bring it on,” to X.

Tim Ferriss: So I wonder if Josh got this from you. It wouldn’t surprise me if you guys independently arrived at this. But with his son, he would take cold showers. And he would always say, “It’s so good.” And he taught his son to say, “It’s so good,” with these short, freezing cold showers. And I don’t know. His son’s probably – I’m making this up – four years old at the time. And also taught his son to enjoy going out in what other people would consider bad weather, the rain storms and so on.

Graham Duncan: Yeah. So that’s an example of just making the rain object. So I think what Josh is observing is that for most people, they are subject to the weather. And they’re experiencing the weather as acting on them. And a hack around that is to say basically, “No. I enjoy the rain. I’m going to find what I enjoy in it and make it not the world happening to me but bringing the locus of control internally,” is what I think he’s doing there. And it’s a good parenting hack.

Tim Ferriss: Are there any other – well, if there are more books behind me, then feel free to mention them.

Graham Duncan: I like Finite and Infinite Games which has been going around a lot. His other book, Breakfast at the Victory

Tim Ferriss: This is James Carse.

Graham Duncan: James Carse is really good. I had him to an event, a hedge fund retreat we had a couple years ago and spent some time with him. And I think he’s a very profound guy. He was observing that – I asked him how he came up with the concept of finite versus infinite games, and he said he was watching his kids play. And he noticed that there were some games like card games or baseball, etc., where their whole motivation and intent was to have the game end and get the trophy. And then he noticed there were other games they were playing where they were more fantasy games, where their goal was to recruit other people to play in that game with them, such as him, as their dad. And the goal was to keep the game going as long as possible. And I think it’s a super profound insight of the different ways you can relate to games in your life if you can see the game you’re playing.

And I asked him for examples of infinite games which he doesn’t give in the book. He mentioned, as a religious studies scholar, he thinks Buddhism and Judaism are two infinite games. I guess in religious studies, neither of those has a central authority or a central army. So it’s unlike Catholicism. They have difficulty making sense of why it persists over time. And so the framework of, “It’s an infinite game,” Buddhists and Jews are recruiting, to various degrees, people into their game and wanting to just keep playing the game for its own sake. I thought that was an interesting framing.

Tim Ferriss: How does the distinction of finite and infinite games apply to finance, if it does?

Graham Duncan: No. I think it does. A finite player who’s an investment manager would be, for instance, trying to hit a certain number of net worth and then leave the game. And that’s okay. But it makes it less valuable of a partner, from my perspective. And the incentives can get weird once they achieve that net worth if they actually stick to it. Now, the reality is most people move the bar. There was a study recently that everybody wants to have – all along the income spectrum, everybody wants to have two times where they are right now.

But I think there are – in general, I seek out partners who I experience as infinite players who are enjoying the game for its own sake and are going to keep playing and want to recruit other people. And that’s back to the distinction between being commercial and transactional. There’s something about the abundance mentality behind somebody who’s commercial who’s trying to create more value than they capture that’s leaving room for other people in this way.

Tim Ferriss: How do you test for that? Or how do you – it might be lower on the hierarchy of needs in assessing talent. But if it is something that you try to assess, how do you assess it?

Graham Duncan: The big one is time horizon. Somebody who’s thinking, “Okay. I found this thing that I love to do. I’m going to do it for the next 20 years. And I’m not going to make short-term accommodations to what’s going on in the market or with my limited partners or with my team –” I experience it around time horizon, mainly.

Tim Ferriss: How do you ask around the question? Especially after this podcast comes out, they’re going to be like, “Okay. Graham wants a long time horizon.”

Graham Duncan: You can see it just in the way they’re setting up their business. I don’t know. There are indications of just subtle, mental framings on – some people start investment firms because it’s the time of their career where their friends have started investment firms, they can no longer stay at the container they’re in, and they need to start – but it’s not an approach goal. It’s almost an avoidant goal. It’s like, “Okay. This is the time where I’m supposed to do this, so I’m going to do this,” versus a different set that are like, “Okay. I found the thing I love. I found the ball I like to hit. And I’m going to do it in this new form because –” and that implies, to me, a longer time horizon and – it’s a cliché – but a love of the game, itself. If you took away David Tepper’s money and made him start at scratch right now, I think he’d enjoy it. He’s just found the thing he loves.

And who else has long-term – Jocko Willink. I would invest in something Jocko did. I think he has that exact – in fact, he has a mantra, right? It is default aggressive. He has that mix of aggressive and integrity or aggressive and humility. And you think of it. He’s coming back from Iraq. He does SEAL Team Three. And then he’s entering your world. “So, there’s a podcast thing.” And then, “Oh, coaching thing.” And from afar – and I don’t know him – I just really admire the way he’s doing his own thing. He has that mix of time horizon, having an idea, executing on it.

Tim Ferriss: You guys should know each other. I’ll introduce you guys. You would get along. I want to stay with this for a little bit more in terms of sniffing around the direct question. And it seems perhaps much like your – “Tell me about what happened in 2008.” You can maybe also – along the lines of looking at how politicians have voted on things as opposed to asking them what they will do. It just made me think that looking at time horizon and intrinsic versus extrinsic motivations and so on, you could also assess kind of along the same lines that Y Combinator has, at least historically, by asking a lot of questions around what people do, what they’ve built in their spare time, and things like that, which will not be a direct answer to the question, but could act as indicators that point to a general pattern of behavior and motivations.

Graham Duncan: Yeah. I find Y Combinator’s and Paul Graham’s and Sam Altman’s stuff high signal from my perspective. So they have this question they ask themselves. “Can you say this person is an animal and not smile, based on the references, based on your interactions with them?” I think they’re keying in on the same quality of aggression or intensity that I am. Buffett uses passion and common sense. Ray Dalio uses assertiveness and open-mindedness. But I think everybody’s homing in on this paradoxical tension that I was talking about earlier. Sorry. Tell me the question again.

Tim Ferriss: Oh, yeah. No. I’m not even sure I asked a question. I think it was more of an observation. And I’m wondering if there are other ways to ask around the direct question of time horizon, which you already gave a few examples of. So I think it’s been answered. So let’s pick up on one thing you also mentioned in passing, which I’ll refresh for people listening by reading a quote. And I’m going to get this name wrong, so maybe you can – this is a quote that you introduced me to. And it was one of two candidates for answering the question what you would put on a gigantic billboard anywhere. And you could put anything on it, metaphorically speaking, a message to get out to millions and billions of people. So could you read this? Because it is stuck in my mind. And I’ve revisited it so many times. But I don’t know the proper pronunciation.

Graham Duncan: Kwame Appiah, who’s a philosopher at NYU – actually, I think he used to be at Princeton – has this quote. “It’s not how well you play the game. It’s deciding what game you want to play.”

Tim Ferriss: Right. And so you had mentioned the game, if you are aware that you’re playing the game. So what is the relevance or importance of this quote for you? And I’ll read it one more time. So “It’s not how well you play the game. It’s deciding what game you want to play.”

Graham Duncan: So I think that’s a way of moving your game from being subject to it to object. So an example would be – I think a huge number of people are obviously playing the game of making money. And they’re keeping score in terms of how much money they make or how much fame they accumulate or how much power they accumulate. And making that game object to them and then just making sure that you still want to play that game is I think what his quote is about. I ended up writing an essay where I tried to capture the various stages of mastery in investment management. It’s a blog that’s on my site.

And to me, that quote allows you to zoom out and say, “Okay. At different stages of my life, I’m going to play different games. What game am I playing right now? And can I see it?” And in effect, that’s what the coaches – and the coach I’ve used in the past – help you do is say, “Okay. You’re clearly optimizing right now for this. Just make sure that that’s the game you want to play.”

Tim Ferriss: So that the ladder you’re climbing is leaning against the right wall. Let’s just make sure –

Graham Duncan: Yeah. Just check in every once in a while. So you can zoo – and it allows you to – it’s like in a video game. What do you call that?

Tim Ferriss: Zoom out?

Graham Duncan: God’s eye view? Yeah. God’s eye view of the game. You’re like, “Okay. I’m down here in this corner of the mountain range. Do I still want to climb this mountain? Or is that a local maximum, and I should actually zoom out and head a completely different direction?”

Tim Ferriss: I think you’ve mentioned this to me before. It may even be in Tribe of Mentors. But it makes me think of the David Foster Wallace commencement speech which has been turned into books and is online in various forms. But here it is right here. “This is Water.” And the story of the two young fish together swimming by the old fish. And the old fish says in passing, “How’s the water, boys?” or something like that. And they’re like, “What’s water?”

Graham Duncan: Yeah. Exactly. I think that’s what he’s capturing so beautifully in that commencement speech is that we all have water. There are things that are water to us in every stage of our life. And the fun project is to try to see it and see it at each stage. And when I think of even your development over the course of the last several years on your podcast, you’re able to see – you’re wrestling with different stuff. You’re able to see your own quirks in a different way than you were five years ago. And I think that’s the process of adult development. That’s what Kegan is pointing to as these different stages.

Tim Ferriss: I do the podcast in part because it helps me to see the water. It forces me to try to ask questions or make statements and articulate things that would otherwise just bounce out of my head consciously or subconsciously. So the podcast is actually a tool for me to try to discern which water I happen to be swimming in which makes it a lot of fun.

Graham Duncan: The Greg McKeown – is that how you say his name?

Tim Ferriss: I said it that way for a long time. McKeown. Greg McKeown.

Graham Duncan: McKeown. Greg McKeown’s podcast recently on Essentialism, when he tells that story of how he felt a ton of pressure to go on the work event on the project with his consulting partners rather than be at the hospital with his wife as she was having a baby, that’s a developmental – in Kegan language, that’s a developmental moment when you’re saying, basically – he’s moving from socialized to self-authoring.

He’s saying basically, “No. My partners don’t define the scorecard here. The scorecard is my scorecard. I decide what’s a priority to me. And I’m going to remind myself of this the rest of my life by embarrassing myself by telling this story over and over again so that I don’t do it again.” I feel like Essentialism is basically – that’s what he’s capturing. And I think in a lot of different moments on your podcast, people are wrestling with what can they see at that moment? What did they used to not be able to see? It’s kind of beautiful. It’s the unfolding that we’re all doing.

Tim Ferriss: And you’ve had an opportunity to observe dozens, hundreds, thousands of careers or at least examine, probably, thousands of careers. How do you think about careers or career advice? I know that we’ve had some exchanges using the metaphor of the river, which might be a good place to start. And then I have some other questions related to that. But maybe we could begin with that.

Graham Duncan: Yeah. I like the image of a river with two banks. One side is chaos, and the other side is order. It’s something Dan Siegel, who’s a neuroscientist, came up with to try to describe what mental health is because he argued that the bank of chaos is schizophrenia, and the bank of rigidity is OCD, and that you could basically put every mental illness on one bank or another and that healthy integration is swimming in the middle of the river in between those two. And I was thinking about how careers are like that.

But you start off along the rigidity bank, apprenticing for somebody. And you’re learning the jargon of that industry. And you’re trying to figure out how people define reality. But you’re in somebody else’s definition of reality. You’re refining reality. And you’re learning to be able to see, whereas the other bank, the chaos bank, is more asserting reality. That’s where people who are swimming right next to that bank are just making stuff up on this mass – I think of Musk as being right along that bank. And if Tesla goes bankrupt, that will mean he lost his feedback with reality and stepped onto the chaos bank. And if he pulls it off, he was swimming right next to it. Steve Jobs, the same way.

Tim Ferriss: Just threading the needle.

Graham Duncan: Right. And you see it in poets. You see it in writers. People who are right next to that bank are super original. They’re coming up with new stuff. We live in their paradigms to some degree. But you’re right on the – if you lose the feedback loop with the way the rest of the world is experiencing reality, all of the sudden, you can seem crazy. And the danger – from a career perspective – of starting your own thing a lot of the times is a project of asserting reality. And if you do it too early, it can be very disorienting. And so you want to just swim back and forth. It’s not to discourage people from starting their own things at a very young age. But just be aware that you’re going to – that’s the project. And you might want to come back and refine reality for a little bit and then go – just see it as fluid.

Tim Ferriss: Right. And it makes me think of – and I’m not saying it’s a direct mapping. But as Pablo Picasso said, “Learn the rules as an amateur so you can break the rules as a professional.” Something along those lines. And you mentioned this bank of chaos and how those who can swim right alongside it can harness this paradigm-shifting originality. But as you’ve also pointed out, that same originality can have unintended consequences if they flop onto the bank, like Steve Jobs and the magical thinking around –

Graham Duncan: Around his illness.

Tim Ferriss: – his illness. If one wants to be top one percent in a given field, just arbitrarily, to pull a number out of my ass, does that mean that they need to swim really, really closely alongside one bank or the other? And is that a mistake in thinking? Or be perceived as being a top performer. Do they swim in the middle? Or do they oscillate between the two? Are there different breeds, just in your experience?

Graham Duncan: I think to be a top one percent – depends maybe on the field.

Tim Ferriss: Let’s say your world.

Graham Duncan: Yeah. I think within financial markets, you need a continual level of innovation and adaptability to stay ahead because the games that were working five years ago no longer work. So for a while, there were a lot of event-driven strategies where people were investing in mergers and acquisitions and making a certain return percentage around that. That game has mainly gone away. And so I would say I think of infinite players as playing with the boundaries of the game. So when Mike Burry came up with the idea of shorting subprime –

Tim Ferriss: Right. Now, Mike Burry, famously played by Christian Bale –

Graham Duncan: Christian Bale in The Big Short. That was an example of innovation and playing with the boundary of the game at that time because he wanted to express a view that would short the housing market. And he found he had no – he didn’t want to short stocks. He wanted to get more leverage on it. And he came up with that. And then the banks offered that to everybody else. And everybody else ended up – everybody else who came into the trade ended up following the trail that he had blazed on that, from my perspective.

There may be other perspectives on that. But that’s my perspective. As Christian Bale portrayed him, he was wrestling with his sanity at various points, having that trade on. At various points, the fund was down a lot. His partners were abandoning him. So I do think there’s something around pushing the edge of your field because people are going to catch up with you that is required. I don’t know that – I’m trying to think of other examples outside of financial markets of being top one percent of something. But I –


Tim Ferriss: It’s less objective. But if we’re looking at successful authors, I think another example that I’ve seen you mention is Pirsig. He wrote Zen and the Art of Motorcycle Maintenance but certainly, towards the end got, one might argue, pretty loopy.

Graham Duncan: Yeah. It’s hard to think of top one percent in –


Graham Duncan: – context. But I think original – you look at Rachel Cusk and Karl Ove Knausgård. I don’t know how to say his name. But those two authors, I think they’re doing original things as novelists. And I don’t think they’re at risk of flopping onto the bank of chaos. But they’re doing original things. I don’t know how to take that.

Tim Ferriss: Yeah. This is more just because I think you’d enjoy it. And I can link to it for people who are interested. But there’s a model of cognitive function – yeah. I suppose we could put it cognitive function – and personality typing that has been just a theory and a model from Robin Carhart-Harris, who’s a scientist in the UK, called the entropic brain, which I think you’d enjoy. So for another time. I’m just looking at my notes here. And I have a short – I have two words based on conversations we’ve had leading up to this. But I don’t have any context here. So time billionaires. What does that refer to?

Graham Duncan: I was listening to a guy introduced a speaker a while ago. And he was saying people don’t really understand the difference between billionaires and millionaires. He said a million seconds is like 11 days. A billion seconds is 31 years. And I remember that –

Tim Ferriss: Oh, shit. That’s a hell of a way to think about it.

Graham Duncan: Right?


Tim Ferriss: Wait. Can you say that one more time?

Graham Duncan: A million seconds is 11 days. A billion seconds is slightly over 31 years. And I was thinking about – Tyler Cowen has a thing about cultural billionaires –

Tim Ferriss: Marginal Revolution?

Graham Duncan: Yeah. In one of his books, he talks about cultural billionaires. I feel like in our culture, we’re so obsessed, as a culture, with money. And we deify dollar billionaires in a way that – it’d be nice to co-opt that term the way Tyler Cowen did with cultural billionaires. And I was thinking of time billionaires that when I see, sometimes, 20-year-olds – the thought I had was they probably have two billion seconds left. But they aren’t relating to themselves as time billionaires. And I was thinking about how if you could – what would Rupert Murdoch, who’s worth $20 billion – he’s 87 years old. What would he pay if he could take the next five years of someone’s 20-year-old healthy body, mind, etc.? And for that 20-year-old, how would they price it? Because I was thinking at various points of my career, I might have sold the next five years for something.

And over time, my pricing has gone vertical because the next five years, if I were to lose – and the key to this question is that you can’t sell the five at the end of your life. You gotta sell them right now. I don’t know how I’d price it because my kids are of a certain age that they’ll never be again. But I don’t know that I live every day that way. But I aspire to. So I was trying to capture – I heard Tim Urban on your podcast. And I started reading his stuff. And I find his writing style and the topics he is interested in just amazing. He has this concept of life calendar. And I bought his life calendar. He sells it as a poster. And what he does is he puts a week – he does a circle for each week. So he has 52 circles on the horizontal and then 90 rows so that you can see a 90-year life in weeks. And what’s startling about the picture – again, to this question of how long is a billion seconds – is how short it actually is.

And so what I did is I went through, and I put where I am right now. And I started filling in the circles as I go. And I put where my eldest daughter goes to college. I put when my dad is going to be 90. And I was actually thinking a good product, if there are any graphic designers out there, would be to partner with Tim and allow you to create a huge poster and select a photo for each week and then – because it’s such a graphical representation of your life in a way that’s hard to convey in words sometimes. So I’ve just been thinking a lot about time and how you live. There’s a quote I like that we’re all very focused on the length of our life. How do you appreciate the width of it as you’re going along? And somehow, keeping that in your consciousness –

Tim Ferriss: Can you elaborate on that? The width?

Graham Duncan: The width, meaning this present moment. We’re sitting here, having –

Tim Ferriss: Stuff like the depth of attention.

Graham Duncan: Yeah. The breadth of sensory inputs. It’s another way of saying trying to stay more present versus being extremely goal-directed of whatever objective you have in your life right now.

Tim Ferriss: And how do you cultivate that in yourself?

Graham Duncan: So one thing is I have that life calendar literally sitting in my kitchen.

Tim Ferriss: Pause quickly. I’ll buy you some time also. So Tim Urban has a blog, Wait But Why. Calling it a blog is funny because some of his pieces are 70,000 words broken up into multiple parts. Also, just since you mentioned Musk, he was, I believe, the only person asked by Musk directly, who was a fan of the blog, to come in and have full access to Tesla. The life calendar is a fantastic place to start as is a piece called “The Tail End,” if you want a really acute sense of time, especially as it relates to how much time you might have left with parents. That is a fantastic piece. So you have the calendar.

Graham Duncan: So reading that piece made me try to engineer having my parents in New York much more frequently. And I tangibly did that –

Tim Ferriss: Oh, no kidding?

Graham Duncan: Yeah. So literally, reading that piece had that big an impact, where I was like, “Oh, my –” because he points out the percentages, how, if your parents don’t live in the same place you do, you will see them – by the time you’ve graduated from high school, you’ve spent 95 percent of the time you’ll ever spend with them –

Tim Ferriss: The total hours you will ever spend with your parents. And I didn’t know that about you and your family. After reading that piece, which was recommended to me by Matt Mullenweg, whose father passed away very unexpectedly – he recommended that piece to me. And that led me to really block out and make a priority a trip or a gathering with my family every six months. That piece, “The Tail End –”

Graham Duncan: It’s pretty profound stuff, I think. So your question is what do I do. So all the standard stuff. I meditate. I use 10% Happier app or Sam Harris’s app.

Tim Ferriss: The Harris brothers, even though they’re not brothers. Dan Harris and Sam Harris.

Graham Duncan: Dan Harris calls that whole crew the Jew Bus, the Jewish Buddhists which I think is a great –

Tim Ferriss: Well, just as a quick side note, I remember I was talking to Jack Kornfield, who’s an incredible teacher. Probably the most empathic human I’ve ever met. Truly walks the walk. And I asked him at one point – I said, “You’ve got Goldstein, Kornfield.” I can’t remember the names. Sharon Salzberg. I’m like, “Why are –” it seems like the entire crew who brought Buddhist mindfulness practices to the US in some – I’m getting the timeframe slightly off probably, but –

Graham Duncan: ‘80s?

Tim Ferriss: Yeah, the ‘70s-‘80s. They’re all Jewish. And he goes, “That is a good question.” This is just us having a private conversation. But he said, “Yeah. It sounds like a law firm.” And we went on to – we won’t get to. But the Jew Bus. Yes. So Dan Harris, Sam Harris. Both of those apps.

Graham Duncan: Yeah. I use both those apps. I try to be nostalgic for spending time with my kids in the present moment. So my youngest right now, I think I can probably carry around my shoulders probably a total of five more times. She’s getting too heavy. And I know because I have an older kid that that’s a distinct phase. Beyond those, keeping track of how much time.

Tim Ferriss: Those are good anchor points.

Graham Duncan: The Gretchen Rubin line about how “The days are long but the years are short,” I think about that a lot.

Tim Ferriss: There’s one that – oh, boy. I wish I could get the attribution right [Ed. Note: Muneeb Ali]. It was in Tribe of Mentors. It was an answer to one of my questions. It was in one of the other profiles, but for a technologist. I know that much. And it was in answer to the question, “What do you do when you feel overwhelmed or unfocused?” And this was a question that he asked himself which was, in effect, “How much would I pay – at age 80-90, looking back at my life, how much would I pay to relive this moment right now?” And I ask that a lot, whether it’s just sitting on the grass, watching my dog play with a stick, or any number of times. That’s a question that I ask myself a lot, like, “Forty years from now, how much would I pay?” And I think about –

Graham Duncan: Sam Harris on his app has a great three-minute gratitude talk. And he says, “Imagine you died yesterday evening. What you would give to be back in this moment of having a shitty dinner with your kids and wife where you’re all in a bad mood, and you’re all in this very contracted state?” And I think that’s such a – it borders on the cliché. But there’s something in just daily reminders of that. I think a lot about the Byron Katie thing of the past and the future are simulations in your head. And the only thing that’s actually real is this current, now moment that we’re in.

Tim Ferriss: So we talked about a little bit earlier – well, we’ll do a couple more questions. And then we can wrap for this round one on this podcast. We talked about your one option for the billboard which was the Kwame quote. Are there any other quotes, statements, questions, words, anything that you might put on a billboard besides that?

Graham Duncan: Yeah. Another candidate would be this quote, “We are not human beings having a spiritual experience. We are spiritual beings having a human experience. Welcome to the party.” And that’s a mashup of Pierre Chardin. He’s a French Jesuit priest and philosopher. And then there’s a meditation on the 10 percent Happier app called “Welcome to the Party” by Jeff Warren where you’re saying to every negative feeling, anything that comes up, “Welcome to the party.”

And he says, “Imagine you’re an affable host. And there was this great moment earlier this week where my son, the seven-year-old who’s still afraid of the dark in his room – and he was running back to get his clothes. And he yelled out, “Welcome to the party, Fear of the Dark,” which made me so proud because he’s able to – that fear is object to him. He can feel his feelings. He can feel his – but anyway, I like that quote because every time I read it, it shifts the, “Oh, this is what it’s like right now. This is a human experience. And somehow, this is our moment to have –” have you heard either of them before?

Tim Ferriss: I like that. No. I haven’t. I really like it. I’ve been reading a lot of writing from Jesuits recently for some reason. And I’m not sure if it’s a Jesuit thing or if it’s just coincidence that I happen to be picking these up. I really don’t know the first thing about the Jesuit Order. But the line, “Welcome to the party,” is so helpful because I’ve certainly read a thousand times in different forms making your emotions an object or not identifying, for instance, with, “I am angry,” but phrasing it in some fairly unnatural way like, “I am currently experiencing anger.” Okay. Fine. But this is much more memorable. And it’s being the affable host to your whole range of emotions, including when the grumpy, cantankerous uncle shows up. And you’re like, “Hey, buddy. Welcome to the party. Right. Look it. You had a hard day. Come over. Have some punch. Welcome to the party.” I love it. I love it. Any others?

Graham Duncan: I also love this quote from Mark Twain right before he died. He was looking back at his life. And he said something like, “There isn’t time, so brief is life, for bickerings, apologies, heartburnings, callings to account. There’s only time for loving and but an instant, so to speak, for that.” And I like that because I think the perspective of somebody who’s really old and dying I find somehow extra high signal because they’re trying to draw your attention to something while you’re still at an earlier place of your life. And somehow, I find myself thinking about that quote a lot that all this stuff that feels so high drama, once you’re – when you’re 90, looking at it, you’re just going to say it was all noise.

Tim Ferriss: Yeah. Or it’s all noise and/or the day after you die if you’re looking down, and you’re like, “God, what I would give to have that shitty meal that I thought was the last place I would want to be. What I would give to have that again.” Graham, I always love spending time together. And thank you for making the time.

Graham Duncan: Thank you for having me. It was fun.

Tim Ferriss: Yeah. This was a lot of fun. I have a ton of notes I’ve taken for myself already and books I want to pick up, “Welcome to the Party” that I want to listen to. People can find you in a number of different places. I’ll just repeat them. Grahamduncan.blog – where they can find that essay that you mentioned earlier – and eastrockcap.com, @GrahamDuncanNYC on Twitter, if they want to wave and say hello on the internet. Is there anything else you’d like to mention, things you’d like people to check out, requests you would have of the audience, suggestions, anything at all that you’d like to say before we wrap up?

Graham Duncan: Well, I’ll just note I help produce this conference call, the SOHN Conference. We do it in partnership with CNBC. And we raise money for pediatric cancer. And we do that by bringing 15 hedge fund managers and venture capitalists together at Lincoln Center. They each bring an actionable investment idea. And we’re doing it this year, May 6th, at Lincoln Center. So anybody listening, if you can afford to donate, come. If you can’t afford to donate, DM me on Twitter, and I’ll come up with some of our free tickets. But it’s a great gift exchange we have where basically, the hedge fund managers bring their ideas, people pay money to come hear them, and then we give that money to the leading pediatric cancer researchers. So that would be one.

Tim Ferriss: That’s the SOHN Conference foundation, S-O-H-N, which I’ve attended before and found endlessly fascinating. I mean endlessly fascinating.

Graham Duncan: Yeah. It’s a fun day.

Tim Ferriss: Yeah. It’s a really mind-stretching experience. Anything else that you’d like to say?

Graham Duncan: No. I think that’s it. No. I got it.

Tim Ferriss: All right. Full stop. Graham, until next time. And we have a lot to otherwise catch up on. But thank you again for being so generous with your time and you caffeinated beverages. And to everybody listening, I will have links to everything in the show notes. So the books, the essays, the various figures and people, thinkers we mentioned which you can find, as always, at tim.blog/podcast. And just search Graham or Duncan, and everything will pop right up. And until next time, pay attention to the present. It’s all you get. All right. Thanks, guys.

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Graham Duncan — Talent Is the Best Asset Class (#362)


Photo by Heidi Gutman/CNBC

“Everyone’s genius is right next to their dysfunction.” Graham Duncan

Graham Duncan (@GrahamDuncanNYC) is the co-founder of East Rock Capital, a multi-family office investment firm that manages $2 billion for a small number of families and their charitable foundations.

Before starting East Rock 14 years ago, Graham worked at two other investment firms and started his career by co-founding an independent Wall Street research firm. Graham graduated from Yale with a B.A. in ethics, politics, and economics. He is a member of the Council on Foreign Relations and serves as co-chair of the SOHN Conference Foundation, which funds pediatric cancer research.

Josh Waitzkin, the chess prodigy who served as the basis for the book and movie Searching for Bobby Fischer, calls Graham “the tip of the spear in the realms of talent tracking and judgment of human potential in high stakes mental arenas.”

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.

#362: Graham Duncan — Talent Is The Best Asset Class

Would you like to hear another episode with an investor who understands the value of quality time? — Check out my conversation with Peter Mallouk, in which we discuss illiquidity as a feature rather than a bug, when the risk of being out of the market is greater than the risk of being in, and much more. (Stream below or right-click here to download.):

#356: Peter Mallouk — Exploring the Worlds of Investing, Assets, and Quality of Life

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

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The Tim Ferriss Show Transcripts: Caterina Fake (#360)

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Please enjoy this transcript of my interview with Caterina Fake (@caterina), a long-time Silicon Valley pioneer. Caterina is a co-founder 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 a co-founder of Flickr. 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). She is an early creator of online communities and a long-time advocate of the responsibility of entrepreneurs for the outcomes of their technologies. Caterina is also the host of the new podcast Should This Exist?, which asks, “What is technology doing to our humanity?” Should This Exist? can be listened to on Apple Podcasts, at shouldthisexist.com, or anywhere podcasts are found. 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.

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


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Tim Ferriss: Caterina, welcome to the show.

Caterina Fake: I’m super excited to be here, Tim.

Tim Ferriss: And you’ve been long requested as a guest on the show, and I am really so thrilled to finally have a chance to spend some time together because I feel like it’s been many many years in the making.

Caterina Fake: It has. I remember, actually, when you first moved out to San Francisco, and you and I had some conversation or email exchanged very early on. So indeed.

Tim Ferriss: And I remember I was so impressed with, at one point, one of your responses because I asked if you would, I think, be a panelist or a speaker at some conference. It might have been South by Southwest, could have been another, and you said, “I’m taking a year break from conferences.” And I was so impressed by the categorical decision to not do any speaking engagements that I made a mental note of that.

There’re so many places we could start, but in the process of doing homework for this, I found mentioned, and I wanted to do a fact check on this, of you having plane tickets automatically cancelled, and other issues related to your last name. Is that accurate? Did those things actually happen?

Caterina Fake: This has happened to me many times, in fact. And I discovered that it was actually the systems at KLM and Northwest that would throw my ticket out, my last name being “Fake.” And I have missed flights and have spent way too many hours with customer service trying to fix this problem. Here’s another thing too, is that I was unable for the first two years of Facebook to make an account there also. And probably  all of my relatives.

Tim Ferriss: Do you use a workaround now to prevent these types of problems? Or has it just been resolved at this point?

Caterina Fake: It has been resolved by my not taking those airlines anymore. I’m serious. I actually will see a flight on KLM or Northwest, and will not take it. I’m not even sure if those airlines are around anymore.

Tim Ferriss: I’m not up to speed on the airlines. It’s like, magazines and airlines, which go out of business faster? Despite these travel challenges, you somehow manage to land in Silicon Valley. And we were chatting before we started recording about your, I think the term was “stochastic” path and eclectic background that you have. But could you describe for people how you ended up in Silicon Valley? Did you do Stanford MBA and study computer science before that, and it was the objective all along? How did it come to be?

Caterina Fake: That’s actually not my path, the Stanford MBA. However, what happened was I was living in New York and had spent the summer in Arkansas rock climbing, and was big into rock climbing, and had hooked up with a group of people there, and we were on our way to Nepal to do a big climb.

And so I showed up at my sister’s apartment in San Francisco; she had moved there first. I am from the east coast originally, and I had my ice pick, and my crampons, and my backpack full of gear, and was planning on doing a big climb in the Himalayas. So she, being my older sister, put me up for a couple weeks in her house, and I was visiting her on my way out to Asia. But what happened was my trip was delayed because one of our head climbers had become injured. And then the trip was delayed, and delayed, and then finally it was avalanche season and it was no longer possible for us to do the trek through the Himalayas, and so I ended up staying in my sister’s spare bedroom.

At the time, San Francisco was cheap enough that people had spare bedrooms, and so I just stayed. And my delightful sister, who I love dearly and has always taken care of me throughout my life, her little sister shows up and six months into my stay there, she suggests to me, “Hey, Caterina, you might want to think about getting a job.” So this being 1994, the most interesting thing that was going on at the time in San Francisco was the internet. And so I got started then as a web designer.

Tim Ferriss: And did you have a design background? Let’s flash back six months. So you’re landing in San Francisco en route to this climbing expedition. At that point in time, what did you think you were going to do when you grew up, so to speak? Or over the following five to ten years? Did you have an idea of where you thought you were going prior to the internet entering the picture?

Caterina Fake: Oh, yeah. My background is in art and literature, mostly. And from the age of, I would say, probably about 10 or 11, I had decided that I was going to be an artist and a writer. I was an art school dropout. I graduated from Vassar with a degree in English literature. And I had applied to grad school at Berkeley before this whole internet thing happened, and was planning on getting a PhD in renaissance literature. That was really my true love; I’ve always loved poetry. And the internet, which I’ve always had an interest in, had a computer and had been hacking around with it since I was young, was another alternate path that I took. So I had actually been very interested, and there were a bunch of professors that I went and interviewed with at Berkley. Renaissance literature was my great love.

Tim Ferriss: Do you think that your background, which is in some respects, I suppose atypical for someone who ends up in tech, did you feel that, say, literature has provided you with some type of advantage, or context, or perspective, or other aspects of your background that ended up really assisting you with both operating in the tech world, and investing in the tech world? Do you feel like those things have been in any way an advantage?

Caterina Fake: I really think that people who come from outside of the industry have a superpower that people who have lived within the industry their whole lives, or have spent all of their time in that mindset, it does give you a super power, it does give you an ability outside, to be able to see things in a different way. And if you look at all of the companies that I’ve been involved with, and the investments that I’ve made, they are companies that emphasize creativity, communication, connection, collaboration, and community. And a lot of that comes from this background in humanities that I have.

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. And in many ways, I’ve always encouraged entrepreneurs, and investors, and people who are interested in entering technology to come at it from a different field, and really emphasize those parts of themselves that are different from the mainstream expectation of who you’re supposed to be, and what you’re supposed to know, and where you’re supposed to go to school. Coming from a different direction is almost always an advantage.

Tim Ferriss: Coming from the interrupted climbing expedition, as you did six months or so after landing in San Francisco, then being encouraged – sounds like very gently and understandingly – by your sister to go consider getting a job, what did the subsequent 12 months or so look like for you when you stepped into that world?

Caterina Fake: This was a very early stage in the internet, and there were no manuals, or guides, or blog posts, or anything like that to help you shape your approach to the industry, and so you had to make it up yourself. It was a very small community of people that were interested in the web at that time, they were all centered down in South Park, which we, at that time, called Multimedia Gulch, which is a funny terminology. It was very early stages. And so I had to teach myself HTML, I had to figure out how to design for the internet. And it was a very experimental, DIY self-education. At the time, getting involved in that at that very early stage, it was such a small community that I just happened to be really lucky that my friend’s roommate, actually, worked at one of the very first web companies and was able to teach me HTML.

Tim Ferriss: And where and when did Flickr enter the scene, or the embryonic stages of Flickr? When did that come onto the radar?

Caterina Fake: It’s interesting because we were actually in the process of building something different when Flickr came about. Everybody calls it pivoting these days, but it was a pivot, and came out of an unsuccessful game. It was also built during the lull after the .com boom, there was the .com bust in 2000, 2001, 2002 was when things were actually looking very bad for technology, and technology businesses, and startups, and the ability to get funding. We were unable to get funding for the game that we were working on, and so Flickr was a kind of Hail Mary that we were able to turn into a very successful business and then lead into the whole web 2.0 era, social media as we know it now. Although when we conceived of it, it was not social media, it was an online community.

Tim Ferriss: And if we look at Flickr as a successful Hail Mary, and we survey the landscape of Hail Marys in the entrepreneurial world, a lot of them don’t work out. A lot of these Hail Marys don’t work out. These sort of death knell, last gasps for breath as funding is running out, often those do not work out, but some do. And there are some examples of these pivots, whether it’s Twitter, or Flickr, or others that did work out. Can you discern what, perhaps, the ingredients were that made it a successful pivot/Hail Mary? Is there a particular way you guys thought about it? Anything at all that you might attribute the success to?

Caterina Fake: You know, it’s funny because there’s a conversation I once had with another investor who said that, “There are some entrepreneurs that are just so bull-headed, and stubborn, and they won’t quit, that companies really go out of business when the founder just quits. When they just stop. When they’re like, ‘I can’t take it anymore.’” And when I was in the Valley, I saw several examples of this. I was dating Ev Williams, the Twitter founder at the time, and it was an amazing thing to see, actually, because Ev had completely run out of cash; it’s the story of startups everywhere: it’s a race against the bank account, really, and he had nothing left when he was starting Blogger, but he just kept on going. It was a miracle. It was amazing to watch.

Blogger was eventually acquired by Google. Google went public, he then had more cash, was able to start the Obvious Corp., which then incubated Twitter. Having seen that first hand, close up, that kind of willful determination, I see that again and again. And when you see things like the pivot that we went through, we were living on cup noodles and not getting paid, and the only guy that was getting paid was the guy who had three kids on our team. Talk about fumes, we were really driving on fumes. And then a miracle happened.

What happened was, we had submitted an application to the Canadian government. Flickr was started in Vancouver Canada, and we had been rejected, actually, for this funding for our startup Game Neverending. And we had apparently checked a little box that said, “Re-submit next year.” Because what happened was, we were truly going out of business. I think we had taken money from our friends and family, and all of that money had been spent. And I remember this, it was December 23rd, it was two days before Christmas, a letter arrived saying, “Congratulations, we are giving you this start-up grant.” And it came out of nowhere. Really, we had a month or two left to pay our front-end engineer, and that was it. So this came out of nowhere, and that was what enabled Flickr to get off the ground.

Tim Ferriss: That’s so wild.

Caterina Fake: Yeah, it was. It was a super scrappy operation. This is days before AWS, and we just didn’t have a lot of cash, and literally the servers were in a colocation center, and we literally had the phone number of the woman who worked down at customs who would call us up and say, “Hey, your new server has arrived from Austin, Texas. Dell has sent you the new server.” We would rush down there, plug in our new server at the colocation center, and load up the software, and keep going. It was a super sketchy foundation on which all of this stuff was built.

Tim Ferriss: There’s certainly some luck involved with the checking of this box, but there were, I would imagine, also some good and probably some bad decisions that were made, but probably some good decisions that were made that in retrospect contributed to what Flickr then became. I was wondering if maybe we could explore one that I have just here under the exploratory bullets, which talks about you and, I think it’s George Oates, spending 24 hours a day, seven days a week, greeting every single person who came to the site. Is that true? Is that something you guys did; manually greeting everyone who came to the site in an effort to build community? Or what was the rationale behind that, if that’s true?

Caterina Fake: Yeah, I think that’s to some degree true. We had, I remember, I looked back in the first three months of Flickr, the team each had posted something like 50 posts a day in the forums on people’s photographs and had really been very strong participants in the community as it was being built. And I really am a big believer in this. I actually wrote an article for Wired at one time talking about how if you read the Bible, Abraham, so and so begat, so and so begat, so and so and it goes on for pages and pages, and I really do believe that the entrepreneur is the Abraham of the company, and so therefore is dictating what the practices are of the community. How everybody behaves; how people respond to other people’s photos.

All of those things I think are basically how communities are built, and staying involved, and being involved, and having that conversation, and being live in that conversation all the time is a really important part of building an online community. And all of this went off the rails a bit when online community was renamed and repackaged as social media. Because then it became a media platform in which people’s attention could be sold, and as we later discovered, people’s data could be harvested, and also sold. And that a very different way of building something than building a community from the ground up, which is, I think, what we were trying to do.

And so I think the community, even now, it’s been acquired by SmugMug, it’s got a new life ahead of it, that’s really the foundation of why it was such a strong community, and how, even after the Yahoo acquisition, and many years later, continued to be a very strong community, and a model of community online.

Tim Ferriss: It also strikes me how many companies that later become viewed as very large, like Airbnb, in the beginning, this also reminds me of this, whether it’s Brian or Joe Gebbia, I know better, talk about the early days of Airbnb, it was highly highly manual. And they would to things that didn’t scale very deliberately until they had to create a system for it. But in the beginning, it was really, really high-touch to build that community in the very early days, and it seems to be something that is sometimes missed by entrepreneurs who start something, and beginning on day one want to scale it to a million users, or 10 million users, or however many million users. Are there any other decisions or behaviors, best practices that you had in those early days that you think were critically important? Or mistakes, either one.

Caterina Fake: Yeah, it’s hard to say. It’s funny because when you look back at something that has been successful, I think there’s a tendency among entrepreneurs to attribute it to some action that they took. And one of the things you mentioned earlier, which I think is actually very important is that we were extraordinarily lucky. We had invented this at exactly the right time. And what had happened was, all of these things were converging at all of the same time. Friendster had come out, had gotten people accustomed to the idea of having a profile of themselves online, and more than half of the households in America had broadband for the first time, more than half of the phones were being shipped with a camera on them. It was just an unstoppable juggernaut because of the time in which it was intended, right? And part of that was being smart, and addressing that market, but a lot of it was also, I think, we were extremely lucky and well positioned to be taken advantage of all of these flows of information.

And Bill Gross, who started Idealab and has been the progenitor of, I don’t know, 500 companies? Many, many companies. He looked at the success of those businesses, many of them succeeded, many of the failed, and tried to figure out what it was about the companies that succeeded that helped them to succeed. And he looked at the team, execution, the financing, the market they were addressing, the timing, all of the things that potentially contribute to a startup’s success, and what he discovered was that more than anything, timing, timing was the thing that made those companies successful. And I think that if this had happened 10 years before to 10 years after, even five years before, or five years after, it wouldn’t have had the same momentum as it does now.

And I look at this as an investor now with Yes VC, my investment firm, and we’re always looking for companies that have timed it just right. That have found a parade and gotten in front of it. That are part of a movement. Because when you have that kind of a movement behind you, there’s some kind of cultural change that’s happening, there’s something that people believe very strongly in, there’s a change that society wants, it makes it so much easier to get ahead. People are more inclined to want the product or the service. They’re more inclined to talk about it. It’s already in a flow that’s moving forward.

Tim Ferriss: How do you, actually maybe we can look at this in a specific example, so let’s take – and this may not be an example of this, but it could be, if we look at Kickstarter. So you were the first investor in Kickstarter, or one of the first?

Caterina Fake: One of the first. And I actually invested in it when it was still a PowerPoint deck. It was not built yet, and Perry, and Yancey, and it was actually brought to me by Sunny Bates, who I think remains on the board now, it was so clear that that had to happen. And it was something that you felt in the culture. Something that you felt around conversations that were happening online. And this was a possibility that needed to bear fruit. It was very clear. And I think a lot of the things, if you look at, for example, Etsy. Etsy was at the forefront of the DIY, handmade movement. It was a rebellion against big-box retail and a return to the marketplace, which has always been a very person to person community-oriented place.

I traveled in Seria and went to those souks, the big marketplaces in Aleppo, which have now been destroyed, tragically. That was one of the most ancient marketplaces in the world. It was like a caravansary, people would bring their camels in medieval times and form a market there, and you could see that that was the genesis of, you talk about the genesis of Airbnb, or Flickr, or all those other companies, the genesis of markets was really sitting down, having a cup of tea, and negotiating for your rug. And Etsy had that, right? Etsy had that. And Kickstarter had that.

And there were these very person-to-person experiences that were manifested in places like Etsy, and Kickstarter, and Flickr, and a lot of these products at the very outset. And I think that that’s another thing that happened at the very beginning of Airbnb, it was very much about people coming together in a very essential and human way. And that was what set those companies on such a strong foundation.

Tim Ferriss: And what did you see that other people didn’t see, or what enabled you to see what you saw that got you to yes with, say, Kickstarter or Etsy, or other examples that might come to mind? Because a lot of these companies that are name brand now faced a lot of rejection and a lot of nos and people didn’t get it. Including people that most folks would consider quite smart. It’s true for Airbnb. Uber was turned down by hundreds of people on AngelList when it went out. What did you see that other people missed? Or did you have – that could be in the companies themselves, or in the founders, or anything else, but what did you see that got you to yes? Because, I’m sorry to interrupt myself and you, because a lot of founders will come in and a very high percentage will claim that they’ve found that parade, right? That they’re in front of these three converging trends that are inevitably going to sweep the world. So how do you end up betting on the right horses?

Caterina Fake: Like we were saying earlier, my difference helps me. I’m also a woman in a male dominated industry. I’m a mom. There’re many things about me that are nontypical. And when I first saw Etsy, it was the beautiful thing, and I actually took it to Reid Hoffman, who had invested in my first company Flickr, and a bunch of other people in the Valley, and they lifted their eyebrows and they said, “Okay, let me get this straight. This is a bunch of women, mostly, knitting sweaters and selling it to each other?” And I said, “Exactly. Don’t you see the opportunity here?” And I think coming from this humanities background where I had spent a lot of time studying culture and society and people, and what was happening around me, and human interactions, and how the culture was changing gave me a special view into that world that was missing, that somehow other people weren’t seeing, that were nontypical, was outside of the pattern recognition of Silicon Valley.

And a lot of the investments that I have made have fallen outside of the typical pattern recognition that everybody takes advantage of in order to spot success. And I think I’ve always had that. My partners at Founder Collective used to tell me this all the time. I would bring in deals, they’d say, “Your deals don’t look like anybody else’s deals. Your deals look very different. The people that you’re backing, the people that you consider as potential entrepreneurs fall far outside of what is typically understood in the Valley as a typical investment.” And they said this to me over and over again, like, “Wow, where did you find these folks?” And most of the time they found me.

And I think part of the reason we started Yes VC, and that we wanted to start a brand new firm, was because we saw that there was a sea change happening in technology, and that people that were nontypical, people that didn’t fit the typical pattern of an entrepreneur as defined by the Valley culture, were now liberated from a lot of prejudices that they’d been working against before. And if there had been an investor in 2004 when I was raising money for Flickr that looked like me, I would have gone straight to her, but there just weren’t that many. And so I think things have changed a lot. And nontypical investors, people from outside of the Valley, people that are in different regions, people of color, women, I think there’s so much more opportunity right now for those kinds of businesses to flourish and are being given a voice. And when all of those companies were starting, it was actually much harder to find people who understood those business models, those founders, and their orientation.

Tim Ferriss: Let’s talk about atypical, and you as an atypical investor for a second because this is part of the reason I was so excited to talk, and I’d love to chat a bit more about a few things you’d mentioned. So you mentioned your familiarity with culture, society, people. And then, whatever it was, five or 10 minutes ago, we talked a little bit about timing. And this is going to be a bit of a long question, so bear with me, was how could someone who wants to cultivate that type of awareness go about developing a better perspective, or a different lens on culture, society, people, and changes that end up getting, in some way, represented by these fantastic opportunities like Kickstarter or Etsy? I’ve read, in doing homework for this interview, that you’ve recommended for entrepreneurs books like The Innovator’s Dilemma. But I’ve also read on your site, caterina.net, a paragraph, I think you’ll recognize this, this is from 2018, but a comment on Stewart Brand’s work, and I’ll just read this because it’s pretty short.

So “Through Stewart Brand’s work, beginning with How Buildings Learn (one of my favorite books) and his work with the Long Now Foundation, I learned to look at time differently, and technology differently, and to think about how time is cooked into everything we do today, especially as regards the ephemeral nature of all the time spent on computers and in online media.”

So I’m curious, if, say, How Buildings Learn, or Stewart Brand’s work, would be something that you would recommend to people coming out of more of the CS, or prototypical Silicon Valley background? If they wanted to develop some of the perspective that you have, are there any resources, or books, or way that you would suggest people explore?

Caterina Fake: I love that you brought this up, Tim, because part of the reason I was super excited to talk to you about this is because I think you and I share an obsession with time.

Tim Ferriss: Yes.

Caterina Fake: And your books are The 4-Hour Workweek, The 4-Hour Body, all of these things having to do with time. Managing your time; thinking about time. And when you really look at it, kind of from the 35,000-foot view, time is all we’ve got. And time management is possibly the thing that I’ve done most in my life in terms of generating the kind of life that I have wanted to lead. And it went way back. Back to when I was young, and I was actually forbidden by the dean at my school from taking any classes before noon because I’m just one of those people, I work really well at night. I’m a night owl, and I could not make it to my classes in the morning. I actually failed a photography class because it was at 8:00 a.m. No way. I couldn’t do it.

And I honestly believe that one of the reasons I’m an entrepreneur, and that I have always worked for myself, is so that I can manage my own time. And I have always thought that the highest standard of living really come from being the master of your own time. Deciding where you want to go in the morning, what you want to do, and that that is so important. And knowing that when you have the energy to put into your work, you can do that. Whether or not it happens at 8:00 a.m. or if it happened at 10:00 p.m. And I actually gave an interview at Businessweek once about my peculiar schedule, in that I wake up in the middle of the night between 2:00 and 5:00 in the morning, and I do three hours of work. I don’t turn on the computer. I write everything on paper; I do my best thinking and writing and ideation during those hours in the middle of the night, and then I go back to sleep and get up and carry on with my day. But without that, that talkative time where I’m uninterrupted, I’m offline. I’m free and liberated in a way that you just don’t get during the work day; it’s a magical time.

Tim Ferriss: I have so many questions. This is great. This is great. So I was going to ask you about this waking up between 2:00 a.m. and 5:00 a.m. I didn’t realize that you went back to sleep. I’ve been reading up, I’ll explain why maybe another time, but on the history of lucid dreaming, and it appears that biphasic sleeping, where people would have a first sleep, wake up and then go back to bed, at various points in history has been quite common. It’s not something that I’ve done a whole lot of. But could you give us an example of what you might work on, on paper in those three hours? So you wake up at some point between 2:00 a.m. and 5:00 a.m. specifically, what do you then do? Is it something that you’ve already planted at the top of a piece of paper as a prompt, and you know you’re going to work on a specific problem? Is it like long-hand stream of consciousness? What do you do during those handful of hours?

Caterina Fake: It really depends. Sometimes I wake up and – I’ve always written books, so I’ve been working on a book now for the past three months, a new book. I write sometimes poetry, I sometimes just open up my journal and start writing. I can be working on a big problem. The five-year plan for my startup or something like that. Any kind of big picture thinking, any kind of thinking that involves creativity, intuition, all of that. The right brain, and not the left brain. And I’ve studied all of these people. I come across these articles, there was an article that was recently sent to me that was about this, I actually forget his name, but he was an AI guru, I think he’s from Cambridge. I did not manage to read the whole article because I got stuck on the very first half where it described how this Cambridge AI genius woke up and he didn’t communicate with anybody until noon. And that he managed to have a relationship with his family and they have developed a language of grunts and smiles, so that his thoughts didn’t get interrupted. And then, when he finally went to work around noon, he had one meeting.

And I was like, “Oh my god, this is a master of time management.” And preserving that flow state in your head, and preserving the ability of yourself to think, and wonder, and ideate is so precious and should be defended ferociously at all costs. And I’ve always felt that way. I’ve always had this – I call it cognitive defense. Really powerful cognitive defense. It’s interesting because this also shows up in some of the investments that we’ve made. For example, one of my theories about cultural movements right now is that there’s this very strong desire to simplify your life. We’re being constantly bombarded with information, with marketing, with new products, and you walk into a grocery store, and you’re confronted with 108 different kinds of toothpaste, right? And like a thousand articles that you could be reading at any given moment of the day.

And one of the investments that we’ve made is this company called Public Goods, which basically give you one shampoo, one conditioner, one dish soap, and sends it to your house so you’re not confronted with all of this paradox of choice, right? Which actually people want to reduce. And people want to constantly reduce the amount of stimulation so that they can focus, and so that they can live a more deep and fulfilled life. And I really think that in our society today, and you depict your podcast and hopefully my podcast, and eliminate all the others. You see what I’m saying? You have to focus in and narrow down and eliminate a lot of the noise in your life as much as possible. It’s a very difficult thing to do. And so I see the time management part of our lives as being just a crucial thing to defend our space, our happiness, and our individual lives.

Tim Ferriss: I was looking at your site earlier today, and found an example of removing noise. And it was a simple example, but might be a jumping off point for exploring other examples. This is DF Tube – that is Distraction Free Tube – which is a plug-in that you use to clean up YouTube. Removes the recommendations on the sidebar, the crap on the homepage, inane commentary, poof. And so I made a note to use that myself. Are there any other tools, or books that you found helpful, or approaches that you believe very strongly in? The waking up in the witching hour and working for a few hours without a screen is, I think, a great example. Then you have the very tactical, like the micro tool, something like this extension. Are there other things that come to mind that you found or find particularly helpful?

Caterina Fake: When I am at my most flourishing and productive self, I’m actually online a lot less. And there’s now all of these tools, Screen Time on Apple, and the Apple phone, and all of these things that I think are great. And during the periods in which I think I’m most flourishing, most productive, what I’m doing is I’m going – I did this for as long as I can, and then I fall out of the practice, occasionally, but I always try to get back is, I would schedule a time to do my email in the morning, 10:30 a.m. to 12:00 p.m. and then again in the evening, 4:30 p.m. to 6:00 p.m. and I would be offline as much as I could in the times in between. Now a lot of us have work that we need to do, and things that we need to do online, but to be super disciplined about the time that you spend online, I think is really important. And I’ve always done this, and I have a notebook that I keep next to my computer and it says WNO on the cover, which stands for When Next Online. And you just write a list, and it says “I need to email my accountant. I need to look up what the name of Bob Dylan’s second album was. I need to go fix this misinformation on this Wikipedia page.” You have the urges during the course of the day to go online, and then the next thing you know, three hours have passed and you’re watching unboxing videos on YouTube, right? And you’re like, “What happened? Where did it go?”

And so I think that you just need to get on top of that. I think that’s one really important thing that you can do. This is kind of a major thing. I fall out of this all the time, you see me watching unboxing videos on YouTube all the time, so you just constantly have to bring yourself back to that and realize how much of a time-suck that is and it can be. And realize also that it’s that kind of activity that’s taking you away from a life fully lived. I remember reading an article on Quora, where somebody said, “I want to be an entrepreneur, as successful as Steve Jobs and Elon Musk. How do I do that?” Right? Many people would like to know the answer to that question.

And one of the respondents was Justine Musk, Elon Musk’s ex-wife. I thought this was wonderful, right? Because she knows firsthand actually what it takes to be Elon Musk, and she responded, “Well, first of all, Elon Musk would never be asking this question in a Quora forum.” And that response stuck with me because it’s true. He was off building PayPal, he was building Tesla, and was off doing that, and not wondering how. You see what I’m saying? He wasn’t reading forums endlessly about that, but was out instantiating those ideas, and that really stuck with me because I think it’s true. You can spend a lot of time in preparation, and I think that’s good to an extent and to a degree, but really living it, really being in it, I think is the most important thing.

Tim Ferriss: Yeah, I always have to reel myself in, in a sense, because I love reading and reading is a very socially acceptable form of procrastinating. So I don’t do it as much online, although I’m certainly guilty of that at times. But Kathy Sierra a long time ago said to me, or it might have been in a presentation she gave, but I was sitting in the audience, about focusing on just in time information, not just in case information, and that really stuck with me because I have a tendency to try and stockpile information in case of the one percent chance that I need A, B, and C in the next six months, but it’s not a great use of time.

Let me ask you about poetry. So you mentioned you sometimes write poetry. And correct me if I’m wrong here, but I have some of your favorite poets including, Wallace Stevens, Shakespeare, Emily Dickinson. Why do you write poetry? What do you get out of writing poetry? What does that do for you?

Caterina Fake: It seems to be an external expression of an internal state. It seems to be the recognition of, and valuing of the inner life. I read something that somebody had written, let me try to figure out who it was…I can’t remember. It was something that I’d read just the other day that was worrying and was very concerned that our modern world made it impossible for people to have an inner life. That the inner life was vanishing from the world. That our life was so much of the time that we would normally spend with ourselves, with our dreams, with our thoughts, was vanishing because it was being filled up constantly with stimulation, entertainment, and our compulsion to be online. And basically, what I see is security exploits of the brain that the internet has managed to insinuate into our lives. And that poetry, writing, dreaming, paying attention to those kinds of things, and the cultivation of an inner life, is something that you have to deliberately do, that you have to protect in your life, and make time for, and recognize as important. And frankly, not do many things.

Many of the opportunities that present themselves, it’s just terrible how much FOMO is created by the internet. It’s endless. And there’s a thousand places that you and I could be right now. And a thousand experiences that we could be having and things that we could be doing. And those of us who are like you, like me, like a lot of the listeners are optimists, we’re possibilists, we’re people who believe in living life to the fullest. And the internet both cultivates that and makes those opportunities available to more and more people, hopefully, and yet too much possibility, as we’ve discovered, shuts us down and deprives us of fully lived experiences.

And so it’s interesting because poetry has always been part of my life. I was a bit of a rebel as a kid and as a student, and I’ve always had a very difficult relationship with institutions. I think my very anti-authoritarian nature is also one of the things that led me to becoming an entrepreneur. And I rebelled against these structures, and one of the very earliest instances of this was in the first grade when all of the other kids were learning to read, and I already knew how to read, and I was basically becoming trouble in the classroom for the teacher because I was impatient and I wanted to read. So I went to the library and I sat and I read poetry with the librarian.

I was only five or six years old, and I still remember some of those poems from when I was a kid. And they were just rhymes. Here’s one I remember [Eletelephony by Laura Elizabeth Richards]:

Once there was an elephant,

Who tried to use the telephant —

No! No! I mean an elephone

Who tried to use the telephone —

(Dear me! I am not certain quite

That even now I’ve got it right.)

Howe’er it was, he got his trunk

Entangled in the telephunk;

The more he tried to get it free,

The louder buzzed the telephee —

(I fear I’d better drop the song

Of elephop and telephong!)

Tim Ferriss: It sounds like a great metaphor for what happens to brains when they encounter the internet for hours a day.

Caterina Fake: Exactly.

Tim Ferriss: How on earth do you remember that? That’s incredible.

Caterina Fake: I have this crazy memory. And I have for a long time, I think, since I was in my early teens, I decided that I would memorize poetry as a way of bringing the beauty of thought and language, and I always felt that poetry was one of the highest achievements of human thought, and beauty, and an embrace of the world. And so I wanted it to be part of me. And so I started memorizing poetry as a way of bringing it into my unconscious. As a way of having it always with me from a very young age, and so I started memorizing poetry as a bit of an eccentric teenager. And I have a lot of that love of poetry, but It’s deep inside. And I can recover a lot of this poetry at times when it’s needed. When you’re going through some kind of crisis or difficult times, or depression, or some kind of bad state you find yourself in. suddenly, some oracle from deep in the unconscious will come out, and Shakespeare will have said exactly the right thing, and you’ll then know what to do. It’s kind of this amazing strategy I’ve carried with me my whole life.

Tim Ferriss: For those people listening who, like me, who have minimal exposure to poetry, or at more point were introduced to the wrong poetry, which was just completely confusing and seemingly designed to remain abstract, and obscure, and confusing, are there any poets or collections you might recommend people start with if they wanted to dip their toe in the water of poetry?

Caterina Fake: I honestly think that there’s no one poet for everybody. And that the best way to start is to just go to, I think it’s poetry.org. It’s this wonderful font of poetry, and just start digging around and find what you love. You mentioned some of the ones that I love. I love Wallace Stevens, I love Emily Dickinson, I love Shakespeare. I wrote my thesis in college on James Merrill. I love W.H. Auden. It just goes on and on. We could talk for hours about this. but it’s important that we do this. I’m going to, Tim, if you don’t mind, dig up this quote from Charles Darwin.

Tim Ferriss: I do not mind.

Caterina Fake: Hang on a second, I’m going to Chrome here and I’m going to say… there is this beautiful thing that he says…I’ll find it, it’s online somewhere.

Tim Ferriss: Yeah, take your time.

Caterina Fake: Okay, I think that this is a beautiful thing because he is an amazing scientist. And he lived the life of the mind. And Darwin’s regret was that he had become, he said, “a machine for grinding out facts a figures.” He had become machine-like in his thinking, and he said, later on in his life, “If I had to live my life over again, I would make it a rule to read some poetry, listen to some music, and see some painting or drawing at least once a week for, perhaps, the part of my brain now atrophied would then have been kept alive through life. The loss of these tastes is the loss of happiness.” And I think that’s pretty powerful coming from as great a scientist as Charles Darwin because we live it, what I call, the technic. We live in a world of mechanistic being and thought and science. And all of those passions that throughout, since time immemorial, has sustained humanity, are getting lost somehow, or they’re slipping away, or they’re not part of our daily life. And I think we have to deliberately put it back in and continually put it back in, and make sure that we don’t lose it.

Tim Ferriss: How much of the poetry that you write for yourself remains just for you, and how much of it do you show to other people?

Caterina Fake: I would say 100 percent of it remains just for me. It’s interesting because many people have asked me this over the years because I’ve actually written half a dozen novels; I have written, probably at this point, two or three books of poetry if it were to be in published form. But I have somehow never let any of that out into the world. And part of it is that it’s such a precious part of me that in some ways, I have a very strong tendency and desire to be successful in the world, and I worry that it will go out into the world and it will be subject to the same laws as have led to my success in business, which it’s a very different thing. And so it’s funny because I find that everyone’s like, “Oh my gosh, this is great, you should publish this,” when it’s encountered. And I’m kind of like, “Well, maybe.” But in the end, it’s so valuable to me, that in some ways, if it were to escape out into the world, it would lose some of its power.

Tim Ferriss: Yeah, I think that’s very wise to protect that. After my first book, I’ve run into a lot of entrepreneurs who talk about, say, taking as a lifestyle business, something they love doing in their spare time, on say, Saturday afternoons. Going surfing, or something like that, and turning it into a business. And I’m always very hesitant to recommend that because if it’s something that is this creative outlet that is pure in a sense, and gives them some reprieve from the expectations and pressure of the outside world, I think it’s very smart to keep that for yourself. And you talked about very deliberately building these things into your life.

And you also mentioned a name, and I might be pronouncing this correctly, but W.H. Auden, am I getting that right? And there’s a quote of Auden’s that I pulled up because I could only remember the first line, but I’d love to talk a little bit about your routines. And the quote goes as follows: “Routine in an intelligent man is a sign of ambition.” Of course, it’s blessed everybody, but, “Routine in an intelligent man is a sign of ambition. A modern stoic knows that the surest way to discipline passion is to discipline time; decide what you want or ought to do during the day, then always do it at exactly the same moment every day, and passion will give you no trouble.”

Okay. I’ve read that you very often will eat the same entrée at certain restaurants if you decide you like something. Are there routines that are particularly important to you aside from those that we’ve already discussed? Anything that you make sure you do in the mornings, or that you make sure you do in winding down, or that you do once a month, once a week, once a quarter? Are there any particular routines that help you in structuring your life and your time that you can think of?

Caterina Fake: I have a very idiosyncratic schedule. And the reason for that is that I have, like you say, I find that thing in the restaurant that I love, and I always order it. Because it’s been proven again and again that the burden of decision-making wears you down. And that the fewer decisions that you make over the course of the day, the better decisions that you can make, and the more energy that you have left over for the important decisions in your life. And so famously, Albert Einstein had one suit of which he had five different versions, or something like this, so he didn’t have to think about what he’s going to wear in the morning. Eat the same food. I kind of feel as if these patterns – if you figure out what it is that you’re happy no longer making the decisions about. It’s one of the principles behind Public Goods, this company that I mentioned earlier, is that you don’t have to think about what shampoo to buy. You just don’t have to think about it anymore. You kind of check that box, it’s done, you’ve got a default.

And so building these defaults into your life is super important. Things that you don’t want to think about anymore. And whether that be what you eat, what you wear, things that you’re less invested in. So that, when you’re in like my witching hour, or the hour of the wolf, or whatever you call that, when I’m in that state, I can go wide, right? I can make a thousand decisions. I have freedom to go into dark corners that I haven’t yet explored that I can think really broadly in, be more creative, and have dreams and revelations that are just not possible if you’re crowded into tiny decisions all the time.

Tim Ferriss: Let me take a step back. So you mentioned in passing something when we were discussing poetry, and how certain poems or phrases would come to mind at seemingly the perfect moment when you need it the most. And you mentioned depression very briefly, and that’s certainly something that I have some personal experience with; is that something that you also have personal experience with?

Caterina Fake: Yeah. When I was a teenager, I was actually quite a depressed teenager. I went through a super bad period of my life when I was in that state that’s familiar to a lot of depressed people where I just couldn’t get out of bed in the morning, and just wanted to stay there all day, and was reluctant to expose myself to the world because I felt very vulnerable and needed to basically hide in my cave. And I think that many of us go through these. It’s just common to the human experience that this be a state. And I honestly think there’s a reason for it, right? I dislike like the term depression, because I think a lot of it is better described as melancholy, or despair, or there are older words that seem to describe it. It seems so clinical to talk about it in terms of depression, because I think that it’s part of a fully lived life to go through these periods of deep unhappiness, and dissatisfaction, and questioning, and despair, even.

And without that, you live always on the sunny side of life, I talk about this in the Jungian sense of the shadow. If you’re constantly rejecting the shadow, if you’re constantly living life on the sunny side – this is what happens on social media, and this is why social media can be so diminishing of people’s humanity is that people are always, I call it social peacocking, right? They’re showing how great their life is. They’re showing all of their happy moments. They’re showing all of their successes and not their failures. All other triumphs, and not their doubts. And basically, providing a highlights reel of their life, and this is very damaging to the psyche, to people’s humanity of not acknowledging, living, and frankly, giving time and space to those parts of yourself that are less savory. That are mistakes. I see it all around. And you see it all around, right? You look a all of your happy, successful friends on Facebook, or Instagram, or what have you, they’re always going fabulous places and doing fabulous things. But what about the shadow, right? What about the shadow?

There’s this really wonderful essay that I encourage everybody to read by the science fiction writer Ursula Le Guin, about the shadow. I talk about it, there’s a blog post on my website that’s called Social Peacocking and the Shadow. And in it I link to a short story by Ursula Le Guin about the shadow, which I think is a very important part of people’s humanity, which somehow is not being given space online.

Tim Ferriss: I’ve not yet read the piece, but how would you suggest, you can either suggest or talk about your personal experience, people accept the shadow, or work with it without falling into a dangerously deeper extended state of despair?

Caterina Fake: Like a pit of despair?

Tim Ferriss: Yeah, exactly.

Caterina Fake: Well, it’s interesting because I actually think that the way to start out with that is to accept the shadow in other people. Because we have this idea of other people as being more rich, successful, beautiful, happy, they’re in a better relationship, they have better teeth, they have thicker hair, I don’t know what the thing is, right? Some insecurity that we have we see in others as something that we don’t have. And there’s a wonderful sonnet by Shakespeare on the subject. I think it’s sonnet…what is it? Hang on a second…

Tim Ferriss: Take your time.

Caterina Fake: Sonnet Shakespeare, which one is it? That’s what I mean about the poems that come back. I think it’s 29. Sonnet 29, yes. Here it is. Can I give you this poem?

Tim Ferriss: Yes, please.

Caterina Fake: Okay. It’s Sonnet 29 by Shakespeare.

When, in disgrace with fortune and men’s eyes,

I all alone beweep my outcast state,

And trouble deaf heaven with my bootless cries,

And look upon myself and curse my fate,

Wishing me like to one more rich in hope,

Featured like him, like him with friends possessed,

Desiring this man’s art and that man’s scope,

With what I most enjoy contented least;

Yet in these thoughts myself almost despising,

Haply I think on thee, and then my state,

(Like to the lark at break of day arising

From sullen earth) sings hymns at heaven’s gate;

For thy sweet love remembered such wealth brings

That then I scorn to change my state with kings.

Tim Ferriss: Beautiful.

Caterina Fake: It’s a beautiful poem, and I think what it speaks to is the envy, you know, “Wishing me like to one more rich in hope.” “Featured like him, like him with friends possessed,” and you see it all around you, especially when you’re in the state of despair. And it seems as if the world all around you is full of delight, and success, and happiness that is somehow unavailable to you. But what this poem does is it – “Haply I think on thee.” Right? And often this is ready as a loved poem as a celebration of the relationship that Shakespeare is presumably in when he’s writing all of these sonnets, but when you really think about it…

Mr. Rogers famously says, “Think about all of the people that loved you into being.” Right? Those people are not necessarily your lover, but they’re your mother, they’re your sister, there’s that teacher that saw something in you that other people didn’t see. It’s your friend. And it’s all around you. All you have to do is stop looking at those people that have the things that you wished you had, and look at those people that saw that in you, and realize that they’re all around you. So that’s what that poem does to me. And I feel as if, if you have all of these poems deep inside you, that they will come to you when you need them.

Tim Ferriss: You’re making me think a bit, I hadn’t thought about it in those terms, but only in the last few years I’ve started reading some very easy to read, very easily digested poetry by people like Hafez, and a lot of Sufi poetry.

Caterina Fake: Rumi?

Tim Ferriss: Yeah, Rumi as well. And they do stick. They really do stick. And they seem to have a particular stickiness. A greater stickiness than, perhaps, more clinical nonfiction. Something that is really artfully woven into beautiful language just has a higher stickiness factor because these poems do come to mind at the right time. Just never thought of it quite the way that you’re presenting it.

Have you found anything else useful for embracing the shadow, but not falling into a pit of despair? Or if you’ve run into entrepreneurs who are going through a pit of despair, which is certainly not uncommon. Are there any particular recommendations that you’ve made or would be prone to make?

Caterina Fake: Well, I think that when people are depressed, they’re also in some ways ashamed of it. And I think that’s one of the things that makes it feel so isolating, is that we feel that other people will judge us. That bad things could happen as a result of our revealing these parts of our self that are so troubled, or despairing, or unhappy, or failing, or unsuccessful. And that we always feel as if we’ve got to present our best face to the world. And this can be one of the things that makes it impossible to get out of it. And so one of the things that’s most important, especially in our world of diminished relationships with others is to constantly be in communication with others, to know who our friends are. To revive those lost friendships that we’ve had in the past that are very meaningful to us. To resume our closeness to others, and frankly, as Rumi would say in one of his beautiful poems, “Cry out in your weakness.” Of course, there’s a poem for everything. But this one is: “Cry out in your weakness because there are helpers in the world who will rush to save anyone who cries out. Like mercy itself, they run towards the screaming and cannot be bought off.” And if you address your suffering to others, you find that the suffering is universal. That we all go through these moments of shame, indignity, depression, unhappiness, failure. And that anybody who’s pretending that they don’t is just not true.

Crying out loud and weeping, Rumi says, are great resources. Right? Give your weakness to one who helps. It’s a beautiful poem. I think if you search for it, it’s called Cry Out in Your Weakness. And that is a very meaningful poem, I think, for people who are suffering because it’s basically giving you permission, which I think a lot of people need, to cry out in your weakness.

Tim Ferriss: Yeah. I really appreciate you being willing to talk about this and explore it a bit because it is a constant, like you said, and it’s come up so many time sin these podcasts, whether it’s with these brutal stories of rejection that Brandon Stanton of Humans of New York is telling, or any number of hundreds of examples that have come up. Like you said, it’s an illusion, and a really crippling illusion when you’re not only depressed, but are ashamed of it, feeling like you’re somehow uniquely flawed because that’s just not the case. So I appreciate you being willing to chat about this. and maybe we can continue on the shadow side for just a few more minutes and then we’ll shift gears.

You have an incredible memory; you have an incredible track record. I think a lot of the people listening, or some people, would certainly find that intimidating, which is part of the reason why also I wanted to bring up the depression just to humanize the profile a bit. Are there any failures, we’ve talked a lot about successes and known names, but are there any failures or apparent failures of yours that have set you up in some way for later success? Any noteworthy failures that come to mind? And if you don’t like the word failure, you can use something else.

Caterina Fake: It’s perpetual. It’s hard to single out a single failure. You look back at your miseries, your failures, the companies that didn’t succeed, the relationships that didn’t succeed, the great hope that you had for this or for that, and realize that you spent years and years working toward some failed project, or relationship that didn’t work out, or some kind of track that you fell into and it was a struggle to free yourself. It’s funny because I think that my orientation as a perpetual optimist leaves me with a sense of forward motion from all of those things.

One of the things that we talked about was how when I was a teenager I went through a very deep depression, and a state of despair and melancholy, to use different terminology around it. And I think always those periods were very formative. They are very important. You go back to them and those moments when you’re at your worst, at your weakest, at your least successful, and most alone, and look back at the path that you took out of them, and the ability to emerge from them, and to keep going in spite of them are some of the most meaningful parts of your life. Is that you have, really, reached the depths of despair, and have recovered from them. And the importance that that gives you, going forward, and your strength comes from that. And if you’re never tested, and you’re never in that kind of situation, God help you. It’s not a good state, right? The fullness of your humanity is emerging from those depths.

I’ve always felt that. And without that, without that experience when I was a teenager, without some of those experiences from my childhood, without those experiences perpetually throughout life, life cycles through highs and lows like that, and to appreciate those periods and not struggle to ignore them or somehow eliminate them from your life, is, I think, one of the healthiest things that you can do.

Tim Ferriss: And from people listening who are willing to have that broad spectrum of experience, including the dark moments, but are listening with envy to your talk of optimism, are there any books – I know this is the type of question that won’t die from me, but are there any tools, habits, books, anything that you would recommend to people who want to cultivate a more constant optimism? If they might have been just beaten into cynicism by spending too much time on the internet or whatever it might be, what would you recommend to those people?

Caterina Fake: Honestly, I think that a great deal of emphasis on long form reading, I think you and I both embrace this, and love books and love reading, and I know you read philosophy and Seneca, and I read Jung and poetry, go long-form, not short-form. Go deep, right? And not broad. I think that this is actually a really important thing. There’re a dozen books, and I can even write a list of these and you can post it in the podcast.

Tim Ferriss: In the show notes.

Caterina Fake: In the show notes, exactly. I can write you, oh my gosh, a list of a dozen or more books that have helped me throughout my life.

Tim Ferriss: Oh, for sure. 100 percent yes and yes. If you can mention any of them now, you don’t have to mention all of them, but all of them that come to mind right now, that was going to be the next place I went, so…

Caterina Fake: Yes. Good. So let’s just start. Part of the reason that I’m actually on the internet and love the internet so much is because of Jorge Luis Borges, who I’m a huge fan of, and actually was the motivation for me going online because I had discovered a community of Borges fanatics in Denmark that I communicated with very early on in my internet career. So that’s a big one. I think the best book of his to start with is Labyrinths. And it’s so much about the internet. It’s kind of the internet before the internet. It’s a beautiful thing. As I mentioned, poetry has been a huge part of my life, I love all of the ones mentioned previously: W.H. Auden, Wallace Stevens, Emily Dickinson, Paul Celan, Shakespeare, of course, and contemporary poets. There are wonderful poets out there that I look forward to their work. Natalie Shapero, Brenda Shaughnessy, the list goes on. I can put together a list for you of poets that I love and respect. I love, also, the ones you were talking about: Hafiz, Rumi, Kahlil Gibran; there’s a lot of really wonderful poets from the east that I think bear attention from us.

Tim Ferriss: Are there any other, whether it’s fiction or nonfiction long reads that you would recommend? And for people listening, I’ll definitely put all these in the show notes, so you’ll be able to access all these, but if any other come to mind. Jorge Luis Borges is just incredible in terms of the wordsmithing, and the art of his prose is really staggering. So I definitely second that.

Caterina Fake: I use Goodreads. And goodreads.com is actually a really great place for people looking to discover new books. It’s actually now owned by Amazon, and I put all of the books that I read there because I read a lot. I read at least a book a week. And I’m re-reading, currently, The Odyssey by Homer in a new translation by Emily Wilson. Other books that I have found to be really great that I’ve read in the past year are — a really wonderful book, A Tomb for Boris Davidovich by Danilo Kis; Hannah Versus the Tree by Leland de la Durantaye; Ethan Frome by Edith Wharton. I’m honestly just going through this because I have this massive list. The White Goddess, which is a very meaningful book by Robert Graves, which is about poetry and its sources. I’ve reread The Upanishads. There’s the writer who I just adore, W.G. Sebald, I don’t know if you’re familiar with him.

Tim Ferriss: I’m not.

Caterina Fake: But The Emigrants by him is just an amazing book. I could go on and on.

Tim Ferriss: What books, they could be from that list or otherwise, have you gifted the most to other people, if you gift books?

Caterina Fake: There’s a couple of wonderful books that are actually illustrated books that I have given out to many people, and I think it’s unfortunately out of print. There’s one called Drawings and Observations by the artist Louise Bourgeois, which is fantastic, and I’ve given that to so many people, as well as The Principles of Uncertainty by Maira Kalman. She’s famously an illustrator. Really beautiful books and full of life-giving thoughts. And you can tell that these women have lived very rich, profound lives, very thoughtful lives, very meaningful lives, and it’s there in the books. There’s another really wonderful book that I’ve also given out to a lot of people called Letters of Note. And that is letters that have been collected throughout the ages.

Tim Ferriss: I’ve been meaning to grab that compendium, so I’m really glad that you just mentioned that, Letters of Note. Check and check. To add to my ever-growing reading list. So you were just mentioning rich lives. We were discussing, or you were mentioning earlier the paradox of choice that many of us face, and certainly, you have more opportunities than you could possibly ever take advantage of in subtotal. Why decide to do a podcast? What was the catalyst or the reasoning behind that? Why Should This Exist? You have finite time, why apply it to that?

Caterina Fake: Well, I think that there’s a super important conversation going on in technology going on right now in the culture in which we live, that needs to be had. I was on my friend Reid Hoffman’s podcast, Masters of Scale, and I loved that experience. I love podcasts just in general, but this one was very gratifying for me because I had done what I thought of as a fairly garden-variety interview with Reid, and they had turned it into a story with conflict, and suspense, and drama, and made it super interesting. I loved it. I loved the podcast, I thought, these producers are geniuses, and June Cohen of Wait What, who produces Masters of Scale started a conversation about this new podcast and realized that the next conversation to be had in technology was about the human consequences of the technology that we’ve been building.

And I think that there has been, going back to the theme of the sun and the shadow, has been all about the sun. And we’re suddenly realizing that the shadow, which is always there, has now emerged. And we’ve seen what damage technology can potentially do to our humanity. And it was time for this podcast to come into being. So it just seemed as if, in some ways, this podcast is inevitable. It seems as if this is a conversation that’s happening now that needs to be emphasized and can potentially build a future that we’re deliberately building, and not lead us into unintended consequences that we’ve seen happen over and over again, most recently in the story of technology.

Tim Ferriss: Can you describe one of the episodes that comes to mind? Whoever is featured, what does the structure of a sample episode look like? What type of technologies, or topics, or entrepreneurs are you discussing?

Caterina Fake: So what we do is we find an entrepreneur who’s building a new interesting technology. And some of the interesting things have to do with AI, or CRISPR, or gene editing, and neuroscientific supplements to help us learn faster. Technologies which are in development where there’re entrepreneurs who are actually building it currently. And we have those conversations, and we bring in people from the industry, from outside the industry, people who have different ideas, psychologists, sociologists, historians, perhaps, and people who have a different perspective on technology and how it might impact our humanity. And then we have a conversation workshop with the entrepreneur about the potential outcomes, utopian or dystopian, of this technology, and how to steer it towards its best possible future.

That is really the best format of the show. And I think that this conversation, hopefully, will become part of the dialog about how companies are built — how they’re thought about — and how, at the very beginning of building these technologies are, frankly, carried out throughout the process of building these technologies that we not only ask the question: can this exist? Because so much of technology has made it possible for so many things to exist, but should this exist?

Tim Ferriss: Do you think there are safeguards or externally enforced constraints, or regulations of any type that could or should steer technology development and company formation? Or are we dependent on the internal ethics and moral compasses of the people who are developing these companies? Certainly, it’s a false dichotomy, you could have both, but I’m curious how you think about that.

Caterina Fake: I do think that we have, in Silicon Valley, enjoyed incredible latitude, and have been, basically, assuming that we have the ability to self-regulate. I don’t think that anybody starts off with this idea of being the supervillain, right? I don’t think anybody starts off in, “Haha, I’m kind of a Bond villain in my hideaway. I’m going to bring about the destruction of the earth!” Nobody starts out that way. I think that we all start out with best intentions and as Baudelaire has said in one of his many beautiful poems, we descend to hell by short steps, and we end up loving what we hate, and hating what we love. We end up doing things that we don’t intend.

And the constant questioning, the constant vigilance, the practice of asking ourselves the question, “Should this exist? Who is this harming? How do I remove bias from my AI? How do I make sure that this doesn’t fall into the hand of the wrong people? How is it that I continually think about the outcomes of my technology and its effect on people and what it might do to them and their behavior, and constantly having that as part of the process of building something new is a very important part of putting it on its right track and building the kind of future that everybody had hoped to build from the outset?”

Tim Ferriss: Well, I am very much looking forward to hearing these episodes, and also seeing how the conversations develop over time, right? I think it’s an important conversation and an increasingly important set of questions, and maybe just lens through which to look at building. And I’m particularly interested in your CRISPR episode. Could you describe for a moment, for people who don’t recognize the term, what CRISPR is, or what it represents?

Caterina Fake: Well CRISPR is, in short, it’s gene editing. It’s the ability to change people’s genes, DNA. And this has incredible possibility and Frankenstein-like potential. I think that people have become very alert to and alarmed by the possibilities, the unintended consequences of introducing edited people, edited animals, edited any form of life, really.

Tim Ferriss: Yeah, virus, bacteria, you name it.

Caterina Fake: You name it, viruses, bacteria. Introducing, basically, the human touch into it. Assuming what, in prior eras and in current eras are actually thought of as the hand of God. And putting that in human hands. And this kind of Promethean impulse that people have to seize the power. Prometheus famously using the power of fire from the gods and wreaking untold destruction upon the earth. There’re just constant warnings throughout historical literature, and Greek mythology, and biblical literature, and modern-day nonfiction, about what happens when we enter the anti-pristine, we enter the era of humankind manipulating the world in a way that is potentially leading us to conflagration and the end. And some say the world will end in fire, some say in ice, right? This is the wonderful poem by Robert Frost. We will somehow bring about our own destruction. And because of our incredible power and ability, I think that we should take responsibility for having that power. And Stewart Brand, who you mentioned earlier, he was one of the progenitors of the Whole Earth Catalog, and in it he said that we are as gods and might as well get good at it.

Tim Ferriss: I have a copy of the updated last Whole Earth Catalog, which was given to me as a Christmas present by my mom about 10 feet from my right side right now. It’s an incredible book and a very good statement on Brand’s part. It’s mind boggling to think about the promise and perils of many of these technologies.

Caterina Fake: Right. Stewart Brand is now working on bringing extinct lifeforms back to life. bringing back the saber-tooth tiger, and the woolly mammoth, amazingly. And that kind of awakened possibility, and dreams, and excitement in the sense of, wow, wonder, the wonder of technology, the wonder of science, right? And then also, terror and fear.

Tim Ferriss: Exciting and scary time to be alive. So I look forward to listening to you explore it with these various entrepreneurs and commentators. Let me ask one more question. It’s sometimes one that’s tough to answer, but I’ll ask it and then we’ll wrap up in just the next few minutes. But the question is one I like to ask, and that is if you could have gigantic billboard, metaphorically speaking, anywhere with anything on it, it could be a quote, it could be a word, it could be a question, anything noncommercial, but in the interest of getting a message of some type out to, say, billions of people, what might you put on that billboard?

Caterina Fake: It’s funny. I think of the basic truths as being a fairly straightforward, frankly boring statement, right? You should brush your teeth regularly; you should not let the grass grow on the path to your friend’s door; you should be kind to one another — they should like platitudes when you say them, when you see them on billboards, and yet they are profoundly true. So frankly, nothing exciting. Mainly, be kind.  

Tim Ferriss: Yeah. Yeah, I think it’s two very important words, and I think that your capacity for being kind may be inversely proportionate to the amount of time you spend on the internet getting poked in the brain by really short form drivel that is weaponized and commercialized, which comes back to the long-form recommendations, and the poetry, and all the other things. I really enjoy having a chance to chat with you like this, in long-form. And I thank you for taking the time to have the conversation. So thank you very much.

Caterina Fake: Yeah. No, this has been a great conversation. Thank you so much for inviting me.

Tim Ferriss: And people can find you on Twitter @caterina, find the podcast, shouldthisexist.com, or on Apple podcasts, and anywhere else podcasts might be found. Caterina.net is where they can find your writing including the Social Peacocking and the Shadow, and the other posts that have come up in this episode for people listening, of course, I’ll add links to everything, including the books that Caterina, I would love for you to send me, and I’ll put them in the show notes. I’ll put those at tim.blog/podcast, and you can just search Caterina or Fake, it will pop right up. Is there anything else you’d like to say? Any parting comments, things you’d like to suggest of people listening, anything you’d like to ask of them, anything at all you’d like to mention before we wrap up?

Caterina Fake: Well, I think that the biggest thing I’ve been working on recently has been the Should This Exist? Podcast, so listen, respond, subscribe, that’s a big thing, and engage in that conversation.

Tim Ferriss: Great. Well, we’ll send plenty of people in that direction. And once again, I really appreciate you making the time to have this conversation. I’ve really really enjoyed it. So hopefully, we’ll have a chance to break bread, or have coffee in person at some point, and I really look forward to listening to the show. So thank you again for that. And to everybody listening, be kind. Be kind. Experiment, go deep, not necessarily wider, and check out some of the books that I’m gonna put into the show notes that Caterina has recommended. And until next time, thank you for listening.

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The Tim Ferriss Show Transcripts: Jim Collins (#361)

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Please enjoy this transcript of my interview with Jim Collins (jimcollins.com), a student and teacher of what makes great companies tick, a Socratic advisor to leaders in the business and social sectors, and one of the 100 Greatest Living Business Minds, according to Forbes (2017). He has authored or coauthored eight books that have together sold 10+ million copies worldwide, including Good to Great, Good to Great and the Social Sectors, Built to Last, How the Mighty Fall, Great by Choice, and his newest work, Turning the Flywheel. 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.

#361: Jim Collins — A Rare Interview with a Reclusive Polymath


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Tim Ferriss: Jim, welcome to the show.

Jim Collins: I’m really happy to be here. I’m hoping that you wouldn’t mind if I start by exercising a bit of my own curiosity just to ask you some questions to begin our conversation.

Tim Ferriss: I would love to jump into it any way that you would like. I’m game for questions.

Jim Collins: I’m dying to ask what did you do your Princeton senior thesis on?

Tim Ferriss: My senior thesis, which took some extra time to complete, was on the phonetic and semantic acquisition of Chinese characters by native English speakers. It was looking at language acquisition, but specifically what most people in the West would consider ideograms. There are a few different layers of meaning or context for each character that one might acquire so the thesis was about the different approaches, the pros and cons of various methods for acquiring these characters.

Jim Collins: What is language acquisition? It’s a major I’ve never quite heard of and I’d be curious what its essence is.

Tim Ferriss: So within the East Asian studies department you had to pick a primary language. I chose Japanese because I had spent a year in high school in Japan going to a Japanese school as an exchange student but I ended up taking primarily Chinese classes because my Japanese level was already decently high. Within the context of that department, language acquisition would be focusing on — and this is a very good question because the way that I look at language is really acquiring concepts and almost an operating system for thinking that is associated with a different culture.

That would generally in, say a language like Chinese and most languages, start with the phonemes, the sounds themselves. In the case of something tonal like Mandarin, you’re actually going to be doing a lot of training. It’s almost like going to the gym and lifting weights because to produce a sound or a word like Yexu, which is maybe, or if you wanted to ask with a retroflexive tongue, Nà shì shénme dongxi? like, what is that thing? You really need to develop musculature that you have not developed before as a native English speaker.

Then after you’ve developed the basic phonetics and pronunciation, verbally you would move into the writing. The writing tells you a lot about the thinking of a given culture. I think of culture as sort of a collection of shared beliefs and habits. Some are purely phonetic, like we have our Romanized alphabet and then others have multiple layers like Chinese where you have a character that’s composed of radicals, each of which has a particular connotation in terms of meaning and the etymology. So all of that, those would all comprise ingredients in the recipe that is language acquisition.

Jim Collins: And forgive me for asking you a follow up question on that. I’m curious just because you’ve clearly come from both a love of language but also a study of language. How much do you think the language in which you are operating, whether that be mathematics or whether it be Japanese or Chinese or English either constrains or enhances the concepts that we develop?

Tim Ferriss: I would say almost completely. I can’t remember who was — Wittgenstein or-

Jim Collins: Wittgenstein, yep.

Tim Ferriss: He said, what is it, “The limits of our language are the limits of our world.” There’s something to that effect. I really feel like language and thinking are inseparable and therefore part of the appeal to me in acquiring other languages, studying other languages, even if I only use them temporarily like I did when I visited Turkey or Greece, these places. I still study the languages very intensely because it gives you, in my experience a different lens through which to process the world and to absorb stimuli and to react to things differently.

So in my experience, you can very often tell a lot about someone by not just the language they speak but the particular dialect within that language that they choose. That can apply to English and the particular nuances or predilection someone has in their own say, grammar vernacular even in a given family, but it can also apply to coding  — and then within coding you have different coding languages. They tend to reflect in many instances different personalities and different value systems, different priorities. So that’s how I would think about that.

Jim Collins: You mentioned Wittgenstein, I am no expert on Wittgenstein. I had a quarter in college, which the main focus of the work I was learning in was in Wittgenstein and I remember the professor saying to me, “Well, what’s marvelous about Wittgenstein,” is he said something along the lines of, “He lays out very clinically what we can meaningfully talk about.” Then the professor adds, “And of course then there’s the great punchline, which is that most of what’s really important we can’t talk about.” Because the words can’t go to the mystical. So very, very interesting.

I’ve often thought about this when I wrestle with concepts as I’m wrestling in my own research. One of the first questions I ask people, I often ask people, I say, “How do you develop a concept or how do you decide to come at something that would allow you to articulate something you’re seeing through the lens of say the Level 5 hierarchy or preserve the course, stimulate progress, duality or whatever?” The first question I always ask myself is, “What’s the conceptual vessel?” Right, because to get a concept there’s different kinds of concepts.

You’ve got dialectics, you’ve got hierarchies, you have stages, you have equations, you have categories. One of the first, most important things to do is to say well, if you’re looking at something, “What’s the best kind of conceptual vessel?” Then from there you develop the concept. Now just one thing on language. It’s not really about language per se, it’s about the really hard world of writing. As I was looking about your background, Tim, I noted if I read it right that you had crossed paths with one of our great nonfiction writers John McPhee, is that right?

Tim Ferriss: That is correct. I was very, very lucky and got to take a class called The Literature of Fact, which was a seminar that McPhee used to teach. I don’t know if he still teaches it. I did have a chance to spend some time with the incredible McPhee.

Jim Collins: Yeah, just before we launch into our broad conversation I — what was it like to have a class from McPhee? I have never met McPhee, but I’ve been a huge, almost student of how he writes. Of course, and I love the most recent work, I think it was called Draft No. 4, where he describes to all of us who struggle with words the struggle of writing, but he’s got those great books from years ago. A Sense of Where You Are about Bill Bradley, and he has the Archdruid book and he has The Control of Nature, which recently, with all of the fires and so forth happening in California, I actually went back to read to kind of remind myself how McPhee was writing about these things before.

He had just such a marvelous way of being able to use words to really exercise his curiosity and see things and then put them in these marvelous forms. I’ve often thought, “Boy, if you could learn from him how to write.” As a proxy for that, what would you — as those of us who write, we all know how hard writing is. Nobody would ever say writing is fun. What did you take from McPhee being able to really learn directly from him?

Tim Ferriss: I never get tired of talking about McPhee, although I worry about invoking his name in a sense because I feel like I am such a shameful repetitive writer full of all sorts of fluff compared to his tight prose.

Jim Collins: His prose is tight. I mean, he’s the consummate version of that Twain line about the difference between almost the right word and the right word is the difference between a lightning bug and a lightning bolt.

Tim Ferriss: Right, so with the preface that I in no way compare myself to McPhee or claim to have had all of his magic rub off on me, the class was absolutely — this is me looking for the right word, looking for the lightning and not the lightning bug. I don’t use this expression much, but it was really paradigm shifting for me in many respects when it came to writing and thinking. I’ll mention a few things before I directly answer your question. Number one is I’ve carried my notes from that class with me everywhere, meaning in every place I have lived since I took the class, which would have been in ’98 or ’99. So I’ve been carrying these notes for 20 years now. So that should tell you about how highly I value them.

The second is I remember very clearly when we had our first round of feedback on some initial writing task that we had been assigned, we had three, I think it was three to five page writing assignments each week. We would have a seminar with all the students together and then we would have one-on-one sessions with McPhee. I remember the first time he handed out in class the red-lined versions of our assignments. The printouts with his red ink on them. In almost every case he led into it by saying, “I just want you to know before I hand these back that you are all good writers. I don’t want you to take this the wrong way,” or something like that. There was more red ink on the page than black ink.

Over time it was remarkable how quickly you could hone your observation to identify superfluous words, to identify the fat on the sentences that you’re putting on the page. What ended up happening, I should say that’s on the micro level. On the macro level, and we can come back to this and I do have questions about your conceptual vessel comment earlier, it was structure. It was thinking about structure visually that really changed the game for me with respect to all types of writing. For those people who do like to get into the weeds I think that Draft No. 4 gives plenty of examples of how intricately he thinks about structure.

He did a number of interviews with The Paris Review on nonfiction writing, which are also really worth reading, but my grades in every other class went up. Yes, it’s multifactorial. There are all sorts of other things that could have contributed, but the correlation between starting that class and all of my other grades improving in all of my other classes was really uncanny. I think that is very specifically because it was tightening up my thinking and it was forcing me to, on a weekly basis, justify the use of specific words. McPhee is a real stickler for the right word. If you use something that is vague, that seems like a lazy backup option that you tend to default to a lot, he will spot that very, very quickly.

It was a wonderful, wonderful class. He is a very entertaining teacher as well. It’s not like having a clinical autopsy done of your work each week, although he is also very dispassionate and certainly not trying to just make you feel good with his feedback, but he over the years has developed a very entertaining style. I remember at one point he was riffing on the various ways that one can convey he said or she said. He brought up the very real example of when people say, “She ejaculated,” then he just went on this riff about how unnecessary that was and it got a good chuckle out of the students of course because there was a lot of heavy lifting to come 20 minutes later when we were actually going to jump into some type of task.

So long answer, but McPhee is along with a handful of other people I can point to very specifically one of the people who has had the biggest impact on my writing, but more importantly, on my thinking and how I think about structured thought. I want to say one thing about Wittgenstein really quickly before I forget. That is a surprising number of the people I respect for clear thinking have an affinity for Wittgenstein. Reid Hoffman the co-founder of LinkedIn would be another example of that. I think that’s worth mentioning just because I think philosophy, there are certain categories or labels of fields of study that sometimes get pushed to the wayside as impractical. I think the study of language and the concepts that language represent is extremely, extremely valuable. It’s kind of one step above consciousness if we’re looking at the foundational layers upon which everything else is built. So let me ask a question if I may.

Jim Collins: Yeah, please. Thank you for letting me start with exercising my curiosity. It’s wonderful to have a chance to begin with questions but questions working both directions.

Tim Ferriss: For sure. I have so many questions but I’m going to try to prioritize them a bit. The conceptual vessel term that you used, or phrase I should say, could you give an example of choosing the right conceptual vessel?

Jim Collins: Yeah. So maybe I’ll use a couple but let me start with one. So back when we were working on the research for what became Good to Great, a little bit of a story of what was happening. When we went into the Good to Great research, and everything we do has a research base to it. I had really given the research team the instruction that I didn’t really want to have a leadership answer. The reason for that is because I was always skeptical, especially from the Built to Last research, which had come before of placing too much emphasis on having a single leader. Number one, if you’re going to build something truly enduring, it has to transcend the leader. They all go away. They all die. You can’t have a system based on a single leader.

The second is you can go around in a big circle where you can say, “Hey, if that company was successful, it must have been a great leader.” Then if it’s not successful you say, “They weren’t a good leader after all.” You’re just in a big circle, you’re not learning. I said to the research team, “I don’t want to study. I don’t want to have a leadership answer.” My research team, which is usually composed of somewhat I would say highly irreverent, smart people who just work really hard, they love to challenge me. And we had these what we call “recharge chimposiums” because Curious George is kind of our mascot of curiosity. We would have chimposiums.

So we would be talking about the research and one day the research team kind of essentially joined hands when I came in. I said, “What’s up?” They said, “We’re going to tell you today that you’re wrong.” I said, “Well, what about?” They said, “About this anti-leadership bias that you have. Each of us, we’re responsible for studying the Good to Great journey, the inflection of these companies that were average that made that leap. We see that at that point of inflection, the leader played a huge role. To ignore that is to ignore the evidence. You always tell us Jim, ‘Pay attention to the evidence.’ We invoke that here today. You’re wrong.”

I responded to the team by saying, “Well, let me ask you a question. You remember your high school algebra?” They all of course did. I said, “And remember if you have the same variable in the numerator as the denominator, the variable goes away,” so as a relevant differentiator. I went to the whiteboard and I put a little line up there for the numerator and the denominator and I put “good to great companies” in the numerator and “comparison companies in the denominator.” Now our research method, this all gets to the conceptual vessel, but I kind of have to sort of know how we get there. So our research is always based on a method that developed with a great mentor of mine.

One of the themes by the way I think that’s going to come up in our conversation is what I see as the incredible that who luck, the luck of the right people that intersect your life plays in the journey. I had great who luck in a research mentor named Jerry Porras at Stanford when we were doing Built to Last together. Jerry pushed us to develop this method where he said, “Look, if you study successful companies or companies that achieve certain things but you only study the successes, you’re going to find they all have buildings. Does that mean having buildings will make you a successful company?”

Tim Ferriss: Right, right.

Jim Collins: So he said, “What we have to have is a comparison set,” and we developed this historical method where you study the entire history of two evenly matched companies at the start of the journey that are in the same place, same time, same resources, same potential and then one breaks out to a totally different level than the other and holds it long enough that you can have confidence in it. The other that was a virtually identical twin at that time does not. At the birth of any industry for example you have an explosion of new entrants, so all the early semiconductor companies and in there you’re going to find a twin pair of companies that are virtually the same, but one of them becomes Intel and the other one doesn’t. Why?

So he said, “You always have to ask what’s really different? Compared to what?” It adds huge amounts to the work, just the magnitude of work you have to do to do the comparison because it basically more than doubles everything you do, but that’s how you see. Of course you find all the comparisons also have buildings. So buildings can’t be the answer. So I went to the whiteboard and I said, “Okay, so we have the good to great companies, have these remarkable people that led them through the transition. Let’s look at the comparison companies,” and started ticking through the list and found, sure enough, the comparison companies had some remarkable leaders and some of them were even really extraordinary leaders.

Jack Eckerd, who had built Eckerd, and Stanley Gault at Rubbermaid, these were really, really good leaders. I wrote leadership in the numerator and I wrote leadership in the denominator and I said, “Guess what? The variable drops out. We have it in both. It doesn’t really matter as a variable. Now let’s go back to work and do something useful.” The team, that’s the wonderful thing about smart, irreverent young people, they sort of closed ranks on me. They said, “We knew you would do that to us. So we came prepared.” This is when the team — this is the value of having a great research team — saw something that then led to this notion of what eventually became the Level Five idea and the conceptual vessel for it.

The team said, “Jim, you’re right. Both sets of companies, the good to greats and the comparisons at the critical moment in time had leaders and there’s no evidence that the leaders were any less exceptional in terms of their pure leadership ability, but there’s something different about the good to great leaders. They’re cut from a different cloth. It’s not about their personality. Many of them were shy and reserved and soft spoken, never drew attention to themselves.” So it wasn’t about that. There’s something different about them. That became interesting.

Essentially what happened then was the question was: what’s the difference between these leaders? It wasn’t leadership, because they were both leaders who did leadership. There was something different about the leaders. So there was this signature of their humility, and then their fierce will on behalf of something that’s not about them. They were able to subsume their ego into the company and that blend of humility and will is what stood out. That was different from the comparisons. That was interesting. So you kind of step back and you say, “Okay, now how do we capture that conceptually?” I went out onto my porch and I started thinking, “Okay, is this just an idea? They’re just humble leaders?” No, that’s not quite it. There’s something about this duality. “Is it a dialectic?” didn’t seem to be quite right.

I started playing around with different things and I had this flash that went through my mind of “It’s a hierarchy. It’s a pyramid of capabilities and you kind of climb up this hierarchy.” It was sort of almost like a Maslow’s Hierarchy, except it was of leadership and there were levels to it. I thought, “This is a hierarchy of levels. Level one would be individual capabilities. That would be at the base of the pyramid, and then you go from individual capabilities to level two, which is you get really good at playing well with others. Good team skills. Level three, you would learn how to manage.

By the way, as an aside, never denigrate great management. Anybody who’s had a poor manager knows how awful that is to work for one and how great it is to work for a great manager. Then above level three becomes level four. You go from managing to learning to lead. Then there was a higher level. That higher level was the Level 5. The Level 5, well you could be a leader as a level four. To be a Level 5 leader you had to go to the next level of the hierarchy and add in this ambition for some things bigger than yourself with humility and with will.

When you stand back and you looked at that, you could look at it and say the right way to convey this idea is as a hierarchy that you grow through as distinct from some other way. I had to kind of find the way of capturing and then the critical thing is: it’s not leading, it’s are you a five or a four? Here’s sort of the overall pyramid. Just to illustrate, let me just invoke somebody who wrote their Princeton thesis on what became a Level 5 journey. One of the great leaders that I’ve gotten to know is Wendy Kopp, the founder of Teach for America.

Tim Ferriss: Sure, Teach for America.

Jim Collins: She wrote her senior thesis on it, which is why I’m always curious. Jack Bogle wrote his senior thesis on mutual funds and ended up creating an amazing thing. Wendy Kopp wrote hers on what became Teach for America.

Tim Ferriss: Yeah.

Jim Collins: But if you look at Wendy Kopp, if you were to ask the question, “Where is she on that?” She went through all the levels, but she’s not just a leader. She has that extra dimension where she’s got that genuine personal humility and an absolutely ferocious resolve for the overall cause that is not about her. If anybody that’s met Wendy or seen her, you would never think, “This is about Wendy Kopp.” You would never think — but if you ever doubted her resolve, there’s that image of her sitting there trying to get her first funding for Teach for America where her image is “I put glue stick on the bottom of my pants and I would not leave the chair until I got a $25,000 check.” Just sheer will. And will for, ultimately, the kids and how the kids’ lives could be changed. And yet, genuine humility. So she went to the top of the hierarchy. So when I stand back, I look at it and say, “That’s the right conceptual vessel for this journey of what we had seen.” Other concepts-

Tim Ferriss: May I jump in for one second?

Jim Collins: Yes, sure, please.

Tim Ferriss: The question was genuine humility. How do you identify genuine humility? What are the characteristics and how do you separate it from false humility or what someone presents as humility? I guess I’m wondering how you-

Jim Collins: How we imputed that from the research data?

Tim Ferriss: Correct.

Jim Collins: Yeah, that’s a great question. So first of all, in all of our work we start not surprisingly with a question of curiosity. It always has to be something; I just am really curious enough to go through the years of suffering to get some insights. Then you translate that into the research method, the comparison method, the historical method and so forth. Then you collect vast amounts of information. And the key is you’re not looking for anything in particular. You’re looking for patterns of difference.

Why did one set of companies, what was different about them versus the others as you walk through time and/or what kinds of decisions they made and so forth, always going to that difference question. So what we began to notice is that the good to great leaders — what’s fascinating, that number one, you can do what’s called event analysis. So you can do something like say, let’s call an event the number of times in speeches you use the vertical pronoun versus you don’t over the course of a career. That’s something you can count. So you can look at it and say, “Let’s take the good to great CEOs and let’s take the comparison CEOs and look at every letter they wrote that you can get hold of. Let’s look at every speech they ever gave. Every interview they ever gave.”

I mean, you’ve got mountains and mountains of information. “Now let’s go through and literally count how many times they tend to take credit themselves, how many times they give the credit to others, how many times they don’t use the vertical pronoun I, how many times they do.” Later of course, if somebody had read Level Five, they could try to pretend to be Level 5. I’ll never forget when somebody sent me an email that says, “Help.” I open it up and it says, “Dear Jim, our CEO just walked in and announced he’s Level 5. What do we do?” Have him reread the chapter. But these are people that, they were just doing what they were doing.

They weren’t trying to show themselves one way or another. That’s the thing of looking over the course of an entire history or career. You can count things. How many times did they allow themselves to be on the cover of a magazine? How many times when they’re in discussions about things that did not go well, you can look at window and mirror events. Things that did not go well. One approach is when something does not go well you can point out the window and subtly or not so subtly attribute the reason it didn’t go well, the factor is outside yourself. The economy or somebody let you down or a partner didn’t come through or whatever it happens to be, but somehow it’s not you.

Or there’s the window approach, which is your kind of natural tendency is, “All that might be true. It doesn’t change the fact that I’m responsible and I’m owning this and this is the mistake I made,” and so on and so forth. You can look, and again, it’s comparative. What did the comparison CEOs do? You can count a lot of events of some version of pointing out the window. What did the good to great CEOs do? You can count a lot of versions of pointing in the mirror. So you begin to add all this up, and over the course of decades — because we look sometimes over 50, 60 years — some CEOs were in harness for multiple decades and since they’re all publicly traded companies people often ask, “Well why do you only study publicly traded companies?” My answer is, “Because that’s where the data is,” right?

Tim Ferriss: Right.

Jim Collins: Because that’s the beauty. They all have to report the same way. They all have annual reports. They all have earnings calls. They all have all of these things over time that you can then use as data sets. I’m not really a business author; I just happen to have used companies as the method to study human systems because there’s great data. So that’s where the data is, and if you do that — and we have 6,000 years of combined corporate history in the research database — pretty soon you can start counting a lot of things. Then you can begin to say there’s a substantial amount of quantitative evidence that adds up to a greater level of humility in these than those and that’s how you get there.

Tim Ferriss: May I ask you a question about counting?

Jim Collins: Yeah.

Tim Ferriss: All right, so we have a number of books we could talk about and we are going to talk about some of them, but Build to Last has a subtitle, Successful Habits of Visionary Companies.

Jim Collins: Yeah.

Tim Ferriss: I’m very fascinated by what might be the successful habits of Jim Collins. This is a question about counting. In the course of doing some of the homework for this conversation, I have come across different ways that you seem to measure your time and your days. I’d love to explore that for just a little bit.

Jim Collins: Sure.

Tim Ferriss: So the first was I read that you had, and this may have evolved or changed by this point, but a stopwatch with three timers in your pocket.

Jim Collins: Mm-hmm (affirmative).

Tim Ferriss: And that it was sort of indicative of creative teaching and other.

Jim Collins: Yes.

Tim Ferriss: Could you explain that habit, please, for people who are not familiar?

Jim Collins: Sure. So actually let me tell you the story of how it began, what the three were about, and then how it’s evolved into something a little simpler and a little more powerful and what I do with it every single day.

Tim Ferriss: Perfect.

Jim Collins: So I don’t want to pretend that I’m normal. Okay, so what I’m going to describe is not normal behavior, but this is it. So when I was 36 years old, I made the decision, and we can come back to this later if you want to talk about big bets and doing scary things, such as betting our career, betting our lives. Joanne and I on an entrepreneurial path. Let me just kind of step back and kind of share the origins of this.

Tim Ferriss: Yeah.

Jim Collins: So I was teaching at Stanford and it was a marvelous journey and of course I had great mentors and learned how to do my research there. That’s where Jerry and I did Built to Last. But I had another mentor who encouraged me to think about whether I wanted to do a self-directed path or not. And I used to say to my students, because I taught entrepreneurship and small business, I always said to my students, “Why don’t you go do something on your own? Why give over all your creative energies for somebody else’s thing?” I would at least challenge them to think about that.

And I would say, if you’re really interested in business, you don’t have to go to work for IBM to be in business. You can do your own. So my students, and this is the wonderful thing about great students, they hold you to account, right?

Tim Ferriss: Right.

Jim Collins: They say, “Well what are you doing that’s entrepreneurial? This doesn’t look like a very entrepreneurial thing — teaching these classes and being here.” And so I started thinking a minute and a realized something about myself, which is I like the independent path and I like betting on myself. So I had this idea, “Well gee, if you don’t have to be at IBM to be in business, why do I have to be at a university to be a professor?” So I said to Joanne, I said, “You know I think I have this idea of I’d like to be a self-employed professor to endow my own chair and to grant myself tenure.”

So Joanne — who, we’ve done these things together through life — she went on with this idea. And the idea was to try to pursue really big questions that wouldn’t be constrained by things you could do in only a year. And the first big bet on that was the research in Built to Last and it was coming out. And I said, “Let’s just bet everything; let’s go.” And so we launched this huge bet. We bet everything on that book. Didn’t know if it would work, we were down to less than $10,000. We were actually really scared. We call it our Thelma and Louise moment. We were launching off the cliff together, except we wanted to get to the other side.

But it was a huge bet and we didn’t know if it would work. But I was very clear about one thing. I did not want to have a half life of qualify in the work. And one of the wonderful things about working on Built to Last with Jerry back at Stanford, no one knew who I was. No one called, no one paid any attention. So for six years of working on that research project, I could just go into the cave and work and work and work. And that kind of deep work, you have to go deep into the data, deep into the research, deep into the thinking, the long cycles of reflection, that’s how you get the ideas. And that’s how you do good stuff.

And what I was worried that what would happen is if I went from being invisible to being visible, and that if I was fortunate enough to have a success, that I might wake up in five or six or seven years and have not gone back to the wellspring of the deep, quiet solitude of work. And then your second book is half as good. Right? And then the next book after that is only half as good again. I wanted the quality to always get better. And so I thought well you know, what’s interesting is a professor, or a university is a place that really encourages that because it’s sort of designed to allow you to spend your life in that tranquility.

And so I went to some faculty members who I greatly respect and I said, “How do the people in the academy that you most respect in yourself spend their time?” And I got a consistent answer: 50, 30, 20. 50 percent of your time in new, intellectual, creative work. 30 percent of your time in teaching. And 20 percent of your time in other stuff that just has to get done — serving on committees, whatever it happens to be that you have to do. And so I thought, “That sounds good. I’m just going to start doing that.” So I started — as I was heading out on the Thelma and Louise leap — counting my hours every day. And I would count how many hours in the day were creative, new, intellectual. And the goal was that had to be above 50 percent.

Then how many hours would be in teaching, and how many hours would be in other stuff like, somebody’s got to balance the QuickBooks, right? And so I started counting and that’s where the triple stopwatch came in. I found this wonderful triple stopwatch where I could constantly go back and forth and at the end of the day I would have the total. Later I came to the realization that what really mattered was the first bucket, the creative work. And so I eventually simplified it. There’s a concept in Great by Choice called the 20 mile march. And so I kind of had a 20 mile march, I just didn’t know that concept yet. And the idea of it being something that you just do really consistently over time that imposes a very high level of discipline that accumulates to results.

And so I simplified it and I just simply said, “Can I just simply count the number of creative hours I get every day and then hold myself to an account?” So at the end of every single day, I open a spreadsheet and that spreadsheet has three cells on a line; that’s for the day. The first thing is just a simple accounting of what happened that day. Where did my time go? What did I do? etc.

Tim Ferriss: Can you give — sorry to interrupt, but I would love…this is the stuff I love. What might a description for the day look like? Is it three sentences, four sentences, what might it look like?

Jim Collins: It sort of depends on — actually the very best days don’t have much in it at all. They are: “Got up early, two hours of really great creative work, breakfast with Joanne, five hours creative work, work out, nap, three hours of creative work, enjoyed dinner with Joanne, bed.” That’s like a great day. But other days are full of lots of other choppy things. And so what I tend to do is try to capture a bit of what happened this week, what happened with the main tasks of the day. If there were some really interesting conversations that happened or something that hit in those. I’ll notes those. They’re markers so that I can always go back and I’ll just share with you how I use those in a minute because I actually do these correlations with all of that.

And then the second cell is the number of creative hours I got that day. Now there’s no rule about how many you get in a day. Sometimes there’s zero and sometimes they can be nine or 10, which would be a huge number. But then it calculates back over the last 365 days. And the march, which I don’t think I’ve missed for well over 30 years, and I hope to hit for a lot longer now is every single 365 days cycle, every single one, every single day, if you calculate back the last 365 days, the total number of creative hours must exceed 1,000. No matter what.

It doesn’t matter if you’re sick. It doesn’t matter if there’s other stuff you’d like — 1,000 creative hours a year as a minimum baseline. Now you can be above that, that’s fine. But never once, there can’t be a single day in any 365-day cycle, January two to January two, July 22 to July 22, September nine to September nine, it doesn’t matter. Always has to be above 1,000 creative hours. And you watch it — and I put on the whiteboard here at the lab — the three-month pace. So you take the last three months multiply it times four, the six month pace. And then the current 365. And that is a way to kind of monitor. If I start seeing those numbers start to go down, I’ll change my behavior. And sometimes I have a big buffer and sometimes I don’t.

And the idea is, if you stay with that, eventually you’re going to have work. Now there’s a third cell that I put in there that most people don’t know as much about because people know about the hours thing somewhat. But all of us have dark times, difficult times. All of us have good times, right? But here’s an interesting thing I noticed, which is that if you’re kind of going through a funk, it colors your whole life. And you tend to think your whole life is a funk because you’re looking through that lens.

And so I thought, “But actually I feel like my life is really pretty good.” But when you’re in that other place, it doesn’t feel that way, right? And so what I started to do is I started creating a code, which is plus two, plus one, zero minus one, minus two. And the other thing I put in — and the key on all this by the way is you have to do it every day in real time. You can’t five days later look back and say, “How did I feel that day?” And what this is, is a totally subjective “How quality was the day?” A plus two is a super positive day.

Tim Ferriss: This is emotionally speaking?

Jim Collins: Exactly. Just like: “Was it a great day?” A plus two is just a great day. Doesn’t mean it wasn’t — there might not have been a really difficult day. It might’ve been a day of a really hard rock climb. It might’ve been a day of really hard writing. But it felt really good, right? It might’ve been a day of an intense conversation, but really meaningful with a friend or something. But what it adds up to is a plus two. Plus one is another positive day. Zero is meh. Minus one is kind of a net tone negative. And minus two is, those are bad days, right? And you put it in before you go to bed because if you try to remember, if I were to ask you Tim, right now, 17 days ago, or even five days ago to give the score, you’re going to be distorted by how you’re feeling today.

Tim Ferriss: Oh for sure. Yeah, memory, if you ask people what they ate two days ago, they’re going to be off by 40 percent, 50 percent calories for sure. Yeah.

Jim Collins: Exactly. So I write it down, and now I start to have — I’ve got the creative hours marked, which is, it’s kind of discipline in service of creativity. And it’s relentless, right? It just stays with me constantly. You never get a break from it. You can take breaks, but you can never get a break from the thousandth floor. But that other has proved to be incredibly useful for me because now what you can do is sort the spreadsheet. And you can say, over the last five years, what’s going on in all the plus two days? Oh, and over the last five years …

Tim Ferriss: Ah, that’s where the descriptions come in.

Jim Collins: Yeah, exactly. And over the last five years, what’s going on in the minus two days? And now as I navigate, it’s kind of like the Simplex Method in operations research where you find optimal by never really knowing that optimal is ahead of time. You do it by a series of iterative steps of the next best step.

Tim Ferriss: Hold on, could you explain that? I’m from Long Island, so sometimes it takes me a minute. Could you explain what that was one more time?

Jim Collins: Yeah, sure. So my undergraduate was a thing called mathematical sciences with a heavy dose of philosophy. And math science was pure mathematics, computer science, statistics, and operations research. And in operations research there’s a method developed by a guy named George Dantzig called the Simplex Method. And essentially the idea is that if you’re really trying to find the optimal answer to a multi-variant problem where there’s lots and lots of variables, even the biggest computers couldn’t basically do a giant spreadsheet and sort. There are just too many permutations. And what he showed was under certain conditions, all you have to do is find the local optimum — what’s the best next step?

Tim Ferriss: Right.

Jim Collins: And then you reset and then what’s the next best step? And that he showed that under certain conditions that is mathematically guaranteed to navigate you to the optimal end point. And that was the Simplex Method as I understand it. It was 30, 40 years ago when I was in the class. So I’ve always had that idea in mind. So you kind of navigate step by step. And so I think about it as in navigating life, I want more of the things that create the plus twos, and less of the things that create the minus twos. But the difference that’s helped me is I know what they are.

Tim Ferriss: Yeah.

Jim Collins: And I can start — it’s not that life is never perfect, but you can do a simple more of this, less of that. And more of this, less of that. If that makes any sense.

Tim Ferriss: It makes perfect sense. What are some of the patterns that you found for either the do more column or the do less column for yourself?

Jim Collins: Yeah. So when I look at those patterns, I would say on the plus twos there are almost two contradictory components. And not contradictory, but they’re just really different flavors. One is the solitude of really hard work. And sometimes one of my favorite days will be I get up, I never leave the house. And I basically get to just lose myself in the research or in the writing or in the making sense of things. It’s a very incredible simplicity of the day. I’m 61 now and I think about what comes next. And I tend to keep creating. I want to stay in some version of that march for a really long time. My role models have all done that.

But I think about life as having three things at least that I think are really important, and one of them is increasing simplicity. Just sheer simplicity. Two is time in flow state. And flow state’s not easy. And the third is time with people I love. And so when I look at those plus twos, a lot of the days would be days of high simplicity, not much happened. There were very few moving parts. But a lot of deep hard work in flow state. I might’ve been writing or doing a concept or creating something. Just you’re lost in the work.

Tim Ferriss: Or rock climbing probably.

Jim Collins: Or rock climbing, exactly. Exactly. It’s arduous but you’re lost in it. Those are great. The other though, for me, is the time with people I love. And the other dimension, while I wouldn’t describe myself as a highly social type person — I love the solitude of the hard work — the other side is the people in my life and there are many; I have great friends. Really great friends that many decade friends. Friends back to third grade, seventh grade, all my college roommates, my personal band of brothers. I have friends. And my wife, we’ve been married 38 years. Got engaged four days after our first date.

Tim Ferriss: What? Four days after your first date?

Jim Collins: Yes, that’s true.

Tim Ferriss: Wow, okay. We might come back to that.

Jim Collins: We might, but the thing is, when you have those days where you’re really present and engaged with people you really love, those are plus two days. You may not have accomplished anything, or in the case of climbing it might that I went out climbing with one of my best friends, and I don’t even necessarily remember the climb. It was with a friend. And so my plus two days are either very solitude or very connected. But connected to people that have these long, enduring really, really wonderful relationships in life. And those make plus twos.

Tim Ferriss: I love it. You at some point in life need to meet my friend, Josh Waitzkin, who you and he have very similar heuristics. He was the basis for the book and the movie Searching for Bobby Fischer. So his first life was in chess. But I won’t take us too far off track but at some point, I think you guys would really, really get along. Okay, let me dive into a couple of clarifying questions if I may.

Jim Collins: Yes. Sure.

Tim Ferriss: Because this is so juicy, I can’t — I don’t want to just move on to the next thing.

Jim Collins: We can have all these people now creating spreadsheets.

Tim Ferriss: I was going to say, if this writing thing doesn’t work out for you, you should create — you have a spreadsheet company, you have a journaling company available to you.

Jim Collins: Right.

Tim Ferriss: Creative: this is a word that means different things to different people. What are the main activities or what are some of the activities that are squarely in the creative bucket for you? And the reason I’m asking is I’m thinking about how I spend my own time. And you have a team — I suspect a much smaller team — but for instance if you are working on a book that requires interviews, would spending time scheduling those interviews count as creative or is there a cutoff? Even if it’s in service of a larger creative project where you have admin and then you have creative. So for you, what counts towards the hours marked creative?

Jim Collins: So you’ve hit upon exactly where the gray zone is on this. And in general, in order to — again, I have to go back to what’s the overall objective? The overall objective is that over time there’s quality work. And so I can’t start calling things “creative” that in the end wouldn’t lead to some kind of creative output. And by the way, sometimes that creative output ends up in a drawer because it just doesn’t make it to the world. But you have to just keep working. And I think of it like being an artist in a studio. And so, is getting the paintbrushes ready to paint part of the creative? I would say yes. I would say that organizing the tools and maybe even ordering paint, because it’s in direct service to the creation of what ultimately might be on a canvas.

Whether the world sees it or not, I define creative as any activity that has a reasonably direct link to the creation of something that is new and potentially replicable or durable.

Tim Ferriss: Oh, I like that. Yeah, please expand on that.

Jim Collins: So for example, if we have in this conversation, right, there’s already elements that will count as somewhat creative because just even you start thinking about if an idea pops into my head. And then that leads to supporting some other concept or piece of work that I’m working on. Because a lot of times — I’m sure you find this too — is there’s a seed of an insight that’s lurking in the back of your brain. And then in the process of conversation or in the process of trying to articulate something, or in some other mechanism, it gets jarred out of your brain and all of a sudden you see it bounce on the table.

Jim Collins: And then you go, “Oh, I need to put that in the bag and not forget it,” right?

Tim Ferriss: Right.

Jim Collins: Right? And sometimes that happens. I’ll give you an example of how something that turns out to be a kind of a creative moment, I wasn’t anticipating as a creative moment. I was meeting with a — I can’t say who it is, but  — it was a very towering, super charismatic, super genius founder who is sort of, to his world, the way say Walt Disney might have been to his world. Just truly a once in a generation. But unlike Disney, this person never really started thinking about the systems that would allow him to build a company that could really ultimately go beyond him. And there were challenges with that. And so we were talking about, I was trying to figure out “How do I get through to this?”

And there are other people on the team who didn’t really want to step up into certain roles. And a whole bunch of other stuff. And so he could kind of picture that as I’m challenging, I’m trying to teach them, set the stage for making a Built to Last company. And so you could you view that as “Well, what’s creative in that? You’re just kind of wrestling with these people.” And all of a sudden in the middle of the conversation, I remember I just turned and I looked at him. I said, “Here’s the problem. You, sir, are a genius. So let’s just start. There’s the problem. You are a genius. And what you have is 1,000 helpers.

Now so long as you’re still a genius, and so long as all these helpers want to help you, being a genius with a thousand helpers, that’s going to work really well until either A, someday you’re not a genius, or B, you’re gone. In which case, this company just hollows out, there’s nothing left. There is no company. All this is, is a genius with a thousand helpers in sort of a vessel called a company. It’s nothing more.” Well right then, that was when this thing came out of my head, bounced on the table. I had never used that phrase before. And I immediately, I made a note on my notepad. And I went back, and if you look in Good to Great, there’s a section when I’m trying to describe the comparison CEOs in contrast to the good to great CEOs where I talk about the genius with a thousand helpers.

And I contrast how the Level 5 leaders come at it as that’s the last thing they’d want to be, right? And how they’d want to build a culture and a company and ultimately be the architect of a great system versus being the genius with a thousand helpers. And there’s a flowchart in there that’s hard to describe, it’s a different set up. That came out of that conversation. So I got to count that conversation as creative even though when I went into it I didn’t know that that would happen. So I wouldn’t have counted it normally. There’s other times where sure, I was doing some research on K12 education recently and the process of really deciding who I wanted to interview, that would count.

That was like assembling the paintbrushes. If I’m balancing the QuickBooks account because I have to do that or I’m I don’t know — there are things that just sort of clearly fall outside of it. And I don’t count it. I try to be a hard counter so that I stay on the march.

Tim Ferriss: This is super helpful. And it also made me think about how if someone were to — and I was thinking about this earlier as well, how the 50 percent creative, 30 percent teaching, 20 percent other in some respects have a — well, we will get to this. Maybe it’s not —

Jim Collins: Yeah, go ahead.

Tim Ferriss: No, I wasn’t going to say maybe it’s not flywheel exactly, but the creativity can lead into teaching. The teaching then can lead back into the creativity because it forces you in some respects or at least catalyzes you to express things in ways that you might not otherwise. And also points out things that are unclearly formed if you then try to convey them to somebody else.

Jim Collins: And in fact it’s interesting, in preparing for today, and I love to prepare for a conversation by thinking clearly what we might chat about. But then it’s not a script, it’s like having different plays you can have in a football game. What might happen in a game, and then that’s conversation. Even when, if I get together with a really good friend, I usually will write down three things I’d love to chat about today. We may or may not get to them, but one of the things I did for today was I thought, “I wonder if Tim will ask me what’s my own flywheel?” And so I actually took account of writing it down; if we come back to that later I’d be happy to.

Tim Ferriss: Yeah, we will absolutely come back to that. And I have a path there.

Jim Collins: Yeah.

Tim Ferriss: So you mentioned a while back — actually before, I just have to check this box or it’s going to bug me.

Jim Collins: Yeah.

Tim Ferriss: Sleep tracking. So you mentioned sleep.

Jim Collins: Yes.

Tim Ferriss: How do you note or modify or have you modified your sleep? Can you talk to us about — I think most people would agree, it’s important. But how have you monitored and modified your sleep?

Jim Collins: Well again, I’m not normal, okay?

Tim Ferriss: That’s precisely why I’m asking you these questions.

Jim Collins: No, but one of the things that struck me a number of years ago is that we spend so much time thinking about time management. And I’m not really a — even though I describe this counting and stuff, I’m not really a time management sort of person. I’m a — I don’t have kind of — I have to organize my time a certain way or whatever. That 1,000 creative hours, as long as I stay there, there’s millions of ways I can get there, right? So it’s like a constraint within which now I can have a ton of freedom, right? So I’m not overly regimented, I’m just disciplined. And there’s a big difference. And so when I was thinking, “Well, wait a minute. If a third of our lives approximately are spent related to sleep, why don’t we put as much thought into time management of sleep as we do into the rest of our day?”

It’s just ignoring a huge piece of it. So one of the things I did was, without to my knowledge having a sleep issue, and my insurance wouldn’t pay for this or anything, I just was curious. There’s a sleep center at I think it’s the National Jewish Hospital here in Denver. They have a sleep lab where they’ll do sleep tests and stuff. And I just said, “Hey, can I come and get sleep tested?” And so I went down there and just scheduled myself in and spent the night and had them put the electrodes on and I kind of feel like I’m my own rat in life. My own lab rat where I’m always studying myself somehow, right?

And I used to have a little book called the bug book, where I’m the bug and I’m studying the bug called Jim. That’s how I figured out where I was going to go in life. And so anyway, so I went down to the sleep lab and I said, “I’m going to study—” I didn’t. To study sleep is too strong of a word. “I’m going to be a student of the science of sleep. And so because it’s a third of my life, why don’t I understand it?” So I got the sleep test and I found out I didn’t have any serious sleep pathologies. I learned about the different aspects of sleep.

And what the big takeaway I got about sleep was we tend to think of this idea of seven hours a day or eight hours a day. And what I learned from this little journey, and again, I want to underscore, it’s not like I’m a sleep expert or anything. I was just trying to figure it out for myself. It’s actually the number of hours that you get over say a 10-day cycle. So if you go up and you do a big climb, like when Tommy and I did our climb at El Capitan together and do it in a day, that means 24 hours. You’re going to be awake for 36 hours.

And so if you’re basically like, “Oh I couldn’t do it without sleep,” well you’re never going to do it. You could perform at really high levels with zero sleep over a day. You wouldn’t want to do it over 10 days though. And so I started thinking is what really matters is the amount of quality sleep I get over, say, a 10-day cycle. So early on after all this I actually started counting and I would count naps and I would count to just try to keep again, very much like the 20-mile march of the creative hours. As long as I was staying above 70 over a 10-day cycle, however I got there, that was fine.

I’ve since found that what really — I probably still hit that number, but having counted it for about a decade meant that I ingrained the patterns of how to come at it. And what I’ve learned is I guess two or three things specifically about the sleep process for me. This is just personal. One, the 20-minute rule. If you wake up in the middle of the night and you check the time — first of all, it’s also by the way fun to see if you can guess what time it is, right? But then check the time. And then if you’re not back to sleep in 20 minutes, get up.

And go — and then I love, I’ll sometimes go lose myself in again — back to the simple work, whatever. There’s something really quiet, I get up at three or four in the morning and you’re just there with the creative stuff you’re doing. That’s a great time. Sometimes you wake up at three, sometimes you wake up at seven. The second is, for me I’m really, really lucky. I have the genetic ability to nap in any situation. I took a nap, I woke up eight minutes before our conversation today. I’m serious.

Tim Ferriss: No, I know you are.

Jim Collins: And so for me, my little secret extra capability that I just was born with was I can nap pretty much anywhere under any conditions and I can dream. You give me 12 minutes, I’ll dream. Give me 55 minutes, I’ll dream. And I can wake up and boom, be fine. It’s just genetic. But naps are my sort of saving — they give me this sense of like “Oh, whatever happens, I’ll be fine because I can always close my eyes.”

Tim Ferriss: When do you nap?

Jim Collins: I can nap sitting up.

Tim Ferriss: When do you choose to nap?

Jim Collins: Well I have two favorite times of napping. Three favorite times of napping. One is airplanes are great for napping. So I never eat anything on a plane or do any of that. I’m either trying to do something creative or sleep. And I have a sleeping kit, which includes Bose noise canceling headphones, and eye covers, and a donut pillow that the headphone can go in. So it’s actually really like kind of creating a micro environment so you can sleep on an airplane or wherever you happen to be. The second place if I’m not traveling, which I try not to do too much anymore, afternoons are great for a nap because you have a really good morning and then you get that wonderful afternoon glow of creative time.

Sometimes if you took a nap from say two to three or three to four, and then you have that marvelous four to seven in the evening. And it somehow coincides with the end of the day. It’s like a second morning. But my favorite absolute sleeping pattern is — so when Joanne’s doing one of her bike rides across the country, and she’s gone for six or seven weeks doing it — I’ll fall into a pattern where on a lot of days I’ll go to bed and 11 and get up at three. I’ll roll out of bed and then I’ll do the creative work stuff usually. Creative or preparing teaching from say three until seven.

You don’t eat anything, you don’t drink anything, you don’t have a cup of coffee, just go roll right in. And then you go back to sleep from seven or eight until 10 or 11. And if you’ve ever been under general anesthetic, that second sleep is like general anesthetic. You blink and it’s just like that deep, dark bang and all of a sudden three hours are gone. And then I get a second morning because mornings are the best. I get a second morning when I get up and then you have breakfast, and then you get this really great energetic day. That for me is a perfect sleep day.

Tim Ferriss: Wow. I have these things that I’m dying to get to, but then you keep bringing up interesting things, which I’ve —

Jim Collins: Well, go ahead.

Tim Ferriss: No, no, I squarely blame you for that, but I’m glad you’re doing it. The bug book.

Jim Collins: Yes.

Tim Ferriss: You mentioned it in passing: what is the bug book? Can you please elaborate on the bug book?

Jim Collins: On the bug book. I think a lot of us, and I certainly was one of them, have a — we struggle in our 20s to get clarity about how to deploy ourselves in the world. Because everything up until you finish high school, or college, or graduate school, or whatever, it’s structured. You don’t really have to think about it. It’s like, “Oh, I gotta figure out how to do these math problems,” or whatever. But life isn’t really like that. And then all of a sudden, you hit life and life is much more ambiguous. And so, you’re trying to navigate through it. So I, like a lot of people, was trying to figure out how to best to deploy myself in my 20s. And I had multiple things that helped me do that. But one of them …

Let me just introduce a concept, okay? And then, I’ll tie it into the bug book. Because this is how I challenge young people to think about it. There’s a concept in Good to Great called the Hedgehog Concept. And the idea of the Hedgehog Concept is to simply down — we found it by studying companies. We found that when they really focus on one or a few really big things, and made very disciplined decisions over time, those would accumulate and begin to build some real results. And eventually what would become the Flywheel Effect, which we’ll chat about a little bit later. And the Hedgehog Concept is the intersection of three circles. For a company, it’s doing what you’re deeply passionate about, because if you’re not passionate about it, you can’t endure long enough to really, really do something exceptional.

The second circle is what you can be the best in the world at. And if you can’t be the best in the world at it, leave it to others. So, for example — it doesn’t mean being big. Right? You could have a truly great local restaurant. It’s never going to be big, but it’s the absolute best in the world at a particular thing that it does in its specific community. And no large company could come in and be better than them at that. That’s very Hedgehog, even though it’s not big. And then the third is that you have an economic engine, and you know how it works. And so, if you have the intersection of those three, our energy is going to go into things that we’re passionate about, and we can be the best in the world at, and that drive our economic engine, you’re in your Hedgehog. Now there’s a personal analogy to the Hedgehog, and this gets back to the bug book.

I’m not a big believer in thinking of traditional careers, I’m a big believer in thinking of finding your Hedgehog, and then really building flywheel momentum with that over time. And so the personal version of the Hedgehog is, again, doing circle one, what you’re passionate about and love to do. The kinds of stuff that when you do it, you say, “I sure hope I get a long life, because I really love doing this.” The second circle isn’t best in the world, because if you said, “Well, if I can’t be the best orthopedic surgeon, I won’t do it,” well, then we’d only have one. Right? That’s not good. So it’s what you are encoded for. And what you are encoded for is different than what you’re good at. So when I went to college, I thought I was going to be a mathematician. Because I was one of those kids that was good at math. That’s why I majored in math sciences.

But then I met, at Stanford, the people who are genetically encoded for math. They were not me. I was good at math, they were encoded for math. It’s like being an athlete where you thought you were a good athlete until you met the incredible, naturally gifted athlete, and you realized, “I could never see to spin to the basket like he did.” Or, “I could never see to put the ball there running down the field, playing soccer, in the way she did, I just wouldn’t have seen it.” There’s a gift. That’s the encoding. And so you have to find what you’re encoded for as distinct from just what you’re good at. And then the third is, you have an economic engine. And you can fund your goals, your objectives, the things you are trying to get done. When you have all three of those, I’m passionate about it, I’m encoded for it, and I have an economic engine in it, now you’re in your Hedgehog.

Now, when you’re in your 20s, there’s all these paint-by-numbers kits approach to life. Right? You can be a professor. You can be a businessman, you can be a lawyer, you can be whatever, right? And the nice thing about a paint-by-numbers kit is you actually don’t have to think about it that much. Because as long as you stay in the lines and you paint, you’re going to and up with a nice picture at the end. But the only way to paint a masterpiece is to start with a blank canvas. And that is from figuring out those three circles, and then making your own unique series of decisions consistent with the Hedgehog of those three circles. And they may or may not fall into a traditional bucket. And so I was trying to find my way.

And I started this little book, and it was inspired by a mentor named Rochelle Myers, who suggested that what I do is I study myself like a bug. And imagine with dispassionate objectivity as you’re going through life, you’re making notes where you’re observing the bug called Jim. But very scientifically, clinically. And so I remember, I was working at HP for a couple years out of graduate school. Great company at the time, for sure. But I wasn’t really constructed to be in a large company. But I was trying to navigate my way. And one day, I had to give a presentation on how network computers work. And this was back in the 1980s, when it was early on in that. And I had to figure out how to communicate to everyone, really, the essence — and on our team — of how network computering was going to work and how it fit together. And I had to sort of conceptualize it. And then I had to teach it.

And all of a sudden, I had this day where it was like, “Wow, that was really fun, to figure it out, to figure out how to conceptualize it, to figure out how to put it in concepts everybody could understand, to share it with everyone, to teaching it.” My bug book, what I’m then writing, “The bug Jim really loves making sense of something difficult, breaking it down into understandable pieces, and teaching it to others.” It was an observation in the journal. The other thing might be something like, “The bug Jim would really languish if he had to spend a lot of time in senseless meetings. This is not good.” And constantly observing, and then eventually that allowed me to — it was that sort of observation, clinical, that allowed me to eventually head back to teaching at Stanford when I was 30, which then became really the start of the real journey of what happened.

Tim Ferriss: With the bug book, did you write things in the bug book each evening, did you do it — keep it in your back pocket, and when there was an outlying, impactful, or emotional notable event you’d write in it? What was the structure to how you used it, if there was any?

Jim Collins: At that time, and I’m more now just kind of in the coding we described earlier, because I’m one of those really lucky people that I found this stuff early. And I remember the moment I hit the classroom at Stanford, first teaching a small business and entrepreneurship class, I just knew, “I’m home. I’m in the three circles. I know what’s going to guide, in some version, some permeation of this, probably for the rest of my life.” And I just knew it. But until then, I had to kind of get to where I could see that. And so, for those years, I would say — I bet if I went back and looked at it, and I haven’t done that, they’re in my basement — I’ll bet you that probably five out of seven days there’s reasonably thorough entries in there.

And those entries would also be things like noting, sort of projecting out — and a lot of it was often what I would describe as pattern recognition. Where you’d be noting things, but I would also always be scanning for people that — I could see them — people much older than me. And the question is, I could somehow picture that some version of what they do, somehow resonated. And I would note that. What was it about it that resonated? Why did I look up to that person? I’d spent a lot of it not just on my own experiences, but also very much on people that I admired. Not people from afar, people I knew and observed. Not their achievements, but something about the quality if what they were. And that was also a big part of that observation process.

Tim Ferriss: Okay. This is the perfect lay up segue, so thank you for what you just said, to a follow on to you mentioning that you’re 61 years old …

Jim Collins: Yep.

Tim Ferriss: And I read in a piece in The Irish Times, and you can feel free to fact check this, but you were quoted as saying, “The big years are 60 to 90, to me. I want to dwarf what happened before this with what comes next.” And in between — that quote was broken up in two pieces. It says, “He adds, pointing out that when he first met Peter Drucker, then aged 86, the Vienna-born sage still had 10 books left in him.” So what McPhee is to you, in a way, wanting to know what it was like to study under him, Peter Drucker is to me. So I have a copy of The Effective Executive, and I’ve read it more times than I can count. I’m fascinated by this man, but I’ve never actually spoken to anyone who has spent any time with him. Would you mind just explaining who he is, for people who don’t know, and then, just talking about your history with Drucker?

Jim Collins: Well, first of all, on The Effective Executive, I was very honored to have the opportunity to write the foreward to the 50th anniversary edition.

Tim Ferriss: No kidding!

Jim Collins: Yep. Yep. And you might want to look it up, because I stood back and I essentially said, “I’m going to distill 10 things I learned from Peter Drucker” in that foreward, some of which tie into The Effective Executive, but some were sort of broader than that. And it was very interesting to sit down and sort of think about some of those things I learned from Peter. So let’s just sort of intersect a little bit with Peter. And Peter was — boy. So, let’s talk about who luck, okay, as an intro to that. I have been so who lucky. And it didn’t start that way, because I didn’t really have a great relationship with my dad, and he died young. And so I kind of decided I would create my own father by reading biographies and people that I really looked up to.

And I formed a personal board of directors, came up with that idea in the 1980s. And started putting people on it. And they’re often people who I just admired for their character more than their accomplishments. And I would let them shape me. And I hope a little bit later we might have a chance to talk about one really amazing person in that, a fellow named Bill Lazier, one of my mentors I learned from. But Peter was a person who I just — if somebody said to me — well, somebody did say to me. A fellow named Tom Brown, from IndustryWeek magazine, way, way back when — I don’t even think we published Built to Last yet. Did an interview with me and Jerry at Stanford, and he said, “Who was most of a role model for you, that you most looked up to?” And I said Peter Drucker. He said, “Why?” And I said, “Well, because he really asks big questions.”

And so, Tom, unbeknownst to me, had previously interviewed Peter for something. And he calls up Peter and he says, “There’s this guy, he’s maybe going to take his own path. He really admires you. He’s 35 years old. He’s up there teaching at Stanford. Would you be willing to spend some time with him?” So out of the blue, I get this voicemail.

Tim Ferriss: Oh my god.

Jim Collins: I get this voicemail, and I hesitate to try to mimic the Austrian accent, because it just sounds terrible, but it was something long the lines of, “This is Peter Drucker.” It’s coming through my voicemail. And he says, “Would you please give me a call, I would love for you to meet with me.” Okay. So he’s almost exactly 50 years older than me at this point. I’m heading to 36, he’s heading to 86. And I call him back from the Seattle airport. And I call him up, and I said, “Mr. Drucker, this is Jim Collins,” and he yells into the phone, “Speak up, I’m not young anymore!” And so I’m yelling into the phone. We arrange this day, and I think it was December 10, 1994, if I recall correctly. And I get on a plane and I go down to Claremont.

And by the way, this was — let me just pause here for something, for anybody, you, anyone that’s listening. If somebody is willing to give you mentor time like that, you owe it to them — and to you — to go prepared and then to do a lot of writing after. So I put an entire couple, three days, into preparing for being able to meet with Peter. And then when I came home, I still probably have, I’m sure, my notes. I mean, I sat down, and I just processed, and wrote, and wrote, and wrote everything I gleaned from that meeting, and there were other interactions later, but that meeting. And that notion of you owe them the respect of going prepared. It’s not like, “Hey, I want to hang out, let’s network,” it’s not like that. Like you need to go. And then you need to process, and then you need to make good on it.

And I, last year went — I had the great privilege of being able to spend a day with Jack Bogle. And that’s an interesting story how that came about. But I spent two weeks preparing. And then probably three days codifying all my notes after, of what you learned from this great man, who only had, it turned out, one year left to live. And so, if you get that — you need to do it. Because that’s how you get the return on the who luck, and it’s also how you honor them, that you’re not taking their time; you have to make good on what the time they spend with you. So I went down there, and I knocked on the door, and he lived in this modest house. You gotta picture it. It’s this modest house in Claremont. And there’s a little bit of paint needed on the door.

And I knock on the door, and nothing happens. And then, finally, he sort of yells, wants me to be patient, he’s kind of curmudgeonly, and the door flings open, and there’s Peter. And he grabs my hand, in two of his. And he says, “I’m so very pleased to meet you. Please come inside.” And we went and we sat, and I have, still, this image of myself of, this is the model I still have in my mind, of the next 30 years. In many ways, just to pattern after, that way he had some sense of grace, but also the simplicity. He sat in a wicker chair. And a few years ago, they had — when they turned his house into a museum, they had the first ever wicker chair lecture, where you get to sit in Peter’s wicker chair and get a lecture. And I got to give the inaugural wicker chair lecture.

Tim Ferriss: That’s amazing.

Jim Collins: Which was — well, and the chair felt really big, by the way. It was Peter’s chair. And he was asking, “Why do you want to do this work? Why do you want to pursue these questions?” And I kept trying to ask him questions, but he kept asking me questions. And then finally we got to go to lunch. And I got a chance to start asking questions. And I asked him at that lunch which of his 26 books he was most proud of. “The next one!” He did write 10 more. He was 86. And years later, when I, again a great privilege, had the chance to keynote the Drucker centennial —

He died at 92, and Claremont asked me to come and give a keynote talk at his inaugural. I mean, at his centennial of his birth. He was born in 1909. And it’s actually — I think this is on YouTube, they put it up on YouTube, I went — I said, “I want to go see the shelf.” And the shelf was all of Peter’s books put out chronologically based on when he wrote them, first editions. And I said, “Where on the shelf is he aged 65?” And the answer was, when you pointed to it, 1/3 of the way across the shelf.

Tim Ferriss: Oh my god. That’s amazing.

Jim Collins: Isn’t it? And after that, they were so kind. They sent me a photograph of the shelf, this kind of a long version photograph, it kind of goes all the way across. I have it above my writing desk. And I look at it, and I picture a little note, that I’m not to 65 yet, right? I picture a little note which is, “You are here.” And it’s about 25 percent of the way across. And I don’t know if I’ll ever be as prolific as Peter was. But I’ll share with you what I think was — there’s so many things that were great about Peter. But here’s what I think was really great. People think he was a management thinker.

And he was. He was the greatest management thinker of all time. But as I stood back and looked at all of his work, and tried to think about what he was really doing, I think he was in pursuit of a giant question. And the best way you can articulate that question is, “How do you make society both more productive and more humane?” If you think about it, that is one of the great social questions. How do you make our society both, simultaneously, more productive and more humane? And I think when you look across the arc of his life, it was guided by a gigantic, beautiful, beautiful question.

Tim Ferriss: Thank you so much for that story. I’m just envisioning you seeing him sitting in that chair, and then later sitting in the chair, and how surreal that must have felt.

Jim Collins: It was surreal. And in a way, it almost felt, no, this is Peter’s chair. Although I recently have started this thing around here where, what I describe as wicker chair meetings. I don’t have a wicker chair, but I’ll just sometimes meet with people that just — there’s something, we’ve crossed paths, and it’s just like, “Oh, we’re going to sit down and have tea for a little while.” I think of those as wicker chair conversations.

Tim Ferriss: Well, I could spend the next hour on more questions about your experience with Peter, experiences, I should say, but I will go read the foreward, because I must have an older edition. I will go find the foreward with some of the lessons learned. Could you give us one of the things that — whatever comes to mind, that you learned from Peter, if you wouldn’t mind sharing that. And then —

Jim Collins: I’ll share with you two.

Tim Ferriss: Perfect.

Jim Collins: Actually — there are so many, because I had 10 of them, but won’t do all 10. One is: don’t make a hundred decisions when one will do. And the idea of that is that Peter believed that you tend to think that you’re making a lot of different decisions. But then actually, if you kind of strip it away, you can begin to realize that a whole lot of decisions that look like different decisions are really part of the same category of a decision. And that what you want to do is to then be able to say, “No, I’m going to make one big decision” that will be replicated many, many times. Because it kind of conceptually captures — for example, one version might be — in my own case, you get — and I’m sure you encounter this too.

You get lots of wonderful, interesting invitations. Things to go do this, or to go do that, or to speak at this, or whatever. They’re wonderful. Never be ungrateful for those opportunities. But you have to be very selective about what you do. And so as I was struggling with how do you decide which to do when you’ve got to say no to most of them, they all can look like a series of individual decisions, but then, actually no, there’s actually a couple of really big decisions. Is it a great teaching moment, potentially? And will you learn something? Okay, that’s like a meta decision.

And now you can sort of strip away — is almost like, actually the question is, “Is it a great teaching moment possibility? Or is it not?” is very different than “Should I go to Austin and do this event?” Right? Or “Should I meet with this person?” They look individual, but they’re really part of a whole. That’s one. And you can think of that as the simple thing, like what you wear. You can make a thousand different decisions, or you can make one big decision and wear the same thing all the time, I suppose. The second is, the one that — and I’ve shared this with some others, but it’s so powerful. At the end of that day with Peter, I asked him how I could pay him back.

And he said, first, I had already paid him back, because he had learned. And then he — and you gotta remember this was when we were doing a Thelma and Louise thing. We were really scared, right? We didn’t know if this was going to work. And I was launching out to try to do this self directed path. And genuinely scared. And Peter said to me, he said, “But I do have a request. That you change your question a little bit. It seems to me you spend a lot of time trying — worrying about if you’re going to survive. Well, you’ll probably survive. And you spend too much time thinking about if you’ll be successful. It’s the wrong question. The question is, “how to be useful?” And that was the last thing he said that day. He just got out of the car, and closed the door, and walked away.

Tim Ferriss: That was the Peter Drucker mic drop.

Jim Collins: Yeah. It was. It was. But you know, I find that I go back to that over, and over, and over again.

Tim Ferriss: We have many, many avenues that we can go down. Hopefully this is not the first and last time that we have a chance to have a conversation like this, but I want to define a term that’s come up a few times already now.

Jim Collins: Mm-hmm (affirmative).

Tim Ferriss: And that is, flywheel.

Jim Collins: Yep.

Tim Ferriss: And you have a monograph, a new monograph which is out, Turning the Flywheel, subtitle Monograph to Accompany Good to Great, but let’s start with the term flywheel itself. What is a flywheel?

Jim Collins: Yeah. And also, describe why I chose to put creative hours into this, because there was lots of other things that are in the pipeline still. And things that haven’t gotten at. Why flywheel extension? Since the flywheel chapter already exists in Good to Great, Why would I then write a monograph? So the idea behind the flywheel, we were looking at — let’s go back to Good to Great. We’re looking at — the question was, “Why do some companies make the leap from good to great, and others who are the same, in the comparison set, of situation, moment in time, resources, industry, customers, did not?” So it’s always the difference. And we went into it. I had this bias towards believing that a dramatic transformation would happen in a dramatic way.

And sort of thinking that there would be an aha moment, a miracle moment, a point of breakthrough. You can really sort of see — there was this grand thing that happened. And that was an assumption. I don’t know if I had it so explicit, but it was kind of in my mind. And then when we started interviewing, we were very lucky because we got to interview all the key executives, many of whom are no longer with us, that were still alive. That had been on those teams when they made those leaps. So what was it like when you were there? What was happening when you were there? We coded all the research, and so forth. And one of the questions was something along the lines of, “How did you know? What was the point of breakthrough?”

And repeatedly, we kept getting a response which was, “I don’t get the question. That’s a stupid question. There was no miracle moment. There was no moment of breakthrough. I don’t think it was a dramatic as it sounds. It was more of a gradual process. It was like an awakening that kind of happened in steps.” We just got this over and over again. It began to dawn on me that the way something really dramatic appears to those looking in from the outside is different than the way it feels to those doing it on the inside. And so it’s like if you’re watching an egg, and nothing’s happening, it just looks like an egg is just sitting there. And then, all of a sudden it cracks open and out jumps a chicken.

Well, you could have a big thing. Radical transformation of egg into chicken. And visionary leader transforms egg into chicken. But what it’s look like from the chicken’s point of view? It’s just kind of one more step after a whole bunch of stuff that’s been happening inside the egg that you couldn’t see until it cracks open. So observing that the way it looked and the way it felt were different. And the way it really happened on the inside, even though you could see the inflection on the outside, the best analogy I could come up with was a series of good decisions, supremely well executed, taken with disciplined thought, that added up one upon another over a very long period of time to produce a great result.

And so I had this image of pushing a giant, heavy flywheel. And you start pushing it in this intelligent and consistent direction. You start pushing on the flywheel, and after a lot of work, you get one giant, slow creaky turn. And then, you don’t stop. You keep pushing in the direction of those three circles we talked about earlier, what you’re passionate about, what you can be best at, what drives your economic engine, so it’s not random pushing. And you eventually get two turns. And then you keep pushing. And eventually you get four. They start to add upon each other. And then eight, and 16, and 31, and 64, and a hundred, and a thousand, and then 10 thousand, and then a hundred thousand. And then, at some point, all that cumulative momentum, all that, sort of like this —

There’s a breakthrough that happens, but how did it happen? “What was the one big push that made it go?” is a nonsense question. It would be like asking, “What was the one investment that made Warren Buffett Warren Buffett?” Doesn’t make sense, right? So it’s a cumulative effect. And then we observed in the comparison companies that they bought into the idea of these dramatic moments, or radical transformations, or cultural revolutions, or whatever — savior CEOs. Anything. They were trying to jump to breakthrough in one big step, rather than the building of the flywheel. And that was the doom loop. And so we wrote this chapter called The Flywheel and the Doom Loop, which was chapter eight of Good to Great. And it really captured —

It was a really neat chapter because it, for me, turned it on its head about how it actually happens. And it came from the research. It was all from the research. So then, after publishing Good to Great, it changed our lives. And I’m very grateful for how many people it reached, but right around the time of its publication, in 2001 — it was published in September/October of 2001, I was invited up to Amazon. And the flywheel principle was embedded in Good to Great, it’s a fundamental principle of how great companies get built over time, ones that last, and so forth. And I knew the principle. And I was there with executives in Amazon, and all I did was teach.

I just taught them the principles in Good to Great, and particularly the flywheel. Coming out of the dot com. It was like, “Don’t respond to this as an event; respond and build a flywheel.” And great students often take things and make them even better. And what they did was they took the flywheel and then made it their own. And what they did was to say, “We’re going to harness the flywheel principle that came from Good to Great, but we’re going to do it by getting clear on ‘What is our flywheel?’” And so, to really harness the flywheel, then you have to be able to say, “Okay, that’s great. The flywheel principle is the principle, but how do you then turn that into your own flywheel?” What is the flywheel?

And what the Amazon people did, kind of in a more simplistic form, and I’ll just grab it here, essentially they had this reinforcing loop. If you lower prices on more offerings, well, then you almost can’t help but go down to the next step in the flywheel. Picture a circle going around to increase customer visits. And if you increase customer visits, well, then you almost can’t help but get more third-party sellers. And if you get more third-party sellers, well, then you almost can’t help but expand the store and expand distribution. And if you do that, you can’t help but grow revenues for fixed costs. And if you do that, you can’t help but be able to lower prices on more offerings, which is going to attract more customer visits, which is going to attract third-party sellers, which is going to expand the store and extend distribution, and you can eventually buy Whole Foods and all the other stuff. You’re going to grow revenues for fixed costs and then, boom, lower prices on more stuff, etc., etc.

Now the beauty of that was that they got very specific. And what I came to understand was the flywheel principle best comes to life when you can really capture it. But here’s the key: people talk about flywheels. We have a flywheel, whatever. And what I came to see is that people didn’t necessarily really have a flywheel, because they didn’t understand something deeply important about what a flywheel really is. A flywheel is an underlying, compelling logic of momentum. It’s not a list of steps. Drawn as a circle, called the flywheel. Rather, there’s an inevitability built in. If you do A, you almost can’t help but do B. And if you do B, you almost can’t help but do C. And if you do C, you almost can’t help but do D. And around and around. And it’s driven around because there’s an underlying connection. There’s a logical sequence that builds dynamic momentum, because A drives B drives C drives D and around back to the top of the loop. Then, if you can kind of stand back and then say, “We need to engage in the very hard thinking of figuring out exactly how our flywheel turns. What is our flywheel?” In a way that truly has that inexorable driving momentum within it. Different organizations will have different flywheels, different people will have different flywheels. You have a flywheel, right?

Then, the key is you build it over a long period of time. The power of a flywheel is that it’s an underlying logic, it’s an underlying architecture. It’s not a single business, it’s something that can be extended. You can then extend it into new things as you experiment and find new things that will drive the flywheel even further, whether it be going from military bombers to commercial jetliners, in the case of Boeing, but the same underlying architecture. Going from memory chips to microprocessors, in the case of Intel, but the same underlying architecture.

What the Flywheel monograph is about is basically after — I like to say to people, “Just because you’re the one who articulated the principle, as we did in Good to Great, we uncovered it, we articulated it, and it’s right, but it doesn’t mean you yet fully understand it, even if you’re the one to bring it forth.” After 15, 17 years of really reflecting on it, I realized that my understanding of the flywheel, back in Good to Great, was right but primitive.

This notion of really, really thinking through the specifics of a flywheel became something that I really wanted to share with people, because I felt that people were talking about it a lot, but not really understanding it. That’s what that’s about.

Tim Ferriss: Just for people who may be wondering, when you say monograph, one way to think of this would be as a short book. It’s, I think, 46 pages.

Jim Collins: About 40 — yeah, yeah.

Tim Ferriss: Yeah, 40 to 46 pages. In that, you also talk about — you give other examples and walk through Vanguard, Cleveland Clinic. You did mention earlier, and I don’t know if this is in the monograph as well, but possibly asking you about what your flywheel is.

Jim Collins: I thought knowing you that you might ask, so in my kind of drive for being prepared, I put a little thought into that so I’d be happy to chat about it. Let me just share one thing though about the different examples that are in there. They cover such a wide range, and we have an elementary school where a school principal uses it to create results for kids basically. You’ve got healthcare and you’ve got startups and whatever, but why a monograph? McPhee, I hope, would like this idea.

A piece of writing has a natural length. A symphony has a length. “Gimme Shelter” by the Stones has a length. You wouldn’t say, “Well we should make ‘Gimme Shelter’ a 72-minute piece.” It’s the wrong length for “Gimme Shelter,” and writing is like music. It has an appropriate length for what the music is trying to do, to be. What I realized back in 2005 was sometimes you could have something that is a powerful extension idea or an ideal, it really shouldn’t be a book. It’s not enough to be a book.

Tim Ferriss: Yeah, 100 percent agreed.

Jim Collins: Yeah, but it shouldn’t be just an article because that’s ephemeral if it’s doable — so we were really struggling. We wrote this thing called Good to Great in the Social Sectors, which was another monograph. I was like, “What are we going to do with this? If we make it an article, it’s too perishable and too short. If we make it a book, it’s too long.” Then, well do you make it a chapter in the back of Good To Great? The problem with that is then all the millions of people who bought Good to Great need to buy another copy of Good to Great. That’s not right.

Joanne, my strategic brain, said, “Well why don’t we create a monograph and publish that and start a thing about remember Common Sense?” Think of the impact of Common Sense by Thomas Paine. it didn’t have to be big. It was the right size. I thought, “Well why don’t we bring back the genre — the monograph size?” and so we wrote Good to Great in the Social Sectors.

I remember printing 50,000 copies and thinking, “I don’t have 50,000 friends to give it to; it won’t sell,” and then it ended up reaching lots of people. We decided to do one on the flywheel here. My own flywheel, if you want to chat about that, I’d be happy to take a cut at describing it.

Tim Ferriss: Yes, please.

Jim Collins: When you do a flywheel, you need to first ask: “Where’s the flywheel going to start?” In the case of Amazon, it’s an economic flywheel that ultimately brings stuff to more customers and so forth. It starts with lower prices on more stuff, right? The Cleveland Clinic begins with getting the right medical professionals that can fit in their culture. Giro Sport Design and Intel start with great innovative products. The start of the flywheel is a key question, and in my case, it’s curiosity-fed big questions.

That’s where my flywheel starts. It all starts with what am I curious about? That has to be at the beginning of everything. If I’m really curious about something, well then I can’t help but want to learn about it and do research on it. That will throw me into the research. If I do the research right and really, really throw ourselves into it and stand those creative hours of the research, well then I can’t help but have ideas and insights, concepts that come out of that research. Then, if I have those, then I can’t help but want to write them and teach them and share them. That means going through the suffering of writing, as you know. Right?

Tim Ferriss: Yeah.

Jim Collins: To write them well and to wrap them well and to get the concepts and the right vessel, I can’t help but want to do that. If I do that, well then I can’t help but have at least some impact on the world if it’s well done. That’s the power of writing. You never know where it goes. If you have impact and reach in the world, well then you can’t help but have funding that comes from that, meaning there’s some economics that comes that allows you to do what?

Fund and feed your next curiosity big questions, which then leads to the research, which then leads to the chaos to concepts, which then leads to writing and teaching, which then leads to impact on the world, which then generates funding, which then allows me to fund the next question. Then, it’s perpetual.

Tim Ferriss: Is it also the case that, in some cases, well I’m struggling with how to ask this question because it just occurred to me, but I suppose it is that are there as many — or is it as true that there are negative flywheels as there are positive? These vicious cycles that are reinforcing within companies that people should be aware of. Or is the flywheel, as you use it, a virtuous cycle? Should people be also looking at disabling flywheels that they might have in their lives personally or organizationally?

Jim Collins: It’s a great question. Actually, I think it could be really interesting to think about dysfunctional flywheels, right? Really think about those. I’ll offer two things. The first is that if a flywheel doesn’t seem to be working, you have to kind of get the diagnosis right. It could be that the flywheel is just — you haven’t got the flywheel right. Or it could be that the flywheel’s fine, but think about the inexorable logic. Imagine you could score each of the five or six components on how well you’re doing it, say one to 10.

Suppose your scores are eight, nine, 10, nine, three, nine. The very nature of the flywheel, the fact that it’s the reinforcing logic that builds incredible momentum over time has a downside, which is that that three stops the whole flywheel. You have to be able to say, “Well maybe we have a flywheel that’s working. It’s a great flywheel, but the problem is we’re not executing on this piece of the flywheel. Therefore, the entire flywheel stalls or stops.” That’s an important thing for people to think about.

If you do 5/6th of the flywheel well, you don’t get 5/6th of the momentum. You get none. That’s sort of the downside of the flywheel, because you’ve got to execute on all of it. Now going to this other question, in Good to Great, this concept came from Good to Great, which is why we go back to it a lot. There are all the other books, Built to Last, Great by Choice, and so forth. In Good to Great, and then later we explored it further in How the Mighty Fall, which is studying how great companies fall, we described this other pattern we saw in the comparison companies or in the companies that fell, which is a doom loop.

You have the flywheel on one hand, and you have the doom loop on the other side. Yes, and the doom loop though tends to have the following pattern. You are grasping for some sort of salvation, a new savior, a new program, a new strategy, a new direction, a new right because things aren’t working. Because it really doesn’t have underlying flywheel logic to it, it doesn’t really get any traction. There’s a burst of hope and, well, gosh maybe this will really work. Then, that’s false hopes dashed by events.

Then that produces kind of a reaction without really understanding what really worked, which then leads to another grasp for salvation. What happens is you drive yourself further and further down in that grasping for salvation, which is stage four of five stages of when great companies fall. That eventually leads to companies really going to the bottom. While you can have actually — because that’s, again, you always have the comparisons, the good to greats and the comparisons, Built to Last and the comparisons. The comparisons often, in fact, double down on the doom loop and drive themselves into the ground.

Tim Ferriss: Thank you for clarifying that. I have just a few more questions. Are you okay to go for another five to 10?

Jim Collins: Sure. You may want to zoom out on something else out of just sheer curiosity.

Tim Ferriss: Oh yes, that’s exactly where I’m going. I’ve observed you to be in the research for this, in your writing, also in this conversation, very data driven, very methodical, someone who trusts in the data, trusts in the data. There are two things that I’d love for you to put in context or explain for me, which at least, at first glance, don’t seem to fit. It could be that I’m misperceiving who you are, or it could be that I’m misperceiving how things transpired.

The first is, well, there are two that jumped out, the first is you having mentioned that you got engaged four days after your first date. The second was around 35, 36, your Thelma and Louise moment where you had less than $10,000 in the bank. You kind of threw this Hail Mary.

Jim Collins: Yeah.

Tim Ferriss: Those both seem very out of character. Is it that you looked at the downsides, decided you could survive, and you ran some type of calculus? How did these two things happen? Given that you seem to be encoded to be very data driven, to think through the contingencies, to test the assumptions, and so on and so forth.

Jim Collins: I think those are related but very different situations. I think one of them is consistent with one of our principles, and one of them I don’t know where to put it. One of the key principles from all of our work is the notion that life, great things build by disciplined people, disciplined thought, disciplined action and building it to last. Then, you multiply times return on luck, luck, L-U-C-K. By the way, the evidence is very clear. The big winners are not luckier. We were able to establish that by quantifying luck and studying it.

The big winners get a higher return on their luck than the comparisons, but they don’t get more luck per se. Now, and I’ve mentioned this notion of who luck all the way through our conversation and lessons from great mentors, one of the key things we’ve learned in our work, everything starts with people, disciplined people, but also just people. I don’t know how you quantify certain aspects of just things about people. I mentioned earlier friends and my marriage and just time with people you love, meaningful work with people you love and respect.

With Joanne, we found each other. We both came from families that were clearly not Built to Last families. We met in Boulder very briefly, but we really met in college at Stanford. Our first date was a run. I wasn’t really a runner, but I really wanted to be around Joanne. I was too shy really to ask her out. She eventually said to me — I said to her, “So you still running?” She said, “Yes.” I said, “Well I’m thinking of upping my mileage,” which was true. I had just thought of it. She said, “Would you like to go for a run?” I said, “Sure.” I went over to her dorm room and she took me out on an eight-mile run.

Tim Ferriss: Oh, you want to run, do you?

Jim Collins: Yeah, you want to run? Anybody who knows the Stanford campus knows that if you go out towards Page Mill Road, you go immediately uphill out of campus. We went three miles uphill. Then, about the three mile mark, it became very clear to her I wasn’t really that much of a runner. We walked five of the eight miles back. We got to know each other really well, and that was my senior year and her junior year. By Thursday, we had simply decided to throw our lives in together.

I don’t know where the data comes from that. I don’t know the evidence. I just had the sense, and I think Joanne did too, of this incredible stroke of luck that these two people had — I mean we found each other, and it was just an instinctive thing. We just did it. It’s funny because Joanne later was the Nike athlete. She won the Ironman in 1985. She was in the original Just Do It campaign, so maybe she was already thinking, “Just do it, right? We’re going to get married.”

Anyways, we got married about six months later. I can’t say where the evidence comes on that but it’s, hands down, the best decision I ever made. Then, the key is the commitment to make it work. Relationships are about, I mean, the unwavering “We will not fail at this marriage no matter what.” You have to have some place in your life — in Good to Great, I wrote in the acknowledgements one of my favorite paragraphs I’ve ever written.

It’s at the end of the acknowledgements. I was going to write about Joanne. I wrote a line which is along the lines of, “Success in the end for me is that my spouse likes and respects me ever more as the years go by. I hope, by that measure, to be as successful as she is.” I don’t know where that comes from.

Tim Ferriss: Yeah. You said at the very beginning of this conversation — or maybe you were quoting Wittgenstein; I can’t recall — many of the most important things transcend the capabilities of language, right?

Jim Collins: Yeah.

Tim Ferriss: This certainly seems to fall into that category in some respects.

Jim Collins: Yeah. One of the things that we learned in Great by Choice with my co-author Morten Hansen — another great stroke of who luck in my life. He’s a genius research methodologist and a great, great partner in Great by Choice. One of the things that we struggled with was the role of big bets and the role of new directions and innovation and so forth. One of the things that we found is the importance of empirical validation, which is really different than pure analysis and it’s a principle we called Fire Bullets, Then Fire Cannonballs.

The idea being you have a certain amount of gunpowder, and you have a ship bearing down on you. Imagine you take all that gunpowder and you put it in a big cannonball. You fire at that ship, and it misses. You turn and you look back and you’re out of gunpowder. Now you’re in real trouble. Imagine if instead what you did was you fired bullets. You fired your first bullet and it’s 30 degrees off. Then, you take another bit of gunpowder and you fire a second bullet. It shoots out there, and now you’re only 10 degrees off.

You take a third bullet and you fire and it hits the side of the ship. Ping. You know you have a calibrated line of sight. Now, you take your gunpowder, whatever you have, and you put it in a cannonball. You fire it on the calibrated line of sight. What we learned is that, and I’ll tie this into the Thelma and Louise moment, because what we learned in our research is that one way you extend a flywheel is you’re firing bullets.

Then, every once in a while, you get calibration and then you fire a big cannonball on a calibrated line of sight, which then adds a big burst of momentum into a whole new — not necessarily new direction, because the flywheel is turning. It gives you an empirically validated big bet that can give you massive momentum.

The key there is, notice though, it’s empirical validation. That empirical validation are the bullets. If we go back to the Thelma and Louise moment, there is the moment of “Gulp!” when you fire the cannonball, right? I mean you can’t just sit there, only fire bullets. There comes a point when you’ve got to fire the cannonball. In that case, I was really scared because if the cannonball didn’t hit, I didn’t know what was going to happen. We really felt out there.

There were also six or seven years of bullets that had been the research we had done, the teaching in the classroom and, also, some early response to Built to Last. There was no guarantees yet, but early response and people really resonating with the ideas, right? It wasn’t like it just came out of the blue. There were bullet, bullet, bullet. There was enough calibration that this was not crazy. The question was: would we have the guts, at that moment then, to take all of our gunpowder, put it into one big cannonball, and to go?

There’s a critical lesson I got from one of my mentors, another stroke of who luck at Stanford, two great professors that were there with me when I was teaching, Bill Lazier, who taught me about the importance of relationships first in life, and there was this guy named Irv Grousbeck. I asked Irv, “Do you think I should keep enough capital alive here at Stanford that if this doesn’t work out, I could come back?” Irv said to me, “An option to come back has negative value.” I said, “I thought options always have positive value.” He said, “No. Not on a creative path.”

Tim Ferriss: Oh that’s such an important point, yeah.

Jim Collins: Exactly. He said, “If you have the option to come back, it will change your behavior. You’re doing a low odds game, which means you have to put all in, 100 percent, full cannonball, go off that cliff. Otherwise, you’re going to hold something in reserve. When it gets really scary, you’re going to pull back. Option is not in your interest.” We took all the gunpowder and fired it out, and there was no retreat. Then, when you’re making the decisions, you’re out there like, “How are we going to get the car to the other side in the Thelma and Louise jump?” There’s no tether back; you have to make it.

Tim Ferriss: The good news is you’ve done a hell of a lot of calibration over six to seven years.

Jim Collins: Exactly, yeah.

Tim Ferriss: Just to underscore for people out there, like, “I’m quitting my job this moment.” It’s like, “Well wait, hold on.”

Jim Collins: Correct. It was calibrated.

Tim Ferriss: There is a burning the ships aspect to it, but it was very calibrated.

Jim Collins: Very calibrated. I don’t know about the four days, but the rest was calibrated.

Tim Ferriss: That was calibrated, just perhaps not with your prefrontal cortex as much.

Jim Collins: Right.

Tim Ferriss: There’s a lot, lot — well anyway, we could talk about, dive into that another time. I mean there’s thinking fast, thinking slow, there’s a lot to decision making, only part of which we’re able to express with language. What a story. Jim, this has been so much fun. I highly encourage people to read all of your work, but the newest, and I think this is a very, very — well, I don’t think. I mean it is a very important concept, the flywheel and the expansion upon that, so Turning the Flywheel. People can find that everywhere books are sold.

They can certainly find you at jimcollins.com. Many more questions I’d love to ask some time, but I think this is a very solid session for me to reflect on. I have tons of notes sitting here in front of me. I’ve been trying to take my notes quietly, but is there anything else you’d like to say, ask of people, suggest? Any parting words before we wrap up this conversation for now?

Jim Collins: If I were to kind of step way back on everything, there’s a line that Joanne uses a lot which is life is people. We’ve talked about who luck and great mentors and personal boards of directors and getting married after four days and great friendships and being on really great Level 5 teams and whatever. We get so wrapped up in all these things we’re doing or things we’re trying to get done, but life is really short.

I mean you know that. You’ve named your company after the guy who wrote Shortness of Life. When you add it all up, the one thing I — with everything we’ve talked about in this, I still think it all goes back to the first who, life is people. Life, at its best, is about doing meaningful things with people you love.

Tim Ferriss: Hear, hear. Time with loved ones, high simplicity, time flow state, but ultimately it’s the people. Jim, is there anywhere online, besides jimcollins.com, where people might learn more about what you’re up to or say hello? Are you on this amazing, yet sometimes dreadful, technology sometimes referred to as social media?

Jim Collins: I’m firing bullets. I fired a few bullets. I’m going to fire some at this point. I haven’t done a lot with it. I’m kind of in the calibration stage. The question I go back to on that with the social media is I’ve been struggling. Remember I said earlier, “Don’t make a thousand decisions where one will do.” What I have been struggling with is “How, if I were to use that tool, do I make it great teaching moments?”

For me, if I can kind of bullet to cannonball to that, then I’ll probably do more with it. If I can’t, well, I’ve been fine without doing a lot.

Tim Ferriss: Mm-hmm (affirmative). Where are you currently firing bullets? I have some thoughts, but is it on Twitter? Is it elsewhere?

Jim Collins: We have a Twitter account, which I think it’s called Level 5 Leaders.

Tim Ferriss: It is, @level5leaders.

Jim Collins: Yeah, Level 5 Leaders. We have a Jim Collins Facebook page where Amy, on my team, helps me think about some postings. We haven’t put up a lot, so I wouldn’t encourage that there’s necessarily a ton there at the moment. We’ll be firing bullets, stay tuned. Our website, jimcollins.com, everything there is designed to share and teach the ideas. It’s all really built around the ideas. When you go there, it’s an ideas driven website. We’ve taken a lot of care to try to make it a place where students of the work can come and have a almost like cyber office hours, if you will, and really learn. That’s what it’s designed to do.

Tim Ferriss: I will say just a few things related to social media.

Jim Collins: Yeah.

Tim Ferriss: The first is I’ve seen some incredible thinkers who have done a lot of deep work go down in flames after tapping the vein of social media. I would say caution is warranted. That would be my first observation. You have a history of saying no so well.

Jim Collins: Yeah.

Tim Ferriss: You have so many policies that have served you in providing the space for the joyful solitude of deep work. I would just say be very careful. I was going to say, when you were talking about burning your bridges, that someone had said to me, “There are three addictions that are the most dangerous addictions of all: heroin, alcohol, and a monthly salary.” I would add to that, social media. There are, however, some examples, and I’ll just give you one, of people who I think do an exceptional job of teaching using short form.

There’s one person on Twitter, there are many, but I’ll point to one who is a close friend of mine. His name is Naval Ravikant. His handle is @naval, N-A-V-A-L, like Naval Academy but @naval. He might be someone to check out. People can follow you at Level 5 Leaders. We will link to, for people listening, all of these various sites, all of the work including, of course, Turning the Flywheel in the show notes as always at tim.blog/podcast. You can just search Jim Collins and this episode and all of its notes will pop right up.

Tim Ferriss: Jim, this has been such a pleasure and has given me so much to think about. I’m so, so grateful for having spent the last two hours with you.

Jim Collins: I’m actually very grateful as well. You’re right, I don’t actually say yes to very much at all. I’ve only fired bullets in this genre. This was one that was like, “I’m going to commit to really preparing and having a good conversation with you.” Part of it is because what I really learned about you is the care and depth of your preparation, and the fact that then you come into it with the idea of really wanting to have a conversation where you are present and engage with ideas and with thoughts. That notion of prepared curiosity, I think, is a great strength and to be able to join you in that, for me, is a real pleasure. We’re going to count at least half of this as creative hours.

Tim Ferriss: Definitely, absolutely. The podcast is certainly — I have to figure out which piece of the puzzle or, I should say rather, which component of the flywheel it is. It is certainly somewhere because I feel drawn, inevitably, to have or to strive for this type of conversation. It just gives me so much joy to be able to spend time with someone like you and share it with everyone listening. Thank you again for that. To everyone listening, you can find links, notes for everything at tim.blog/podcast for all of the goodies that we discussed in this episode. Until next time, thank you for tuning in.



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Jim Collins — A Rare Interview with a Reclusive Polymath (#361)


Photo by George Lange

“I’m not really a business author; I just happen to have used companies as the method to study human systems because there’s great data.” — Jim Collins

My guest for this episode is the incredible (and somewhat reclusive) Jim Collins.

This was a rare treat, as Jim rarely does any media or interviews. I’ve wanted to speak with him for more than a decade, and it was worth the wait. This conversation overdelivered on every level. I hope you enjoy it as much as I did.

So, who is Jim Collins?

Jim Collins (jimcollins.com) is a student and teacher of what makes great companies tick, and a Socratic advisor to leaders in the business and social sectors. He has authored or coauthored eight books that have together sold 10+ million copies worldwide, including Good to Great, Good to Great and the Social Sectors, Built to Last, How the Mighty Fall, Great by Choice, and his newest work, Turning the Flywheel.

Driven by a relentless curiosity, Jim began his research and teaching career on the faculty at the Stanford Graduate School of Business, where he received the Distinguished Teaching Award in 1992. In 1995, he founded a management laboratory in Boulder, Colorado.

In 2017, Forbes selected Jim as one of the 100 Greatest Living Business Minds.

Jim is also an avid rock climber and has completed single-day ascents of El Capitan and Half Dome in Yosemite Valley.

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

#361: Jim Collins — A Rare Interview with a Reclusive Polymath

Want to hear an episode with someone else who likes to ask big questions? — Listen to my conversation with Nick Kokonas, subversive entrepreneur, angel investor, and restaurateur extraordinaire (stream below or right-click here to download):

#341: Nick Kokonas — How to Apply World-Class Creativity to Business, Art, and Life

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.

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

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Caterina Fake — The Outsider Who Built Giants (#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 a co-founder 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 a 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 shouldthisexist.com, 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 athleticgreens.com/tim.

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 Uber.com/Rewards.

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

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