Please enjoy this transcript of my interview with Kevin Systrom (@kevin), an entrepreneur and the co-founder (with Mike Krieger) of Instagram. While at Instagram, Kevin served as the CEO, where he oversaw the company’s vision and strategy and daily operations. Under his leadership, Instagram grew to over one billion users and launched dozens of products including video, live, direct messaging, creative tools, Stories, and IGTV. Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!
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This interview was transcribed by Rev.com.
Tim Ferriss: Kevin, welcome to the Tim Ferriss Show.
Kevin Systrom: Thank you. I’m excited to be here.
Tim Ferriss: For people who don’t know Kevin, allow me to introduce Kevin Systrom, @Kevin on Instagram is an entrepreneur and co-founder of Instagram. While at Instagram, Kevin served as the CEO where he oversaw the company’s vision and strategy, and daily operations. That is a whole lot, which we will talk about. Under his leadership, Instagram grew to over one billion users, that’s with a B, and launched dozens of products including video live, direct messaging, creative tools, stories, and IGTV.
The company also grew to more than 800 employees with a campus in Menlo Park, new offices in New York City, and a new headquarters in San Francisco. Prior to founding Instagram, Kevin graduated from Stanford University with a BS in management science and engineering. He currently lives in San Francisco with his wife and daughter. Where to begin? We spent a little bit of time together. We have a little bit of time, fortunately not three minutes on morning television to explore all sorts of things. I thought we could start with one since you seem to read not just widely, but intelligently. We’ll hopefully get into that. Are there any particular books that you have gifted often to other people?
Kevin Systrom: Yeah, totally. Of course now, all my friends are having kids. I give kids books, but the one I give people that are trying to learn actively is Principles by Ray Dalio. It’s interesting actually. Someone gave me the PDF. It was a PDF before his book. Gave me the PDF and I skimmed over. I was like, “Oh, this is pretty good.” They were like, “No. I seriously think you’re going to love this.”
For some reason, I didn’t get around to it for maybe a year-and-a-half, and then I read the actual book, and I was blown away. It’s both a guide to life, a guide to business, and also I think an insight into Ray and someone who’s built an amazing business. If you guys listening don’t know what he does, he runs a hedge fund called Bridgewater and he’s so much more than just a finance thinker, he’s also just a brilliant philosopher. I give that a lot because I think it’s a great guide to life.
Tim Ferriss: He’s an awesome guy.
Kevin Systrom: Have you read it?
Tim Ferriss: I have actually. Ray has been on the show.
Kevin Systrom: Oh, really? Cool.
Tim Ferriss: For those people who are wondering just how many commas are involved in Bridgewater capital, I think they have $160 billion under management, something along those lines.
Kevin Systrom: It’s a little bit.
Tim Ferriss: He has a lot of very — in some respects — controversial and unusual practices within Bridgewater, like recording meetings and so on, and allowing all employees to have access to the minutes, and so on of such meetings. Are there any other books that helped you in the early days from an entrepreneurial standpoint that you found inspiring?
Kevin Systrom: Totally. Early on, we read — Mike and I both read The Lean Startup. I think it’s called Lean Startup Method or Lean Startup, I can’t remember.
Tim Ferriss: Eric Ries?
Kevin Systrom: By Eric Ries. I remember very early on I went to one of his book talks. I was one of like, 13 people sitting in this little room in Palo Alto. I was like a super fan, still am actually. I don’t know that I read the entire thing, but the principles from Lean Startup, I still apply today. One of which is: do the simple thing first, and that was one, our number one value at — well, actually community first was our number value at Instagram. Number two was do the simple thing first. Still to this day, I come back to that. If I were reading two books, I’d probably read those two books.
Tim Ferriss: If we look at do the simple thing first from a practical standpoint, could you give us an example, and I love that you brought up Eric because I remember also going to —
Kevin Systrom: Has he also been on the show?
Tim Ferriss: He has not.
Kevin Systrom: Okay.
Tim Ferriss: But I remember —
Kevin Systrom: I’m just going to start naming people that have not been on your show.
Tim Ferriss: He’s a great guy. I would have him on. I remember going also to, I think some hotel conference room — probably in Palo Alto — when he was initially testing out the material that later became the book in these workshops.
Kevin Systrom: Yeah, it was like that.
Tim Ferriss: Talking about avatars and all sorts of different things. Doing the simple thing first. The scope of your responsibilities at Instagram, at least reading even just your bio, makes my head spin to imagine what is involved, and how easily distracted you could become. What are some examples or any examples of doing the simple thing first, putting that into practice?
Kevin Systrom: The first thing I will say about doing the simple thing first is people love to make their lives more difficult than it needs to be. It’s like you talk to people who are saving for retirement, and you don’t have to go figure out a hedging strategy for currencies to save for retirement. Turns out just generally putting it in a mutual fund is not a bad idea. The returns you get for ever-more complex strategies — either in life or finance — it’s harder to eke out the incremental value. And I think what I found in a startup is when you’re small, and you’re two people — it’s me and Mike, we’re coding late into the night — you don’t have time to make things complex. You have time to make things work.
What ends up happening is you over-optimize. You might think you know how it’s going to break, so you end up trying to build a bunch of things before it breaks. And then it breaks in a different way. You’re like, “Why did I spend all that time on that fix when actually I needed to be doing something else?” I feel like that’s true in life, I think it’s turned business, it’s turned finance.
Some examples: Early on, maybe the best example at Instagram was we were — here’s the layman’s term version. We were on one computer basically, one server, and we had enough space to store the data on that one server, and Instagram became popular. It turns out all the data couldn’t fit on one server anymore, and we were like, “This is a novel problem. Let’s figure out to split it among two servers or three servers, or four.” Instead of just writing a single file that said like, “Hey, listen. If your user ID is — even, you’re on this server, and if it’s odd, you’re on that server,” which would have sharded the data across two servers very well and deterministically, what ended up happening was we threw everything out and we were like, “You know what? Let’s adopt this crazy new technology that does auto-sharding.” It was fancy and had all these bells and whistles. I won’t name it because I don’t want to throw them under the bus. We spent, I don’t know, four months trying to rewrite our system to be on this new database. Eventually, after it crashing a bunch of times, and us having issues with it, we were about to run out of space and Mike was like, “Screw it.”
He literally spent maybe two hours in the afternoon writing that file that we should have written to begin with, and it all just worked. I’m oversimplifying things a little bit for effect, but that’s basically what happened. And I still think about that story to this day in terms of an executive making the decision with his co-founder about what to do. Always do the simple thing first. It’s amazing to me how many people think the quality of their management, they think is judged based on the complexity of their decisions or the outcomes. It turns out actually the right thing to do is sometimes the simplest, and it’s the most effective. I live that as a value both in life and finance, and at work as well.
Tim Ferriss: I’m going to rewind the clock a little bit because I think this segues —
Kevin Systrom: Please. I assumed you could do that in editing!
Tim Ferriss: Yes, we can, and we can slice and dice, but this will be like watching the movie Memento.
Kevin Systrom: Okay. Got it. It’s basically usually what’s it’s like when I do an interview.
Tim Ferriss: Yeah, exactly. Pretty standard protocol. I would love to talk about — we won’t spend a ton of time on this because as we chatted before recording, I think you’ve talked about the origin story of Instagram a lot, but for people who don’t have any context, I think it’s worth diving into a little bit. Doing the simple thing first makes me think of a common problem that I see in startups and in software development of any type really, which is feature creep. And these products that start off with a focus, lose focus, and it seems to me that you effectively did the opposite in some ways for the creation of Instagram. Could you give people a little bit of background on how Instagram came to be? You can tackle that short version, medium-sized, however you like.
Kevin Systrom: First of all, I’m happy to talk about where Instagram came from. It’s such an interesting story in my life, and that I’ve talked about it a bunch of times, but I forget that it’s actually super interesting to hear for people who might have signed up for Instagram a couple of years ago and think it’s been around forever. Also, I think it has some interesting lessons. I’ll combine both talking about the origin story, but also how we kept it simple.
Instagram came out of, one, wanting to be my own boss. I was like, “You know what? I want to work for myself. I want to work on ideas. I really hope I’m going to make money.” I remember telling at the time my mom, I was like, “Hey, I’m going to go do this thing.” She was like, “What about health insurance?” I was like, “Oh, what about health insurance? You’re right. I totally forgot.” My point is I was a little naïve, but I wanted to do my own thing.
I had a bunch of different ideas, one of which was a terrible idea for check-in app. Actually, it wasn’t terrible. At the time, there were a bunch of check-in apps and we’re sitting in Austin right now, South by Southwest. Zoom back six, seven, eight years ago, it was all about Gowalla and Foursquare, right? Everyone was all about it.
Tim Ferriss: For sure.
Kevin Systrom: I had to have my version. It wasn’t bad, but it wasn’t good, either.
Tim Ferriss: Catchy name.
Kevin Systrom: Yeah. It was called Burbn, B-U-R-B-N. I think I own the domain name somewhere. But anyway we — what happened? I was working on that, I left my job, and I happened to be able to raise money for it. I’m not sure how or why but check-in apps were all the rage, so we raised some money. It a couple well-known firms in the Valley. I had just enough money to work on it. I met my co-founder Mike at the time and I know I needed a bunch of help because I’m like I’m technical, but I’m not a true engineer in the sense — I didn’t study it formally.
I met Mike, and he was one of the power users of Burbn, and he was like, “This will be super fun.” So we decided to join up. We worked on Burbn for maybe, I don’t know three months. It was clear it wasn’t working. It was very clear the startup was going nowhere. We decided to pivot, and this is where keeping it simple comes in. We actually got to the idea for Instagram by taking away features from Burbn, not by changing it all. A bunch of the features of Burbn: one, you could check in at a place, but two, you could add a photo of what you were doing at that place.
So you and I, we’re out to drink somewhere. I check in at the bar. I could post a photo of the beer I’m having or the cocktail, whatever. It turns out people kind of liked the check-ins; they thought it was pretty lame because it was a “me too” thing, but they loved showing people what they were doing. They loved taking a picture of the bar, the restaurant, the whatever. We realized to keep it simple, we were going to have to cut every other feature of Burbn — which we did — and we just kept the photo part.
Tim Ferriss: How did you decide on that feature?
Kevin Systrom: We made a list, and we asked ourselves, “What exists in the world? What sucks?” Meaning you look out in the world, and you say, “What opportunity is there to fill?” If stuff doesn’t exist, and it’s a problem that can be solved, aka the experience sucks, then that’s what you should go do. There were a lot of check-in apps, there were a lot of planners, and meet-up things, and group chat things, but there was no solution for posting great photos to lots of friends all at once. We made the list, we crossed off the things we thought were pretty boring or just there was no opportunity in them, and we circled the photos thing because we saw the confluence of mobile phones being pervasive — again, go back in the day, not everyone had an iPhone, but maybe the iPhone had been out for a couple years at that point, 2007, ’08, right?
Tim Ferriss: Yeah.
Kevin Systrom: We knew that cameras were going to be pervasive in people’s pockets, that people were going to be carrying these camera phones wherever they went. We didn’t know if it would be successful or not to capitalize on that, but it was the only thing that looked like a greenfield opportunity. Everything else felt crowded. That’s a different way of saying it. We got to the idea by cutting everything away from Burbn, circling the one thing that we felt like was the biggest opportunity because it didn’t exist yet and it was a big need. We built the first version of Instagram.
Note, by the way, the first version of Instagram did not have filters. People forget the only reason Instagram worked early on was because of the filters. Filters came about because I was on this walk with my wife. We were taking a small vacation. I had been working on Burbn for a while; I was exhausted. We were taking this walk along the beach and I was like, “You’re excited about this new app we’re building?” We hadn’t called it Instagram yet.
She was like, “Yeah, but I don’t think I’m going to use it because my photos aren’t that good.” I said, “Why don’t you think your photos are good?” She’s like, “Well, all your friends post these amazing photos and they’re all filtered and stuff.” I was like, “That’s because they use filters.” She goes, “Well, you should probably add filters.” We came back from that walk, I went straight to the room, and I just got on my laptop and I made the first filter, which was X-Pro II.
This is a long way of saying we cut features, we focused on what we thought the world needed, and then we got to the heart of the issue of why people wouldn’t use it because people didn’t feel comfortable sharing their photos. By solving those things right in a row and keeping it uber simple, I mean, even that first filter could have been written in OpenGL and could have been a lot faster. You tap on that filter, it took three seconds to show you the filter. No one cared. It was fine. Keep it simple.
Tim Ferriss: Keep it super simple. Now you mentioned Eric Ries; his book is perhaps one of the influences. I’d like to look at — or dig for — lessons learned, best practices observed, anything at all that you took away. Or difficult times, anything from a few previous experiences. We’ll go back to the Mayfield Fellows Program. Was there anything in that program that you found particularly useful? And then the next that I’ll hit — so we can certainly do them in order or not — would be Odeo.
Kevin Systrom: I mean, where do I start? Biggest lesson —
Tim Ferriss: What is the Mayfield Fellows Program?
Kevin Systrom: Mayfield Fellows Program. It’s a program at Stanford where they take, I think they still take 12 a year. 12 typically graduate students — although I snuck in; I’ll explain that in a second — who are interested in entrepreneurship, and they focus on what is called an entrepreneurship education. So they do three months of case studies, kind of like going to Harvard Business School, but case studies on just entrepreneurship. Then three months you spend at a real startup getting real experience.
Then you come back, and the last three months — so it’s a year-long program, meaning three-quarters of the school year — you come back and you debrief on your own experience. You actually write basically a case on your experience over the summer. I did that my junior year. I snuck in by like, I don’t know, I was like, “Hey, I founded this startup.” Not really a startup. It was a website at the time that was a competitor to Craigslist, but for Stanford students only.
I prayed that they would take me because I was so excited about entrepreneurship, and they let me in. Years later by the way, one of the people who ran the program, still runs the program actually, pulled me aside and was like, “Just so you know, we were barely about to let you in.” I was like, “Thank God you did.” She was like, “The thing that made the difference was that you were out there actually trying to start something.” I guess lesson number one is: never expect you’re going to get a “no.”
Always put your name in. Number two is: actually do the thing. Actually, start the startup. Don’t just go to conferences about it, don’t just write articles about starting. Do something. And that carries a lot of weight. That was the Mayfield Fellows Program, and maybe the last lesson on the Mayfield Fellows Program that I got from it was: there’s nothing in the world that can substitute for real experience. It doesn’t matter what we’re talking about.
If you want to be a chef, working in the kitchen is the only way you’re going to learn. Going to culinary school, whatever, I’m sure is great, but working in a kitchen is the way to do it. If you want to be, gosh, like a tech founder, you’ve got to start a startup. You’ve got to know what it feels like to put it all in the line, lose everything, and then come back. You can’t learn about investing unless you invest. I mean, name whatever profession. It’s like real experience is so much better than what’s in a book. That doesn’t mean the books aren’t helpful, but you’ve got to do it.
Tim Ferriss: They’re an adjunct. Very hard to become a professional soccer player by reading books on the physics of soccer.
Kevin Systrom: Although I got to tell you, I took this personality test and the results came back. But one of the main takeaways was “prefers learning by reading,” and I was reading my results to my family because I thought it would be entertaining. My mom was like, “Oh, my God. I remember when you were a kid. You just read everything.” My dad was like, “Yeah. You said you were going to be interested in playing baseball, so I bought a mitt for you and we were going to go play catch, and you were like, ’Dad, I got to go to the library.’ I was like, ’What?’ You were like, ’I got to read about it.’” I literally went to the library, read about how to pitch, and then played. I think that’s my M.O. It’s just I’m wired that way.
Tim Ferriss: Do you remember the —
Kevin Systrom: I was an okay pitcher.
Tim Ferriss: — name of the personality test for the assessment that you did?
Kevin Systrom: Yes. It was the Golden Personality Test.
Tim Ferriss: Golden Personality Test?
Kevin Systrom: Yeah. I think it was Golden, yeah.
Tim Ferriss: Why did you take that test?
Kevin Systrom: It’s a variant on the Myers-Briggs test, but it actually gives you very specific breakdowns of every dimension. For those of you listening that don’t know the Myers-Briggs test, there are basically four main dimensions of the personality test. It tells you for instance whether you’re more casual or if you’re very calculated and punctual, that kind of stuff. I wanted to know more about what I was like. I talked about Ray Dalio before. I spoke with him and he was saying, “Yeah, everyone who joins Bridgewater, we give this personality test.” I was like, “Well, can I take it? I want to know what I am like.”
My co-founder took it, a bunch of our senior execs took it. It was illuminating to learn, see on paper, what you know in the back of your mind. Of course, it helps you work with others, but a big part of it was reading on paper what you’re actually like and realizing, for instance, I do learn by reading. I’m not someone who likes to sit in a lecture hall; I want to have the book. If I’m going to learn something new, the way to learn is not for me to go to a conference, it’s to sit down with the best book possible. That might not apply to you. If you took it, maybe you like learning some other way. But I wanted to know what my API was, so that was helpful.
Tim Ferriss: Your API. I like it. That’s true.
Kevin Systrom: We all learn differently.
Tim Ferriss: Application programming interface, is that right? I used to know some acronyms. On reading, there are different ways to read books, and I had found in some of the research for this conversation a mention of Mortimer Adler’s How to Read a Book. Could you talk about how you read?
Kevin Systrom: How weird is it that I’m so into reading that I have to find a book that’s how to read? Where does it stop? How to read How to Read a Book? Have you read the book?
Tim Ferriss: I haven’t.
Kevin Systrom: It’s fine. I can save you some time. Basically, the idea behind this book is it’s how to read a book most effectively. Most people open the first page, and they start with the first word, and then they go into until either they get bored or they push through, or whatever. The claim in the book is basically that that is not correct, that instead what you should do is familiarize yourself with the structure of the book first. The most important — I would say his thesis is that the most important — part of reading a book is to actually read the table of contents and familiarize yourself with the major structure of the book.
Then familiarize yourself by skimming the book, and figuring out what the main arguments are. In fact, one of the secrets that I love and I still do to this day, is most authors in the last paragraph of every chapter — especially the last paragraph of the book — will not only summarize their main arguments, but make the point they actually have been waiting to make the entire chapter. By reading just those paragraphs, you get a pretty good idea of what the book’s about. Then you go back and you read like you normally read, but with the context of knowing the overall arc of the story rather than guessing where it’s going to go. I don’t recommend doing this with a thriller because it’ll ruin your experience, but with nonfiction, I think it’s fantastic. But that’s How to Read a Book. By the way, for those of you Mortimer fans out there, I probably didn’t do it justice, but go buy the book.
Tim Ferriss: Go buy the book, which will encourage you to buy yet more books.
Kevin Systrom: Seriously, if I could show you my room right now, my bedside table is just stocked with books. I’ve got a book called Mathematics of Politics, because I’m interested in both politics, and also the math behind elections, and that stuff. I think How to Read a Book is probably there. What other books do I have? I’ve got books on flying because I’m learning to be a pilot. I’ve got quantitative finance books. It’s the most fun I ever had just plowing through books. I guess it’s good I don’t have a job right now! I don’t know.
Tim Ferriss: It does create a little space.
Kevin Systrom: A little.
Tim Ferriss: It creates a little.
Kevin Systrom: I’m surprised how quickly it gets filled up.
Tim Ferriss: It does.
Kevin Systrom: Podcasts.
Tim Ferriss: Yeah, the podcasts, especially the long ones.
Kevin Systrom: It’s okay.
Tim Ferriss: Odeo. What did you learn there? What did you observe?
Kevin Systrom: Odeo was the precursor to Twitter. We were talking about Mayfield Fellows Program. My internship was Odeo. That three months over the summer, I spent at Odeo. I remember I showed up the first day, I brought my own computer, because I thought when you worked at a company, you bring your own computer. Because it was like, I don’t know, computers are expensive. You bring your own. They’re like, “Oh, good! You brought your own computer.” I think they were thrilled. It was Evan Williams and Noah Glass were the co-founders of Odeo.
They were like, “I forgot you started today.” I was like, “Yup. Here I am.” Actually, it was one of the best experiences learning from Ev, who’s brilliant, and Noah, who’s also brilliant. Just seeing that startup try to take off, it was a podcast directory, believe it or not. Maybe a little early.
Tim Ferriss: It was the right way, they just paddled a little early.
Kevin Systrom: Yeah, which by the way, another lesson in this whole thing, timing is everything. The number of amazing ideas and teams that either came too early or too late, it’s like you’ve got to have that essential element of timing and it’s the hardest to predict. But it was a podcast directory. Honestly, a lot of the famous podcast folks got started on Odeo, and there are a bunch that are still around, but it turns out back then there wasn’t exactly a business around podcasts and it didn’t go so well.
Tim Ferriss: Yeah. Super small.
Kevin Systrom: But that’s what Odeo was, and that was my experience. It was awesome. I’m very thankful to all those guys.
Tim Ferriss: What do you view as some of, say, just as an example Ev’s superpowers? He’s a very impressive guy, very understated in a lot of ways. What did you observe in the secret sauce of Ev? Because he’s also a repeat player. He’s not a one-hit wonder.
Kevin Systrom: No.
Tim Ferriss: What have you observed in him?
Kevin Systrom: It turns out blogging and communication is a thing, and doesn’t go away. There are lots of companies that can be started around it. What did I observe? It was a really long time ago but —
Tim Ferriss: Or what superpowers do you think he has? You could talk present tense too.
Kevin Systrom: I think he’s super determined, and super calm under fire. There are a lot of CEOs that are very emotionally volatile. And Ev, at least in my experience, is not one of those people. In fact, he’s determined and hard working. I can’t remember his background story, but he’s like, “Yeah. I went to this college. It wasn’t that great. I just worked my ass off to get here, and to build this thing, and then eventually sell it to Google — that was Blogger — and then to be able to start this thing.” I remember his work ethic because at one point I’m pretty sure he was convinced we all weren’t working hard enough. He sent us — he didn’t send us, he offered for us — to go to this seminar by David Allen, the Getting Things Done guy.
Tim Ferriss: Getting Things Done, sure.
Kevin Systrom: I remember sitting in the audience, and it’s like the Odeo crew, they were like, I don’t know six or seven of us at the time, at the David Allen Getting Things Done — not conference, but seminar. I still try to use that stuff today, by the way. But the signal was like, “We work hard here, and we get stuff done.” He was there. He was the first one in, last one out. As a CEO, I understood what that model meant. One, that I could learn from the CEO that if they had ways of getting things done, you could learn that as an employee, and I tried very hard at Instagram to learn stuff and then pass it on. But also just the work ethic that is required to get startups off the ground. It’s incredible.
Plus, willing to call it. He was willing to call Odeo and pivot to this thing called Twitter. Trust me, when we were calling it on Burbn and pivoting to Instagram, I was thinking about that moment. I wasn’t there in the room when they did it, but I can imagine the bravery that it takes to switch like that. It’s hard. Paying attention to people like Ev, and entrepreneurs like that, and entrepreneurs like Jack, I think you begin to learn that there are patterns and you have a little faith in their ways, and you end up trying to mirror it in many ways.
Tim Ferriss: I completely agree on the Ev having calmness as a competitive advantage. He’s very good at pausing and not jumping to respond, so he’s better able to choose his responses instead of being reactive. I think you’re very good at that as well.
Kevin Systrom: Thanks.
Tim Ferriss: I want to talk about — since it’s come up a few times — pivoting or ending projects. There’s in some aspects a fetishizing of perseverance in a lot of places including Silicon Valley and do all the tech, and yet if you look at a lot of the largest public successes, many of them had some type of pivot or shutting down of something that wasn’t working. How do you know it’s the right time to stop, and how does one go about making that difficult decision? Are there telltale signs that it’s not that another 50 percent of effort is required, another X number of hours per day? This is fundamentally flawed in some way that isn’t going to prevent it from working.
Kevin Systrom: Let’s take this question two parts. First is let’s just talk about the premise that most successful things are pivots, which I believe is true. One of the really fun things to do is actually — do you know The Wayback Machine?
Tim Ferriss: I do.
Kevin Systrom: I think it still exists. I haven’t tried it in a long time, but you can go and type any web address, and then I think it allows you to select the date of that website. You can basically see the history of the web. It’s super interesting. Go to YouTube and figure out when YouTube was founded. I can’t remember, but you can look it up on Wikipedia. Go to that date, around the beginning, you will see YouTube was a dating site before it became YouTube — what we know as YouTube.
Do that for most major things that you get excited about or look at the history of Facebook when it was Facemash beforehand, and it was something before that. The only one that I don’t think was a pivot was Google, and they’ve done pretty well. That’s the one counter example. That literally was their project, and they made it a company, and it worked really well, so I don’t know. Most other projects are pivots from an original idea.
I think that’s because, one, it’s really hard to tell, what works a priori. Doing it before anything, before you actually put it into people’s hands, it’s really difficult. You don’t know if it’s going to work. The key to entrepreneurship is failing really quickly. Putting it out there, seeing if it works, if it doesn’t, then diagnosing why, and then focusing on how to improve it from there.
One, I agree with the premise that most things are in fact like second runs, and then two, the importance of pivot, I think is that most of the time, you get it wrong. The question is knowing you’re going to get it wrong, how equipped are you to deal with that failure really quickly before you run out of money? The entrepreneurs that I’ve seen do very well are the ones that are equipped and engaged on the change from something that’s not working to something that is. Far too many people, because ego or whatever, stick with ideas far too long, and I think it ends up really poorly.
Tim Ferriss: Or look at something that isn’t working that might have a different application. If you look at Post-it Notes, it’s actually a failed adhesive. Then you look at, say, Viagra, which was failed — it was a failure from the perspective of whatever it was initially tested for or intended for, which I think was lowering blood pressure and normalizing blood pressure, and then the —
Kevin Systrom: They were like, “Excuse me. Can you check off all the side effects of this blood pressure pill?” “No, I can’t!” There’s a pattern here.
Tim Ferriss: Well, the recipients were asked to send back their samples and all the women sent their samples back and almost none of the men did. They’re like, “Wait a second. What’s going on here?”
Kevin Systrom: I can’t tell if this is a family-friendly show and we should dive into this?
Tim Ferriss: Oh, we can — it is family friendly, but Modern Family!
Kevin Systrom: This will be the director’s cut.
Tim Ferriss: This will be the director’s cut. This is like Blade Runner —
Kevin Systrom: Anyway, pivots are important.
Tim Ferriss: Anyway, pivots are important. How do you train, if you do, the ability to recognize, say, confirmation bias, or — this is something certainly Ray thinks a lot about — is identifying, from the perspective of an investor, where you might have — you’re succumbing to Sunk Cost Fallacy or any of these other things that could steer you to make bad decisions or not stop things? Is that something that you’ve trained in yourself, or is that innate from birth or upbringing?
Kevin Systrom: I was talking with my wife the other day, and I was like, “Nicole, I think one of my failures is that I always think things are not going to work out or I’m wrong in some way,” and we were going back and forth and she was like, “Maybe that’s actually a strength, because you’re so hard on an idea that you’re trying to prove yourself wrong to test the integrity of your idea or test the integrity of your thesis.” You mentioned Ray. I think a big part of knowing that you’re right is working as hard as you can to prove that you’re wrong. And if you can’t, well, there’s only one option left, which is: you’re probably right.
A lot of people I think are afraid to gather feedback. I think Mike and I at Instagram very early on tried our best to be open to feedback. I think as a young executive, I was like, “No. I’m the boss. All ideas are great. All my ideas are great.” After a couple of failures, I think you learn really quickly that, “Hey, listen. I know there’s this myth that the best founders just have the Midas touch, and every idea they have is perfect.” Like Steve Jobs, he touches everything and it just becomes gold.
It turns out that there are a lot of failures in these people’s lives. They just usually get written out of history, and then what you see is a trail of amazing ideas. I mean, someone should write a book on all the bad ideas amazing people have had over the years and just —
Tim Ferriss: Should be a 10-volume set.
Kevin Systrom: Totally. I think people get the wrong idea. There is no Midas touch. One of the things I hated most working in tech was the idea that there’s a product guy or product girl that you’re somehow, someone who just knows what’s going to work. Most of the successful people I know have tons of bad ideas, and it’s about editing them out, and figuring out which one is actually right because honestly, what is the Mendoza Line? It’s like you if you bat 200, above 200, you’re a pretty good batter.
In a world where your average is going to be one percent, you got to generate a ton of ideas before you get one, roughly 100. One percent would be way higher than the average. How do you figure out which is the one? I think it’s by being super, not mean to yourself, but critical on the idea in a constructive way, and pressure testing it with other people. I’m just wired in a way that assumes every, whether it’s idea or a thesis or whatever, I have is wrong. I’m more worried about being wrong than I am looking bad. You know what I mean?
Tim Ferriss: I get it. Do you have any particular questions that you’ve asked yourself or other people when you’re stress testing an idea, or alternatively, how you solicit feedback? I’ll give you an example since I write. I have all these books. I want people to act as proofreaders, but I don’t want them, since they are my friends, to be unnecessarily nice. Polite. One of the questions I’ll ask them is in a given chapter, I’ll say, “If you had to cut 10 to 20 percent, gun to the head, which 10 to 20 would go?”
Kevin Systrom: Nice.
Tim Ferriss: It forces their hand in a sense.
Kevin Systrom: I think that’s smart.
Tim Ferriss: Are there approaches that you like to use, or like others to use, on your ideas for stress testing?
Kevin Systrom: Well, first off, I think it’s important to realize how people are just wired not to be honest. Not that they lie. I mean I guess technically it’s a lie. I don’t think it comes from a bad place. They’re wired to avoid conflict. You go eat in a restaurant, and the server comes by, maybe you didn’t like it. The server comes by. When was the last time you actually, literally told them “Everything was great, but that thing was too salty. That was (I like to eat, by the way) that thing was too salty, that was undercooked.” Next time you go out to eat, and they’re like, “How was everything?”
You’re like, you instinctively just respond “Great, thanks!” Is that actually what you thought? Most people have one or two things they wish they could be better. What’s crazy is I think of myself in that situation. Every time I’m sitting down there, I’m like, “Man, if I were on the other side of this, I’d really want to know the truth. Because without the truth, you can’t improve.” You have to be careful because sometimes people have opinions, and they’re not always right, but if you don’t know, you can’t act on it. I’ve been surprised how many people I’ve met — at least in the food industry where, at least if you do it in a nice way, you’re like, “Listen, if I were on the receiving end of this, I’d want to know, so I’m giving this to you. Do whatever you want with it.” It’s always interesting to see the people that are grateful for that feedback, and you’re like, “That person is going to go kick some ass.”
Tim Ferriss: Totally.
Kevin Systrom: The people who are like, “Well, it’s supposed to be that way.” You’re like, “Well, okay. But what if it isn’t?” I think it’s really important as you mature as an executive, like, I definitely started in a place where I just didn’t listen to feedback. I was headstrong. Then as you have more and more failures — that, by the way, everyone has — you begin to realize it’s really important to collect that data and that information from people. No one would tell me when I was presenting on stage, everyone would be like, “Great talk. Great. Awesome job. Great. You killed it.” It’s like, that’s not possible.
A few talks in a row that happened. Then we hired someone, and I’m not going to pick on them and tell you who they are, but we hired someone who came up to me after and gave me three pieces of feedback. They were like, “You need to smile more. You need to do it. I know you’re a happy person, but you’re not smiling when you’re talking about this really happy subject. Smile!” I was like, “Oh, my God. That person is right.” They literally watched every single interview I had done for the last two years, and just had a list of things. I was so grateful for that, because it was feedback that no one else would give me.
Tim Ferriss: Do you remember any of the other points?
Kevin Systrom: It was “Slow down.” “Pause.” It was “Smile more.” Not because you’re trying to give off a vibe that — but just what’s funny is you can’t overdo smiling, it turns out. Like, it’s hard. I’m just like, I’m a serious person, so I don’t think to smile as much. What would be the other things? I’d have to go back to my notes, but those are the two things that stood out. What if people don’t give you feedback? It’s crazy. By the way, the whole thing is the other thing is the more important your company gets, the higher up you go, the less people are willing to do it.
You actually have to dig for it, and that’s one of the weirdest feelings ever is: “Please tell me something negative!”
But you asked a specific question, which is like: “What are the tools to do it?” I don’t know that there are any specific tools so much as like: When is the last time you, the listener, did that? When is the last time you went out of your way and you said, “Hey, I really want honest feedback on this?” When someone gives you feedback, you don’t respond in a defensive way. You say, “Thank you,” and you encourage the behavior. If you could do that, man, the self-improvement that comes with that…
Tim Ferriss: Yeah. The honesty that comes with it, if — depending on the format, can be a really remarkable — you may have done this before, but I had not done it — a 360 interview.
Kevin Systrom: Yeah. I avoided doing the first one they wanted me to do ever. It was like, “This is just like a management thing.” Then the second one I did, I literally tried hard to do it. I ask people to participate, I said “Please be as honest as possible.”
Tim Ferriss: Everyone is chatting with Joe Gebbia about his first 360 interview. For people who do not know what that is, there are different ways to approach it, but in effect, your superiors, peers/colleagues, and subordinates are all interviewed. The people that you interact with most are all interviewed about your strengths and weaknesses and so on. Very frequently, at least in my case, with my employees and so on, it was anonymized to ratchet up the allowable honesty.
It was a great example of how valuable honesty can be and also how difficult it can be to digest if it’s really full frontal. I think Joe said he went into his car in the parking lot and cried afterwards. I had a tough time. I had a really tough time with it, but it ended up being very helpful. I was able to look at it with a cooler head, not because I was angry, but I was really cut down at the knees by some of the comments, and it was really important. I mean, if you have spinach stuck in your teeth, you need somebody to tell you.
Kevin Systrom: I think the hardest part is how to tell when you’ve got spinach stuck in your teeth or someone just doesn’t like you! You have to be willing to get both, and then ask yourself “Which of these have merit?” And not to write things off, but you have to be able to go through it, and just ask yourself. But yeah, that was hard. I remember my first one. Now I think about it, and no matter what I do, whether it’s another company, whether I’m doing a writing project or a podcast, whatever. I just walked off the stage at South by Southwest, and I could see the screen that was displayed after we left.
They ask people to rate everything, like rate the speakers, rate the host. I was like, “I really want that data. I’m going to ask him for it.” Because I want to know, like, was it interesting to people? What topics didn’t they like? Did we come off as authentic? Inauthentic? Like where were we? It’s funny because no one ever tells you anything. Unless you dig for it, you won’t find it. Honestly, I think letting people know that it’s safe to give feedback, asking for it proactively, et cetera, et cetera, is important. The amount people go out of their way to avoid conflict is pretty wild.
Tim Ferriss: Which often works in the short-term, but can really be caustic and erode relationships in the long-term if you’re avoiding that. And your commenting on the rating on screen made me think of Kyle Maynard, who’s an incredible, incredible guy, who’s also been on the podcast, but he had learned at one point, or was given a piece of advice from very successful CEO of a large company, that if you ever ask somebody to rate something from one to 10, to disallow seven because seven is like, semi-polite.
Kevin Systrom: It’s like Yelp is all three-and-a-half stars, you’re like, “No.”
Tim Ferriss: Exactly. You’re mentioning restaurants. I’ll very often ask people of restaurants if they’re giving me the “Everything is good” response, which is giving no information to act on, I’ll say, “All right. On any — ” I’ll give them two options, and I’ll say one to 10, but no seven, how do you rank?” Then they’re forced, if they’re struggling, that —
Kevin Systrom: I like that.
Tim Ferriss: — to do a barely pass, which is a six. I’m not going to order that. Or an eight, which is a strong — that’s a confident endorsement. That can be applied to all manner of things.
Kevin Systrom: That’s really cool. I’ll do that from now on. No sevens.
Tim Ferriss: Yeah. Let’s talk about tough times, because you mentioned —
Kevin Systrom: There are none. The life of an entrepreneur is golden.
Tim Ferriss: It’s true. It has been said that your life is all highlights. No, I’m kidding. That hasn’t been said.
Kevin Systrom: What company made that happen?
Tim Ferriss: I want to talk about some of the, maybe, tougher times that you’re willing to share if any, some of the maybe darker periods, tough decisions, or any time you had self-doubt or felt lost because — where I’m going with this is I’m very curious how you then recontextualized it, found the silver lining, or just got through it. Because some people get knocked out, and they have a really tough time getting back up, so when people are able to do that, I like to look inside and see what actually happened. Any at all that you’re willing to talk about?
Kevin Systrom: First thing I’ll say is a lot of people assume that businesspeople, entrepreneurs, whether they make a lot of money, or they sell a company, or they go public, or whatever, and they’re CEOs for a long time, or world leaders, whatever, a lot of people assume these people don’t struggle. Somehow they’re inhuman or whatever. I feel like I wake up every day with a lot of the same worries I did before Instagram was a thing. “Am I working on the right thing? Did I do enough today? Is that idea the right idea?”
I still have just as many failures as I did before Instagram, and inside of Instagram as well. Now don’t get me wrong, there are structures around me now that allow me to come back from those failures. I guess my point is like, getting knocked down is a really common thing no matter where you are in your career. No matter where you are in your progress of building something. In fact, it usually happens more, the more important thing you’re doing. Early on at Instagram, I think there were a bunch of times, I remember pitching the idea and having really smart, intelligent folks look at me like I was a crazy person for working on anything related to photos.
I remember trying to hire some of the most amazing designers early on who just wouldn’t join because they didn’t believe in the app. I remember press stories or investors investing in competitors even though they had invested in us. Choosing the other, which is fine. Listen, it’s up to — investors should be able to choose who they think the winner is, that’s their job, but it’s tough to think you’re not the winner. All of these things happened along the way, and we were knocked down multiple times — whether that was in our heads or actually there in reality.
The thing that kept us going was realizing it wasn’t other people we were trying to impress. I mean, of course we wanted a community for the app. The reason we got back up each and every time was because we loved what we were doing. If your goal is to gain people’s approval, like the startup business is a terrible business to get into. Heck, if you’re a singer, it’s the worst business to be in in the world because everyone is going to tell you your stuff stinks until maybe it doesn’t, but you have to believe in what you’re doing and love what you’re doing, and that itself has to bring you the most amount of gratitude, or that itself has to bring you the most amount of excitement, otherwise getting knocked down is going to knock you off the horse and you’re off forever.
I often think, was it determination that got us to where we got, or luck, or some combination of both of them? Because I don’t know. If you have a bad idea and you’re determined on it, and don’t listen to anyone, it’s not great. At the same time, we wouldn’t where we are if I listened to most people. It’s crazy. I don’t know if there’s a secret to getting back up, otherwise other than maybe creating no choice but to get back up. I didn’t have another job. What was I going to do? Sign up for business school? I don’t know. I had quit my job and raised a bunch of money. I really loved what I was doing, so every time one of those failures would occur, what was the other option?
Tim Ferriss: Can you think of one?
Kevin Systrom: A desk job.
Tim Ferriss: A desk job. Can you think of an example of a tough time, a tough decision, a tough rejection from an investor, a designer, anything, and what you then said to yourself? I’m very curious about self-talk. Whether it’s like Shaun White on the final run in the Olympics, and I asked him what he said before he left the gate to himself, and it was “Who cares?” He explained why it’s like “Who cares?” I didn’t expect that answer and —
Kevin Systrom: Me neither!
Tim Ferriss: — found it really interesting in a sense that he’s done all the preparation he could possibly do. He’s either ready or he isn’t, and there’s an entire explanation for it. What fighters say before they get in the ring if there is some type of self-talk.
Kevin Systrom: I got one. let’s go straight to the interesting topics, selling our company. We sold our company and it was April of 2012. By all accounts if you start a company, for a lot of entrepreneurs, “winning,” quote-unquote — by the way, I don’t agree with this definition, but winning is, quote-unquote, selling your company or having a public offering, an IPO for a lot of people. That’s like the traditional outcome for a startup. We had sold — and we were 13 people and it was a billion dollars. It was really exciting.
I remember right afterwards, everyone being like, “So it’s over.” I feel like that was the most painful thing to hear because I had no intention on not doing Instagram. I wanted to work on it for the next whatever years, but everyone I met was like, “So you’re done now. So it’s over.” I was like, “No, no, no.” We would try to hire people and they’d be like, “No. It’s over.”
I remember people working at the company telling me it was over. A couple of people ended up leaving pretty soon after that. I remember one of them saying, “Yeah, there’s nothing else to learn here. Where can we go from here?” Mind you, at the time we had, I don’t know, 50 million users. We got to a billion, by the way. We had no revenue. We got to a lot more than no revenue. We grew to a thousand people on the team. We opened up multiple law offices all around the world. I got to do everything from meeting the Pope to meeting some idols. It was crazy. The idea that in 2012, we sold our company, and then everyone just counted us out, that was painful.
Tim Ferriss: How did you contend with that? What was your response to that?
Kevin Systrom: I think with me it usually comes with the competitive nature of proving people wrong. If you look at the histogram, sorry to use that word, but of how long founders stay after they sell their company, I’m pretty sure there’s a giant lump around one month to one year. We were there for six years after we sold it, which I think goes to show how incredibly determined we were to show people that Instagram wasn’t done. That we were at the beginning, not the end, and that it didn’t matter if we sold the company. We were going to make something out of this thing.
For me, I think the motivation comes with proving people wrong, because I hate when people discount us. I hate when people tell us we’re not going to be something, that because we’ve sold, it’s all over. Looking from the outside, I get their perspective. I just wanted to prove them wrong.
Tim Ferriss: Yeah. It’s a powerful motivator.
Kevin Systrom: Yeah. Part of taking that personality test we talked about is understanding what your motivators are. Because if you know what your motivators are, then you know how to get yourself up in the morning, how to work hard. You know what things are not motivating, but competition is one. Actually, it’s interesting. There were two dimensions of the personality test. There’s competition, and then there’s challenge. I always thought I was competitive. It turns out I’m actually not competitive at all. I mean, I’m a little competitive, but not that competitive. I have very high scores on challenge, which means setting goals for yourself and trying to meet them, but it’s like self-imposed rather than comparative.
Tim Ferriss: Right. Sort of an intrinsic motivator.
Kevin Systrom: Yeah. It’s an internal motivator of “I want to go get this thing done.” For me, I think at that moment, it was more about self-challenge to prove to myself that I could do it, and that we could build this thing. It worked.
Tim Ferriss: How did you learn to manage?
Kevin Systrom: Man, I had to.
Tim Ferriss: Yeah. How does one learn to manage? Because you — and it’s not just time within a larger company, because you can find plenty of people who make the same mistakes for 20 years in a row, and somehow manage to limp along and do decently despite their weaknesses. But when you sold the company, how many employees did you have?
Kevin Systrom: 13.
Tim Ferriss: 13. And then —
Kevin Systrom: I think I managed three of them.
Tim Ferriss: Right. You then went through —
Kevin Systrom: Why do you think companies have hierarchy? They’re like, “I don’t want to manage people! You manage them.” Before you know it, you’ve got a tree 90 layers deep. I’m joking.
Tim Ferriss: I mean, there is some truth to that, but how do you learn to manage? Were there any particular lessons, resources?
Kevin Systrom: I have to say —
Tim Ferriss: Anything at all.
Kevin Systrom: I was going to say my job is different than most, which obviously is an understatement. I’m going to tell you the philosophy I subscribed to, and then I think the listeners can decide if it makes sense for them. It might. I decided that I had nothing to lose because — or at least, I didn’t think I had anything to lose — because I had my job. I was excited about it. I was running this thing, and I knew what I didn’t know — or at least knew that I didn’t know a bunch of stuff. My philosophy was hiring the smartest possible people who are way better than me to work for me.
That feels weird because you’re like, “I have no experience. I’ve been doing this for two years. How do I hire someone that has maybe 15 years of experience in engineering or 15 in operations, or…” The list goes on. The ironic thing is, by hiring people that were way better than me, that I would see myself working for someday if they started a company, that actually you end up creating the best possible team. I think that works because I felt like I had job security.
A lot of people are worried, “If I hire great people beneath me, then maybe one of them will take my job.” I don’t know where the reality is on that spectrum in the real world. I don’t know, but I think that’s actually one of the issues I looked for most in the company, which was people hiring down on purpose. People do it reflexively. They hire down. They’re like, “No. I need someone with less experience than me. They should be younger, they should have fewer years of experience, because I should coach them.” Actually, if everyone hired up, you’d have the most badass company in the world. How do you manage that?
I guess my point is I found people that were way better than me, and the way I managed was by managing division and direction of the company, and then asking those people how to get there, and making sure those two things were connected at all times. I didn’t have the regular job of managing a bunch of new grads out of college and coaching them on their careers, which exists en masse in Silicon Valley. I’m not sure my management experience mirrored that of most, but I think there’s a lot to learn, which is: hire really great people, that someday you want to have — they should have your job.
Tim Ferriss: You hire these people if you subscribe to this philosophy, and then I imagine there are different strategies and routines and rules and so on that you put in place to give structure and direction to this team of all stars. One that I could ask about would be meeting structures. In the course of prepping for this, and I found this a few places, but in The New York Times — feel free to fact-check this, but I’ll just read this briefly. I’d love to hear you elaborate on what the meeting actually looks like and how you handle it.
This is from The New York Times. “Some of the bottlenecks the company has addressed in the past year are internal. For example, Mr. Systrom and his co-founder realized that one of the primary holdups was their own decision-making. So in the past three months, they started holding meetings in which they just make a bunch of decisions.
’We have a doc in which we list out the inventory of decisions on products — as if it’s stacked up in front of a machine, waiting to be processed,’ Mr. Systrom said. ’And then we have sessions where we sit down and we decide. You just work through the decisions.’”
This is something that you might be able to do in an informal, unbatched way when you have three direct reports, or have 13 employees, but as it grows, it seems like this type of systematizing could be really important. Can you describe how a meeting like this functioned?
Kevin Systrom: Totally.
Tim Ferriss: And why.
Kevin Systrom: It’s really funny for me to think of myself as being referenced as “Mr. Systrom.” It’s very formal. “Mr. Systrom with an inventory of decisions.” Okay. Here’s the context. Have you ever read the book The Goal?
Tim Ferriss: The Goal?
Kevin Systrom: The Goal.
Tim Ferriss: I have not.
Kevin Systrom: It is a book about basically manufacturing and supply chain management. It sounds really boring, but I promise you it’s really good. Last name is Goldratt. I think it’s Goldratt who wrote the book. In fact, if you talk to business people, a lot of people will say it’s their favorite book. I wrote in one of my weekly updates to the team, I wrote that I was reading this book, and that I loved it. A bunch of people were like, “Oh, I love that book too.” It’s a business book that talks about how to optimize supply chains, basically. But it’s written in narrative form, which is kind of cheeky.
Tim Ferriss: It is cheeky.
Kevin Systrom: It’s not like a business — it’s a business book, but it’s written with a narrative. There are characters. It’s actually pretty fun, so I say go have a read. What I realized in reading this was that any system is most constrained — or at least the thesis of the book is most constrained — by the slowest process. I think they called it a Herbie.
Tim Ferriss: Herbie, yeah.
Kevin Systrom: Have you ever heard that?
Tim Ferriss: I have, yes.
Kevin Systrom: It’s because the beginning of the book, it’s the Boy Scouts.
Tim Ferriss: Yeah, exactly. You want to explain what Herbie is?
Kevin Systrom: Yeah, I know. We’re getting there. How many times are Boy Scouts going to come up in our podcast? The narrative is that they’re on some trip, and they have these Boy Scouts lined up. I think the main character’s son or something is in the line of Boy Scouts. Herbie, it might not be PC to talk about now, but Herbie is a little overweight and he’s at — is he at the back? I don’t know. Basically, they figure — I think the way it goes is no matter where they put him in the line, the line can only move as fast as the slowest process. That’s the takeaway.
Again, people who are super fans of The Goal can correct me on this, but the essence of it is your slowest part in the chain is always going to limit output. In this case, the slowest Boy Scout limits the progress the troop makes, which isn’t actually all that intuitive until you read this book, and you go through it. With decision-making, what we realize is that a lot of things were coming to us. Unless we would decide on an important decision, it was basically like inventory stacking up in front of a machine that wasn’t moving.
Of course the machine can’t output products that people want to go use until those decisions get made. It sounds again really intuitive, but if you think about a company as the raw materials go in, and raw materials are ideas. They go through machines that transform them into reality, so they go from an idea to a mock, to a final draft, to a version, to out testing with the beta testers, out to the real world, that actually what you need to do is make sure all machines are running at highest capacity, including the one that moves ideas from the idea pile to mocks, from mocks to actual — right? You work down the chain, and we realized very early on in reading this book that a lot of the lessons that usually apply to manufacturing actually apply to making decisions at a company as well. I had actually forgotten about that book until you mentioned it.
Tim Ferriss: I’ll have to pick it up, The Goal. I have a long list of books to tackle. How do you choose books that you’re going to read? I know you have a few examples of things that you’re interested in. How do you filter the universe of books to those you end up reading? You could pull up a few real examples from those you’ve read, and indicate how you got to those, but do you have a process for selecting books?
Kevin Systrom: Well, first —
Tim Ferriss: Or disqualifying those.
Kevin Systrom: First, I don’t read fiction. Not that there’s anything wrong with fiction. I know people that read a lot will be like, “What? You don’t read fiction? Come on. There’s so many greats.” I don’t know. It just doesn’t get me up in the morning. There we go. There goes a good portion of books down to nonfiction books. Then I ask myself what topics I care deeply about or what things I really want to learn.
For instance, learning to fly. What are the best books to learn to fly? Or if I want to learn about investing or finance, what are the best books? Or if I want to learn about productivity, what are the best books? Obviously, Amazon is great for that, and you can read through reviews. Honestly, a big part me reading is just like there’s usually some outcome I want like, “I want to be able to do X. What do I have to read that will teach me as fast as possible?”
With a book — okay, with a class, you’ve got to wait until the class happens, go to a class, and then wait until the next class. But with a book you can literally just get through it in a week or a day. Then you can reread it, and then reread it. I find that if you want to learn a new skill, there’s nothing like sitting down with a nonfiction book on that topic that’s well laid out. Sometimes you’ve got to call it. I’ve been a quarter away through a bunch of books on topics that I thought I was going to like, and just thrown them out because I’m like, “These are trash.” It doesn’t always work that way.
Tim Ferriss: Do you read, and if you don’t, this isn’t a value judgment, biographies? Do you ever read biographies?
Kevin Systrom: Okay. I have not read, no. But I really want to. The one area that I want to spend way more time on is history, including biographies, which I consider a form of history. Although biographies can be fairly selective in the history they tell, that’s true of all history books. I feel like — how old are you?
Tim Ferriss: 41. I’m pretty sure I’m 41.
Kevin Systrom: It’s okay. Well, fact-check that one. I’ll get back to you. I’m 35. Our lives are really short compared to the recorded history. It turns out if you look back in history, patterns emerge. I read this great book called Lessons of History.
Tim Ferriss: That’s Will and Ariel Durant.
Kevin Systrom: Yeah.
Tim Ferriss: Fantastic book.
Kevin Systrom: It’s short.
Tim Ferriss: It’s excellent.
Kevin Systrom: It’s like a leaflet. You can read it in a day. There’s some parts that I just go through it, but for the most —
Tim Ferriss: Actually, I read that because Ray Dalio recommended it.
Kevin Systrom: It’s a great book. The number of people I meet that are like, they’ve read it, and — anyway, the takeaway is that things happen over and over again, or at least certain patterns emerge. I guess what I’m saying is if you look back at history, you can learn a lot from reading people’s history whether it’s a biography or the history of a specific segment of companies. For instance, I think if you want to study the acquisitions of companies and where those founders have gone, and what they’ve done, and more importantly, what do most founders do next after selling a company, and taking some months off.
How many take one month off? How many take a year? How many take five years? How many never emerge again? What are the differences between those that decide to do something and those that don’t? Even in my own exploration of what’s next in my life, I find myself not reading necessarily biographies, but I do read accounts of entrepreneurs that have launched big things, and done new things in the future and those who haven’t. I start asking myself like, “What are the patterns that emerge?” No, I don’t read biographies yet, but I want to, and history, I think more generally, is a super interesting topic.
Tim Ferriss: There’s some excellent biographies out there. I think you might enjoy Genghis Khan and the Making of the Modern World.
Kevin Systrom: Okay.
Tim Ferriss: Excellent, excellent book for a lot of reasons.
Kevin Systrom: I’m trying to think of the ones that have been recommended to me. I’ll have to get back to you on that.
Tim Ferriss: David McCullough has a lot of really good biographies, and the Wright Brothers and so on. It was actually given to me by a very, very successful consumer packaged goods entrepreneur here in Austin, which turns out to be sort of ground zero or the epicenter of a lot of CPG stuff.
Kevin Systrom: That’s so cool.
Tim Ferriss: Yeah.
Kevin Systrom: Isn’t it interesting how many people have so many similar patterns in their lives? I think there’s this great equalizer when you realize what you are doing or going through or whatever, while that might be super unique to you in your 35 or 41 years, it actually turns out it happens over and over again to people in their lives. Not everyone, but it’s occurred in the past, and you have a lot to learn from it. That’s basically my point.
Tim Ferriss: I think it’s a 120-page book; Lessons of History is a fantastic place to start. I actually downloaded it as Kindle book and let it sit there for months because I expected it to be very dry, and it’s a beautifully written book. I was very impressed. Then if you like that as a taste test, then you can go into their, what is it like 10 or 20-volume encyclopedic —
Kevin Systrom: It’s a summary of their volumes, right?
Tim Ferriss: That’s right.
Kevin Systrom: It’s like the Cliffs Notes.
Tim Ferriss: The Cliffs Notes. This is one of the questions that I’ve been hoping to ask ever since we booked the podcast, and that is about advice that you give to entrepreneurs that very few actually take, and I’ll explain just by way of example. I’m asked all the time how various folks should launch books. People come to me asking, “How should I launch a book? How should I write a book? How should I get a book published?” I might tell them, for instance, don’t try to write for the entire world. If your goal is to hit The New York Times Best Sellers list, write for 10,000 to 20,000 people per week. In other words, you really only need to get the flywheel spinning, because people use the Best Sellers list as a shopping list to write a book that at least 20,000 people will love.
Kevin Systrom: But they end up writing something too general.
Tim Ferriss: They end up writing something too general. I tell them to give themselves a ton of buffer before the book is published, and to write it in such a way that for instance, it can be read modularly. Then they don’t do that, and they wonder why they can’t run excerpts. It’s been incredible to me how I put together a blog post, which is how to write a bestselling book this year, where I lay out the exact playlist — or not playlist, rather, but playbook — and nonetheless it’s like one out of 100 who actually implement even a portion of the steps. Are there any particular bits of advice or recommendations that you give to entrepreneurs that you’re surprised aren’t taken more seriously or actually followed?
Kevin Systrom: Yeah. Number one advice I always give is to solve a problem. So many people, when they found a company, they found a company just to found a company. Or they’re like, “I’ve got an idea.” Ideas are not companies. Ideas are not products. You’re like, “Well, I’m going to combine this thing with this trend and we’re going to do this. It’s a cool idea.” Usually the warning signs are they include some element of a current fad, like AI or something. Not that AI is a fad, but it’s a wave that’s happening right now that I think it’s easy to make your company sound more interesting if you’re just like, “And it uses AI,” or like, crypto.
There are always warning signs that I see with the pitches that I hear from people when they include those words and it’s not backed up by a clear problem that you’re solving for the person on the other side or the company on the other side. The counterparty, right? I always say, “Make sure you’re actually solving a problem.” Now there are different ways that can be wrong. It can be solved already, really well, in which case you’re not solving a problem. The idea might be great, but you’re not solving a problem. It can be a really neat idea with not a lot of people that need that problem to be solved, in which case, it’s not really a problem for the world. Maybe we could broaden this by saying, “Solve a problem for the world.”
Or it just misunderstands what people need. Or it doesn’t even take into account what people need. You’re just like, “It sounds really cool. I’m going to do this, this, and this, and it’s a hot market so I’m going to figure it out.” The number of times I’ve seen entrepreneurs go that direction because it feels good to be part of the trend, it feels good to say you have a cool idea without asking yourself “Does this actually solve someone’s problem? If I go talk to people, does this literally relieve people that this now exists?” The number of times I’ve seen people ignore this advice is countless. What’s crazy to me is I feel like it’s our secret sauce at Instagram and I’m like, “This is great. We can just keep doing this.” Every product we work on, hopefully is solving someone’s problem, and I feel like I’m giving this advice away for free, but no one is taking it.
Tim Ferriss: It’s also true for nonfiction books, right?
Kevin Systrom: Yeah.
Tim Ferriss: The number of books you pick up, it’s like, “I bought the book because I have the problem. You don’t have to spend 80 percent of the book describing the problem!”
Kevin Systrom: You got it. You got it.
Tim Ferriss: What are other common mistakes that you observe among entrepreneurs or creators? We can make it broader, it doesn’t have to be broader, but people who are trying to do their own thing, entrepreneurs or otherwise. What are some common mistakes that you see? It could be within the venture-backed startup world, but it could also be broader than that.
Kevin Systrom: I think going at a loan is often a mistake. That doesn’t mean you have to have a co-founder, but not having a team is a mistake I see a bunch. People feeling like, “I’m just going to do this by myself. I’m just going to — ” There’s an incredible power in having people around you. Even individuals who are maybe the face of their company have an incredible team around them. I think trying to do it all yourself is not only a recipe for getting it wrong, but also a recipe for not being able to get back up.
I mean, how do you get up with you get punched down? Sometimes having someone else in the room with you, to be like, “Let’s get up and get them,” it helps. I think that’s a mistake I see a lot, but the crazy thing is that having gone through it, and making mistakes yourself, it’s not clear to me that those were all mistakes in every other situation. I’m trying to be careful in overprescribing my situation, because there are counter examples as well.
Tim Ferriss: Sure. That’s a really important point, actually, that I think is worth underscoring for folks, and that is for nearly every rule that someone might prescribe, there’s probably a counter example that the, say, leader of which would prescribe the exact opposite. It’s, I suppose, in part finding the rules that are compatible, also, with what you hold to be the core values or philosophies that guide you, like being passionate about the product or the service or the company, because that has some real practical implications. If you’re not passionate, are you in fact going to be able to summon the endurance, like you said, to walk through, around, or climb over the various walls that are going to pop up? Probably not.
Then you can find the examples that suit your personality and the set of values that you set out for a given company. This is a metaphor question, but if you could, and just a few more questions, and then we’ll wrap up, if you could put a message, a quote, a word, a question, anything non-commercial on a billboard, and really what I’m asking is to get a message to billions of people, which it’s crazy to think that you can actually do that now on some of these platforms like Instagram, but to get a message simultaneously to billions of people — could be an image — what might you put on that billboard?
Kevin Systrom: I don’t know if it sounds cheesy, but the advice that I got that has driven me the entire way is “Follow your passion.” I cared so deeply about social media and so deeply about photography, and there were so many people that were like, “Social media is crowded; photography is lame,” you know what I mean? The only way to get through those is by loving the thing or the mission that you’re on. Again, it sounds cheesy. Maybe we could wordsmith this “Follow your passion” thing, but the number of people that don’t follow their passion because people talk them out of it, and I think that’s a crime.
Of course you can’t follow your passion and not expect consequences. Listen, if your passion is to go fly fishing, and you want to do that all the time, that’s great, but you have to know, okay, “Can I pay my bills?” There are constraints, but if you thought through it, and you love it, there should be no one standing in your way. The number of people that tried to stand in our way, like they still — listen, even long into Instagram, there were people predicting our demise.
I don’t know. At a certain point, it’s not like, “Ignore the haters.” That could be the other billboard by the way. It’s like you’ve got to follow your passion as long as you’ve thought through it, you’ve done the math, you think about it, like go for it. Don’t let people stand in your way. It’s just so sad when people don’t do that.
Tim Ferriss: Life is short like you said. I mean, our lives are so short relative to the span of human history. I think that’s another benefit of reading history, is it puts that into perspective. Like these lives are the flicker of — I think Naval Ravikant put it this way — “Like the flicker of a firefly in the scope of history.” It’s really short in time.
Kevin Systrom: Really tiny. I had this one coach who said to me, he’s like, “Often people wake up when they have someone close to them that dies, or they come down with some really serious illness, and they realize all the little things they were spending all this time worried about, don’t matter compared to these grave, big things in life. It’s important to keep that perspective. I’m not trying to get all serious here, but I think it’s really important to keep things in perspective and I think that, I don’t know, I guess it’s another word for maturity. The faster you can get there, the faster you realize a lot of what you think matters doesn’t matter.
The things that you’re not thinking about matter a lot more than you’re giving them credit for, which is why you should follow your passion and love what you do every day. Don’t get me wrong. By the way, I want to clarify, a lot of people are like, “You should love what you do,” and I agree, but I think it’s more “You should love what you’re shooting for,” because work is hard! It can be miserable at times. Nothing great in this world ever came easy. If you want to be an amazing guitarist, you’re not going to get there easily. You got to train really hard, get shot down a bunch.
It’s a universal law in the world that great things come with a lot of work. What you have to do is I think love the thing you’re shooting for rather than the every day of the thing. But I think a lot of people are like, “I should love every day.” It’s like “No. There are lot of hard days ahead, but the thing that gets you through those days is loving the outcome you’re shooting for, and being excited to get there someday.”
Tim Ferriss: Well, Kevin, I’m excited to see what you hatch next.
Kevin Systrom: Thank you.
Tim Ferriss: After you’ve done your pattern recognition on this meta-analysis of founders who do various things at various points, I’ll be curious to see where you end up. Do you have any closing remarks, anything you’d like to ask people to do? Anything at all that you like to say before we wrap up?
Kevin Systrom: No pressure, right?
Tim Ferriss: You don’t have to —
Kevin Systrom: Go tell your friends about this podcast.
Tim Ferriss: Perfect. I like that recommendation.
Kevin Systrom: Awesome. Thanks for having me. This was a lot of fun.
Tim Ferriss: Yeah. Good to see you again. To everybody listening, for links to everything that came up, the books, and all sorts of other things, the names of people and so on, we will provide links to all of that in the show notes as always at tim.blog/podcast. You can just search Kevin or Systrom, and it will pop right up. Until next time, thank you for listening.
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