The Tim Ferriss Show - #369: Kevin Systrom — Tactics, Books, and the Path to a Billion Users

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Starting point is 00:03:13 warranty and you can test drive your mattress for 100 nights risk-free. Right now, Helix is offering up to $125 off of all mattress orders. So check it out. Get up to $125 off at helixsleep.com forward slash Tim. That's helixsleep.com forward slash Tim for $125 off your mattress order. Take a look. helixsleep.com forward slash Tim. Kevin, welcome to the Tim Ferriss Show. Thank you. Excited to be here. And for people who don't know Kevin, allow me to introduce Kevin. Systrom, at Kevin, on Instagram, is an entrepreneur and co-founder of Instagram.

Starting point is 00:03:56 While at Instagram, Kevin served as the CEO where he oversaw the company's vision and strategy in daily operations. That is a whole lot, which we will talk about. Under his leadership, Instagram grew to over 1 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.

Starting point is 00:04:30 He currently lives in San Francisco with his wife and daughter. Where to begin? So we've 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. And I thought we could start with one since you seem to read, not just widely, but intelligently, and we'll hopefully get into that. Are there any particular books that you have gifted often to other people? Yeah,

Starting point is 00:04:59 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 it. I was like, oh, this is pretty good. And they were like, no, I seriously think you're going to love this.

Starting point is 00:05:22 And 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 hedge fund called Bridgewater. And he's, he's so much more than, you know, just a finance thinker. He's also just a brilliant philosopher. So I give that a lot, because I think it's a great guide to life. Yeah, he's a fascinating guy.

Starting point is 00:05:55 I have, I have actually, and Ray's been on the show. And for those people who are wondering, just just how many commas are involved in Bridgewater Capital. They think they have $160 billion under management, something along those lines. It's a little bit. And 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 and allowing uh all employees to have access to uh the the minutes and so on of such meetings uh are there any other books that helped you in the early days from an entrepreneurial standpoint or that you found inspiring totally early on um we read uh

Starting point is 00:06:42 mike and i both read the lean startup i. I think it's called Lean Startup Method or Lean Startup. Can't remember. Eric Reese. Eric Reese. And I remember very early on, I went to one of his book talks. And I was one of 13 people sitting in this little room in Palo Alto. And I was a super fan. Still am, actually.

Starting point is 00:07:02 And so I don't know that I read the entire thing, but the principles from Lean Startup, I still apply today. One of which is like, do the simple thing first. And that was our number one value at, well, actually community first was our number one value at Instagram. Number two was do the simple thing first.

Starting point is 00:07:22 And still to this day, I come back to that. So if I were reading two books, I'd probably read those two books. And 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-

Starting point is 00:07:40 Has he also been on the show? He has not. Okay. But I remember- I'm just gonna start naming people. He's a great guy. i would have him on uh 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 yeah yeah it was like that yeah talking about avatars and all

Starting point is 00:08:01 sorts of different things uh Doing the simple thing first. The scope of your responsibilities at Instagram, at least reading even just your bio kind of 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? Yeah. The first thing I'll 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 know, you talk to people who are saving for retirement and, you know, you don't have to go figure out a hedging strategy, right? Like for currencies to save for retirement, turns out just like generally putting in a mutual fund

Starting point is 00:08:52 is like not a bad idea. And the returns you get for ever more complex strategies, either in life or finance, they're like, 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 like you don't have time to make things complex you have time to make things work and what ends up happening is you over optimize so 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. And you're like, why did I spend all that time on that fix when actually I needed to be doing something else?

Starting point is 00:09:36 I feel like that's true in life. I think it's true in business. It's true in finance. But so 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, right? And 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 how to split it among two servers or three servers or four. And instead of just like writing a single file that said like, hey, listen, if your user ID is, you know, even you're on this server, and if it's odd, you're on that server,

Starting point is 00:10:18 which would have sharded the data across two servers very well and deterministically. What ended up happening was was we threw everything out. We were like, you know what? Let's adopt this crazy new technology that does auto sharding. And 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. But we spent, I don't know, four months trying to rewrite our system to be on this new database.

Starting point is 00:10:48 And eventually after 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. And 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. So I'm oversimplifying things a little bit for effect, but like, that's basically what happened. And I still think about that story to this day, in terms of an executive making a decision with his co founder about what to do, always do the simple thing first. And 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. And it turns out

Starting point is 00:11:25 actually the right thing to do is sometimes the simplest and it's the most effective. So I live that as a value both in life, finance, and at work as well. So I'm going to rewind the clock a little bit because I think this segues. I assumed you could do that in editing but yes we can and we can slice and dice but this will be like watching the movie memento okay got it uh it's basically usually what it's like when i do an interview yeah exactly so a pretty pretty standard protocol uh i would love to talk about and we won't spend a ton of time on this uh because as 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.

Starting point is 00:12:23 And these products that start off with a focus, lose focus. And it, it seems to me that you effectively did the opposite in some ways for the creation of Instagram. Could you, can you give people a little bit of background on how Instagram came to be? And you can tackle that short version, medium sized, however you like. Well, first of all, I'm happy to talk about where instagram came from i just um 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 years ago i think it's been around forever right um but also I think it has some interesting lessons.

Starting point is 00:13:05 So I'll combine both talking about the origin story, but also how we kept it simple. Um, 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. Um, and I remember, uh, telling at the time my mom, uh, I was like, Hey, I'm gonna go do this thing. And she was like, What about health insurance? I was like, Oh, what about health insurance? You're right. Like, I totally forgot. So my point is, I was a little naive, but I wanted to do my own thing. And I had a bunch of different ideas, one of which was a terrible idea for a check in app. Actually, it wasn't terrible. But like for at the time, there were a bunch of check ideas one of which was a terrible idea for a check-in app actually wasn't terrible but like for at the time there were a bunch of check-in apps and we're sitting in austin

Starting point is 00:13:49 right now it's south by southwest you know zoom back six seven eight years ago it was all about gowalla and foursquare right everyone was all about sure so i had to have my version um and it wasn't bad but you know it wasn't good either. And, uh, catchy name. Yeah. It was called bourbon. Um, and B U R B N. I still, I think I own the domain name somewhere. Um, but anyway, we, uh, what, what happened? I was working on that. I left my job. Um, and I happened to be able to raise money for it and I'm not sure how or why, but, um, checking apps were all the rage. So we raised some money. It was, you know, a couple well-known firms in the Valley and I had just enough money to

Starting point is 00:14:30 work on it. And 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 not like, you know, I'm not a true engineer in the sense, like I didn't study it formally. So I met Mike and he was one of the power users of bourbon. And, uh, he was like, yeah, this will be super fun. So we decided to join up. We worked on bourbon for maybe, I don't know, three months and it was clear it wasn't working. Okay. It was like very clear. The startup was going nowhere. And, uh, 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 bourbon, not by changing at all. So a bunch of the features of bourbon, one, you could check in at a place, but two, you could add a photo of what you were

Starting point is 00:15:20 doing at that place. So you and I were out to drink somewhere. I check in at the bar. I could post a photo of the beer I'm having or the cocktail or whatever. Right. Um, and 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. And, uh, and we realized to keep it simple, we were going to have to cut every other feature of bourbon which we did and we just kept the photo part how did you decide on that feature uh because 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

Starting point is 00:16:06 solved, AKA like 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 meetup things and group chat things, but there was no solution for posting great photos to like lots of friends all at once. So 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 both mobile phones being pervasive. Like again, go back in the day, not everyone had an iPhone. Like maybe the iPhone had been out for a couple of years at that point, 2007, eight, right? So, um, we knew that cameras were going to be pervasive in people's pockets, that people were

Starting point is 00:16:51 going to be carrying these camera phones, you know, wherever they went, but 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. So we got to the idea by cutting everything away from bourbon, circling the one thing that we felt like was the biggest opportunity because it didn't exist yet and it was a big need. And we built the first version of Instagram. Note, by the way, the first version of Instagram did not have filters. Um, and people forget the only reason Instagram worked early on was because of the filters and filters came about because I was on this walk with my wife. Uh, we were taking a small vacation. I had been working on bourbon for a while. I was exhausted. Um, and we were taking this walk along the beach and I was like, oh,

Starting point is 00:17:41 so you're excited about this new app we're building. We haven't called it Instagram yet. She was like, yeah, but I don't think I new app we're building? We haven'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 was like, okay, well, why don't you think your photos are good? And she's like, well, all your friends, you know, you post these amazing photos and they're all like filtered and stuff. And I was like, oh, that's because they use filters. And she goes, oh, well, you should probably add filters.

Starting point is 00:18:02 And we came back from that walk. I went straight to the room and I just like got on my laptop and I made the first filter, which was X-Pro2. 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 open GL and could have been a lot faster. You tap on that filter. It took like three seconds to show you the filter. No one cared.

Starting point is 00:18:40 It was fine. Yeah. Keep it simple. Keep it super simple. Now, you mentioned Eric Ries, his book, as 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 very difficult times, anything from a few previous experiences. So 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. Yeah. I mean, where do I start?

Starting point is 00:19:26 Okay, so... And what is the Mayfield Fellows Program? Yeah, 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 and I'll

Starting point is 00:19:42 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. And 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. And you actually write basically a case on your experience

Starting point is 00:20:18 over the summer. So I did that. I my junior year, I snuck in by like, I don't know. I basically, I was like, hey, but like I founded this startup, not really a startup. It was a website at the time that was like a competitor to Craigslist, but for Stanford students only. And I prayed that they would take me because I was so excited about entrepreneurship

Starting point is 00:20:38 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. 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. And I was like, thank God you did. And she was like, but the thing that made the difference was that you were out there actually trying to start something. And I guess lesson number one is like, never expect you're going to get a no, like always put your name in right. Number two is

Starting point is 00:21:05 actually do the thing, like actually start the startup. Don't just go to conferences about it. Don't just like write articles about started do something. Um, and that carries a lot of weight. Um, but that was the Mayfield fellows program. And maybe the last lesson on the, um, Mayfield fellows program that I got from it was it was there's nothing in the world that can substitute for real experience. Doesn't matter what we're talking about. If you want to be a chef, working in a 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, right? You got to start a startup. You got to know what it feels

Starting point is 00:21:47 like to put it all on the line, lose everything and then come back, right? 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 that books aren't helpful, but you got to do it. They're an adjunct. Yeah. Yeah. Very hard to become a professional soccer player by reading books on the physics of soccer. Although I got to tell you, I took this personality test, um, and the results came back. But one of the main takeaways was like prefers learning by reading. And I was reading my results to my family because I thought it would be entertaining. And my mom was like, Oh my God. Like, I remember when you were a kid, you just read everything. And my dad was like, yeah, like you said when you were a kid you just read everything and my dad was like

Starting point is 00:22:25 yeah like you said you were going to be interested in playing baseball so uh uh i was like i bought a mitt for you and we were going to go play catch and you're like dad i gotta go to the library and i my dad was like what he's like i gotta read about it so i literally went to the library read about how to pitch and then played and i think that's my MO. It's just, I'm wired that way. Do you remember the, the name of the personality test or the assessment that you did? Um, yes, it was the, uh, golden personality test. Golden personality. Yeah. I think it was golden. Yeah. Why did you take that test?

Starting point is 00:23:00 It's a, uh, it's a variant on the Myers-Briggs test, but it actually gives you very specific breakdowns of every dimension. So for those of you listening that don't know the Myers-Briggs test, there are basically four main dimensions of the personality test. And it tells you, for instance, whether you're more casual or if you're like very calculated and punctual, that kind of stuff. I wanted to know more about what I was like. I had talked about Ray Dalio before. I spoke with him and he was saying, yeah, everyone who joins Bridgewater, we give this personality test. And I was like, well, can I take it? Like, I want to know what I am like. And my co-founder took it. A bunch of our senior execs took it. And it was

Starting point is 00:23:42 illuminating to learn, see on paper, what you know in the back of your mind. And bunch of our senior execs took it. And it was illuminating to learn, see on paper, what you know in the back of your mind. And then 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. So I'm not someone who likes to sit in a lecture hall. I want to have the book. So if I'm going to learn something new, like the way to learn is not for me to go to like a conference. It's to like sit down with the best book possible. And that might not apply to you, right? Like if you took it, maybe you like learning some other way, but I wanted to know what my API was. So that was helpful. Your API. Yeah. I like it.

Starting point is 00:24:22 That's true. Yeah. we all learned application programming interface is that right he used to know some acronyms uh on reading there are different ways to read books and i had uh found in some of the research for this conversation a mention of mortimer adler's how to read a book yeah could you talk about how read? How weird is it that I'm like so into reading that I have to find a book that's how to read? Like, where does it stop? How to read? How to read a book? Have you ever read the book? I haven't. Okay. It's fine. I can save you some time. Yeah. 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 until either

Starting point is 00:25:14 that they get bored or they push through or whatever. And 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. So 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 like the major structure of the book. And 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 points they actually have been waiting to make the entire

Starting point is 00:26:02 chapter. And 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 you'll ruin your experience, but with nonfiction, I think it's fantastic. But that's how to read a book. And by the way, for those of you Mortimer fans out there, I probably didn't do it justice, but go buy the book. Go buy the book, which will encourage you to buy yet more books. Seriously, if I could show you my room right now, my bedside table is just stacked with books.

Starting point is 00:26:50 I've got a book called Mathematics of politics. Cause I'm interested in both politics and also the math behind elections and that stuff. Um, I think how to read a book's probably there. Um, what are the books do I have? I've got books on, uh, on flying. Cause I I'm learning to be a pilot. Um, it like, it ranges. Oh, I've got a quantitative finance books i've got but like it's the most fun i've ever had just like plowing through books i guess it's good i don't have a job right now i don't i don't know like it does create a little space a little it creates a surprise how quickly it gets filled up it does well i mean're not, I don't think you're the podcast, especially the long ones. No, it's okay. Uh, audio, what was audio and, and, uh, what did you learn there? What did you observe? Yeah. Audio is the precursor to Twitter. So, um, you, we were talking about Mayfield

Starting point is 00:27:42 fellows program. Uh, my internship was audio. So that three months over the summer I spent at audio. Um, I remember I showed up the first day I brought my own computer. Cause I thought when you worked at a company, you bring your own computer. Cause it was like, I don't know, computers are expensive, right? Like you bring your own. Um, and they were like, Oh good. You brought your own computer. I think they were thrilled. Um, and it was, uh, Evan Williams and Noah glass were the co-founders of audio. And, uh, they were like, Oh, I forgot you started today. And I was like, yep, here I am. And actually it was one of the best experiences learning from Ev who's brilliant. Um, and Noah, who's also brilliant. And like just seeing that startup try to take off, it was a podcast directory, believe it or not,

Starting point is 00:28:26 maybe a little early. It was the right way, but they just paddled a little early. 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 got to have that essential element of timing and it's the hardest to predict but it

Starting point is 00:28:46 was a podcast directory and you know honestly a lot of the the famous podcast folks got started on audio and there are a bunch that are still around but turns out back then there wasn't exactly a business around podcasts and it didn't go so well and they ended up pivoting to an idea started by an engineer there, Jack Dorsey, who, by the way, also started, I think, like maybe my first or second day. And I remember him walking in. I'm like, I'm the intern. He's like, Oh, I'm Jack. And I learned actually, he gave me a couple of coding assignments over the summer. I remember learning some JavaScript from him. So it's a small world, it turns out. Yeah, super small. But that's what Odeo was.

Starting point is 00:29:26 And that was my experience. It was awesome. And I'm very thankful to all those guys. What do you view as some of, say, just as an example, Ev's superpowers? I mean, 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, right? I mean, he's not a one-hit wonder.

Starting point is 00:29:52 So what have you observed in him? Turns out blogging and communication is a thing and doesn't go away. And there are lots of companies that can be started around it. What did I observe? Well, it was a really long time ago, but... Or what superpowers do you think he has? You could talk present tense too. So I think he's super determined and super calm under fire. There are a lot of CEOs that are very emotionally volatile.

Starting point is 00:30:28 And Ev, at least in my experience, is not one of those people. In fact, he's determined and hardworking. And I can't remember his background story, but he's like, yeah, I went to this college. It wasn't that great. And 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. And I remember his work ethic, because at one point, I'm pretty sure he was convinced we all weren't

Starting point is 00:30:54 working hard enough. So he sent us, he didn't send us he offered for us to go to this seminar by David Allen, the getting things done. So I remember sitting in the audience and just like the ODO crew, there were like, I don't know, six or seven of us at the time at the David Allen Getting Things Done, you know, not conference, but seminar. I still try to use that stuff today, by the way.

Starting point is 00:31:18 But the signal was like, we work hard here and we get stuff done. And he was there, you know, he was the first one in, last stuff done. And he was there, you know, he was the first one in last one out. And 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 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.

Starting point is 00:31:46 It's incredible. Plus willing to call it like he was willing to call ODO and pivot to this thing called Twitter. And trust me, when we were calling it on bourbon 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, you know, the, the bravery that it takes to switch like that. It's hard, but, uh, but 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, you end up trying to mirror it in many ways. I completely agree on the the ev having uh calmness as a competitive advantage he's very good at pausing and not jumping to respond uh so he's he's better able to choose

Starting point is 00:32:38 his response i suppose instead of being reactive i think you're very good at that as well thanks and um i want to talk about since it's come up a few times, pivoting or ending projects. Yeah. Because there's, in some aspects, a fetishizing of perseverance in a lot of places, including Silicon Valley and the world of tech.

Starting point is 00:33:00 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? Like, are there telltale signs that this is just, it's not that another 50% of effort is required and another X number of hours per day, but like this is fundamentally flawed in some way that is going to prevent it from working. I think let's take this question in two parts. First is let's just talk about the premise that most successful things are pivots, which I believe is true.

Starting point is 00:33:42 One of the really fun things to do is actually, do you know the Wayback Machine? I do. Right. I think it still exists. I haven't tried it in a long time, but you can go and type in any web address. And then I think it allows you to like select the date of that website. So 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, right? And go to that date around the beginning. You will see YouTube was a dating site before it became YouTube, what we know as YouTube, right? Do that for most major things that you get excited about. Or look up the history of Facebook when it was face-mashed beforehand.

Starting point is 00:34:28 It was something before that. The only one that I don't think was a pivot was Google, and they've done pretty well. So that's the one counterexample. That literally was their project, and they made it a company, and it worked really well. So I don't know. But most other projects are pivots from an original idea.

Starting point is 00:34:47 And I think that's because one, it's really hard to tell what works a priori, like doing it before anything, before you actually, you know, put it into, into people's hands. It's really difficult. Like you don't know if it's going to work. The key to entrepreneurship is failing really quickly. So putting it out there, seeing if it works, if it doesn't, then diagnosing why, and then like focusing on how to improve it from there. Um, so one, I agree with the premise that most things are in fact, uh, like second runs. And then two, the importance of pivot, I think is that most of the time you get it wrong. So 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? And the entrepreneurs that I've seen

Starting point is 00:35:37 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 of ego or whatever, stick with ideas far too long. And I think, you know, it ends up really poorly. Yeah. Or look at something that isn't working that might have a different

Starting point is 00:35:56 application, right? If you look at post-it notes, you're actually a failed adhesive, right? And 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

Starting point is 00:36:15 lowering blood pressure and normalizing broke blood pressure. And then the... They were like, excuse me, can you check off all the side effects of this blood pressure pill? They're like, huh, there's a pattern here well the the recipients were asked to send back their samples and all the women sent their samples back and almost none of them ended and they're like wait a second what's going on here i can't tell if this is a family friendly show and we should dive into this or oh we can we can we can uh it is family friendly but uh modern family this will be the director's cut this will be the director's cut this This will be the director's cut. Anyway, pivots are important.

Starting point is 00:36:48 Pivots are important. And 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 be 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? I was talking with my wife the other day and I was like, Nicole, I think one of

Starting point is 00:37:29 my failures is that like, 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, oh, well, maybe that's actually a strength because like you're so hard on an idea that you're like trying to prove yourself wrong to test the integrity of your idea or test the integrity of your thesis or, and like, so you mentioned Ray, like, 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. But a lot of people I think are afraid to gather feedback. I think Mike and I at Instagram very early on tried our best

Starting point is 00:38:20 to be open to feedback. I think as a young executive, I was like, no, I'm the boss. Like all ideas are great. All my ideas are great. Right. And after a couple of failures, I think you learn really quickly that like, Hey, listen, I know there's this myth that like the best founders just have like the Midas touch and every idea they have is perfect. You know, like Steve Jobs, he touches everything and it just becomes gold and it's right but it turns out 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 is a trail of amazing ideas i mean someone should write a book on all the bad ideas amazing people have had right over the years. Could be a 10-volume set. Totally. But I think people get the wrong idea. There is no Midas touch. One of the things I hated most working in tech

Starting point is 00:39:12 was the idea that there's a product guy or a 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, if you bat 200, like above 200, you're like a pretty good batter, right? Like in a world where your average is going to be 1%, you got to generate a ton of ideas before you get one, roughly 100, right? Yeah. So and 1% would be like way higher than the average. So how do you figure out which

Starting point is 00:39:52 is the one it's 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. But I just, I like always have, I don't know, I'm just wired in a way that assumes every, whether it's idea or thesis or whatever I have is wrong. And I'm more worried about being wrong than I am looking bad. You know what I mean? No, I get it. Do you have any particular questions that you ask yourself or other people when you're stress testing an idea? Or alternatively, how you solicit feedback? And I give 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. Because what they all are. Yeah.

Starting point is 00:40:52 And so one of the questions I'll ask them is in a given chapter, I'll say, if you had to cut 10 to 20%, gun to the head, which 10 to 20 would go? Nice. Right? And it forces their hand,

Starting point is 00:41:00 in a sense. I think that's smart. So are there other approaches that you like to use or like others to use on your ideas for stress testing? Well, first off, I think it's important to realize how people are just wired not to be honest. Not that they lie.

Starting point is 00:41:21 I mean, I guess technically it's a lie, but I don't think it like comes from a bad place. They're wired to avoid conflict. So like you go in a restaurant and the server comes by, you know, maybe you didn't like a dish. The server comes by. When's the last time you actually literally told them like everything was great, but that thing was too salty. That was, you know, I like to eat by the way. Um, that thing was too salty. That was undercooked. Like next time you go out to eat and they're like, how was everything? And you're like, you instinctively just respond. Great. Thanks. If it is that actually what you thought? Like most people have one or two things they wish

Starting point is 00:41:59 could be better. And 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. Right. And 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. And I've been surprised how many people I've met, at least in the food industry, right? Where at least if you do it in a nice way, you're like, listen, I just, 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. And it's always interesting to see the people that are like grateful for that feedback. And you're like, that person's going to go kick some ass. Totally. And the people who are like grateful for that feedback. And you're like, that person's going to go kick some ass.

Starting point is 00:42:45 And the people who are like, what's supposed to be that way? You know, and you're like, well, okay. Like, but like, what if it isn't? And I think it's really important as you mature as an executive, like I definitely started in the place where I just like didn't listen to feedback.

Starting point is 00:43:04 I was, you know, headstrong. And 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 like when I was presenting on stage, everyone would be like, great talk, great, awesome job. Great. You killed it. And I was like, that's not possible. Like, like a few talks in a row that happened it. And I was like, that's not possible. Like, like a few talks in a row that happened. And 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 that. Like, I know you're a happy person, but you're not smiling when you're talking about this really happy subject,

Starting point is 00:43:43 like smile. And I was like, Oh my God, that person's right. They literally watched every single interview I had done for like the last two years and just had a list of things. And I was so grateful for that because it was feedback that no one else would give me. Do you remember any of the other points? It was slow down, pause, right? 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.

Starting point is 00:44:12 Like it's hard. And I'm just like, I'm a serious person. So I don't think to smile as much. What were the other things? I'd have to go back to my notes, but those are the two things that stood out. Yeah, it's- People don't give you feedback.

Starting point is 00:44:24 It's crazy. And by the way, the thing is, the more important your company gets, the higher up you go, the less people are willing to do it. Yeah. So you actually have to like 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 like specific tools so much as like, when's the last time you, the listener did that? When's the last time you went out of your way and you said, Hey, like I really want honest feedback on this. And when someone gives you feedback,

Starting point is 00:44:54 you don't respond in a defensive way. You say, thank you. And you encourage the behavior. If you could do that, man, like the self-improvement that comes with that. Yeah. And the honesty that comes with it, if depending on the format can be really remarkable. I, you may have done this before, but I had not done a 360 interview. Oh yeah. I avoided doing the first one they wanted me to do ever. I was like, ah, this is just like a management thing. And then the second one I did, I literally tried like hard to do it. Like I asked people to participate. I said, please be as honest as possible. Yeah.

Starting point is 00:45:31 And I remember I was chatting with Joe Gabia about his first 360 interview. And for people who do not know what that is, there are different ways to approach it. But in effect, your superiors, peers, slash colleagues, and subordinates are all interviewed. So the people you interact with most are all interviewed about your strengths and weaknesses and so on. And very frequently, at least in my case, with my employees and so on, it was anonymized to ratchet up the like allowable honesty. And 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.

Starting point is 00:46:16 And 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 when I was able to look at it with a cooler head. I had a really tough time with it, but it ended up being very helpful when I was able to look at it with a cooler head, not because I was angry, but I was really sort of like 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.

Starting point is 00:46:39 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 and but you have to be willing to get both yeah 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 um but yeah that was hard yeah i remember my first one and i just but now I think about it and like no matter what I do whether it's another company whether I'm doing a writing project or a podcast whatever like so I just walked off the stage at South by Southwest and I could see the screen that was displayed after we left and they asked people to rate the rate everything everything like rate, the speakers, rate the host. Like, and I was like, Oh, I really want that data. I'm going to ask him for it. Uh, because I want to know, like,

Starting point is 00:47:30 was it interesting to people? What topics didn't they like? Like, did we come off as authentic, inauthentic? Like where were we? Um, but it's funny because no one ever tells you anything and it's, unless you dig for it, you won't find it um but honestly i think letting people know that it's safe to give feedback asking for it proactively etc etc is important i just the amount people go out of their way to avoid conflict is pretty wild yeah which which often works in the short term but can really be caustic and erode relationships in the long term. And if you're avoiding that, your comment 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

Starting point is 00:48:25 from a very successful CEO of a large company, that if you ever ask somebody to rate something from one to 10 to disallow a seven, because seven's just like semi-polite. It's like Yelp is all three and a half stars. You're like, no. Exactly. So you're mentioning restaurants.

Starting point is 00:48:40 So what I'll very often ask people in restaurants, if they're giving me the everything is good response which is gives me no information to act on as i'll say all right on any i'll give them two options and i'll say one to ten but no seven how do you rank and it's sort of bare then they're they're forced if they're straddling that to do a barely pass which is a six i'm not going to order that or or an eight, which is a strong, that's a confident endorsement. And so that can be applied to all manner of things. That's really cool. I'll do that from now on.

Starting point is 00:49:15 No sevens. Yeah, let's talk about tough times. As you mentioned- There are none. The life of an entrepreneur is golden. It's true. It has been said that your life is all highlights. No, I'm kidding. That hasn't been said.

Starting point is 00:49:33 What company made that happen? But 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 where anytime you had kind of self-doubt or felt lost uh because and where i'm going with this i'm very curious how you then recontextualized it found the silver lining or just got through it um because it's uh some people get knocked down and they have a really tough time getting back up. So when people are able to do that, I like to look, look inside and

Starting point is 00:50:10 see what actually happened. Uh, so yeah, any, any at all that you're willing to talk about. First thing I'll say is a lot of people assume that like business people, entrepreneurs, like whether they make money, like a lot of money, or they sell a company or they go public or whatever, and their CEOs for a long time or world leaders, whatever, a lot of people assume these people don't struggle, right? That somehow they're inhuman or whatever. Like I, 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? And I still have just as many failures as I did before Instagram and well inside of Instagram as well. Now, don't get me wrong. There are structures around me now that allow me to like come back from those failures. Um, but I guess my point is like

Starting point is 00:51:01 getting knocked down is like a really common thing, no matter where you are in your career, no matter where you are in your progress of building something. And in fact, it usually happens more the more important thing you're doing. Right. 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 like the most amazing designers early on, who just like 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. So choosing the other, which is fine. Listen, like it's up to like investors should be able to choose who they

Starting point is 00:51:58 think the winner is. That's their job, but it's tough, right? 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. But 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 to impress, I mean, of course we wanted a community for the app. The reason we got

Starting point is 00:52:25 back up each and every time was because we loved what we were doing, right? Like if your goal is to gain people's approval, like the startup business is a terrible business to get into. Heck, like if you're a singer, like it's the worst business to be in in the world because everyone's going to tell you your stuff stinks until maybe it doesn't, right? But you have to believe in what you're doing and love what you're doing. 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. And I often think like, 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,

Starting point is 00:53:10 it's like not great. Right. But at the same time, we wouldn't be where we are if I listened to most people. It's crazy. So, um, 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. Like I didn't have another job. What was I going to do? Like sign up for business school. I don't know. Like I had quit my job and raised a bunch of money and I really loved what I was doing. So every time one of these failures would occur, what was the other option? Can you think of one? A desk job?

Starting point is 00:53:46 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, right? So it's like like whether it's like

Starting point is 00:54:07 sean 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 and he like explained why it's like who cares and i didn't expect that answer and me neither found it really interesting i mean in the sense that like he's done all the preparation he could possibly do he's either either ready or he isn't. And there's an entire explanation for it. And what fighters say before they get in the ring, if there is some type of self-talk. I got one. Yeah.

Starting point is 00:54:36 Yeah. Let's go straight to the interesting topic, selling our company. Yeah. So we sold our company, and it was April of 2012. And by all accounts, if you start a company, for a lot of entrepreneurs, winning, quote unquote, and by the way, I don't agree with this definition,

Starting point is 00:54:55 but winning is, quote unquote, either selling your company or having a public offering, an IPO, for a lot of people. That's like the traditional outcome for a startup. And we had sold and we were 13 people and it was a billion dollars. It was really exciting. And I remember like right afterwards, everyone being like, so it's over. And I feel like that was the most painful thing to hear because I had no intention on, you know, not doing Instagram. I like wanted to work on it for the next, you know, whatever years, but everyone I met was like, so you're done now. So it's over. I was like, no, no, no, no, no. And like, we would try to hire people and they'd be like, no, it's over. And I remember people working at the company telling me it was over. And a couple of people ended up leaving pretty soon

Starting point is 00:55:58 after that. And I remember one of them saying, yeah, there's like nothing else to learn here. Like, 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 offices all around the world. I got to do everything from meeting the Pope to meeting some idols. Like I got to, it was crazy. So the idea that in 2012, we sold our company and then everyone just kind of counted us out. That was painful. What, what, how did you contend with that? Like, what was your response to that? I think with me, it usually comes with the competitive nature of proving people wrong.

Starting point is 00:56:45 If you look at the like histogram, sorry to use that word, but of how long founders stay after they sell their company, I'm pretty sure there's like a giant like lump around one month to one year, right? We were there for six years after we sold, 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. And for me, I think the motivation comes with proving people wrong. Because I hate when people discount us. I hate when people, you know, tell us we're not going to be something,

Starting point is 00:57:29 you know, that because we've sold, it's all over. But looking from the outset, I get their perspective. I just wanted to prove them wrong. Yeah. Yeah. It's a powerful motivator. Yeah. I think, and part of taking that personality test we talked about

Starting point is 00:57:45 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, how to write, and you know what things are not motivating. But competition is one. Actually, it's interesting. There are two dimensions of the personality test. There's competition and then there's challenge and i didn't 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 right Right. Sort of an intrinsic motivator. It's an internal motivator of like, I want to go get this thing done. So for me, I think at that

Starting point is 00:58:33 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. How did you learn to manage? Oh man, and I had to. Yeah, so how does one learn to manage? And it's not just time within a larger company, right? 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 sort of do decently despite their

Starting point is 00:59:08 weaknesses. But when you sold the company, how many employees do you have? 13. 13. Yeah. I think I managed like three of them. Right.

Starting point is 00:59:20 So you then went through. Why do you think companies have hierarchy? They're like, I don't want to manage people, you manage them. And before you know it, you've got like a tree, you know, 90 layers deep. I'm joking. Well, I mean, there is some truth to that, I think. But how did you learn to manage? Were there any particular lessons, resources?

Starting point is 00:59:41 So I have to say... Anything at all? Well, I was going to say my job was different than most, which obviously is an understatement, but like, I'm going to tell you the philosophy I subscribe to. And then I think the listeners can decide if it makes sense for them. It might.

Starting point is 00:59:58 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. And 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. But the ironic thing is by hiring people that were way

Starting point is 01:00:42 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. And I think that works because I felt like I had job security. So a lot of people are worried, well, if I hire great people beneath me, then maybe one of them will take my job. And 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 who they should be younger. They should have fewer years of experience,

Starting point is 01:01:30 right? Cause I should coach them. And actually if everyone hired up, you'd have like the most bad-ass company in the world. So 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 the vision 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. But I didn't have the regular job of like, you know, managing a bunch of new grads out of college

Starting point is 01:01:57 and like coaching them on their careers, which exists in mass in Silicon Valley. So 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. So 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. And so one that I could ask about would be meeting structure.

Starting point is 01:02:47 So 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 and then I'd love to hear you elaborate on what the meeting actually looks like and how you handle it. So some of the bottlenecks,

Starting point is 01:03:03 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. And then this is quoting Mr. Systrom, we have a dock 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. So this is something that you might be able to do in an informal, unbatched way when you have three direct reports or 13 employees. But as it grows,

Starting point is 01:03:40 it seems like this type of systematizing could be really important. Could you describe how a meeting like this functioned? Totally. And why? And it's really funny for me to think of myself as being referenced as Mr. Systrom. So it's very formal. Mr. Systrom with inventory of decisions. Okay, so here's the context. Have you ever read the book, The Goal?

Starting point is 01:04:11 The Goal. The Goal. I have not. Yeah. 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 Goldrat. I think it's really good. Um, last name is

Starting point is 01:04:25 gold rat. Uh, I think it's gold rat. Yeah. Who wrote the book? And it's kind of, in fact, if you talk to business people, a lot of people will say it's their favorite book. Like I wrote in one of my weekly updates to the team, I wrote that I was reading this book and that I loved it. And a bunch of people were like, Oh, I love that book too. So 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, right? Yeah, that is very cheeky. It's not like a business. It's a business book, but it's written with a narrative.

Starting point is 01:04:59 There are characters. And it's actually pretty fun. So I say, go have a read um but what i realized in reading this was that uh any system is most constrained or at least the thesis of the book is most constrained by the slowest process um i think they called it a herbie herbie have you ever heard that i have yes so it's because the beginning of the book is the Boy Scouts. Yeah, exactly. You want to explain what Herbie is?

Starting point is 01:05:29 I know, we're getting there. How many times are Boy Scouts going to come up in a podcast, right? So the narrative is that they're on some trip and they have these Boy Scouts lined up. I think it's like the main character's son or something is in the line of Boy Scouts. And Herbie, it might not be PC to talk about now, but Herbie is a little overweight

Starting point is 01:05:50 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 kind of the takeaway, okay? Again, people who are super fans of the goal can correct me on this, but the essence of it is your slowest, um, your slowest part in

Starting point is 01:06:12 the chain is always going to limit output. In this case, the slowest boy scout limits the progress the troop makes, um, which isn't actually all that, um, isn't all that intuitive until you read this book and you go through it. So with decision making, what we realized is a lot of things were coming to us, but unless we would decide on an important decision, it was basically like inventory stacking up in front of a machine that wasn't moving. And of course, the machine can't output products that people want to go use until those decisions get made. So it sounds, again, really intuitive. But if you think about a company as, you know, the raw materials go in and raw materials are ideas, okay? And 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 beta testers out to the real world.

Starting point is 01:07:14 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? So 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. Off to pick it up. Yeah. The goal of a long list of books to tackle. actually forgotten about that book until you mentioned it off to pick it up yeah the goal

Starting point is 01:07:45 uh of a long list of books to tackle how do you choose books that you're going to read i know you give a few examples of things that you're interested in uh but how do you filter the universe of books to those you end up reading and i mean you could maybe just pull up you could pull a few real examples from from uh those you've read and kind of indicate how you got to those but is do you have a process for selecting books well first uh or disqualifying well first i don't read fiction um not that there's anything wrong with fiction and 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.

Starting point is 01:08:26 So 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. So for instance, learning to fly. Like, OK, 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? And obviously, Amazon's great for that.

Starting point is 01:08:54 And you can read through reviews. But honestly, a big part of 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? Because like with a book, okay. So with a class, you got to like wait until the class happens, go to a class and then wait until the next class with a book, you can literally like just get through it in a week or a day or, and then you can reread it and then reread it. And I just, I find that like, if you want to learn

Starting point is 01:09:25 a new skill, there's nothing like sitting down with a nonfiction book on that topic. That's, uh, you know, well laid out and, but sometimes, you know, you gotta call it. I've, 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. Uh, so they don't, it doesn't always work that way. Do you read, uh, and if you don't, this isn't a value judgment, uh, biographies, do you ever read biographies? Okay. So, um, I have not read, no, but I really want to. Okay. So 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 they're, how old are you? 41. Pretty sure i'm 41 yeah it's okay we'll fact check that one i'll get back to you uh i'm 35 okay uh our lives are really short compared to the history uh recorded history and it turns out

Starting point is 01:10:35 if you look back in history things patterns emerge i read this great book called lessons of history i was just have you read it will and a Ariel Duran. Yeah. It's short. It's excellent. It's like a leaflet. Like you could read it in a day. It's great. There's some parts that I disagree with, but for the most- Actually, I read that because Ray Dalio recommended it. It's a great book. Yeah. 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. And 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 a history of a specific segment of companies. So for instance, I think if you want to study the acquisitions of companies and where those founders have gone

Starting point is 01:11:26 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, right? But what are the differences between those that decide to do something and those that don't? So 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. And I start asking myself, what are the patterns that emerge? So no, I don't read biographies yet, but I want to. And I started asking myself, like, what are the patterns that emerge? So no,

Starting point is 01:12:05 I don't read biographies yet, but I want to. And history, I think more generally is a super interesting topic. There's some excellent biographies out there. I think you might enjoy Genghis Khan and the Making of the Modern World. Okay. Excellent, excellent book for a lot of reasons. I'm trying to think of the ones that have been recommended to me. Yeah, I'll have to get back to you on that. David McCullough has a lot of really good biographies on 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 cbg stuff so cool yeah uh and there's but isn't it interesting how many people have so many similar patterns in their lives and

Starting point is 01:12:49 i think there's this like great equalizer when you realize what you are doing or going through or whatever well it might be super unique to you in your 35 or 41 years it actually turns out like it happens over and over again to people on their lives. Not everyone, but like it's occurred in the past and you have a lot to learn from it. That's basically my point. And that, I think it's 120 page book, Lessons of History is a fantastic place to start. I expected it. I actually downloaded it as a Kindle book and let it sit there for months because I expected it to be very dry and it's a beautifully

Starting point is 01:13:26 written book. I was very impressed. And then if, if you like that as a, as a taste test, and then you can go into there, what is it like 10 or 20 volume? Uh, it's a summary of their volumes, right? That's right. Yeah. It's like the cliff notes, the cliff. Yeah. Okay. Uh, so I'd like to ask you, uh, 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, or people come to me asking, how should I launch a book? How should I write a book? How should I get a book published? And I might tell them, for instance, don't try to write for the entire world. If your goal is to hit

Starting point is 01:14:20 the New York Times bestseller list, write for like 10 to 20,000 people per week. In other words, you really only need to get the flywheel spinning because people use the bestseller list as a shopping list to write a book that at least 20,000 people will love. But they end up writing something too general? They end up writing something too general.

Starting point is 01:14:41 And 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 and then they don't do that and they wonder why they can't run excerpts uh and uh it's it's it's been incredible to me how you know i put together a blog post which is like how to write a best-selling 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? Yeah. Number one advice I always give is to solve

Starting point is 01:15:32 a problem. So many people, uh, when they found a company, 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. Like 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. And, you know, usually the warning signs are that includes some element of a current fad, like AI or something.

Starting point is 01:16:01 Not that AI is a fad, but like, you know, 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 or like there are always warning signs that I see with the pitches that I, 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? So I always say, make sure you're actually solving a problem. Now, there are different ways that can be wrong. It could 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,

Starting point is 01:16:51 in which case it's not really a problem for the world, right? 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, oh, it sounds really cool. I'm going to do this, this, and it's a hot market. So I'm going to figure it out. And 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? Like if I go talk to people, does this literally like relieve people that this now exists?

Starting point is 01:17:28 The number of times I've seen people ignore this advice, it's countless. And what's crazy to me is I feel like it's our secret sauce at Instagram. And I'm like, this is great. Like we could just keep doing this, right? Like every product we work on hopefully is solving someone's problem.

Starting point is 01:17:43 And I feel like I'm giving this advice away for free, but no one's taking it. It's also true for nonfiction books, right? Yeah. The number of books you pick up and it's like, I bought the book because I have the problem. You don't have to spend 80% of the book describing the problem. You got it. You got it. What are other common mistakes that you observe among entrepreneurs or creators?

Starting point is 01:18:08 So we can make it, 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 you see? And it could be, it could be within the venture backed startup world,

Starting point is 01:18:21 but it could also be broader than that. I think going it alone is often a mistake. And 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, oh, 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 like maybe the face of their company

Starting point is 01:18:44 have an incredible team around them. Uh, and I think trying to do it all yourself is like 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 when you get punched down? Well, sometimes having someone else in the room with you to be like, yeah, let's get up and get them. You know, it helps. Um, I think that's a mistake I see a lot, but, uh, you know, the crazy thing is that having gone through it and making mistakes yourself, it's not clear to me that like, those are all mistakes in every other situation. So I'm trying to be careful in over-prescribing my situation because there are counter-examples as well.

Starting point is 01:19:29 That's the 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, the leader of which would prescribe the exact opposite yeah right and so it's 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 with the company because that has some real practical implications if you're not passionate

Starting point is 01:20:11 are you in fact going to be able to summon the endurance like you said to sort of walk through or around or climb over the various walls are going to pop up probably not right so then you can find the examples that sort of suit your personality and the set of values that you've set out for a given company. This is a metaphor question, but if you could, just a few more questions and then we'll wrap up.

Starting point is 01:20:39 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, 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. Well, what might you put on that billboard? I don't know if it sounds cheesy, but, uh, the advice that I got that has driven me the entire way is follow your passion. Like 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? That like the only way to get through those is by loving the thing or the mission that you're

Starting point is 01:21:32 on. And well, it, again, it sounds kind of cheesy. Maybe we could wordsmith this follow your passion thing, but like the number of people that don't follow their passion because people talk them out of it. And I think that's a crime, right? Of course you can't follow your passion and not expect consequences. Like, 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, like, can I pay my bills? Right? Like, can I, there are, there are constraints, but if you thought through it and you love it, there should be no one standing in your way. Yeah. And like the number of people that tried to stand in our way, like they still like, listen, even long into Instagram, there were people, you know, predicting our demise. And so I don't know, like at a certain point point it's not like ignore

Starting point is 01:22:25 the haters that could be the other billboard by the way um it's it's like you 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 and don't let people stand in your way you know like it's just so sad when people don't do that and life is short. Like you said, I mean, our lives are so short relative to sort of the span of human history. And I think that's another benefit of reading history is it puts that in perspective.

Starting point is 01:22:53 Like these lives are sort of the, the, the flicker of, I think, and of all Ravikant put it this way, like the flicker of a firefly in the sort of scope of, of history. It's really short. Really tiny. And I had this one coach who said to me, he's like, often people

Starting point is 01:23:15 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 like grave, big things in life. And it's important to keep that perspective. So I'm not trying to get all like serious here, but like, I think it's really important

Starting point is 01:23:41 to keep things in perspective. And I think that, I don't know, like, I guess it's another word for maturity, right? But, um, the faster you can get there, the faster you realize a lot of what you think matters doesn't matter. And the things that you're not thinking about matter a lot more than you're giving them credit for. Yeah. Um, which is why you should follow your passion and, and, 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. Yeah. Cause work is hard. Yeah. It can be miserable at times. I mean, nothing great in this world ever came easy.

Starting point is 01:24:26 Like 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, right? Like they're all like, it's a universal law in the world that great things come with a lot of work. And what you have to do is I think love the thing you're shooting for rather than the everyday of the thing. But I think a lot of work. And 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, oh, I should love every day.

Starting point is 01:24:50 It's like, no, no, every day can be, there are a lot of hard days ahead. The thing that gets you through those days is loving the outcome you're shooting for and being excited to get there someday. Well, Kevin, I'm excited to see what you hatch next. Thank you. We'll see if after you've done your pattern recognition on this, uh, meta analysis of founders who do various things at various points, I'll be curious to see where you end up. Uh, but,. But do you have any closing remarks, anything you'd like to ask people to do, anything at all that you'd like to say before we wrap up? No pressure, right?

Starting point is 01:25:34 You don't have to have... Go tell your friends about this podcast. Perfect. I like that recommendation. Awesome. Thanks for having me. This was a lot of fun. Yeah, good to see you again.

Starting point is 01:25:43 And 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 forward slash podcast. You can just search Kevin or Systrom and it will pop right up. And until next time, thank you for listening. Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me?

Starting point is 01:26:17 And would you enjoy getting a short email from me every Friday that provides a little morsel of fun for the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little

Starting point is 01:26:51 tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out. Just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by Helix Sleep. Last year, I focused on dramatically improving a few things. Surprise, surprise. Most notably, the quality of my sleep, which seems to affect just about everything.

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Starting point is 01:28:16 mattress orders. Check it out. Get up to $125 off at helixsleep.com forward slash Tim. That's helixsleep.com forward slash Tim for $125 off your mattress order. Take a look, helixsleep.com forward slash Tim. This episode is brought to you by FreshBooks. FreshBooks has become the go-to cloud accounting software for literally millions of small business owners who found a faster, more efficient, and much less stressful way to deal with their numbers. And ultimately, this helps you to focus on what you are best at. It is used by many of the fastest growing startups I've invested in or advise, and it's equally used by many of the best freelancers I work with on a daily or weekly basis. It is one of the easiest ways to send invoices, get paid, track your time, and track

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The Tim Ferriss Show - #369: Kevin Systrom — Tactics, Books, and the Path to a Billion Users

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The Tim Ferriss Show - #369: Kevin Systrom — Tactics, Books, and the Path to a Billion Users

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