Kevin Systrom — Tactics, Books, and the Path to a Billion Users | The Tim Ferriss Show | Transcription

Transcription for the video titled "Kevin Systrom — Tactics, Books, and the Path to a Billion Users | The Tim Ferriss Show".


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Intro (00:00)

Kevin, welcome to the Tim Ferrish Show. Thank you. I'm excited to be here. And for people who don't know Kevin, allow me to introduce Kevin Sistram @ Kevin on Instagram as 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 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. 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.

Kevin'S Journey And Lessons Learned

The book Kevin gifted most frequently (01:16)

We'll hopefully get into that. Are there any particular books that you have gifted often to other people? 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 it. I was like, "That was pretty good." And they were like, "No, I seriously think you're going to love this." 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. 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. Yeah, he's fascinating. I have actually. Ray's been on the show. Oh, really cool. For those people who are wondering just how many commas are involved in Bridgewater Capital, they think they have $160 billion under management. Something along those lines. 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 or that you found inspiring?

A book that helped Kevin in his early days (03:03)

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 by Eric Rees. I remember very early on I went to one of his book talks. I was one of 13 people sitting in this little Roman paul. 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. 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. Still to this day, I come back to that. If I were reading two books, I'd probably read those two books.

Doing the simple thing first (04:02)

If we look at do the simple thing first from a practical standpoint, could you give us an example? I love that you brought up Eric because I remember also going to. Has he also been on the show? He has not. I'm just going to start naming people. 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. Yeah, it was like that. 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 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. 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. 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. It turns out just like generally putting in a mutual fund is not a bad idea. It's harder to eke out the incremental value. 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. You end up trying to build a bunch of things before it breaks. 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 true in business. It's true in 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. 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. We were like, "This is a novel problem. Let's figure out how to split it among two servers or three servers or four." Instead of just writing a single file that said, "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. We were like, "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 four months trying to rewrite our system to be on this new database. Eventually, after it crashed a bunch of times and us having issues with it, we were about to run into 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. 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. 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, finance, and at work as well.

Instagram’s origin story (08:09)

I'm going to rewind the clock a little bit because I think this segment... I think you could do that in editing. Yes, we can, and we can slice and dice, but this will be like watching the movie Memento. Okay, got it. It's basically usually what it's like when I do an interview. Yeah, exactly. So, pretty standard protocol. I would love to talk about, and 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? 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... It's such an interesting story in my life 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? But also, I think it has some interesting lessons. So I'll combine both talking about the origin story, but also how we kept it simple.

How Kevin and Mike decided which features to keep or eliminate (09:42)

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." And I remember telling at the time my mom, I was like, "Hey, I'm going to go do this thing." And she was like, "What about health insurance?" I was like, "Oh, what about health insurance?" You're right. 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. It actually wasn't terrible. But at the time, there were a bunch of check-in apps, and we're sitting in Austin right now, south by southwest. You know, Zoom back six, seven, eight years ago. It was all about Gawala and Four Square, right? Everyone was all about them. So I had to have my version. And it wasn't bad, but it wasn't good either. So what? So what, Ketchy Name? Yeah, it was called Bourbon and B-U-R-B-N. I still think I own the domain name somewhere. But anyway, what happened? I was working on that. I left my job, and I happened to be able to raise money for it. And I'm not sure how or why, but checking apps were all the rage, so we raised some money. You know, a couple of well-known firms in the valley. And I had just enough money to 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 he was like, yeah, this will be super fun. So we decided to join up. And 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 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 it 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 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? 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 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? 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 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 meet-up 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, '08, right? So 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. 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.

How filters became part of Instagram’s big picture (13:37)

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. 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. We were taking a small vacation. I had been working on bourbon for a while. I was exhausted. And we were taking this walk along the beach. And I was like, oh, 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'm going to use it because my photos aren't that good. I was like, OK, well, why don't you think your photos are good? And she was like, well, all your friends, you post these amazing photos. And they're all filtered and stuff. And I was like, oh, that's because they use filters. And she goes, oh, well, you should probably add filters. And 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 2. 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 like three seconds to show you the filter. No one cared. It was fine. Yeah. Keep it simple. Keep it super simple.

Important lessons from Stanford’s Mayfield Fellows Program (15:16)

Now, you mentioned Eric Rees, 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 could certainly do them in order or not would be ODO. Yeah. I mean, where do I start? Okay. 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, typically graduate students, although I'm not going to 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 over the summer. So I did that, my junior year, I stuck 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 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. 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 actually do the thing, like actually start the startup. Don't just go to conferences about it. Don't just like write articles about start it. Do something. And that carries a lot of weight. But that was the Mayfield Fellows program. And maybe the last lesson on the Mayfield Fellows program that I got from it was really, 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 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. But they're an adjunct. 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 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 I 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 you were going to be interested in playing baseball." So I was like, "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." And my dad was like, "What?" He was like, "I got to read about it." So I literally went to the library and read about how to pitch and then played. And I think that's my ammo. It's just, I'm wired that way. Did you remember the...

Insights from the Golden Personality Test (19:16)

I was an okay pitcher. The name of the personality test or the assessment that you did? Yes. It was the golden personality test. Golden personality test. Yeah. I think it was golden. Yeah. Why did you take that test? 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 the 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 illuminating to learn C on paper, which 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 a conference, it's to 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. That's true. We all learned application programming interface. Is that right? Houston, SNM acronyms. On reading, there are different ways to read books.

How Mortimer Adler recommends reading nonfiction books (21:00)

And I had found in some of the research for this conversation a mention of Mortimer Adlers, "How to Read a Book." Yeah. Could you talk about how you read? How weird is it that I'm 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 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 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 point they actually have been waiting to make the entire chapter. And by reading just those paragraphs, you get a pretty good idea of what the book is 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. Yeah, go buy the book, which will encourage you to buy yet more books.

A sampling of the kind of books currently occupying Kevin’s nightstand (23:08)

I have this seriously. If I could show you my room right now, my bedside table is just stacked 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. It ranges, oh, I've got quantitative finance books. I've got, but it's the most fun I've ever had just like plowing through books. I guess it's good. I don't know a job right now. I don't know. It does create a little space. It creates a little bit. It cries out quickly. It gets filled out. It does. Well, I mean, you're not podcast. I don't think you have a podcast. Especially the long ones. No, it's okay. Odeo.

The precursor to Twitter (Odeo) and what Kevin did there (23:58)

What was Odeo? How are you? And what did you learn there? What did you observe? Yeah, 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 were a company. You bring your own computer because I was like, I don't know. Computers are expensive, right? You bring your own. And they're like, oh, good. You brought your own computer. I think they were thrilled. And it was Evan Williams and Noah Glass were the co-founders of Odeo. And 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. And Noah, who's also brilliant. And just seeing that startup try to take off, it was a podcast directory. Believe it or not, maybe a little early. It was the right way that they just paddled a little early. Yeah, which by the way, another lesson in this whole thing, timing is everything. Like 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 was a podcast directory. And you know, honestly, a lot of the famous podcast folks got started on Odeo 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, on 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 and that was my experience. It was awesome and I'm very thankful to all those guys.

Evan Williams’ superpowers (26:01)

What do you view as some of, say, just as an example, Ev's superpowers? You know, 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. 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. 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, you know, 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 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. Getting Things Done. So I remember sitting in the audience and just like the ODO crew, they 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. 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 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 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. 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 bravery that it takes to switch like that. It's hard. 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 end up trying to mirror it in many ways. I completely agree on that.

Business Strategy And The Importance Of Feedback

Some of the most successful pivots in recent history (28:51)

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 response, I suppose, instead of being reactive. I think you're very good at that as well. And I want to talk about, since it's come up a few times, pivoting or ending projects. Because in some aspects, a fetishizing of perseverance in a lot of places, including Silicon Valley and the world of 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 if something 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. 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. One of the really fun things to do is actually, do you know the way back 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 at 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 is funded. I can't remember, but like you can look it up on Wikipedia, right? And go to that date like around the beginning. You will see YouTube as 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 like look up the history of Facebook when it was, you know, it was face-mashed beforehand. 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 counter example. Like 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. 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 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. So 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. 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 have 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 of ego or whatever, stick with ideas far too long. And I think it, you know, it ends up really poorly. Yeah. Or look at something that isn't working that might have a different 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 lowering blood pressure and normalizing 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." 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. Oh, we can... We can... It is family-friendly, but modern family. This will be the director's cut. This will be the director's cut. Anyway, pivots are important. Pivots are important.

Can you train to make the right call to pivot? (33:20)

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 identifying from the perspective of an investor where you might be succumbing to some 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 think... 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 I was... She was like, "Oh, well, 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." And so 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. 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 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." And after a couple of failures, I think you learn really quickly that like, "Hey, listen, I know there's this myth that the best founders just have the mightiest touch and every idea they have is perfect. 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 trail of amazing ideas. I mean, so much you write a book on all the bad ideas amazing people have had over the years and could be just 10 volumes set. Totally. But I think people will get the wrong idea. There is no mightiest touch. One of the things I hated most working in tech was the idea that there's a product guy or a product girl. Like that you're like 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. In a world where your average is going to be 1%, you've got to generate a ton of ideas before you get one. Roughly 100, right? So 1% would be way higher than the average. So 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. But I always have, I don't know, I'm just wired in a way that assumes 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.

How to get honest feedback (36:51)

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. And so one of the questions I'll ask is in a given chapter, I'll say you had to cut 10 to 20%. Yeah. I'll say you had 10 to 20. Which 10 to 20 would go? Nice. Right? And it forces their hand. I think that's smart. So are there other approaches that you like to use or 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. I mean, I guess technically it's a lie. But I don't think it comes from a bad place. They're wired to avoid conflict. So you go in in a restaurant and the server comes by, 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, 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 is everything? They're like, you instinctively just respond great things. If it is that actually what you thought? Like most people have one or two things they wish could be better. And what's crazy is I think of myself in that situation every time I was 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?

Some honest feedback Kevin was grateful to get (38:44)

And you have to be careful because sometimes people have opinions and they're not always right. They 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. 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. 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 it's like, that's not possible. Like, like a few talks in a row that happen. 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, 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. 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 a... People don't give you feedback. 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 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's the last time you, the listener, did that? When's the last time you went out of your way and you said, "Hey, I really want honest feedback on this." And 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? Yeah.

What is a 360 interview, and what can it teach us? (41:36)

And the honesty that comes with it, depending on the format, can be really remarkable. 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, "Oh, this is just like a management thing." And then the second one I did, I literally tried hard to do it. Like I asked people to participate. I said, "Please be as honest as possible." Yeah, 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/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 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. And I think Joe said he went into his car in the parking lot like quite average. 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, 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. 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. 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. 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, like rate the speakers or the host like, and I was like, oh, I really want that data. I'm going to ask them for it because I want to know like, was it interesting to people? What topics didn't they like? Like, did we come off as authentic, inauthentic? Like, where were we? But it's funny because no one ever tells you anything and it's unless you dig for it, you won't find it. But honestly, I think letting people know that it's safe to give feedback, asking for it proactively, et cetera, et cetera, is important. I just, the amount people go out of their way to avoid conflict is pretty wild.

Disallowing seven on a one-to-10 scale (44:29)

Yeah, 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 and you're coming on the rating on screen, made me think of Kyle Maynard, who's an incredible, incredible guy, who's also been on the podcast. And he had learned at one point, or was given a piece of advice from a very successful CEO of a large company, that if you ever ask somebody to rate something from one to ten to disallow seven, because seven's is like semi polite. Like Yelp is all three and a half stars? You're like, no. Exactly. So you're mentioning restaurants. So it all very often asks people in restaurants if they're giving me the, everything is good response, which 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 forced if they're struggling that 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, 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.

Overcoming Challenges And Personal Growth

How Kevin has bounced back from tough times (45:46)

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's, it has been, it has been said that your life is all highlights. No, I'm kidding. That hasn't been said. What company made that happen? But I want to, I want to talk about, I want to talk about some of the, maybe tougher times that you're willing to share, if any, some of the, maybe, of course, darker period. Tough decisions were any time you had kind of self-doubt or felt lost. 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. Because it's, 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 see what actually happened. Yeah. So yeah, any, any at all that you're willing to talk about. The 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 COs 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. But I guess my point is like 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? So 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 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 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, 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. It's like not great, right? But at the same time we wouldn't be where we are if I had listened to most people. It's crazy. So 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. 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. So it's like whether it's like 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 found it really interesting. I mean in the sense that like 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. And what fighters say before they get in the ring if there is some type of self-talk? I got one.

Selling Instagram for $1B—not everything you'd think it would be (51:06)

Yeah. 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. But winning is quote unquote either selling your company or you know 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 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. 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 people ended up leaving pretty soon 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. We're meeting the pope to meeting some idols. Like I got 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. How did you contend with that?

The power of understanding your own motivators (53:06)

Like what was your response to that? I think with me it usually comes with the competitive nature of proving people wrong. 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. 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 but looking from the outside I get their perspective. I just wanted to prove them wrong. It's a powerful motivator. 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, how to write and 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 self-imposed rather than comparative. Right. It's an intranzic motivator. It's an internal motivator of like I want to go get this thing done. For me I think at that moment it was more about self-challenged to prove to myself that I could do it and that we could build this thing. It worked.

How did Kevin learn to manage? (55:12)

How did you learn to manage? That's a... Oh man and I had to. Yeah. So 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? 13. 13 and then... I think I managed like three of them. Right. 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 do you learn to manage? Were there any particular lessons, resources? 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 subscribed to you 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 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 were way better than me to work for me. It 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 you know operations or the list goes on? But the ironic thing is by hiring people that were way better than me but like 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. 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. 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 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 managing a bunch of new grads out of college and coaching them on their careers which exist in mass 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 they should have your job. If you hire these people, if you subscribe to this philosophy.

On getting through decision-making bottlenecks (58:45)

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. 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. Some of the bottlenecks, this is from the New York Times. Some of the bottlenecks companies addressed in the past year are internal. For example, Mr. Sistrom and his co-founder realized that one of the primary holdups was their own decision making. In the past three months they started holding meetings in which they just make a bunch of decisions and then this is quoting Mr. Sistrom. 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. Sistrom 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 un-batched way when you have three direct reports or 13 employees. But as it grows, it seems like this type of systematizing could be really important. Could you describe how a meeting like this functioned and why? It's really funny for me to think of myself as being referenced as Mr. Sistrom. It's very formal. Mr. Sistrom with inventory of decisions. Okay. So here's the context. Have you ever read the book The Goal? 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 Goldrat, yeah, who wrote the book. 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 like written with a narrative. There are characters. And 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. 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? 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 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 and he's 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 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. So with decision making, what we realize is a lot of things were coming to us, but unless we would decide on an important decision, it was basically inventory stacking up in front of a machine that wasn't moving. And of course, the machine can 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 the raw materials go in and raw materials are ideas. 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, 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. I'll have to pick it up. Yeah. The goal of a long list of books to tackle.

How does Kevin choose the books he’s going to read? (01:04:17)

How do you choose books that you're going to read? I know you've given a few examples of things that you're interested in, 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 those you've read and it can indicate how you got to those. But do you have a process for selecting books? Well, first, I don't read fiction. 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. So there we go. There goes a good portion of books down to nonfiction books. Then I asked myself what topics I care deeply about or what things I really want to learn. So for instance, learning to fly. Like, okay, 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 and you can read through reviews. But honestly, a big part of me reading is just like there's usually some outcome I want. 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 get to like wait until a 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 a new skill, there's nothing like sitting down with a nonfiction book on that topic that's well laid out. But sometimes, you know, you 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, "Did you crash?" So they don't... It doesn't always work that way.

Entrepreneurial Advice And Reading Recommendations

What Kevin gets most out of reading history books (01:06:14)

Do you read... If you don't, this is an evaluate judgment. Biographies? Do you ever read biographies? Okay, so I have not read... No, but I really want you. 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. I'm 35. Okay. Our lives are really short compared to the history, recorded history. When it turns out, if you look back in history, patterns emerge. I read this great book called Lessons of History. I was just... Have you read it? Willing-er-old read. Yeah. It's short. It's excellent. It's like a leaflet. Yeah. You could read it in a day. It's great. There are some parts that I disagree with, but for the most... Actually, I read that because Reed Dolly recommended it. It's a great book. Yeah. The number of people I meet that are like, they've read it. 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 a 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, 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. There's some excellent biographies out there.

I think you might enjoy a Genghis Khan in the making of the modern world. Excellent, excellent book for a lot of reasons. I'm trying to think of the ones that have been recommended to me. 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 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. But 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, 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 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 a 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 beautifully written book. It's very impressed. And then if you like that as a taste test, then you can go into there, what is it like, 10 or 20 volume and so it's a summary of their volumes, right? That's right. Yeah, it's like the cliff notes. It's the cliff notes.

Advice Kevin gives to entrepreneurs that very few actually take (01:10:09)

Yeah. So I'd like to ask you, this is one of the questions that I've been hoping to ask ever since we book 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 the New York Times Bicellar 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 best seller 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. 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. And it's been incredible to me how 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 play book. 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 a problem. So many people when they found a company, found a company just to find 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 usually the warning signs are that includes some element of a current fad, like AI or something. Not that AI is a fad. 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 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. So 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, 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? The number of times I've seen people ignore this advice, it's 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 could just keep doing this, right? Like 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'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.

Other mistakes Kevin sees entrepreneurs and creators making (01:14:29)

What are other common mistakes that you observe among entrepreneurs or creators? So, we could 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? It could be within the venture-backed startup world, 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 are feeling like, I'm just going to do this by myself. There's an incredible power in having people around you. Even individuals who are like maybe the face of their company have an incredible team around them. 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. 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." It helps. I think that's a mistake I see a lot. The crazy thing is that having gone through it and making mistakes yourself, it's not clear to me that those are all mistakes in every other situation. I'm trying to be careful and over-prescribing my situation because there are counter examples as well. Sure. That's the really important point actually that I think is worth underscoring for folks. 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. 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 of 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 or 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'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.

What would Kevin’s billboard say? (01:16:58)

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 so many platforms, like Instagram. But to get a message simultaneously to billions of people could be an image. What might you put on that billboard? 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. There were so many people that were like, "Social media is crowded. Photography is lame." You don't even mean that the only way to get through those is by loving 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, "Can I pay my bills?" There are constraints, but if you've 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, 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. Go for it, and don't let people stand in your way. It's just so sad when people don't do that. Life is short. Like you said, our lives are so short, relative to the span of human history. I think that's another benefit of reading history, as it puts that in perspective. These lives are the flicker of, I think, and of all the rovacompa, but it's the flicker of a firefly in the scope of history. It's really short. Really tiny. I had this one coach who said to me, "Often people wake up when they have someone close to them that dies, or they come down with some really serious illness." 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. 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." 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 love the thing you're shooting for rather than the everyday of the thing. I think a lot of people are like, "I should love everyday." It's like, "No. No, everyday 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.

Concluding Remarks

Parting thoughts (01:21:32)

Thank you. We'll see if after you've done your pattern recognition on this meta-analysis of founders who do various things, of various points. I'll be curious to see where you end up. 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? You don't have to have-- You don't have to have-- Guys, I'll 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. 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 You can just search Kevin or Systrom and it will pop right up. And until next time, thank you for listening.

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