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Tim FerrissTim Ferriss

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

Kevin Systrom (@kevin) is an entrepreneur and the co-founder of Instagram. While at Instagram, Kevin served as the CEO, where he oversaw the company’s vision and strategy and daily operations. Under his leadership, Instagram grew to over one billion users and launched dozens of products including video, live, direct messaging, creative tools, Stories, and IGTV. The company also grew to over 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. Kevin currently lives in San Francisco with his wife and daughter. Please enjoy! Intro [00:00] The book Kevin gifted most frequently [01:16] A book that helped Kevin in his early days [03:03] Doing the simple thing first [04:02] Instagram’s origin story [08:09] How Kevin and Mike decided which features to keep or eliminate [09:42] How filters became part of Instagram’s big picture [13:37] Important lessons from Stanford’s Mayfield Fellows Program [15:16] Insights from the Golden Personality Test [19:16] How Mortimer Adler recommends reading nonfiction books [21:00] A sampling of the kind of books currently occupying Kevin’s nightstand [23:08] The precursor to Twitter (Odeo) and what Kevin did there [23:58] Evan Williams’ superpowers [26:01] Some of the most successful pivots in recent history [28:51] Can you train to make the right call to pivot? [33:20] How to get honest feedback [36:51] Some honest feedback Kevin was grateful to get [38:44] What is a 360 interview, and what can it teach us? [41:36] Disallowing seven on a one-to-10 scale [44:29] How Kevin has bounced back from tough times [45:46] Selling Instagram for $1B—not everything you'd think it would be [51:06] The power of understanding your own motivators [53:06] How did Kevin learn to manage? [55:12] On getting through decision-making bottlenecks [58:45] How does Kevin choose the books he’s going to read? [1:04:17] What Kevin gets most out of reading history books [1:06:14] Some of my recommended biographies and histories [1:08:40] Advice Kevin gives to entrepreneurs that very few actually take [1:10:09] Other mistakes Kevin sees entrepreneurs and creators making [1:14:29] What would Kevin’s billboard say? [1:16:58] Parting thoughts [1:21:32] This podcast is brought to you by Helix Sleep. Visit Helixsleep.com/TIM and take the simple 2-3 minute sleep quiz to get started, and the team there will build a mattress you’ll love. The mattress arrives within a week, and the shipping is completely free. You can try the mattress for 100 nights, and if you’re not happy, they’ll pick it up and offer a full refund. To personalize your sleep experience, visit Helixsleep.com/TIM and you’ll receive up to $125 off your custom mattress. This podcast is brought to you by FreshBooks. FreshBooks is the #1 cloud bookkeeping software and the easiest way to send invoices, get paid, track your time, and track your clients. Right now you can get a free month of complete and unrestricted use. You do not need a credit card for the trial. To claim your free month and see how the brand new Freshbooks can change your business, go to FreshBooks.com/Tim and enter “Tim Ferriss” in the “how did you hear about us” section. SUBSCRIBE: http://bit.ly/1dSzTkW About Tim Ferriss: Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 300 million downloads and been selected for “Best of iTunes” three years running. Connect with Tim Ferriss: Sign up for "5-Bullet Friday" (Tim's email newsletter): https://go.tim.blog/5-bullet-friday-1/ Visit the Tim Ferriss PODCAST: https://tim.blog/podcast/ Visit the Tim Ferriss BLOG: https://tim.blog/ Follow Tim Ferriss on TWITTER: https://twitter.com/tferriss/ Follow Tim Ferriss on INSTAGRAM: https://www.instagram.com/timferriss/ Like Tim Ferriss on FACEBOOK: https://www.facebook.com/TimFerriss/

Tim FerrisshostKevin Systromguest
Apr 25, 20191h 22mWatch on YouTube ↗

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

EVERY SPOKEN WORD

  1. 0:00 – 0:15

    Intro

    1. TF

      [upbeat music]

  2. 0:15 – 4:53

    Books Kevin Gifts: Principles and The Lean Startup

    1. TF

      Kevin, welcome to The Tim Ferriss Show.

    2. KS

      Thank you. Excited to be here.

    3. TF

      And, uh, for people who don't know Kevin, allow me to introduce Kevin Systrom, @kevin on Instagram, is an entrepreneur and co-founder of Instagram. While at Instagram, Kevin served as the CEO, where he oversaw the company's vision and strategy and daily operations. That is a whole lot, which we will talk about. [laughs] Under his leadership, Instagram grew to over one billion users, that's with a B, and launched dozens of products, including video, live, direct messaging, creative tools, Stories, and IGTV. The company also grew to more than 800 employees, with a campus in Menlo Park, new offices in New York City, and a new headquarters in San Francisco. Prior to founding Instagram, Kevin graduated from Stanford University with a BS in management science and engineering. He currently lives in San Francisco with his wife and daughter. Where to begin? 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.

    4. KS

      Yeah.

    5. TF

      And I thought we could start with one, since you seem to read not just wi- uh, widely, but intelligently, and we'll hopefully get into that. Are there any particular books that you have gifted often to other people?

    6. KS

      Yeah, totally. Um, of course, now all my friends are having kids, I, I give kids books, but, uh, the one I give people that are, are trying to learn actively is Principles by Ray Dalio.

    7. TF

      Hmm.

    8. KS

      Um, it's interesting actually, someone gave me the PDF, it was a PDF before it was a book, gave me the PDF and I, like, skimmed over it. I was like, "Oh, this is pretty good." And they were like, "No, I seriously think you're gonna love this." And I, 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. Uh, it's both a guide to life, a guide to business, and also I think an insight into, uh, Ray and, and someone who's built an amazing business. If you guys listening don't know what he does, he, uh, runs a hedge fund called Bridgewater, and he's, um, he's so much more than, you know, just a, a finance thinker. He's also just a brilliant philosopher. So I give that a lot because I think it's a, a great guide to life.

    9. TF

      Hmm. Yeah, he's a fascinating guy.

    10. KS

      Have you read it?

    11. TF

      I have. I have actually. And, uh, Ray's been on the show.

    12. KS

      Oh, really? Cool.

    13. TF

      And for those people who are wondering, uh, just, just how many commas are involved in Bridgewater Capital, I think they have $160 billion under management. Something along those lines.

    14. KS

      It's a little bit.

    15. TF

      And, uh, he has a lot of very, uh, in some respects, controversial and unusual practices within Bridgewater, like recording-

    16. KS

      Yeah

    17. TF

      ... meetings and so on, and allowing, uh, all employees to have access to, uh, the, [laughs] 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?

    18. KS

      Totally. Early on, um, we read, uh, Mike and I both read The Lean Startup. I think it's called Lean Startup Method or Lean Startup, can't remember.

    19. TF

      Mm-hmm. Eric Ries?

    20. KS

      By Eric Ries. Um, and, uh, I remember very early on, um, I was, I went to, like, one of his, like, book talks, and I was, like, one of, like, 13 people sitting in this little room in Palo Alto, and I was, like, a super fan. Still am, actually. And, uh, so I don't know that I read the entire thing, but the principles from Lean Startup I still apply today, um, one of which is, like, do the simple thing first, and that was our number one value at, uh ... Well, actually, community first was our number one value at, uh, Instagram. Number two was, um, do the simple thing first, and still to this day, I, I, I come back to that. So if I were reading two books, I'd probably read those two books.

    21. TF

      [laughs] And if we, if we, 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-

    22. KS

      Has he also been on the show?

    23. TF

      He has not.

    24. KS

      Okay.

    25. TF

      But I remember go-

    26. KS

      I'm just gonna start naming people that have not been on the show. [laughs]

    27. TF

      He, he's a great, 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.

    28. KS

      Yeah.

    29. TF

      And-

    30. KS

      Yeah, it was like that.

  3. 4:53 – 8:10

    Do the Simple Thing First: The Server Sharding Story

    1. TF

      what i- what are some examples or any examples of doing the simple thing first, putting that into practice?

    2. KS

      Yeah. The first thing, uh, the first thing I'll say about doing the simple thing first is, um, 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 it in a mutual fund is, like, not a bad idea. And the returns you get for ever more complex strategies, e- 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. [laughs] And w- 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- And then it breaks in a different way, and you're like, "Why'd I spend all that time on, you know, that fix when actually I needed to be doing something else?" I feel like that- that's true in life. I think it's true in business, it's true in finance. But so some examples, um, early on, uh, uh, maybe the best example at Instagram was we were, uh, here's the layman's term version. We were on one computer, basically, one server, and, uh, 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. Uh, 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," um, which would have sharded the data across two servers very well and deterministically, uh, what ended up happening was we threw everything out and we were like, "You know what? Let's adopt this crazy new technology that does auto sharding," and it was fancy and had all these bells and whistles. I won't name it 'cause I don't wanna-

    3. TF

      [laughs]

    4. KS

      ... throw them under the bus. Um, but we spent, I don't know, four months trying to rewrite our system to be on this new, uh, database. And eventually, after it crashing a bunch of times and us having issues with it, we were about to run out of space, and Mike was like, "Screw it." 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-

    5. TF

      [laughs]

    6. KS

      ... 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, 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, uh, and at work as well.

  4. 8:10 – 15:16

    The Origin of Instagram: From Burbn to Photos and Filters

    1. TF

      So I'm going to rewind the clock a little bit-

    2. KS

      Please

    3. TF

      ... uh, because I think this segues-

    4. KS

      I assumed you could do that in editing, but [laughs]

    5. TF

      Yes, we can, and we can slice and dice, but this will be like watching the movie Memento.

    6. KS

      Okay, got it.

    7. TF

      Uh-

    8. KS

      It's basically usually what it's like when I do an interview.

    9. TF

      Yeah, exactly.

    10. KS

      [laughs]

    11. TF

      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. Uh, 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, it seems to me that you effectively did the opposite in some ways for the creation of Instagram. Could you, could you give people a little bit of background on how Instagram came to be? And you can tackle that-

    12. KS

      Sure

    13. TF

      ... short version, medium sized-

    14. KS

      Yeah

    15. TF

      ... however you like.

    16. KS

      Well, first of all, I'm happy to talk about where Instagram came from. I just, um, it's such an interesting story f- 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 think it's been around forever, [laughs] right? Um, but also I think it has some interesting lessons. So I'll combine both talking about the sto- 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 wanna work for myself. I wanna work on ideas. I really hope I'm gonna make money." [laughs] 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?" And I was like, "Oh, what about health insurance? You're right."

    17. TF

      [laughs]

    18. KS

      "Like, I totally forgot." Um, 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-in apps, and we're sitting in Austin right now. It's South by Southwest. You know, zoom back six yea- seven, eight years ago, it was all about Gowalla and Foursquare, right?

    19. TF

      Oh, that's for sure.

    20. KS

      Everyone was all about them. So I had to have my version. Um, and it wasn't bad, but, you know, it wasn't good either. And, uh, so I-

    21. TF

      Catchy, catchy name.

    22. KS

      Yeah, it was called Burbn, 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, check-in 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 work on it, and I met my co-founder, Mike, at the time, and I know I needed a bunch of help. 'Cause 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 Burbn, and, uh, he was like, "Yeah, this'll be super fun." So w- we decided to join up. We worked on Burbn 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, um, comes in. We actually got to the idea for Instagram by taking away features from Burbn, not by changing it all. So a bunch of the features of Burbn, one, you could check in at a place, but two, you could add a photo of what you were doing at that place. So you and I 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 kinda liked the check-ins. They thought it was pretty lame 'cause 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 gonna have to cut every other feature of Burbn, which we did, and we just kept the photo part.

    23. TF

      How did you decide on that feature?

    24. KS

      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 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, um, and we circled the photos thing, 'cause 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 years at that point, 2007, '8, right?

    25. TF

      Yeah.

    26. KS

      So, um, we knew that cameras were going to be pervasive in people's pockets, that people were gonna 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 Burbn, circling the one thing that we felt like was the biggest opportunity because it didn't exist yet, and it was a big need. Um, and we built the first version of Instagram. Uh, 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 Burbn for a while. I was exhausted. Um, and we were taking this walk along the beach, and I was like, "Oh, so are you excited about this new app we're building?" We haven't called it Instagram yet. She's like, "Yeah, but I don't think I'm gonna use it, 'cause 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." [laughs]

    27. TF

      [laughs]

    28. KS

      And, uh, 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. Um, 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've been written in OpenGL and could've been a lot faster. You tap on that filter, it took like three seconds to show you the filter. No one cared.

    29. TF

      Yeah.

    30. KS

      It was fine.

  5. 15:16 – 19:30

    Mayfield Fellows Lessons and Learning by Doing

    1. TF

      Now, you mentioned, you mentioned Eric Ries, his book as, as perhaps one of the influences. Uh, 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, a few previous experiences. So go back to the, uh, Mayfield Fellows program. Uh, was there anything in that program that you found particularly useful? Uh, and then the next that I'll hit, so, uh, we can certainly do them in order or not, would be Odeo.

    2. KS

      Yeah.

    3. TF

      Uh-

    4. KS

      I mean, where, where do I start? I... Okay, so biggest lessons-

    5. TF

      And what is the Mayfield Fellows program?

    6. KS

      Yeah, Mayfield Fellows program, uh, it's a program at Stanford where they take, I think they still take 12 a year, 12, uh, typically graduate students, um, although I snuck in, and I'll explain that [laughs] in a second, um, who are interested in entrepreneurship, and they, um, they focus on what is called an entrepreneurship education. So they do three months of case studies, kinda like going to Harvard Business School, but case studies on just entrepreneurship. Then three months, uh, you spend, um, at a real startup getting real experience, and then you come back, and the last three months, so it's a year-long program, uh, meaning three-quarters of the school year, um, you come back and you, uh, debrief on your own experience, and you actually write basically a case on your, um, experience over the summer. So I did that, uh, I, my junior year. I snuck in by, like, ah, I don't know. I basically... I, 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, uh, I prayed that they would take me, 'cause I was so excited about entrepreneurship, and they let me in. Um, years later, by the way, uh, 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." [laughs]

    7. TF

      [laughs]

    8. KS

      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 gonna 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 it. Start it. 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, I got from it was, uh, real- there's nothing in the world that can substitute for real experience. Doesn't matter what we're talking about. If you wanna be a chef, working in a kitchen is the only way you're gonna 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. Um, like a, like a tech founder, right? You gotta start a startup. You gotta 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 gotta do it.

    9. TF

      But they're an adjunct.

    10. KS

      Yeah, yeah.

    11. TF

      Very hard to become a professional soccer player by reading books on the physics of soccer.

    12. KS

      Although, I, I gotta 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, 'cause 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 you were gonna be interested in playing baseball, so, uh, uh, I was like, I bought a mitt for you and we were gonna go play catch, and you're like, 'Dad, I gotta go to the library.'" And I was ... My dad was like, "What?" And he's like, "I gotta read about it." So I literally went to the library-

    13. TF

      [laughs]

    14. KS

      ... read about how to pitch, and then played, and I think that's my MO. It's just I'm wired that way.

    15. TF

      Do you remember the-

    16. KS

      I was an okay pitcher

    17. TF

      ... the, the name of the personality test or the assessment that you did?

    18. KS

      Um, yes. It was the, uh, Golden Personality Test.

    19. TF

      Golden Personality Test.

    20. KS

      Yeah. I think it was Golden. Yeah, mm-hmm.

  6. 19:30 – 23:57

    Personality Testing and How Kevin Reads

    1. TF

      Why did you take that test?

    2. KS

      It's a, uh, it's a variant on the Myers-Briggs test, uh, 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, uh, there are basically four main dimensions, uh, 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. Um, I wanted to know more about what I was like. I had talked about Ray Dalio before. Um, 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 wanna know what I am like." And my co-founder took it. A bunch of our senior execs took it. Um, 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 uh, 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 wanna have the book. So if I'm gonna learn something new, like, the way to learn is not for me to go to, like, a, 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.

    3. TF

      Your API.

    4. KS

      Yeah.

    5. TF

      I like it. No, that's true. Yeah.

    6. KS

      We all learn differently.

    7. TF

      Application programming interface. Is that right? I 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.

    8. KS

      Yeah.

    9. TF

      Could you talk about how you read?

    10. KS

      How weird is it that I'm, like, so into reading that I have to find a book-

    11. TF

      [laughs]

    12. KS

      ... that's how to read? Like, where does it stop?

    13. TF

      [laughs] Right.

    14. KS

      How to read how to read a book.

    15. TF

      Right.

    16. KS

      Um, have you ever read the book?

    17. TF

      I haven't.

    18. KS

      Okay. Um, it's fine. Um, uh, I can save you some time.

    19. TF

      Yeah. [laughs]

    20. KS

      Basically, the idea behind this book is, uh, 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 they, they get bored or they push through or whatever. Um, 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, uh, I, I would say his thesis, the f- the mo- 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, th- 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, uh, paragraph of the book, will not only summarize their main arguments, but make the points 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'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 gonna go. I don't recommend doing this with a thriller, because you'll ruin your experience. [laughs]

    21. TF

      [laughs]

    22. KS

      But with nonfiction, I think it's fantastic. Um, but that's, uh, 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.

    23. TF

      [laughs] Go-

    24. KS

      I, uh ... Yeah.

    25. TF

      Go buy the book, which will encourage you to buy yet more books. Uh-

    26. KS

      I have this, uh ... Seriously, if I could show you my room right now, my bedside table is just stacked with books. I've got a book called, uh, 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 other 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, uh, quantitative finance books. I've got ... But, like, it's the most fun I've ever had just, like, plowing through books.

    27. TF

      [laughs]

    28. KS

      I, I guess it's good-

    29. TF

      No, I feel the same way

    30. KS

      ... I don't have a job right now. I don't, [laughs] I don't know. Like ...

  7. 23:57 – 29:13

    Odeo and Lessons from Ev Williams

    1. TF

      Uh, Odeo.

    2. KS

      Mm-hmm.

    3. TF

      What was Odeo?

    4. KS

      Oh, Odeo.

    5. TF

      And, and, uh, what did you learn there? What did you observe?

    6. KS

      Yeah. Odeo was the precursor to Twitter. So, um, you ... We were talking about Mayfield Fellows program. Uh, my internship was Odeo, so that three months over the summer I spent at Odeo, um- I remember I showed up the first day. I brought my own computer, 'cause I, 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, and Noah Glass were the co-founders of Odeo, and, uh, they were like, "Oh, I forgot you started today." [laughs] 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. Maybe a little early.

    7. TF

      Yep.

    8. KS

      Um-

    9. TF

      It was the right wave, they just paddled a little early.

    10. KS

      Yeah, which by the way, another lesson in, 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 gotta 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, 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, uh, 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 and I'm like, "I'm the intern." He's like, "Oh, I'm Jack." And, uh, I learned... Actually, he gave me a couple of coding assignments over the summer. Um, I remember learning some JavaScript from him, so it's a small world it turns out.

    11. TF

      Yeah, super small.

    12. KS

      But that's what Odeo was, and that was my experience. It was awesome, and I, I'm very thankful to all those guys.

    13. TF

      What do you view as some of, say, just as an example, Ev's superpowers? I mean, uh, he's a very impressive guy, very understated in a lot of ways. Uh, what did you, what did you observe, uh, i- in the secret sauce of, of Ev? Because he, he's also a repeat player, right? I mean, this is-

    14. KS

      Yeah

    15. TF

      ... he's not a one-hit wonder.

    16. KS

      No. [laughs]

    17. TF

      So w- what, uh, what have you observed in him?

    18. KS

      Turns out blogging and communication is a thing and doesn't go away.

    19. TF

      Yeah. [laughs] Yeah.

    20. KS

      Um, and there are lots of companies that can be started around it. Um, what did I observe? Uh, well, it was a really long time ago, but, um-

    21. TF

      Or, or what superpowers do you think he has? You could talk present tense too.

    22. KS

      So I think he's super determined, um, and super calm under fire. There are a lot of, uh, there [laughs] there are a lot of CEOs that, um, are very like, uh, 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, 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... Uh, he didn't send us. He, he offered for us to go to this, uh, seminar by David Allen, the getting things done thing.

    23. TF

      Getting things done, sure.

    24. KS

      So I remember sitting in the audience, and it's just like the Odeo 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, uh, uh, not conference, but seminar. I still try to use that stuff today, by the way.

    25. TF

      Mm-hmm.

    26. KS

      Um, 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. Um, and as a CEO, I, 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, it's incredible. Plus, willing to call it. Like he was willing to call Odeo 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, and you, you end up trying to mirror it in many ways.

    27. TF

      I, I completely agree on the, the Ev having a 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 his response, I suppose, instead of being reactive. I think you're very good at that as well.

    28. KS

      Thanks.

  8. 29:13 – 33:54

    Why Most Successes Are Pivots

    1. TF

      And, um, I wanna talk about, since it's come up a few times, uh, pivoting or ending projects.

    2. KS

      Yeah.

    3. TF

      Because in, there's a, in some aspects, a fetishizing of perseverance in a lot of places, including Silicon Valley and the world of tech. And yet if you, 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. Uh, how do you know it's the right time to stop? And when... 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 gonna prevent it from working.

    4. KS

      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 Wayback Machine?

    5. TF

      I do.

    6. KS

      Right? Uh, I think it still exists.

    7. TF

      Yeah.

    8. KS

      I haven't tried it in a long time, but you can go and type in, in any we- 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, uh, YouTube and figure out when YouTube was founded. I, 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 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, like, look up the history of Facebook when it was, you know, it was Facemash beforehand, it was something before that. Um, 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.

    9. TF

      [laughs]

    10. KS

      Um, like, that literally was their project, and they made it a company, and it worked really well, so I don't know. Um, but most other projects are, um, 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, uh, before you actually, you know, put it into, into people's hands is really difficult. Like, you don't know if it's gonna 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 gonna 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 it, that is. Far too many people, because of ego or whatever, stick with ideas far too long, and, uh, I think, you know, it ends up really poorly.

    11. TF

      Yeah, or look at something that isn't working that might have a different application, right? If you look at Post-It Notes-

    12. KS

      Yeah

    13. TF

      ... you actually have failed adhesive, right?

    14. KS

      Yep.

    15. TF

      And, uh, then you look at, say, Viagra, which was failed [laughs] it was a, a failure from the perspective of whatever it was initially, uh, tested for or intended for, which I think was lowering blood pressure and normalizing blood pressure, and then the, the-

    16. KS

      They were like, "Excuse me, can you check off all the side effects-

    17. TF

      [laughs]

    18. KS

      ... of this blood pressure pill?"

    19. TF

      The, the-

    20. KS

      And they're like, "Huh, there's a pattern here." Anyway.

    21. TF

      Well, the, the recipients were asked to send back their samples, and all the women sent their samples back [laughs] and almost none of the men did, and they're like, "Wait a second, what's going on here?" [laughs]

    22. KS

      I can't tell if this is a family-friendly show and we should dive into this or-

    23. TF

      Oh, we can, we can, we can, uh-

    24. KS

      I'm sure we-

    25. TF

      It is family-friendly-

    26. KS

      Yeah

    27. TF

      ... but, uh, modern family-friendly.

    28. KS

      This will be the director's cut?

    29. TF

      This will be the-

    30. KS

      I got it

  9. 33:54 – 45:47

    Pressure-Testing Ideas and Seeking Honest Feedback

    1. KS

      I, uh, think... I was talking with my wife the other day, [laughs] and I was like, "Nicole, I think one of my failures is that, like, I always think things are not gonna work out or I'm wrong in some way." And, and we were going back and forth, and I was... 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. Um, but a lot of people, I think, are afraid to gather feedback. One of... 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. Like, all ideas are great. All my ideas are great," right? And after a couple 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 and just-

    2. TF

      Could be a 10-volume set, yeah.

    3. KS

      Totally, but, like, I think people get the wrong idea. There is no Midas touch. Like, the... One of the things I hated most working in tech was the idea that there's, like, a product guy or a product girl, right? Like, that you're, like, somehow someone who just knows what's gonna work. Most of the successful people I know have tons of bad ideas, and it's about editing them out, um, 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?

    4. TF

      Yeah.

    5. KS

      Like, in a world where your average is gonna be 1%, you gotta generate a ton of ideas before you get one. Roughly 100, right?

    6. TF

      Yeah.

    7. KS

      So... And 1% would be, like, way higher than the average. So how do you figure out which is the one? It's... I think it's by being super not mean to yourself, but critical on the idea in a, in a constructive way and pressure testing it with other people. Um, but I just, I, 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, I have is wrong, and I'm, I'm more worried about being wrong than I am looking bad.

    8. TF

      Yeah.

    9. KS

      You know what I mean?

    10. TF

      No, I get it. Do you have any, uh, particular questions that you ask yourself or other people when you're stress testing an idea, or alternatively how you solicit feedback? And, um, I'll give you an example. Since I write, I have all these books, I want people to act as proofreaders. Uh, but I don't want them, since they are my friends, to be unnecessarily nice-

    11. KS

      But guess what? They all are

    12. TF

      ... uh, polite. Yeah. And so I will a- one of the questions I'll ask them I'll, I, is in a given chapter, I'll say, "If you had to cut 10 to 20%-"

    13. KS

      Yeah

    14. TF

      ... gun to the head, which 10 to 20 would go?

    15. KS

      Nice.

    16. TF

      Right? And it forces their hand, right, in, in a sense.

    17. KS

      I think that's smart.

    18. TF

      So i- i- are there other approaches that, that you like to use or like others to use on your ideas for stress testing?

    19. KS

      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 like comes from a bad place. They're wired to avoid conflict. So like you go in, 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, i- 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'm sitting down there, I'm like, man, if I were on the other side of this, I'd really wanna know the truth, because without the truth, you can't improve, right? And you have to be careful 'cause sometimes people have opinions, and they're not always right, but at lea- if you don't know, you can't act on it. And I've been surprised how many people I've met, um, 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 wanna 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 gonna go kick some ass."

    20. TF

      Totally.

    21. KS

      And the people who are like, "Well, it's supposed to be that way," you know? And you're like, "Well, okay," like, "but like what if it isn't?" [laughs] You know? Like... Um, 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 a- awesome job. Great, you killed it." And I was like, that's not possible. Like the, like a few talks in a row that happened, and then we hired someone, and I'm not gonna pick on them and, 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 this." Like, "I know you're a happy person, but you, 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.

    22. TF

      Do you remember any of the other points?

    23. KS

      Uh, it was, um, slow down. Pause, right? Uh, 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.

    24. TF

      Yeah.

    25. KS

      Like, it's, it's hard. Um, and I'm just like, "I'm a serious person, so I don't think to smile as much." Uh, what were the other things? I'd have to go back to my notes, but those are the two things that stood out.

    26. TF

      Mm-hmm. Yeah. It's, uh-

    27. KS

      But 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.

    28. TF

      Yeah.

    29. KS

      So you actually have to like dig for it, and that's one of the weirdest feelings ever is, "Please tell me something negative."

    30. TF

      [laughs]

  10. 45:47 – 55:13

    Tough Times: Getting Back Up and Selling Instagram

    1. TF

      let's, let's talk about tough times. Uh, so you mentioned-

    2. KS

      There are none. The life of an entrepreneur is golden.

    3. TF

      It's true. It-

    4. KS

      Yeah

    5. TF

      ... you know, I've, it's, it, it has been, uh, it has been said that your life is all highlights. No, I'm kidding. That hasn't been said. Um, but-

    6. KS

      What company made that happen?

    7. TF

      But I want to, I wanna talk about, [laughs] I wanna talk about some of the maybe tougher times that, uh, that you're willing to share, if any, some of the maybe-

    8. KS

      Of course

    9. TF

      ... darker periods, tough decisions, where, uh, any time you had kinda self-doubt or felt lost. Uh, because a- and where I'm going with this is I'm very curious how you then recontextualized it, found the silver lining, or just got through it. 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 see what actually happened.

    10. KS

      Yeah.

    11. TF

      Uh, so yeah, any, any at all that you're willing to talk about.

    12. KS

      First thing I'll say is a lot of people assume that, like, business people, entrepreneurs, like, whether they make money, uh, like a lot of money, or they sell a company, or they go public or whatever, and they're CEOs for a long time or world leaders, whatever, a lot of people assume these people don't struggle. 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, 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, getting knocked down is, like, a really common thing no matter where you are in your career, no matter where you are, um, 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, uh, 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. [laughs] Um, I remember trying to hire some of, like, the most amazing designers early on, um, who just, like, wouldn't join because they didn't believe in the app. I remember press stories, um, or investors investing in competitors even though they had invested in us.

    13. TF

      Oh.

    14. KS

      So choosing the other, which is fine. Listen-

    15. TF

      Yeah

    16. KS

      ... 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-

    17. TF

      Yeah

    18. KS

      ... to think you're not the winner. Um, all of these things happened along the way, and we were knocked down multiple times, um, whether that was in our heads or actually there, uh, r- in reality. Um, 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. [laughs] Heck, like, if you're a singer, like, it's the worst business to be in in the world because everyone's gonna 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 gonna knock you off the horse and you're off forever. And I, 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, [laughs] it's, like, not great, right?

    19. TF

      Yeah.

    20. KS

      But at the same time, we wouldn't be where we are if I had listened to, to most people.

    21. TF

      Mm.

    22. KS

      It's crazy.

    23. TF

      Yeah.

    24. KS

      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. [laughs]

    25. TF

      Mm.

    26. KS

      Like, I didn't have another job. What was I gonna 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-

    27. TF

      Mm-hmm

    28. KS

      ... what was the other option?

    29. TF

      Can you think of one-

    30. KS

      A desk job. [laughs]

  11. 55:13 – 1:04:18

    Learning to Manage: Hiring Up and The Goal

    1. TF

      How did you learn to manage? Uh, that's, that's a-

    2. KS

      Oh, man, and I had to.

    3. TF

      Yeah. So how do you-

    4. KS

      [laughs]

    5. TF

      How does one learn to manage? Because, uh, you... And it's not just time within a larger company, right? Because you can, you can find plenty of people who make the same mistakes for 20 years in a row-

    6. KS

      Yeah

    7. TF

      ... and somehow manage to limp along and sort of do decently despite their weaknesses. But when you sold the company, how many employees did you have?

    8. KS

      13.

    9. TF

      13.

    10. KS

      Yeah.

    11. TF

      And then-

    12. KS

      I think I managed like three of them, [laughs] so.

    13. TF

      Yeah. Right. So, so you then went through-

    14. KS

      Why do you think co- companies have hierarchy? They're like, "I don't wanna manage people. You manage them."

    15. TF

      [laughs]

    16. KS

      And before you know it, you've got like a tree, you know, 90 layers deep. I'm joking.

    17. TF

      [laughs] Well, I'd be, I don't... I mean, there, there is some truth to that, I, I think, but how did you learn to manage? Were there any particular lessons, resources, um-

    18. KS

      So I have to say-

    19. TF

      Anything at all

    20. KS

      ... well, I was gonna say my job was different than most, which obviously is an understatement, but like, I'm gonna tell you the philosophy I subscribe to, and then I think your, the listeners can decide if it makes sense for them. It might. I decided that I, uh, had nothing to lose because, or at least I didn't think I had anything to lose, um, 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, um, 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, you know, operations or..." The list goes on. Um, but the ironic thing is, by hiring people that were way better than me, that like 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, then maybe one of them will take my job." And I don't know where like the reality is on that spectrum in the real world. Like I, I don't know. Um, but I think that's actually one of the issues I looked for most in the company, which was, um, people hiring down on purpose. Like, people do it reflexively. They hire down. They're like, "No, I need someone with less experience than me who l- they should be younger, they should have le- fewer years of experience," right? "Because I should coach them." And actually, if everyone hired up, you'd have like the most badass company in the world. So how do you manage that? The, 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 a- at all times. But I didn't have the regular job of like, you know, managing a bunch of new grads out of college and like coaching them on their careers, um, which exist in mass in Silicon Valley. Um, so I'm not sure my management like experience mirrored that, um, of most, but I think there's a lot to learn, which is hire really great people that someday you wanna have, you know, they should have your job.

    21. TF

      So you hire these people if you subscribe to this philosophy, and then I, 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, right? And so, so one that I could ask about would be meeting structure. So i- in the course of prepping for this, uh, and I found this a f- a few places, but in the, in the New York Times, feel free to fact-check this. [laughs] But, uh, I'll just read this briefly and then we can... I'd love to hear you elaborate on what the meeting actually looks like and, and how you, how you handle it. So some of the bottlenecks, this is from The New York Times, some of the bottlenecks the company's addressed in the la- in the past year are internal. For example, Mr. Systrom and his co-founder realized that one of the primary hold-ups 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 doc in which we list out the inventory of decisions on products as if it's stacked up in front of a machine waiting to be processed," Mr. Systrom said, "And then we have sessions where we sit down and we decide. You just work through the decisions." So, 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, it seems like this type of systematizing could be really important. Could you describe how a meeting like this functioned?

    22. KS

      Totally.

    23. TF

      And why it's-

    24. KS

      And it's really funny for me to think of myself as being, uh, referenced as Mr. Systrom.

    25. TF

      [laughs]

    26. KS

      Sounds very, sounds very formal. Mr. Systrom with inventory of decisions. Um, okay, so here's the context. Have you ever read the book The Goal?

    27. TF

      The Goal.

    28. KS

      The Goal.

    29. TF

      I have not.

    30. KS

      Yeah. Um, it is a book about basically manufacturing and supply chain management. Sounds really boring, but I promise you it's really good. Um- Last name is Goldratt. Uh, I think it's Goldratt, yeah, who wrote the book, and it's kind of... And, 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, uh, supply chains basically. Um, but it's written in narrative form, which is kind of cheeky, right? Like-

  12. 1:04:18 – 1:10:09

    Choosing Books: Nonfiction, History, and Lessons of History

    1. TF

      How do you choose books that you're going to read? I know you gave an, a, a few examples of things that you're interested in. Uh, but how, how do you filter the universe of books to those you end up reading? And I mean-

    2. KS

      Yeah

    3. TF

      ... you could maybe just pull up, you could pull a few real examples from, from, uh, those you've read and, uh, kind of indicate how you got to those, but is, do you have a process for selecting books?

    4. KS

      Well, first, uh-

    5. TF

      Or disqualifying books

    6. KS

      ... I don't, 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, uh, there we go. There goes, you know, a good portion of books-

    7. TF

      Yeah

    8. KS

      ... uh, down to nonfiction, nonfiction books. Then I ask myself what topics I care deeply about or what things I really wanna learn. So for instance, learning to fly. Like, okay, what are the best books to learn to fly, or, uh, if I wanna learn about investing or finance, what are the best books? Or if I wanna learn about productivity, what are the best books? And obviously, Amazon's great for that, and you can read through reviews and, um... But honestly, a big part of me reading is just like there's usually some outcome I want. Like, I wanna 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 gotta 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 wanna learn 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 of the way through a bunch of books on topics that I thought I was gonna like and just thrown them out because I'm like, "These are trash." [laughs]

    9. TF

      [laughs]

    10. KS

      Uh, so they don't, it doesn't always work that way.

    11. TF

      Do you read, uh, and, and if you don't, this isn't a value judgment, uh, biographies? Do you ever read biographies?

    12. KS

      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. Um, although biographies can be fairly selective in the history they tell, that's true of all history books, um, I feel like they're... How old are you?

    13. TF

      Uh, 41. Pretty sure I'm 41. [laughs]

    14. KS

      Yeah, it's okay. We'll fact check that one. I'll get back to you.

    15. TF

      [laughs]

    16. KS

      Uh, I'm 35. Okay. Uh- Our lives are really short compared to the history, uh, recorded history. And it turns out if you look back in history, things, patterns emerge. I read this great book called Lessons of History.

    17. TF

      I was just gonna-

    18. KS

      Have you read it?

    19. TF

      Will and Ariel Durant.

    20. KS

      Yeah.

    21. TF

      A fantastic book.

    22. KS

      It's, it's short.

    23. TF

      It's excellent, yeah.

    24. KS

      Like, it's, it's like a leaflet.

    25. TF

      Yeah.

    26. KS

      Like, you could read it in a day. Um-

    27. TF

      It's great

    28. KS

      ... there's some po- parts that I disagree with, but for the most-

    29. TF

      Actually, I read that because Ray Dalio recommended it.

    30. KS

      It's a great book.

  13. 1:10:09 – 1:16:58

    Advice Entrepreneurs Ignore: Solve a Problem and Don't Go Alone

    1. TF

      s- so I'd like to ask you, uh, this is one of the questions that I'd, uh, 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. Uh, I'm asked all the time how, how, uh, 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 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 f- to write a book that at least 20,000 people will love.

    2. KS

      But they end up writing something too general.

    3. TF

      They end up writing something too general.

    4. KS

      Yeah.

    5. TF

      Uh, and, uh, 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.

    6. KS

      Mm-hmm.

    7. TF

      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 bestselling book this year, where I lay out the exact playlist, uh, or not playlist rather, but playbook, and nonetheless, it's like one out of 100 who actually implement even a portion of the steps. Do... Uh, 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?

    8. KS

      Yeah. Number one advice I always give is to solve 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." I- ideas are not companies. Ideas are not products. Like, you're like, "Well, I'm gonna combine this thing with this trend, and we're gonna 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. 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, um, 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? Um, so- 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, 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. Um, 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 gonna do this, this, and it's a hot market, so I'm gonna 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. And what's crazy to me is I feel like it's our secret sauce at Instagram [laughs] 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, and I feel like I'm giving this advice away for free, but no one's taking it. That's, that's-

    9. TF

      It's, it's als- also true for nonfiction books, right?

    10. KS

      Yeah.

    11. TF

      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.

    12. KS

      You got it.

    13. TF

      [laughs]

    14. KS

      You got it.

    15. TF

      Uh, what are other common mistakes that you observe among entrepreneurs or creators? So we can make it, make it broader.

    16. KS

      Yeah.

    17. TF

      It doesn't have to be broader, but people who are trying to do their own thing, entrepreneurs or otherwise, uh, what are some common mistakes you, you see? And it could be, it could be within the venture-backed startup world, but it c- could also be broader than that.

    18. KS

      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 gonna do this by myself. I'm just gonna..." It, um... 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. 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 'em," you know?

    19. TF

      Yeah.

    20. KS

      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, I'm trying to be careful in over-prescribing my situation 'cause there are counter examples as well.

    21. TF

      Sure.

    22. KS

      Um...

    23. TF

      That's the really important point, actually, uh, e- that I think is worth underscoring for folks, and that is for, for nearly every rule that someone might prescribe, there's probably a counter example, you know, the, say, leader of which would prescribe the exact opposite.

    24. KS

      Yeah.

    25. TF

      Right? And so it's, it's, I suppose, in part finding, uh, the rules that are compatible also with, uh, what you hold to be the core values or philosophies of... that guide you, like being passionate about the product, uh, or the service or the company, because that has some real practical implications. If you're not passionate, are you, in fact, going to be able to summon the endurance, like you said, to sort of walk through or around or climb over the various walls that are gonna 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. Uh,

  14. 1:16:58 – 1:22:34

    The Billboard Message: Follow Your Passion and Closing

    1. TF

      what... This is, this is a, um, a metaphorical question, but i- if you could in just a few more questions and then we'll-

    2. KS

      Yeah

    3. TF

      ... we'll wrap up. If you could put a message, a quote, a word, a question, anything non-commercial on a billboard, and really what I'm asking is to get a, a message to billions of people, which it's crazy to think that you, you can actually [laughs] do that now on some of these platforms like, like Instagram. Um, but to get a message simultaneously to billions of people, could be an image, what, what might you put on that billboard?

    4. KS

      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." [laughs] 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 on. And while it... Again, it sounds kinda cheesy, m- 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.

    5. TF

      Yeah.

    6. KS

      Right? It's... Of course you can't follow your passion and not expect consequences. Like, listen, if your passion is to go fly fishing and you wanna 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've thought through it and you love it, there should be no one standing in your way.

    7. TF

      Yeah.

    8. KS

      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 it's not like ignore the haters. That could be the other billboard, by the way. Um-

    9. TF

      [laughs]

    10. KS

      ... it's, it's like you gotta 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? [laughs]

    11. TF

      Yeah.

    12. KS

      Like it's just so sad when people don't do that.

    13. TF

      And life is short. Um, like you said, I mean, our, our lives are so short relative to sort of the span of human history, and, uh, I think that's another benefit of reading history is it puts that in perspective. Like, these lives are sort of the, the, the flicker of, I think Naval Ravikant put it this way, like the flicker of a firefly in the sort of scope of, of history. It's really short, the, the timeline.

    14. KS

      Really tiny. And I had this, uh, this one coach who said to me, he's like, "Often people wake up when they have someone close to them that dies or, um, 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 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-

    15. TF

      Yeah

    16. KS

      ... 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 wanna clarify, a lot of people are like, "You should love what you do," and I agree, but I, I think it's more you should love what you're shooting for.

    17. TF

      Yeah.

    18. KS

      'Cause work is hard. [laughs]

    19. TF

      Yeah.

    20. KS

      It can be miserable at times. I mean, nothing great in this world ever came easy. Like, if you want to be a, an amazing guitarist, you're not gonna get there easily. You gotta train really hard, get shot down a bunch, right? Like, there are all ... Like, it's a universal law in the world that great things come with a lot of work.

    21. TF

      Yeah.

    22. KS

      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 people are like, "Oh, I should love every day." It's like, no.

    23. TF

      No, no, no.

    24. KS

      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, uh, being excited to get there someday.

    25. TF

      Well, Kevin, I'm excited to see what you hatch next.

    26. KS

      Thank you.

    27. TF

      We'll see if after you've done your pattern recognition on this, uh, ana- meta-analysis of founders who do various things at various points, I'll be curious to see where you end up. Uh, but, uh, 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?

    28. KS

      No pressure, right?

    29. TF

      [laughs] You don't, you don't have to have-

    30. KS

      Go tell your friends about this podcast. [laughs]

Episode duration: 1:22:57

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