#369: Kevin Systrom — Tactics, Books, and the Path to a Billion Users

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Tim. Kevin, welcome to the Tim Ferris Show. Thank you. Excited to be here. And uh for people who don't know Kevin. Allow me to introduce Kevin Sistram at Kevin.

On Instagram is an entrepreneur and co-founder of Instagram. While at Instagram, Kevin served as the CEO where he oversaw the company's vision and strategy and daily operations. That is a whole lot, which we will talk about. Under his leadership, Instagram grew to over one billion users, that's with a B. And launched dozens of products including video, live, direct messaging, creative tools, stories, and IG TV. The company also grew to more than eight hundred 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 w uh widely but intelligently and we'll hopefully get into that.

Are there any particular books that you have Gifted. Often to other people. Yeah, totally. Um Of course now all my friends are having kids. I I give kids books, but uh

Mm. The one I give people that are are trying to learn actively is Principles by Ray Dalio. Um It's interesting actually. Someone gave me the PDF. It was a PDF before his 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. Mm. Yeah, he's a fascinating guy. I have. I have actually. And uh Ray's been on the show. Oh, really cool. And uh for those people who were wondering Uh just

Just to how many commas are involved in Bridgewater Capital. They think they have$160 billion under management, something along those lines. A little bit. And uh he has a lot of very Uh In some respects controversial and unusual practices within Bridgewater, like recording meetings and so on and allowing Uh all

Employees to have access. to uh the the minutes and so on of such meetings. Uh Are there any other books that helped you in the early days from an entrepreneurial standpoint or that you found inspiring? Totally. Early on, um, we read uh Mike and I both read the Lean Startup. I think it's called Lean Startup method or lean startup, can't remember by Eric Reese. Um and

I I remember very early on um I was I went to like one of his like book talks. I was like one of like thirteen 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 So if I were reading two books, I'd probably read those two books. 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 Has he also been on the show? He has not. Okay. But I remember naming the great guy. I would have him on. Uh I remember going also to I think some hotel conference room probably in Paulo Alto when he was initially testing out the material that later became the book. in these workshops. Yeah. Yeah, it was like that. Yeah. Talking about avatars and all sorts of different things. Uh doing the simple thing first. Uh

The Scope of your responsibilities. Uh Instagram. At least

reading even just your bio kinda makes my head spin to imagine what is involved and how easily distracted you could become. Uh What are some examples or any examples of doing the simple thing first, putting that into practice? Yeah. The first thing I'll say about doing the simple thing first is 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 in a mutual fund is like not a bad idea. And the returns you get for ever more complex strategies, either in life or finance, they're like it's harder to eke out the incremental value. And I think what I found in in a startup is When you're small And you're two people, it's me and Mike. We're coding late into the night.

Like you don't have time to make things complex, you have time to make things work. And What ends up happen is you over optimized. 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 did 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 I maybe the best example at Instagram was we were uh

Yeah. 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're like, this is a novel problem. Uh let's figure out how to split it among Yeah. 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. We were like, you know what, let's adopt this crazy new technology that does auto sharding and was fancy and had all these spells and whistles. I won't name it because I don't wanna 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 a 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 a fact, but like that's basically what happened. And I still think about that story to this day in terms of an executive making a decision with his co-founder about what to do. Always do the simple thing first. And it's amazing to me how many people think the quality of their management they think is judged based on the complexity of their decisions or the outcomes. And it turns out 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. So I'm going to Rewind the clock a little bit, because I think this is you could do that in editing, but Yes, we can and we can slice and dice, but this will be like watching the movie Memento. Okay, got it.

I do an interview. Yeah, exactly. So a pretty pretty standard protocol. Uh I would love to talk about and we won't spend a ton of time on this, uh, because as as we chatted before recording, I think you've talked about the origin story of Instagram a lot, but For people who don't have any context, I think it's worth diving into a little bit. 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 short version, medium sized, however you like. Well, first of all, I'm happy to talk about where Instagram came from. I just

Um It's such an interesting story 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, right? Um But also I think it has some interesting lessons. So I'll combine both talking about the store 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. Um And I remember uh telling at the time my mom, uh I was like, Hey And she was like, What about health insurance? I was like, Oh, what about health insurance? You're right. 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. South by South West. You know, zoom back six seven, eight years ago, it was all about Goala and Foursquare, right? Everyone was all about it. So I had to have my version. Um and it wasn't bad, but you know, it wasn't good either. And uh catchy name. Yeah, it was called Bourbon. Um and B U R B N. I still I think I own the domain name somewhere. Um but anyway we Uh

What what happened? I was working on that. I left my job, um, and I happened to be able to raise money for it. And I'm not sure how or why, but Um checking out's for 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. Because I'm like I'm technical, but Not like, you know, I'm not a true engineer in the sense, like I didn't study it formally. So I met Mike and he was one of the power users of Bourbon. And uh he was like, Yeah, this will be super fun. So w we decided to join up. We worked on Bourbon for maybe I don't know, three months and it was clear it wasn't working. Okay, it was like very clear the startup was going nowhere.

And uh we decided to pivot. And this is where keeping it simple um comes in. We actually got to the idea for Instagram by taking away features from Bourbon, not by changing it all. 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? Um And it turns out people kinda liked the check-ins. They thought it was pretty lame because it was a me too thing, but they loved showing people. What they were doing.

They loved taking a picture of the bar, the restaurant, the whatever. And uh and we realized to keep it simple, we were gonna have to cut every other feature of bourbon, which we did. And we just kept the photo part. How did you decide on that feature? Uh, because we made a list and we asked ourselves what exists in the world.

What sucks. Meaning You look out in the world and you say What opportunity is there to fill? If stuff doesn't exist and it's a problem that can be solved, a K like the experience sucks.

Then that's what you should go do. There were a lot of check and apps, there were a lot of planners and meetup things and group chat things. But there was no solution for posting great photos to like lots of friends all at once. So we made the list, we crossed off the things we thought were pretty boring or just There was no opportunity in them.

Um 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, two thousand seven, eight, right? 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 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. 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 bourbon for a while. I was exhausted. Um and we're 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 was like Yeah, but I don't think I'm gonna use it'cause my photos aren't that good. 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. 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 Pro Two.

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 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.

Yeah. Now you mentioned you mentioned Eric Reese, 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 f a few previous Experiences. So we'll 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 could certainly do them in order or not would be Odeo. Yeah. Uh I mean where where do I start? I Okay, so Mayfield Fellows program. Yeah, Mayfield Fellows Program uh

It's a program at Stanford where they take I think they still take twelve a year. twelve uh typically graduate students, um, although I'm not gonna I'll explain that 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 I 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 because 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. 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 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 real 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 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. Yeah. Yeah. Very hard to become a professional soccer player by reading books on the physics of soccer. 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 because I thought it would be entertaining. And my mom was like, Oh my God, like I remember when you were a kid, you just read everything. And my dad was like, Yeah, like you said you were going to be interested in playing baseball. So uh uh I was like I bought a mitt for you and we were gonna go play catching you're like, Dad, I gotta go to the library and I my dad was like what? He's like I gotta read about it. So I literally went to the library, read about how to pitch

And then played. And I think that's my MO. It's just I'm wired that way. Do you remember the It was an okay picture. Personality test or the assessment that you did? Um Yes, it was the uh golden personality test. Golden personality test. Yeah. I think it was golden. Yeah. Mm-hmm. Why did you take that test? 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.

Mm-hmm. 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 those personality tests 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 want to 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. Your API. Yeah. I like it. That's true. Yeah. Application programming interface. Is that right? Houston as some acronyms. On reading.

There are different ways to read books. And I had uh found in some of the research for this conversation. A mention of Mortimer Adler's How to Read a Book. Yeah. Could you talk about how you read?

How Weird is it that I'm like so into reading that I have to find a book that's how to read. Like where does it stop? How to read how to read a book. Um have you ever read the book? I haven't. Okay. Um, it's fine. Um

I I can save you some time. Yeah. 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 that 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 familiarise 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, the one of the secrets that I love and I can still do to this day

Is Most authors І на last параграф в ери чай 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. 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. Yeah. Go buy the book, which will encourage you to buy yet more books. 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 Uh Mathematics 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. I guess it's good I don't have a job right now. I don't I don't know. It it does create a little space.

Yeah, but Audio. Mm-hmm. What was Odeo? And And uh

What did you learn there? What did you observe? Yeah, Odeo is the precursor to Twitter. So Um You we were talking about Mayfield Fellows Programme. Uh My internship was ODO. So that three months over the summer.

I spent it ODO. 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. 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. 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. Yep. Um It was the right way if they just paddled a little early 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 ODO 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, Oh, 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.

Yeah, super small. But that's what ODIA was, and that was my experience. It was awesome and I I'm very thankful to all those guys. What do you view as some of Say Just as an example, Ev's superpowers. I mean I he's very impressive guy, very understated in a lot of ways. Uh what did you

What did you observe uh in the secret sauce of of Ev? Because he he's also a repeat player, right? I mean this is he's not a one hit wonder. No. So w what uh What have you observed in him? Turns out blogging and communication is a thing and doesn't go away. 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 Or what superpowers do you think he has? You could talk present tense too.

So I think he's super determined. Um and super calm under fire. There are a lot of uh 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 hard working 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 w 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. So I remember sitting in the audience and just like the ODO crew. There were like I don't know, six or seven of us at the time at the David Allen getting things done, you know. Uh Not conference, but seminar. I still try to use that stuff today, by the way.

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 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.

I I completely agree on the the ev Having uh Calmness. As a 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. Thanks. And um I wanna talk about since it's come up a few times

Uh pivoting or ending projects. Yeah. In some aspects a fetishing 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. Mm. How do you know?

It's the right time. To stop. And when w how does one go about making that difficult decision? Like are there Telltale signs that this is just it's not that another fifty percent 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. 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? I do. Right? Uh I think it still exists. I haven't tried in a long time, but you can go and type in any w 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 ютюba за 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 mash 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. 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 the people's hands, it's 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 poor. 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 uh then you look at say Viagra, which was failed. 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 brood pressure, and then the They were like, Excuse me, can you check off all the side effects of this blood pressure pill? Huh, there's a pattern here. Well the the recipients were asked to send back their samples and all the women sent their samples back and almost none of the men did. And they're like, Wait a second, what's going on here? I can't tell if this is a family friendly show and we should dive into this or Oh we can we can we can uh it is family friendly but uh modern family This will be the director's cut? This will be the director's cutter important Pivots are important.

How do you train If you do the ability to recognize say Confirmation bias or This is something certainly Ray thinks a lot about.

is identifying from the perspective of of an investor where you might have uh you be succumbing to some cost fallacy or any of these other things that could steer you to make bad decisions or or not stop things. Ha has is that something that you've you've Trained in yourself or is that innate from Birth or upbringing. I

Uh thing I was talking with my wife the other day 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. When 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 of failures, I think you learn really quickly that like, hey, listen. I know there's this myth that like The best founders just have like the mightest 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 could be just ten volume set. Totally, but like I think people get the wrong idea. There is no Midas touch. Like the w 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 two hundred. Like above two hundred, you're like a pretty good daughter, right? Like

In a world where your average is gonna be one percent, you gotta generate a ton of ideas before you get one. Roughly a hundred, right? Yeah. So and one percent 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. Then I am looking bad.

You know what I mean? 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 give 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 un Necessarily. Nice.

But guess what they're doing. Yeah. And so I will a uh one of the questions I'll ask them, I is in a given chapter I'll say if you had to cut ten to twenty percent. Yeah. Gun to the head, which ten to twenty would go. Nice. Right. And it forces their hand, right in in a sense. I think that's smart. So i are there other approaches that U like to use or like others to use on your ideas for stress testing?

Well, first off, I think it's important to realize How people are just wired not to be honest. Not that they lie. 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 Uh next time you go out to eat and they're like, How is everything? And you're like, you instinctively just respond, Great Thanks. If

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 le 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 listening. 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. Totally. And the people who are like What's supposed to be that way.

You know, and you're like, Well, okay, like But like what if it isn't? 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 awesome job. Great, you killed it. 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 that 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. Do you remember any of the other points? 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. 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.

Yeah, it's uh people don't give you feedback. It's crazy. And by the way, the h thing is the more important your company gets, The higher up you go The less people are willing to do it. Yeah. So you actually have to like dig for it. And that's one of the weirdest feelings ever, is please tell me something negative. But you asked a specific question, which is like what are the tools to do it? I don't know that there are any like specific tools so much as like When's the last time you, the listener, did that?

When's the last time you went out of your way and you said, Hey, like I really want honest feedback on this. And when someone gives you feedback, you don't respond in a defensive way. You say thank you. Mm. And you encourage the behavior. If you could do that.

Man, like the self improvement that comes with that. Yeah. And the honesty that comes with it if uh depending on the format can be uh really remarkable. I you may have done this before, but I had not done a a three sixty interview. Oh yeah.

I avoided doing the first one they wanted me to do ever. It was like oh this is just like a a management thing. And then the second one I did, I literally tried like hard to do it. Like I asked people to participate. I said please be as honest as possible. Yeah. And uh I remember I was chatting with uh Joe Gabby about his first three sixty interview, and for people who do not know what that is. Uh there are different ways to approach it. But in effect your Superiors.

Peers slash colleagues and subordinates are all interviewed. So the people you interact with most are all interviewed about your strengths and weaknesses and so on. And very frequently, at least in my case, With I'm my employees and so on. it was anonymized to ratchet up the like allowable

Honesty and Uh 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. Yeah and I think Joe said he like went into his car in the parking lot like cried afterwards. I had a tough time. I had a really tough time with it, but it ended up being very helpful when I was able to look at it with a cooler head, not because I was angry, but I was really sort of like

Mm. by some of the comments. And uh 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.

And But you have to be willing to get both. Yeah. And then ask yourself which of these have merit. And not to write things off, but you have to be able to go through it and just ask yourself, um, but yeah, that was hard. Yeah, I remember my first one and I just

But now I think about it and like No matter what I do. Whether it's another company whether I'm doing a writing project or a podcast, whatever Like

So I just walked off the stage at South by South West and um I could see the screen that was displayed after we left. And they asked people to rate the rate everything. Like rate the speakers, rate the host, like And I was like Oh, I really want that data.

I'm gonna ask him for it. Uh because I wanna 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? Um But it's funny because No one ever tells you anything. Yeah. It's unless you dig for it, you won't find it. Um

But honestly, I think letting people know that it's safe to give feedback Asking for it proactively. Et cetera, et cetera is important. I just The amount people go out of their way to avoid conflict is pretty wild. Yeah. Which which

Often works in the short term, but can really be caustic and So erode relationships in the long term. Right, if you're avoiding that and you your comment on the rating on screen made me think of

Uh Kyle Maynard, who is an incredible, incredible guy. who's uh who's also been on the podcast. But he had learned at one point, or was given a piece of advice from a very successful CO of a large company. that if you ever ask somebody to rate something from one to ten to disallow seven. Because seven's just like Semi-polite. No. Exactly. So you're mentioning restaurants. So what I'll very often ask people in restaurants if they're giving me the everything is good response, which is gives me no information to act on.

As I'll say, all right, w 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 it's sort of bare then they're they're forced, if they're straddling that, to do a barely pass, which is a six, I'm not gonna order that, or an eight, which is a strong that's a that's a confident endorsement. And uh That can be applied to all manner of things. Um That's really cool. I'll do that from now on. No sevens. Yeah, let's let's talk about Tough times. Uh

There are none. The life of an entrepreneur is golden. It has been uh It has been said that your life is all highlights. No, I'm kidding. That hasn't been said. Uh company made that happen but I want to I want to talk about I wanna talk about some of the maybe tougher times that uh that you're willing to share, if any. Some of the maybe darker

Periods, tough decisions where uh any time you had kind of self doubt or felt lost. Uh, because uh 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.

Yeah. So yeah, any any at all that you're willing to talk about. First thing I'll say is a lot of people assume that Like business people, entrepreneurs, like whether they make money, uh like a lot of money, or they sell a company, or they go public or whatever and They're 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 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. 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. 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. 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 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's 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. It's like not great, right? Yeah. But at the same time we wouldn't be where we are if I had listened to to most people. It's crazy. Yeah. So um

I don't know if there's a secret to getting back up, otherwise Other than maybe creating no choice but to get back up. Like I didn't have another job. What was I gonna do? Like sign up for business school. I don't know. Like I'd 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? Uh Of a tough time, a tough decision.

A tough rejection. From an investor, a designer, anything and What you then said to yourself. I'm very curious about self talk, right? So it's like 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 you 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. Uh And

What fighter say. before they get in the ring if there is some type of self talk. Uh I got one. Yeah. Yeah. Let's go straight to the interesting topic, selling our company. Yeah. So we sold our company and it was April of

Two thousand twelve. Um And by all accounts, if you start a company, uh For a lot of entrepreneurs, winning, quote unquote and by the way, I don't agree with this definition, but um But winning is quote unquote either selling your company or or

Uh You know. Having a public offering, an IPO. Um for a lot of people. That's like the traditional outcome for a startup. Um

And we had sold and we were thirteen people and it was a billionaire. It was really exciting. And uh And I remember Like right afterwards. Everyone being like so it's over.

And I feel like that was the most painful thing to hear. Because I had no intention on you know, not doing Instagram. I like wanted to work on it for the next, you know, whatever years

But Everyone I met was like so you're done now, so it's over. I was like no no no. And like We would try to hire people and they'd be like, No, it's over.

And I remember people working at the company Telling me it was over. And a couple of people ended up leaving pretty soon after that. Um And I remember one of them saying, Yeah, there's like nothing else to learn here.

Uh like where can we go from here? Mind you, at the time we had I don't know, fifty million users. We got to a billion, by the way. We had no revenue. We got to a lot more than no revenue. Um We grew to a thousand people on the team. We opened up multiple offices all around the world.

I got to do everything from meeting the Pope to meeting some idols. Like I I got to It was crazy. So the idea that in two thousand twelve we sold our company and then everyone just Kind of. Counted us out. That was painful.

What what how did you contend with that? Like what was your response to that? I think with me it usually comes with the competitive nature of proving people wrong. 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 gonna make something out of this thing. And for me, I think the motivation comes with proving people wrong. Um Because I hate when people discount us. I hate when people You know, tell us we're not gonna be something or you know.

That because we've sold it's all over. Uh but looking from the outset, I get their perspective. I just wanted to prove them wrong. Yeah. Yeah. It's a powerful motivator. Yeah, I think

And part of taking that personality test we talked about? 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 right, and you know what things are not motivating. But competition is one Actually it's interesting. There were two dimensions uh of the personality test. There's competition and then there's challenge. And I didn't

I always thought I was competitive. It turns out I'm actually not competitive at all. I mean I'm a little competitive, but not that competitive. I I have very high scores on challenge. Which means setting goals for yourself and trying to meet them, but it's like self imposed rather than comparative. Right. Intrinsic motivator. It's an internal motivator of like I want to go get this thing done. So For me, I think at that moment it was more about

self challenge to prove to myself that I could do it. Um and that we could build this thing. Um It worked. How did you learn to

Manage. Uh that's that's it. Oh man, and I had to. Yeah. So how how does one learn to manage? Because it you and it's not just time within a larger company, right? Because you can You can find it.

plenty of people who make the same mistakes for twenty years in a row. Yeah. And somehow manage to limp along And their weaknesses. But When you sold it

The company. How many employees do you have? Thirteen. Thirteen. Yeah I think I manage like three of them. Right. So uh you then went through Why do you think kind 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, ninety layers deep. I'm joking. Well, I be I don't I mean there is some truth to that, I th I think, but how did you learn to manage? Were there any particular lessons, resources, um

So I have to say anything at all. 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 are 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 fifteen years of experience in engineering or fifteen in, you know, operations or The list goes on.

Um But the ironic thing is by hiring people that were way better than me. But like I would see myself working for some day 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. I 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 They should be younger, they should have l 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? That I guess my point is I found people that were way better than me and the way I managed was by managing the vision and direction of the company and then asking those people how to get there. And making sure those two things were connected.

At all times. But I didn't have the regular job of like, you know, managing a bunch of new grads out of college And like coaching them on their careers. Um which exist in mass in Silicon Valley. 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. 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. And so so one that

I could ask about would be meeting structure. 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. 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 y how you handle it. So some of the bottlenecks this is from the New York Times, some of the bottlenecks the companies addressed in the la in the past year are internal. For example

Mr. Sisterman and his co-founder realized that one of the primary holdups was their own decision making. So in the past three months, they started holding meetings in which they just make a bunch of decisions. And then this is quoting Mr. Sistram. 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. Sistram 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 Unbatched way when you have three direct reports.

or thirteen 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. Totally. It's really funny for me to think of myself as being uh Referenced as Mr Sister. Mr. Sistram with inventory of decisions.

Okay, so Here's the context. Have you ever read the book The Goal? The goal. I have not. 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 Goldrat, uh I think it's Goldrat, yeah, who wrote the book. And It's kinda 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 kinda cheeky, right? Like it's uh It's not like a business it's a business book, but it's like written with a narrative. Like there are characters and And it's actually pretty fun. So I say go have a read. Um But what I realized in reading this was that uh

Any system is most constrained, or at least the thesis of the book, is most constrained by the slowest process. Um, I think they called it A Herbie? Herbie. Have you ever heard that? I have, yes. So it's because the beginning of the book is like Boy Scouts. Yeah, exactly. If you you want to explain what Herbie is. I know, we're getting there. How many times are Boy Scouts gonna come up in a podcast, right? So uh

The narrative is that they're on some trip and they like have these uh Boy Scouts lined up. I think it's like, you know, the main character's son or something is in the line of Boy Scouts. And uh and Herbie it might not be P C to talk about now, but Herbie is a a little overweight and he's a Is he at the back? I don't know. Basically they figure I think it 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. Um again, people who are super fans of the goal can correct me on this, but the essence of it is your slowest um

Part in the chain is always gonna limit output. In this case, the slowest boy scout limits the progress the troop makes. Um which Isn't actually all that um Isn't all that intuitive until you read this book and you go through it.

So with decision making, what we realized is a lot of things were coming to us. But unless we would decide on an important decision, it was basically like uh Inventory stacking up in front of a machine that wasn't moving. And of course the machine can output

products that people wanna go use until those decisions get made. So it sounds again really intuitive. But If you think about a company as You know, the raw materials go in and raw materials are ideas.

Okay. And the go through machines that transform them into reality. So they go from an idea to a mock to a You know, uh a final uh 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 um 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. Uh Of a long list. of books to tackle. How do you choose books that you're going to read? I know you give an e a few examples of things that you're interested in.

Uh but h 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 uh those you've read and uh kinda indicate how you got to those, but is do you have a process for selecting books? Well first uh

Or disqualify. 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 great 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, uh, down to nonfiction non fiction 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 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 the 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 want to 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 way through a bunch of books on topics I thought I was gonna like and just throwing them out'cause I'm like these are trash.

Uh so they don't it doesn't always work that way. Do you read uh and if you don't, this isn't a value judgment. Uh Biographies? Do you ever read biographies? Okay, so Um I have not read

No. But I really want to. Okay, so the one Area that I want to spend way more time on is history. Including biographies which I consider a form of history.

Um Although biography is 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? Uh forty one. Yeah, it's okay. We'll fact check that one. I'll get back to you. Uh I'm thirty five. 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. I was just Will and Ariel Durant. Yeah. Fantastic. It's short. Excellent. It's like a leaflet. Like you could read it in a day. It's great. There's some ports that I disagree with, but for the I read that because Ray Dali recommended it. It's a great book. Yeah. Yeah. I the number of people I meet that are like they they've read it and

Anyway. The takeaway is that things happen over and over again. Or at least certain patterns emerge. And I guess what I'm saying is if you look back at history You can learn a lot from reading people's history, whether it's a biography or

History of a specific segment of companies. So for instance I think If you want to study the acquisitions of companies and where those founders have gone 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 how many never emerge again, right? Like But how what are the differences between those who that decide to do something and those that don't? So even in my own exploration of what's next in my life, I find myself

not reading necessarily biographies, but I do read accounts of You know, entrepreneurs that have launch big things and none, you know, new things in in the future, and those who haven't, and I start asking myself, like, what are the patterns that emerge? So No, I don't read biographies yet, but I want to And uh and history, I think, more generally is a super interesting topic.

Uh There's some excellent biographies out there. Uh I I think you might enjoy Genghis Khan in the making of the modern world. Okay. Excellent, excellent book for a lot of reasons. I'm trying to think of the ones that have been recommended to me. Um Yeah, I'll have to get back to you on that. Yeah, David McCullough has a lot of really good biographies on the Wright brothers and so on.

Uh it was actually given to me by very, very successful Uh Consumer package goods entrepreneur here in Austin, which turns out to be sort of ground zero or the epicenter of a lot of CBG stuff. So cool. Yeah. Uh and this But isn't it interesting how many people have so many similar patterns in their lives and I think there's this like great equalizer when you realize what you are doing or going through or whatever while it might be super unique to you in your thirty five or forty one years.

It actually turns out like it happens over and over again to people in their lives. Not everyone, but like it's occurred in the past and you have a lot to learn from it. That's basically my point. And that that I think it's a hundred and twenty page book. Lessons of history is a fantastic place to start. I expected it. I actually downloaded it. As uh Kindle. book and let it sit there for months because I expected it to be very dry. And it's a beautifully written book. I was very impressed. And then if if you like that as a as a taste test, then you can go into their what is it, like ten or twenty volume

Uh instead of the summary of their volumes, right? That's right, yeah. It's like the cliff notes. 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, right for like ten to twenty thousand people per week. In other words, you really only need

To to write a book that at least twenty thousand people will love. But they end up writing something too general. 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. Uh And uh it's it's It's been incredible to me how you know I put together a blog post, which is like how to write a best selling book this year, where I lay out the exact playlist.

uh or not playlist rather, but playbook. And nonetheless, it's like one out of a hundred who actually implement even a portion of the steps. D 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. 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. Uh 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 A I 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 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. 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 Yeah.

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. What's crazy to me is I feel like it's our secret sauce at Instagram. And I'm like

This is great. Like we could just keep doing this, right? Like every product we work on hopefully is solving someone's problem. And I feel like I'm giving this advice away for free, but no one's taking it. That's that's it's all 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 eighty percent of the book describing the problem. You got it. You got it. Uh

What are other common mistakes that you observe. Among Entrepreneurs or creators. So we can make it make it broader. 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 it could also be Broader than that. I think going it alone is often a mistake, and that doesn't mean you have to have a co founder, but Not having a team is a mistake I see a bunch. People feeling like oh I'm just 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? 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. Sure. Um That's the really important point.

Actually. Uh 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.

Yeah, the say leader of which would prescribe the exact opposite. Yeah. 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 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 What

This is this is a a m a metaphorical question, but if you could and just a few more questions and then we'll we'll wrap up. Yeah. 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 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?

I don't know if it sounds cheesy, but uh the advice that I got that has driven me The entire way is follow your passion. Like I cared so deeply about social media and so deeply about photography. And there were so many people that were like

Social media is crowded, photography is lame. You know what I mean? That like The only way to get through those is by loving the thing or the mission that you're on.

And Well, it y again, it sounds kinda cheesy. Maybe we could wordsmith this follow your passion thing, but like The number of people that don't follow their passion because people talk them out of it, and I think that's a crime. Yeah. Of course, you can't follow your passion and not expect consequences. Like listen, if you're

passion is to go fly fishing and you want to do that all the time, that's great, but you have to know, okay, like Can I pay my bills, right? Like can I there are there are constraints. But If you thought through it. And you love it, there should be no one standing in your way.

Yeah. And like the number of people that tried to stand in our way, like They still like listen, even long into Instagram there were people, you know, predicting our demise and So I don't know. Like at a certain point it's not like ignore the haters. That could be the other billboard, by the way. Um 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? Like It's just so sad when people don't do that. 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

Deep. The flicker of I think Naval Rava Kamp is like the flicker of a firefly. In the sort of scope of of history. It's really short. 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. Yeah.

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. Yeah.'Cause work is hard. Yeah. It can be miserable at times. I mean Nothing great in this world ever came easy. Like if you want to be uh

an amazing guitarist, you're not gonna get there easily. Gotta train really hard, get shot down a bunch, right? Like They're all like it's a universal law in the world that great things come with a lot of work. Yeah. And What you have to do is I think love the thing you're shooting for.

Rathery of the thing. But I think a lot of people are like, Oh, I should love every day. It's like no, no, every day can be there are a lot of hard days ahead. The thing that gets you through those days is loving the outcome you're shooting for. And I and being excited to get there someday.

Well Kevin, I'm excited to see. What you hatch next. We'll see if after you've done your Pattern recognition. On this uh

An 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? Any Wrap.

No pressure, right? Go tell your friends about this podcast. Perfect. I like that recommendation. Awesome. Thanks for having me. This was a lot of fun. Yeah. Good to see you again. And to everybody listening. For links to everything that came up, the books and all sorts of other things, the names of people and so on. We will provide links to all of that in the show notes as always at Tim.blog forward slash podcast. You can just search Kevin or Sistram and it will pop right up. And until next time, thank you for listening.

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