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I wish I knew earlier that my company was still my responsibility, no one was going to fix my problems. They were investing because they believed in me and they believed in my potential. But it was up to me to to still sort of take that potential energy and turn it into kinetic energy. It wasn't a handout. It wasn't like, you know, you're going to get these people to come in to your office and help you solve problems day in, day out.

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No one is going to make you rich people. People are busy solving their own problems.

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Welcome to the Knowledge Project podcast. This is Shane Parrish, this podcast and our website, F-stop blog, Help sharpen your mind by mastering the Best what other people have already figured out. If you're hearing this, you're not currently a supporting member. If you'd like early access to the podcast, ad free episodes, transcripts and other subscriber only content, you can join at F-stop Blogs podcast. Check out the Schnitz for an easy to click on. My guest today is Sahil, living in Sahel, was the second employee at Pinterest and left to start building a service that helped creators earn more than 300 million.

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We talk about the hardest skills to succeed in business, what he looks for when hiring, what it's like to try and build a billion dollar business. His worst mistake patterns of success, patterns of failure and so much more. It's time to listen and learn. The Knowledge Project is sponsored by Medlab for a decade, Medlab has helped some of the world's top companies and entrepreneurs build products that millions of people use every day. You probably didn't realize that at the time, but odds are you've used an app that they've helped design or build apps like Slack, Coinbase, Facebook Messenger, Oculus, Lonely Planet and many more.

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Medlab wants to bring their unique design philosophy to your project. Let them take your brainstorm and turn it into the next billion dollar app from ideas sketched on the back of a napkin to a final ship product. Check them out at Medlab Dutko. That's Medlab Dutko. And when you get in touch, tell them Shane sent you.

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This episode has also brought to you by 80, 20, 80, 20 is a new agency focused on helping great companies move faster with code. The team at 80 20 can build your next app or website in a matter of days, not months.

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And see, this episode is supported by Team History, a podcast that tells the stories of unsung teams working together in new and unexpected ways to achieve remarkable things. Each episode highlights lessons that leaders can apply in their organizations. I got a preview of an upcoming episode, and I really enjoyed learning about how researchers, biologies, data scientists and citizens are using A.I. to fight extinction across the globe. Search for team history anywhere you listen to podcast. My thanks to Timestream for their support.

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Sanho man, so happy to have you on. Thanks for having me. Excited to be here.

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You were born in New York, but you grew up in Singapore. What was that like? Yeah, it was interesting.

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Singapore is a very unique place. A lot of people who visit describe it like a city playground where it's just insanely safe, it's super clean. You know, people joke about the fact that, you know, you get beat up for chewing gum or whatever, which is not true, but not inaccurate either. Kind of it is. It is it is a good heuristic to describe Singapore, I think. But yeah, I was just, I think living in a place that felt so different from everywhere else and Singapore because it's such a young country, it doesn't have the same sort of, you know, identity almost issues that a lot of other countries have in terms of like this is the way that we do things.

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Singapore, if you read about Lee Kuan Yew or any of the founding story of the country and things like they just pick and pull ideas from everything. You know, libertarians I know describe it as like a utopia because there is no minimum wage zero. There is basically a flat tax. I think it's around fifteen percent flat. No matter how much you make, there's no capital gains tax. And so libertarians love it. But then you the sort of more progressive socialist kind of people that I know also love Singapore because it's sort of, you know, 80 percent of the housing there is built by the government.

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It's it's a very sort of top down, centrally planned country. It's a single city, state, country. And so I just love it because people love to use it as an example of their viewpoint. Like, it's a really interesting kind of Rorschach test for like the for the things that people like. But, you know, it's young, it's small. And so in terms, you know, it's never been in a war. And so I think there are just things that allow it to do to do things, quote unquote, better than than other folks.

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And then I would say the other thing that I just took away from Singapore is just a pretty ruthless it's like a very pragmatic as a country place. They're very strategic about how do we grow this thing. Right. Like how do we structure this place in a way that if you look at the GDP of Singapore over the last 50, 60 years, it's like the fastest growing startup you've ever seen, you know?

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Well, that was the from third world of first. Right, Lee Kuan Yew. And sort of like his unprecedented taking a country in a generation and basically making it wealthy. Totally.

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And, you know, there's a there's a lot of things you can't control like that. Just, you know, where it's located on the map is really important in terms of the trade routes. Singapore is sort of like the largest port in the in Southeast Asia. But it took a person, I think, just like George Washington, like you need the ingredients, but then you need kind of the chef as well to kind of put them together. How long were you there?

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I was there from age five to seventeen. So most of my childhood. What was school like there? I don't know. I don't know how to compare it because that's the only context. I think it's relatively similar to to schools here, though. Certainly doesn't have some of the same issues around. What you've been reading about racism and anti-Semitism and sexism and all these things like Singapore, it doesn't feel like it has much of the same bag. It has other other issues for sure.

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I would say the emphasis there was so much on getting a secondary education. It was like everyone knew without any doubt that they would go to college. And it's a very it's a very sort of financially motivated place. And so typically, people will pick the jobs that will make them the most money is sort of very, very capitalistic in that way.

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It's interesting how those expectations shape outcomes to you. It's like you're expected to go to college, that you're expected to perform academically, I believe. I think expectations cannot be underrated and I think. In your peer group also can be underrated, like I think there's so much emphasis on on sort of the system that you're a part of, you're sort of that your set of teachers, et cetera. But honestly, I think the biggest thing is just like you're kind of the average of your five friends, you know, and if you hang out with certain people, you're going to end up in a very, very, very different place based on based on that kind of like that osmosis that you'll go through with sort of like this sort of socialization that that you'll have as a kid.

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And I think that happens super early. And certainly Singapore, it just it's a pretty ruthless it's a pretty ruthless place, like the idea that there's no fat people, for example, in Singapore. It just doesn't really exist as a concept. And I don't mean that any sort of derogatory way. But there's just people in general there aren't overweight. And part of that is in in the local school system, if you are overweight, you go through a program like you, part of you skip lunch and you go through a program that you basically run around a track and sort of eat lunch.

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I mean, it's like sort of a regulatory regulatory system. And there's also national service. Everyone who's Singaporean. If you stay in Singapore, I chose to leave and go to school in the US, you have to go through national service. Right. So you spent two years becoming sort of like a perfect adult, quote unquote. Right. Like you learn these things, like in general people who go through that are less likely to to get into trouble and things like that.

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So there was a lot of it's hard to unpack exactly like, oh, we took this and apply to here. It would fix this problem. But there's just so much culturally around just holding holding the people to a very high bar. And then when you do that, the next generation is brought up with these sort of values and is willing to do that for the sort of for the next generation, et cetera, et cetera. I want to explore something you said there about sort of the you are the product of the five closest people you hang around.

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How do you use that information to consciously choose the people that you're hanging around?

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I'm really mindful of of that. Like in terms of the books that I read, the people that I listen to, the tweets that I follow, I think it's it's super important to to really it's sort of like you are what you eat, the companies that you work for. I think, like, I've never read a book and and come out of it being less convinced of the argument, even though I was not on the side of the argument.

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Like when you spend that much time sort of looking at a subject from a specific perspective, you just end up becoming more empathetic to that point of view. And it's like doing that en masse. When you go on the on your phone, you're kind of seeing the way that a certain group of people see certain things. And I think this is actually sort of been accelerated with covid because you don't have maybe some of the back and forth. You're just you can't you know, it's sort of this very asynchronous medium.

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And so you end up just like absorbing all of this content and your perception is your reality. So I think you just inevitably, inevitably kind of become closer to those sorts of people, which I think can be a great thing. If you want to be a great business person, for example, you can read books by great business people. And of course, they're selling things like you kind of have to be mindful of maybe what their incentive structure might be, but you'll get closer to figuring out like what are the sort of attributes that make someone like Jay-Z, Jay-Z or someone like Steve Martin?

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Steve Martin. Right. And I spend a huge amount of time reading those sorts of those sorts of books as well.

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One of the people you physically hang around with, like do you call sort of friendships when you're like this isn't serving me or how do you think of it then?

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Yeah, this is something I struggle with a lot. I think there is a large expectation around friends and what friends mean. And, you know, Silicon Valley is kind of funny because there's this concept of we're friends and I like to joke that we're startup friends because it's such an overused word. And what it means is like we met once in person for coffee, and if I need something from them, I'll send them an email and the reply to my email.

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It's not like we hang out at the bar, you know, like, you know, like all these sorts of things, unless it's sort of some situational thing that arises typically from some sort of business reason. And that might just be a differentiator between friends in school and friends in adult life. I'm not really sure, because that's the only sort of career path that I've sort of taken. But, yeah, it's it's I always struggle with with that idea that we need to be friends with everybody.

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There are people that I talk to all of the time, but I wouldn't consider them even friends of mine. We just happen to be valuable for each other. Very symbiotic relationship. And then there's other people that I'm friends with that I would consider close, close, close friends with that I haven't talked to in months. And so I really I think those can be separated. But yeah, I spent a lot of my time thinking about how do I spend more time with certain.

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People which I think could be a trap because you don't want to get into this, this place where you're just like, how do I meet this person? I don't think that's the right approach, but it's more like, how can I figure out how to become closer to the type of person that this kind of person is. And in general, if you do that over time, I feel like opportunities to meet these kinds of folks will come up and show up in your life organically.

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Where did the idea from Gumm Road come from and how did you get started? Yes, of Gum Road. I wanted to sell this pencil icon that I designed for a Mac app, and I had a Twitter account. I had a dribble account. I had a few thousand followers. This is twenty eleven and I just wanted to sell them this thing. I kind of called it like a lemonade stand. I just I don't need a whole storefront, like, I need to need all of this infrastructure.

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I just needed like a little table and I wanted to sell this icon for a dollar. And and these people who are already following me, you know, I could just share with them and they can choose to buy it or not. And, you know, they enter their credit card information, they get an email receipt with the download or they get the download maybe in line even and just made it super easy. And so I thought that would exist and it just didn't exist.

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If it felt like a very large disconnect where I was like, oh, I'm going to go sell this icon to this audience. And then it wasn't possible. So that was Friday night. And then I ended up building Gummer that weekend and then launched it onto a Monday morning on Hacker News. And it did well, I think. And then a few months later, I ended up starting starting to work on it full time, raise some money from folks like Nabal, etc.

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. That's what I've been doing since.

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What was the process of raising money like? I mean, this is a this is like, I don't know, a really good example. I think of like figuring out how you get to spend time with certain folks, like the way that I structured my life before before I even I wanted to fundraise or thought about it as an idea. I felt like I wanted to be a founder. And so I spent a lot of time hanging out with founders, hanging out with really employees working at an early stage startup.

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I think that's sort of the best thing that you could do. I left USC to go do that, and so I had a network just from building stuff, meeting with people, people wanting to recruit me for their companies. I started to build a relatively strong network of people like Narval and Seth Goldstein from Turntable and and Sumiyoshi from Haystack now. And when I sort of had the opportunity to raise money, when one investor suggested, like, hey, this thing looks really cool.

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Have you thought about doing this full time? I know you're at Pinterest, but this is certainly something you think you'd probably be able to raise money for. And I was like, I really, really have no idea that I could do that. It was not in my mind at all that I could be a founder that early, that quickly. And so I said yes. And then I just told all of these people that I met out of the context of raising money.

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I was like, hey, we met about this three months ago or six months ago or or or what have you. I have a startup like I'm going to raise money for. Are you interested? And it was honestly a relatively smooth transition because I built up these relationships with people around just talking about product and talking about there was no agenda. I wasn't selling them anything. So I sort of already effectively sold them on my abilities to build stuff and be really committed to that path.

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And so when I decided to raise money, I'd almost done all of the work accidentally. And then it was just sort of like going through, like, OK, what are the terms, you know, what sort of like the legal paperwork side of things. But it was a relatively smooth, smooth process. Where do you wish you knew? But raising money that you know?

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No, I mean, I would say I think every founder thinks that raising money is going to change their life. Like you're going to get all of these phenomenal people on your cap table and you're going to hang out with them all the time. And they're going to help you recruit and build product and figure out go to market strategy. And the truth is, like all of these folks are very busy. Some of them are running their own companies. Many of them are in many, many, many companies, of which you are at least on in the beginning, one of their sort of top few.

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And the way venture returns work is it's sort of a power loss. So if you're not there, Uber, you know, it's a different the way they think about you might be a little bit different. So I wish I just knew that I wish I knew earlier that my company was still my responsibility. No one was going to fix my problems. They were investing because they believed in me and they believed in my potential. But it was up to me to to to still sort of take that potential energy and turn it into kinetic energy.

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It wasn't a handout. It wasn't like, you know, you're going to get these people to come in to your office and help you solve problems day in, day out. And this is an experience I've talked to so many founder friends where they feel like because the sales process is so good, this is what they do. Right? They're selling cash to get on your cap table. And they're really good at that. But it's like the second they sell you the car, they've they've sold you the car.

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I mean, they've done the 90 percent of the of the of the work to sort of precede it. Investors. It does change a little bit later on, I think. And so I. I wish I knew not in any in any way that says, oh, these people aren't helpful or whatever, but just the incentives and it's just a model in which they operate. And so I can understand, OK, this is as a founder, what you expect from me, what I owe you, quote unquote, and how I should sort of go about it.

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But you learn you learn pretty pretty quickly that that that was the expectation and that you just need to like anything like no one's going to no one's going to make you rich people people are busy solving their own problems.

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Were the expectations on you that you would become sort of like this billion dollar business that you haven't accomplished yet? Yeah. And what's it been like?

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Yeah, I was I think I mean, Silicon Valley is is a game of finding these crazy outsized returns. It's the sort of common adage is 30 percent of your companies die, 30 percent of your companies return less than one X. And so you kind of need the last third and really the top 10 percent of the best that you make to return over 10 of the sort of initial principal capital and often a lot more if you want to return any meaningful returns to your investors.

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So this is an ill liquid asset class, right? You're giving money to to a to a venture capitalist as an LP and they're going to hold a capital for 10 plus years. Right. So you kind of expect more than market returns if you're if you're if you're signing up for that. So, yeah, that was totally the expectation. And that's not just the expectation. I think some people really focus on venture capitalists in the zeitgeist, but it's also the expectation for the early employees because the early employees might only have half a percent of the company, one percent of the company, two percent of the company.

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And so they also are looking for it. I mean, they're turning down offers from Facebook and Google and Uber and like for hundreds of thousands of dollars to work at your rinky dink startup. There's a there's a whole system I think is modeled off of for this to be worth it for everybody that you need to get signed up to even get to to any end result. That's interesting. You need the promise or the potential of there needs to be a billion dollar plus outcome here.

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That's it's kind of like when you look at the music industry or the NBA or anything, it's not that everyone has the expectation that they're going to become LeBron or Kanye West or anything like that. But the idea that it's possible and that one person is going to win The Hunger Games is going to really kind of drive the level of competition and sort of work ethic that I think you frankly just don't get when you don't have those those those crazy outcomes as a as a possibility.

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Right. Like Jeff Bezos, Disney, two hundred billion dollars or whatever he has now. But for some reason and no one I don't know what you do with that much money, but for some reason it's still like America. I think it still has like this phenomenal culture of innovation that I think is largely driven by this weird, relatively abstract number on the on the wall that everyone can see, you know, did you feel any sort of disappointment or did they make you feel disappointed in terms of not accomplishing that as quickly as maybe it was anticipated?

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I mean, yeah. I mean, there there definitely was some disappointment. I mean, I had I had so many wins so early, I dropped out of school and then I was the second employee at Pinterest at eighteen. And then I started a company nineteen and raised a bunch of money from really great investors and and raised like ten million bucks by the time I was twenty one or something like that. So I just felt like if this was going to work, these are sort of the things that you need to see.

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Right. But that's kind of a delusion. It's like when your team get to the semifinals, you still have to you're still less than halfway there. Right? There's still work to do. But but you have so much evidence that you're like, oh, this you kind of start believing something that might not be true. But it was it was mostly internal disappointment. The nice thing about the portfolio theory that VCs have is they don't care that much about you if it doesn't work either.

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Right. So they're all they're sort of focused on on other things. They're kind of content to let you figure it out, at least the good ones are. They kind of understand that, I think. But it was certainly I mean, it was certainly disappointing, I think, to admit when we did the layoffs, that was like the big moment that there's really no going back from that. Right. Like, you're sort of saying, hey, this thing that we all signed up for, like we literally cannot possibly keep going on this path.

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We need to we cut seventy five percent of the staff from twenty down to five people in twenty fifteen. And then TechCrunch wrote about it. And so it's just like, oh well like the we really we really failed. And, and even though failure is such a meme almost at this point in something you read about when it happens to you and it really, even though you knew the odds coming into it, when it when you realize like, oh, you're part of history, like this is you are the example that other people might be referring to when it feels very, very.

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Do you actually feel like you failed? I did for a long time. Yeah, I mean, you know, I was living in San Francisco, everyone was raising money. And everyone's talking about how many employees they have and how much revenue they're doing and how fast they're growing. So certainly in that cultural context, it feels like you show up and it's like, how come? You know, I mean, that's the those are the questions. It's not malicious.

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These are the questions that people tend to ask. When you go to these house parties, like, you know, like how much of what are you doing? Oh, where do you work? What do you do for them? Just sort of gauging your sort of like where you are.

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Where are you in the hierarchy? How useful are you going to be to me?

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Yeah, something you know, this is I assume it happens in any boom town or like people are there for a specific reason, typically sort of accelerating their career. It definitely when you hear that question on your kind of responding to it a lot, you kind of end up sort of conflating that with your whole identity. And it took me leaving San Francisco and moving to Provo, Utah. And there the questions were very different. You know, it was like, hey, are you married?

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Where are you from? Do you go to church? Just different, different kind of questions. It's maybe a similar things happening. They're also trying to figure out where you stand on the in their own journey. Where do you fit in their journey. Right. And they're also trying to form a connection around the common topics that you both are probably interested in. But after a while of that, you kind of forget, oh, I'm I am a CEO of a company like that, all kind of like I almost forgot about.

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And really that I think distance was what got me to write that article in the first place, because I think if I hadn't, I wouldn't I would not have been able to write that article like sitting at a coffee shop in San Francisco, write like this the the ego, the the self consciousness of it. I think I needed that distance to be in the middle of people who didn't like to be so outside of that to to really kind of look at it and feel like it was almost like an out of body experience.

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So I was kind of like analyzing that life. Like I was writing a biography of of somebody else, know, it was so foreign at that point. There's people that sort of ascribe your value to your position and what you do and what you can do for them. And then there's people who want to know who you are and sort of have a relationship with you. And then I think if we hang out with people that ascribe value to our rank or position or some sort of authority or knowledge that we have, then we become wrapped up in that.

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We have to see ourselves as that. And that can be a very, very bad thing over the long term.

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I'm curious as to what your worst mistake was like, what led to it, how did you recover from it and how did you learn from it? What happened?

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Yeah, I mean, I think I mean, to your point, just quickly, like, it kind of goes back to what we were talking about, Singapore and like the average of your five friends and stuff. Right. Sort of the same thing. The questions that everyone in your group is asking themselves ends up being the question that you're going to start asking yourself to in terms of the worst mistake. Definitely like one one that is very raw because it has a very specific number tied to it is we we started raising the Series B, we started talking to investors about it.

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And so for context, we raised the seed round of a million bucks. We raised a series of seven in twenty twelve from Kleiner Perkins. And then in twenty fourteen, twenty fifteen we're going sixty percent a year. We thought we had it wasn't going to be easy, but we thought we had a shot and we started talking to investors around the series B we wanted to raise maybe 15, 20 or so million dollars to keep going and very quickly realizing this was going to be a pretty hard a hard path if if we were going to succeed at all.

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And concurrently our office was expiring. And so we had this thirty three thousand square foot office. We were spending ten grand a month for and we had the and we were growing startups like you have to signal that you're growing. You can't say, hey, guys, we're going to take a break, figure this thing out, because everyone's going to look at that and say, oh, these guys are venture capitalists. You don't want those people. You don't want to back those people.

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So you're you're sort of it becomes a self-fulfilling prophecy. When you do this. You have to kind of keep going, assuming that things are going to work out for at least a certain period of time. And so that's what we did. We signed a lease for a new office so we could scale from twenty people to forty fifty people or so. It was twenty five thousand dollars a month. We paid a big deposit, six figure deposit on it and moved it.

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And then a few months later it was like, we're probably not going to raise money and we're not. We certainly are freezing hiring now. And what are we going to do it? I mean the office was just this overbearing thing, like walk into a cavern and it felt like, you know, it was it was brutal. And then when we we went down from twenty to five, guess what? We're still in this office. This office could hold forty plus people and there's like four or five of us.

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Day, it was painful, and so ultimately I had to make the decision to kill the least completely and we lost a couple hundred thousand dollars and luckily we found a we found a new tenant to come in, but we still lost. We ended up still losing probably 100 hundred or so thousand dollars through the through that process. And what I should have done in hindsight, of course, hindsight's 20, 20, but what I should have done is told the team, hey, we're not moving offices, we're just going to renew this lease.

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But then again, if I followed that on that advice, who knows what would have happened? Folks might have pulled out even sooner and it could have been it could have been worse, but definitely very painful. And that really that timing is very deep lesson of commitments and debt and like really feeling like you owe someone something like I really don't like being in that place where I have to establish this almost goes back to what we were talking about before, too, where you have these friends and you kind of there's sort of an expectation that you're going to be friends with someone for life or it's bad that you kind of go separate ways.

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Something must have gone wrong or something. We still have in marriage divorce. So maybe that's fine. Maybe just what happens. That might be the right thing. I think we definitely have a lot of attachment to these ideas, and that's another one of them. I think it's the same thing. It's like I really try to form build relationships with people that feel at will. They feel like we're both recopying to keep this thing going on a very frequent basis with my employees, with with my investors, with with other folks that I talk to.

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It should feel very not transactional, it feels transactional and maybe maybe that maybe it is transactional, but it it doesn't I don't know, it feels just voluntary. It feels like something we're signing up for. And that makes that makes me feel a lot better about it. And you guys are profitable now, right. Yeah.

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So we in twenty fifteen we, we, we sort of January we knew this was going to be brutal. We spent nine months, we raised a small bridge around two million dollars at forex liquidation preference from from Kleiner and Mark Cuban and some other folks and spend nine, nine or so months really trying to make it work, like sort of focusing almost completely on what can we do to grow the business faster. And then we we failed to do that.

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And so luckily, I told the team, like, you know, they have full awareness that this is likely the path was going to lead to mass layoffs to save the company. And that's what we did in October, November, we downsized from twenty five, got rid of the office, finally found a new tenant and, you know, got profitable, made ten thousand dollars one month. And it was like a dream because not only do you make ten thousand dollars, your runway goes from a certain finite number to infinity.

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Right. And Excel starts airing out and you're like yes, like this. We can do this forever if we need to. And that's roughly where we've we've been since, where we're kind of growing. We're doing it in a way that we think we can do sustainably without betting the company to. To do anything certainly means we have to we're constrained in many ways. We can't just say, hey, we're going to want this totally new product, but a team of twenty on it.

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But so far, it's it's worked pretty well for us.

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Do you wish you would have done that sooner? Yeah, that is that is a decision that I think. Yeah, I and this is as I sort of do more investing. It's something I communicate to, to founders a lot too is like, look, this is what you need to stay on this path. This is the venture backed path is actually relatively objective. You need to be growing. In the article I say twenty percent month over month, but it can be 10 percent.

[00:30:58]

It just needs to be sort of exponential or or so polynomial or whatever the correct math term is. And if you're doing that, you can stay on this path. If you're not doing that, it's going to be tough. It really maybe and seed a little bit different. But if, you know, sort of at some point around series A, Series B, that becomes sort of like the end all be all it becomes is the most important thing in which all of the other things can't outweigh that.

[00:31:27]

And I I knew that I saw that in the numbers like that was evident to me. But I didn't make the connection with how important it was, how fundamental it was for this path. And I wish, you know, a year before I did or so we said, hey, look, we're not growing as fast as we need to be growing, like, let's pause. We don't have to do anything drastic because it's still early. But let's pause.

[00:31:52]

Let's recalibrate and and let's let's figure this out and certainly out. Certainly wish I would have done that. We would have avoided a lot of a lot of pain. But it is what it is.

[00:32:03]

I've spoken with a few entrepreneurs who sort of been VC backed and then one way or another got off that train and then came to a path of profitability that was sustainable. And it's almost unanimous that everybody wishes they just would have done that. From the get go instead of and maybe that's just a cumbias, right, so you didn't hit this sort of like big massive unicorn, 30 X win, and so you're left with profitability. But lots of companies die trying to get to that stage, too.

[00:32:35]

Yeah, totally. I do think there is a level of outcome bias. I think there is also a level of one of the reasons to raise money is a social one, where it gives you a sort of credential that is very useful. I can still to this day go into a room and say, hey, I raised money from Devall, Max Levchin, Kleiner Perkins, Krosoczka, first round. And people will take me seriously for that.

[00:32:59]

Right, just because of that, the signal value. And so there is like this kind of I think people might sort of forget when you when you get through the whole thing, that you're still taking advantage of some of those things. And maybe, you know, it's kind of like maybe you should get into Harvard and put this, you know, the acceptance letter on the wall, but not actually attend, especially now it's sort of that like maybe you should, like, say that they were going to give you the money and not take it or something.

[00:33:26]

I don't know how you would frame that in a way that doesn't make you sound bad, but or maybe raise a small seed round or something. But again, like being that strategic about it, it feels like venture is such a long term game. You can't you can't think like that. And I wouldn't recommend it. But there is an outcome bias. I mean, I do agree with you.

[00:33:46]

Almost every single person I meet who runs a profitable business, especially one powered by software, they wouldn't trade it for the world. And frankly, they like their cash flow. It looks better than most folks I know who are on paper worth a lot of a lot more money. I still haven't resolved that for myself because I still feel that sort of aspirational quality. Right. Like, I still feel there's something about stripe, like there's something about Airbnb.

[00:34:15]

There's something really cool about building something so meaningful. And I think part of that for me is it's a it's a unique experience. There are a lot of these other businesses and they're great. And they give you a phenomenal quality of life and tons of freedom and time. And certainly if you're if you are running one of these other companies, you don't have a lot of those things. You don't have a lot of freedom. You don't have a lot of time.

[00:34:38]

But you're living in San Francisco regardless of what happens with covid and remote work, because you need to be there. But yet there's still something about that. And I think it is that, like, you have a certain set of experiences when you get to this place that people like me just frankly want like we want to hang out these sorts of people and have these interesting conversations. And it makes it easier to do that. But it is weird.

[00:35:01]

It it does feel like even even acknowledging it, like being aware of it doesn't make it go away.

[00:35:08]

You know, what do you think is the hardest skill to transfer to other people that's necessary for success in business?

[00:35:16]

Yeah, the skill that's been really top of mind for me right now is the ability to save other people time. Basically what I mean is there are certain people that go about their lives. I try to be like this, but they just operate in a way that requires less of everybody else for them, for the equivalent amount of success in that relationship. Right. So, for example, someone who sends calendar invites someone who's very diligent about taking notes and following up.

[00:35:46]

And, you know, people like you, you put like the link to to have this conversation right into the Google calendar, invite a lot of people like they'll just put in the email. They'll find like there's just a level of care. It feels like you're you're almost like it's like a concierge service for like the getting to spend time with this person. And then there are there other folks. They're just being responsive. Like there's just things that lead to a less, less level of stress in everybody else around their lives.

[00:36:14]

And it's so rare. It's so rare. I found and I think it's because everyone else is also trying is very time sensitive, too, about their own time. And so they end up sort of operating in a way that's saving them time by sort of maybe pushing that burden onto other folks. Right. You sort of like playing hot potato with the task that no one really wants to do. But it's the people who are like, I'll do that.

[00:36:35]

I think that I think people underrate and you're that type of person, you know, as a as a as a CEO, as a founder. Those employees that do that will win like they will get whatever they want, because those are the folks I really want to surround myself with, because I care about my quality of life in my time and as a as an investor, even as a I don't know all of these other roles I really like how can I save you?

[00:37:00]

How can I save you time? Like when I send invites, I put my name first instead of the other person so that in their calendar it shows up. In other words, you have all these counteractive, just your name, and you can't see who you're actually talking to, just like small things from like, how can I just really streamline everybody else's life? And the beauty of software is you can now use a lot. Software like Cowley and Xabier in these editable etc.

[00:37:23]

and these tools like hook up these things, but everyone, I think can operate like as if you had a full time E.A. running your life for you. You just now pay a couple hundred bucks to three or four different tools that give you that. That's actually an even better experience because software is often a little bit more foolproof than that than a human being. Yeah, I like how you said that, something I thought a lot about. And I find myself lacking in some areas, but definitely there's a lot of people who are more thoughtful about how they approach it from the other person's point of view, which is how do I make this easy for them, especially if you're you're asking them to come on the podcast or do something for you, like you're doing me a favor.

[00:38:04]

I don't want to send you fifty five emails trying to schedule it. I definitely don't want to, you know, make it hard for you to hop on board and follow the instructions and like do all of that stuff.

[00:38:14]

And but there's a lot of people in life like I remember going through this before when people would be like let's go for coffee. And you know, it's like thirty five emails to go for a minute coffee. And, you know, at the end of the day you're like, that's ridiculous. Like, I don't want to do that anymore. I just stop replying to those.

[00:38:29]

Yeah. It's like when people ask you, even people who I know, they're like, hey, do you want to catch up next week? And I know that they have a reason for this, but they won't tell me the reason.

[00:38:42]

And I always and I just ask people now, I'm like, hey, what what what do you want to talk about?

[00:38:47]

I don't know. It's like a power information asymmetry thing. But I think it's mostly just time. It's mostly like I want to I need to do something. Hey, so how can you talk about this next week? Not really. Maybe even thinking about the fact that, you know. Exactly you're going to show up and know exactly what we're talking about and I'm going to show up and know nothing. And by the way, if you tell me I'm happy to do the work ahead of time, like, I'll go read stuff out, like, I will get you the answers.

[00:39:09]

So when I show up, I can. And then the other great thing is maybe we don't even have to have the meeting. Like maybe everything that you need for me, I can just give you, but you don't give me that opportunity. And so there is this like interesting, like people who view time as the thing that they're trading and then people who sort of like can can transition to value. For example, there's a if you're a founder, you want a hundred thousand dollars from me or something like that.

[00:39:34]

You know, as you mentioned, like, you're doing me a favor and it's it's like, how can I like how easy can you make it for me? How easy can I make it for you? And there's certain founders who make it so easy for me. I just reply to the email and I just say I'm in for that, for that like ceasing Angel to to wire the money. Like they made it so easy for me to give me all of the things that I would want.

[00:39:53]

And then there are other folks who are like, hey, I have a great idea. Do you have time next week in this area different?

[00:40:00]

Yes, I understand there's also another level to this which like outside of maybe professional relationships, but there's people who make it difficult and then there's people who actually like it's not a conscious process, but they make it exceptionally difficult.

[00:40:15]

It's like they want to go to dinner with you, but they want you to convince them to go to dinner with you. You know what I mean? Like, there's a there's another layer to this, which is like it's not easy and it's not middle of the road. It's actually quite complicated. Like you're put on the now, I have to convince you sort of side of this.

[00:40:32]

That is where I want to talk to you. What other skills do you look for when you're hiring? Communication is a huge one. It's similar to that. But people who overcommunicate, people who are always thinking about, you know, the next day, the next week, the next two weeks, the next month, the next year, and telling me what they need for me, how they feel about our relationship, people who are very good at doing that.

[00:40:57]

It's it's it's low stress. It lets me solve their problems before they need them solved potentially. It makes me feel confident that they're in a good place and that they have what they need. It's it's like static electricity where like you don't you ever go too long without touching something. You hit something and you're just like your like skin freeze for a second. It's like but if you did that all the time, it would never happen. Like, that's how I think about communication, especially within within sort of like a high stress, high functioning organization where that's going to happen very quickly.

[00:41:26]

And you need to constantly be like tapping and like being, hey, this is what's happening now. This what's happening. That's what's happening now. And so I think people who are really good at sort of ambient signaling saying, like, I don't need to ever go to them and say what's going on? Like, I just know I wake up a lot, I do whatever. I just know what they're doing. To me, that's the dream.

[00:41:43]

That is just a phenomenal, phenomenal thing. I think an ability to write really, really well is key to that. Part of that is just the medium in which so much of this communication happens is via writing, especially now remote work, et cetera. But in general, I just love when people when people do the work of, you know, not just sending me the email, but writing the email, revising the email, revising the email, sending that email like the the brainwaves that they've sort of like spent on that with the context they were already in, is going to save, netnet, save so much time for everybody involved.

[00:42:17]

And then the level of. Conversation is so much higher because instead of going like that, it's just like I'm going to spend five minutes on this thing, but when you get it, it's going to going to be like level 10 because it's already a level 10. I can get it to level 50 and I'll give you the time that you gave me, like, oh, I'll pay you back very, very quickly and we'll build a very high quality relationship.

[00:42:38]

I would also say, like, I like people who are very kind of transactional, frankly, like I like people who are like, I'm here to do this job. This is what I came here to do. I'm really excited about speeding up the site. That's all I care about. And like ninety nine percent of our conversations are around that. And I spend you I might be working with these people on a daily basis. And so I think I like that too.

[00:43:01]

When people don't feel the need to package up or bundle a relationship and say, hey, we're co-workers, so we need this, this, this, this and this, we need you need to come to my birthday party and like I like and there's definitely a change for me sort of 10 years ago. But I like people who are like this is the way that we interact, like we talk every day. But it's about investing or it's about we talk every day.

[00:43:22]

But it's about this other thing or sometimes it's just like totally random stuff. Like there are people that I would never consider, quote unquote, friends of mine. But like when I need to talk about, like oil painting or something like this is the person that I talked to would talk for hours about it. And then it might be like six months until we talk again. And it's it's fine. Like, we might even forget that the other person exists.

[00:43:43]

And I actually think, like a little life built of relationships like that, it gives you way more relationships. And it's sort of like having a friend group of thousands of people or having a company of all these sorts of people. So I really like people who think like that, where they're very sure about what they want. They feel very good about where they're at in life. And all they're looking for is this is our relation to feel like one thing that they need.

[00:44:05]

They're trading X for Y. And I just I really like knowing that that's what someone is expecting of me. And I can just offer that and feel and feel really good about that and and focus on that. And so it's like when someone's like, how can I help you get nowhere? But if you say, hey, I need help with this very specific thing and intro to X, I can do that. Like, that's I'll do that for me.

[00:44:27]

An email with the blurb in the back and I'll forward it and ask for an opt in like that's purely automated. That's purely a a process that I go through. I could, I could at some point it will automate that completely. Agree.

[00:44:40]

That's also making it easy for you to run through investing and through Gumnut. I mean, you've dealt with probably thousands of entrepreneurs at this point. What are the common patterns of success and failure that you've seen?

[00:44:52]

Yeah, I think one big one is, is they build stuff. They actually build stuff. In the early days, it was the it was the only group of people that I hung out with. Like, I wasn't just hanging out, started people. I was hanging out with the people who went through some stuff to get there. It's like often the people, the best people in the industry are the ones that didn't go to school for that industry because it means that they had to cross all of these things to get into it, if that makes sense.

[00:45:15]

So people who are people who build stuff, I mean, I was surrounded by those people. When I get it started, getting into it more and meeting thousands of people realize a lot of people don't actually build stuff. They don't know how to build stuff. They need help. This kind of goes back to what we're talking about. Again, like, you know, there are people who need all of these things from other people. And I don't like those people.

[00:45:33]

I like the people who are like, I want this for my life. I want to build a company. I want to build an app. I want to be a musician like it could be. I want to write a book. I need all of these things from other people in order for me to do that. I mean, that is a very uncontrollable way to live your life. I like to say it would be the equivalent of saying, like, I want to make a movie.

[00:45:54]

I have a great idea. Right. And the world is full of these kinds of people. And so that's a big one is like, well, make a movie. You have an iPhone, like show me show me like a cool thing that you've made. There's ticktock now. I mean, there's things you can even put this stuff on, like show me what you've made. There's a great book, Rebel Without a Crew, by Robert Rodriguez, who directed a little Battle Angel, a taxi driver.

[00:46:16]

And he basically talks about his journey. And it's like it's like the lean startup apply to filmmaking or something like that, where he just he literally says, OK, I live in this town. These are the things I have in my town. I'm going to make a plot that involves these things because that's what I have right now. And then I'll make another movie like, well, we'll take it one Sundance or whatever, like it. That's what got him started.

[00:46:38]

And that those are the people that I look for, the people who want something so badly that they just figure out how to do it and they're OK with, like, not maybe sort of having their first thing be just like the dream project. They just get started and then they they figure things out as they go into building stuff. People who don't ask for permission, people who have hard skills, people who really try to save people time and are are really feel grateful, you know, like they feel like, wow, I'm so lucky to be in this place.

[00:47:05]

Like, how can I make it as easy as possible for everybody, people who don't think of it like a numbers game. I just need to send one hundred emails and what three people are going to say. Yes. It's like I want to send three emails, I want to spend three hours on each one and all of them are going. So, yes, I think that's possible, I think a lot of people underestimate how possible that is and people who read a lot, I would say this.

[00:47:24]

The other thing is people who, again, sound, I don't know, like when I say these things and it makes it, I'm like, these are just basic expectations. I have almost. But but you might be surprised at how few people deeply read about anything, let alone their subject. I mean, their own industry, their own don't know the set of problems that they're interested in. Someone might say, hey, I'm really interested. Like from their tweets, it seems like they're really interested in health care.

[00:47:52]

Like they think health care is fundamentally broken. It's totally messed up in the US. We need to go. And by the way, this can be someone who is like, we need to go this way or that. Like, I don't know exactly what this is an abstract example, but if you said, hey, OK, cool, what's the best book that you've read on health care in America and why it's gone to the way it is and what the right answer is?

[00:48:11]

A lot of them will say, I haven't read a book. I read a book about it. I've read a lot of tweets. I read a ton of tweets. I read a lot. I listen to a lot of podcasts with politicians about this and celebrities about this. I've read some Atlantic pieces or something like that. I subscribe to a few subsects, but to have you deeply gone into the subject. And the filter that I use is if you remove the social incentive, so much of this you've done because of the social incentive, it's to comment.

[00:48:36]

It's to go to work and talk about something. It's you know, the reason I think people don't often read a lot of these old books is because of the social incentive goes away. You read this book and then you're smarter, but. That's it, you know, but I can't signal that easily to other people. Yeah, I can't. Yeah, exactly. Yeah, it's like, oh, man, like I read this phenomenal book on like I'm reading a book right now on Wailes.

[00:49:01]

I don't know why, like someone I like tweeted about the book and it seemed interesting and it's quite it's interesting is a very interesting book.

[00:49:08]

I don't know why I'm reading it. I haven't talked to anyone about it. It's full of really fascinating stuff, but like very, very few people, I think, do that and but but ironically, almost almost in the sort of paradox, when you do stuff like that short term, I think that's true. But long term, over time, I really think that's clear. I'm doing it like there is still a reason. I'm doing it just like a much larger, longer time horizon.

[00:49:32]

And this has happened so many times. Or I'll randomly run into somebody, someone who maybe is exactly the perfect person to propel me in my career. And they'll be like, what what book you're reading? I'll be like, oh, I'm reading like a face like glass. It's like a young adult fantasy thing or whatever. And they're like, that is my favorite book. That is something that has happened to me so many times. And guess what?

[00:49:53]

I'm now they want to hang out with me all day long and not to talk about this other stuff, but just to talk about, you know, like they finally have someone else that they can talk about. So I do think it's it's sort of that sort of impatient with impatient patients kind of sort of thing. Impatient. You want to be impatient with results, I guess. But I definitely noticed that in people like it's very rare to meet someone who's genuinely just like exploring things that are at the sort of limits of their interest to kind of figure out what's new and different.

[00:50:20]

And it's selfish of me. I like those people because they can teach me about all of this new weird stuff that I can go explore myself. But I find that sort of innate curiosity that isn't tied to a social thing or a financial thing is is is relatively rare. And maybe that's just quote unquote privileged, right? Where it's like, oh, you've achieved X, Y, Z thing is sort of the philosopher king thing. Like now that you're here, you can spend all this time messing around and figuring out these things.

[00:50:46]

But regardless, I mean, that is something that I look for in the people that I hang out. That's interesting.

[00:50:51]

I want to dive a little bit into that. What's your ideal ratio of sort of exploring broadly to diving deep into a certain subject, do you think, for reading?

[00:50:59]

I would say I spend almost all of my time exploring, probably like I go deep very, very, very rarely, even with authors. Like it's pretty rare where I find an author, where I am like, this person is so good I need to read everything that they've written. That's happened a couple of times, like Matt Ridley recently was one of those people for me. But even like when you read his books, it's like every book is different ones about genomics.

[00:51:23]

One's about risk. One's about virtue. One's about evolution. One's about innovation now. And there's clearly a thread, right? Like you can kind of see the rational. Often you can see like what's what's where he's coming from. And certain sort of fingerprint is certainly on those books. But even he is, it seems to me, is just exploring these things broadly because I think, like, it makes those connections when they happen, like just so much more satisfying when you find a connection between, I don't know, the way that mole rats like resemble like the way humans used to be.

[00:51:57]

And maybe like they're sort of we figured out that there's this sort of middle ground of social. There's a pack, there's pack animals. And then there's like you social animals, the college animals that are like these ants and more rats. For some reason, more rats are also part of this group. And then there's humans as a result. And it's just interesting. I just think it's like, oh, maybe maybe there's a way to apply. Like, this is like a startup and this is a mid-sized company.

[00:52:19]

This a large company, I don't know. But I think for me, so many of the insights, like the easy insights, have already been solved. If I just go deep, it's going to take like literally you have to go to the bottom of the ocean to get like if you go deep in quantum theory, there's a lot of books you're going to have to read to get to really the frontier. But if you go abroad, I feel like I feel like there's just so much more avenue there, like there's just so much more freedom.

[00:52:41]

Like it doesn't take that for it to end up in, like, totally unknown territory. And even if there are there people there, there's like four of you, you know, there's like four people on Twitter that are talking about like the commonality between like. Yeah. Like animal relationships and like company organization dynamics. It's yeah. So I always think that like that's a better that's a better approach. I frankly very rarely go deep on on reading at least.

[00:53:09]

What are some of the books that have had the biggest influence on you in terms of your thinking around entrepreneurship or investing.

[00:53:16]

How to Win Friends is my my sort of top recommended book. It's almost kind of a cliché, I feel like at this point to recommend that book. But it is like the canonical example for me of this saving other people time. Like the whole book is about like how do I operate in a way that makes everyone's else's life just really clean, really stress free, really easy. And so then everyone's going to want to work with you and be your friend.

[00:53:41]

And and so I think that is a really great book. Thinking fast and slow is it is a really great one. All of the maritally books I think are really, really, really good. I think understanding your mental prison almost like understanding the constraints of your brain physically and your body, like just where you came from. Like what led to this moment I think is just so helpful in terms of like feeling like, oh, these are the things you have control over.

[00:54:10]

These are the things you don't have. Control over David Deutsch's books. I just read The Beginning of Infinity and the Fabric of reality, those books, it's actually currently the thing that I'm thinking the most about is, is the fabric of reality. Is it like, you know, you learn about parallel universes and sort of quantum mechanics and things in high school, you take an elective or what have you and you kind of get it intellectually, but like really spending hundreds of words, like hundreds of pages in this person's head and the way they think about it and how that relates to free will.

[00:54:46]

And it's just like really been interesting for me, because that's one you know, one question I always I think about a lot is like when you decide to do something like, you know, like when I decided to leave San Francisco and move to Provo, was it the stuff in Provo that made me open minded? Was I open minded when I decided to move? Like, where did I have to learn it? Where is that like, is it a discrete system?

[00:55:06]

Is there a point? And so I've just been thinking a lot about like, you know, like when I have an idea, when I decide to respond to a question you have, where is that even coming from? Like, I just speak. I can't tell you, like where you know, it's very weird. And so I've been, like, really interested in like in the sort of parallel universes and in quantum mechanics, because I really think, like, when you when you learn the answer there, there is an answer like what you got to believe that I think to keep to keep pursuing this kind of stuff.

[00:55:33]

But when you figure it out, like when you realize like, oh, the reason that, like, I don't know, like a hot water, clean stuff faster than cold water, like when you know, the physical reason behind that, it feels good. It feels like you have a grip on your life. You can actually apply it in a way.

[00:55:51]

You know, what is hot water, clean stuff faster than cold water. So I think it's because, you know, temperature and he is just the particles are moving faster. There's just more things moving around, bouncing stuff. So I think when you're cleaning stuff like you just like have more particles, like hitting stuff off, it ends up dislodging these molecules or what have you from the from the material. And so I think it's literally just like the collisions are happening at a faster rate, I think.

[00:56:20]

But just like things like that where you just like I don't know, it feels very satisfying for me to know life is weird. I mean, like, life is very strange. And I think you go through this middle where you're born and you're like, the world is flat and like the skies above us and gravity just makes sense. You can like obviously flying would be weird, like like you just kind of take these and then you learn all of this weird stuff, like we're all on a ball of fire, just like shooting through like a devoid like right now we're like, what?

[00:56:50]

You know, just crazy. And luckily we have like some rock around the ball of fire. The sun doesn't even have that, you know, just like just weird stuff. And then and then I feel like just I'm just like floating like I have no grounding in reality. I'm just like learning all these things. My life is like, what is death? And this and that. Like, it's just crazy. And then once once you start to read that stuff, I feel like I'm going back to that first place where it all actually incredibly simple.

[00:57:14]

It's just a bunch of dots moving around. It's bouncing off each other and at different levels of abstraction. You can use the phenomenon to explain different things, just like the Earth and the sun there. They're just two particles in space, just like when you're cleaning something, just two particles of space and an atom, there's like it kind of goes all the way up and down and it's like a fractal pattern. It just makes me feel like I understand and I can, like, move forward without, like, walking through a wall, me or something, you know, like it just something like that.

[00:57:43]

I don't know where I'm going with this, but I do enjoy, like, really feeling like I understand. And that goes back to the entrepreneurship stuff too. Like just figuring out like what I can what I can deeply understand, like reading the paper I was reading in the Plex. A lot of these books are just really important because you are building a company, you're hiring folks. It's like, why start from scratch when you have all of these resources for people who've done it before?

[00:58:06]

And and the lessons aren't that the world hasn't changed that much in many ways you can sort of like straight up apply a lot of this stuff and copy paste it.

[00:58:15]

There's a lot of timeless lessons from that.

[00:58:17]

As you were talking, I was thinking of his thinking that maybe you can just appreciate the beauty of the the world in a different level with that sort of understanding. And I think that that's really important to be able to do in terms of quality of life. Maybe I want to come to happiness later.

[00:58:33]

But switching gears a little bit here, what are you most insecure about?

[00:58:37]

I am definitely insecure about, like, wanting stuff. I mean, I still think I am driven by a level of ambition and want for something, even though I have read all of these books and I feel relatively good about what I understand about the world and how little it really matters, there is something satisfying about it. And and so I'm definitely kind of like insecure about the fact that I have those wants and desires. Like, I think I don't know if they will go away, but I always try to try to figure that out and unearth like why it's similar.

[00:59:10]

Why like why am I like. I don't have to solve the problem, but just understanding where this comes from, it just gives me a level of sort of like closure, almost like, OK, that's just the way I am. That's because of this thing. I can't change it. I can't get taller. I can't do that. Right. Like, there's certain things. And that's that's that's fine. So that's that's that's that's probably a big one.

[00:59:32]

And then just like figuring out I'm sort of insecure with how much I work, like how I work a lot, I enjoy it a lot. I am insecure about the fact that I enjoy it so much. And even like I go on Twitter and I talk about maybe not working so much, but I just genuinely, really enjoy it, enjoy it. And so, yeah, there's a there's a lot of things like wanting a nice house or whatever to write, like the basic things that people people seem to seem to want.

[00:59:59]

And then starting a family like that's that's a scary prospect as well that I, I hope to make the focus of my life in the next ten years or so. Was it scary?

[01:00:08]

It just feels like it feels like I've been so self centered my whole life. You know, it's it's basically everything I've done was for me and I got married last year in December. And that was like the first time that I, I was like, OK, this is like we're signing up for something pretty. This is very different from the the the ideal relationships that I like with most people for me.

[01:00:32]

Just email me every six months. We'll check it out so that marriage is good.

[01:00:39]

And, you know, like I moved up to Portland, Oregon recently, though the first time I'd ever moved to a place as a group decision, it wasn't just me just saying, hey, I'm going to go do this because I want to. And so that was like that's a there's a set of learnings that I need to go through. I think having children like I think that would be really meaningful. And but I think it is really important for me to figure out, like, how do I live a life that sort of like the vision of what's important is, is is slightly larger.

[01:01:08]

Children are amazing.

[01:01:10]

And yeah, it's just so incredible. I'm excited. I'm people ask me, like, what are you excited about? Road event and always like having kids, like, honestly, like five years from now or so like that. That's definitely like what I am aiming, aiming for. And I think everything else is sort of like a kind of a distraction, almost like just to keep me busy until I get there.

[01:01:31]

Well, let's talk a little bit about your writing process. You're pretty prolific on Twitter. That changed about eighteen months ago or something. It just your style sort of changed a lot. And ever since then, you know, I think you've got a lot of traction on there. So I want to I want to learn about your writing process a little bit, how you come up with ideas, how you put them into pithy sort of like tweets and talk to me about that.

[01:01:55]

I have a lot of conversations. I would say my life is sort of pretty distinct in two distinct buckets. I'm either like having an interesting conversation with someone or I'm spending time totally alone, especially with Kova. There's no kind of like in between or social events or other background noise. Like it's really just like we're talking or we're not talking like sort of feels like that to a lot of a lot of the tweets. Like when I started learning how to how to oil paint, I realized, like the fundamental skill in painting was observation.

[01:02:23]

It wasn't like paint application and like knowing color theory, it was like, can you even see what's in front of you? Well, and if you can do that, then, like copy pasting that onto a piece of paper with some dirt and oil is actually the easy part. And I think the same thing with with writing. It's it's like living a life, like having a conversation with someone. It's almost meditative. You're like having the conversation, but you're also listening to yourself have the conversation.

[01:02:48]

And I think that's really important because you're sort of like your own editor where you can't change what you're doing and saying in the moment. But like, maybe you can note it for future use and that's how you improve as a communicator and a conversationalist. And I think writing is kind of similar where like I'll be having a conversation with someone and I will somehow subconsciously sort of pin that little moment, like bookmark it of, like I said, a sentence within a rant about a certain topic that's I should tweet.

[01:03:14]

I should just literally take that sentence and go tweet it. And that's a lot of my tweets. And then a lot of them are those sentences that I save. And then I just stare out for a long time, or there are things that I just can't stop thinking about. I often feel like it's like food poisoning or something where it's just like in my system and I can't get it out and I can't stop thinking about it. Every day I wake up and I like for some reason that's stupid.

[01:03:39]

It's like a song stuck in your head. It just comes up again. And I found one of the best ways. It's like resolving a problem in therapy or something like that. Like once you figure out, like what it is, why it is, you package up in a way that gives you clarity. It's kind of like untying, you know, a certain like a string with a bunch of knots in it. You finally can see this thing for what it is.

[01:04:00]

And then I would I often share it. And the sharing is is really cathartic for me because it sort of gives it to somebody else. It's like that's your food poisoning now. Like, you go, you go, you go. Talk about this for a while, I'm done, I did the work for myself, I've digested this thing. Here you go. Have fun with it. And that's a lot of how I kind of how I sort of like to think.

[01:04:22]

And that would say the other insight that I think has really worked for me is I always try to figure out, like, does this apply to a lot of the things in my life? Like, I think if you take if you take it from a very sort of entrepreneur business focus, you're going to end up with like a very kind of narrow set of thoughts. But if you if I often will, and that's a lot of the conversations that I'm having, but also as a writer, as a painter, as an investor, as a husband is on the other things that I do now.

[01:04:49]

If I can take the same lesson and apply it to other things and it sort of feels like a universal truth, then I often like those are those sort of sort of a filter that I used to like about the quality of of something that I that I would share as well.

[01:05:04]

One of the things that you said there that struck me was observing and talked to me a little bit about how we can become a better observer of the present.

[01:05:14]

Yeah, I mean, I think a lot of it is is is paying attention and taking notes. This was the one of the first times I had this experience was I was painting a rock. I was in southern Utah with like an oil on canvas. And I was painting a rock and I spent three hours. It takes me roughly like two to three hours to paint something. And I remember like four months I could me probably even today I could draw I could draw that rock out for you, like the angles in the shape, the proportions roughly.

[01:05:48]

If if I asked you to draw a dollar bill like you wouldn't, I wouldn't be able to do it. You wouldn't be able to do it. We've never spent that time genuinely staring and paying attention to a dollar bill. I know what you would draw. I know what I would draw. We draw this rough thing with like a one here and a one here and like a circle on this or something. But like, we we had the silhouette almost like that.

[01:06:08]

We have the shape and the.

[01:06:10]

Yeah, yeah. It's like when you when you're a kid and you draw the sun and you have the rays. Right. Like there's a symbol that you're storing, you have the allemande eyes, you have like the nose that's like three kind of three semicircles. But you never actually studied what this thing actually is and looks like. And so I think a lot of it is just doing that. I think you can improve like the time that you're taking.

[01:06:35]

And that's what being present is to me, is like just really focusing on the present moment and noticing as many things as possible. Which sounds easy. Right. And it's almost paradoxical. You're obviously here like, what does that mean? You're obviously looking out through your eyes. You're selling things through your nose. But like if I said, OK, like, how many times did you blink in the last three seconds? You wouldn't even remember the last time you blinked.

[01:06:57]

Clearly, you blinked somewhere in the last. Like, your eyes aren't drying out. Right. But like, this is something that you literally saw, like you saw yourself do that. But it's gone like your brain didn't even remember any of this stuff. And so I think that's a big part of it, is your brain. Unless you tell the brain, you signal to it, hey, this is important. Like make a note of this, because I'm going to need this later to survive or like some of these very fundamental biological incentives.

[01:07:26]

It's going to forget because guess what? Like you have a finite number of neurons. You have energy to energy is being expended. Like there's the sort of the the famous adage of the sort of like the chess players that burn like eight, nine thousand calories a day, like doing this insanely intense exercise effectively. And so I think that's a big part of it, is like you need to figure out, like what is the uncomfortable what is like the exercise of version of what I'm doing right where I'm not just like, I don't know, drawing dragons out of my head, but I'm actually like, figuring out, like, OK, what are what are the fundamental building blocks that lead to me being able to do a certain skill and then and then kind of a tree structure and then figuring out, OK, that means I need to learn perspective.

[01:08:07]

That means I need to draw hundreds of boxes in perspective. Once I can do that, then I can draw ants because ants are a little bit more structural or something like that. Then I can draw maybe like looser, looser animals, like things with fur and and things like that. And then I can I can do cars and little I like you can scale that up and then you like a dragon is sort of like a cat with wings that breathes fire like it has the body proportions roughly of a cat.

[01:08:31]

And that's where the dragon like comes from. But like some people, I think they just look at they don't do the work of figuring out like what is the path that leads to this? They just say, oh, I want to do that. Right. So it's kind of the same thing. It's like the way you have to learn what you need in the moment. And you can't really it's like you got to learn addition to learn math, to learn multiplication, you've got to learn multiplication, learn division.

[01:08:53]

You got to learn both of those things. To learn algebra. You got to learn algebra, to learn geometry. I think those things to learn trigonometry, you need those things like calculus. And if you miss one of those things, you can still get by in life, like you can still, like ace the tests and and draw the things when you need to. You can memorize, but you don't really have a deep understanding of that. And it's kind of the same thing with with being present.

[01:09:15]

It's just like I think some people go really far and they just they feel like they need to do all of these things. But the truth is, you just need to be there and you need to stop thinking about other stuff. And you just need to really like it has to hurt almost like you have to be so focused, like you're working out like I'm spending an hour trying to figure this problem out. And I think most people, they might think about it like, oh, I just need to meditate.

[01:09:39]

But meditation is almost work like I think it is. It is like a like exercise, physical, physical activity.

[01:09:46]

This has been awesome. And I really appreciate you taking the time. To talk today. You're welcome. Thanks so much for having me. Hey, one more thing before we say goodbye, the knowledge project is produced by the team at Furnham Street. I want to make this the best podcast you listen to, and I'd love to get your feedback. If you have comments, ideas for future shows or topics or just feedback in general, you can email me and Shane F-stop blog or follow me on Twitter.

[01:10:17]

A pair of you can learn more about the show and find past episodes at DOT Blogs podcast.

[01:10:23]

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[01:10:29]

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