We Study Billionaires - The Investor’s Podcast Network - TIP433: The Art and Science of Investing in Startups w/ Jason Calacanis

Episode Date: March 25, 2022

Trey Lockerbie chats with Angel Investing legend, Jason Calacanis. Jason is an entrepreneur who sold his second business Weblogs to AOL for $30MM in 2005. Jason then founded multiple other companies ...and along the way, became an angel investor in companies like Uber, Robinhood, Calm and 300 others give or take. IN THIS EPISODE, YOU'LL LEARN: 01:38 - The advantages of being an outsider. 06:10 - The realities of running a startup. 09:28 -What makes up a star founder and the ingredients for success. 13:32 - Why so many startups fail and how to look for the signs. 37:56 - Startup deal terms and syndicates. 45:31 - Common traits of Jason's many billionaire friends and colleagues. And a whole lot more! *Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences. BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members. Angel Book. This Week In Startups Podcast. All In Podcast. The Syndicate Website. Inside Newsletter Website. Jason Calacanis Twitter. Trey Lockerbie Twitter. NEW TO THE SHOW? Check out our We Study Billionaires Starter Packs. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets. Learn how to better start, manage, and grow your business with the best business podcasts.  SPONSORS Support our free podcast by supporting our sponsors: SimpleMining Hardblock AnchorWatch Human Rights Foundation Unchained Vanta Shopify Onramp HELP US OUT! Help us reach new listeners by leaving us a rating and review on Apple Podcasts! It takes less than 30 seconds, and really helps our show grow, which allows us to bring on even better guests for you all! Thank you – we really appreciate it! Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

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Starting point is 00:00:00 You're listening to TIP. On today's show, we have Angel Investing legend Jason Callicanis. Jason is an entrepreneur who sold his second business web blogs to AOL for $30 million back in 2005, and then he went on to found multiple other companies. And along the way, became an angel investor in companies like Uber, Robin Hood, Calm, and 300 others, give or take. He's the author of Angel, where he lays out his playbook for turning 100,000 into over 100 million.
Starting point is 00:00:27 And you may also know Jason from the All-In Podcast with Chimoth, Paul Hepatia, David Sacks, and David Freedberg, or his other podcast this week in startups. In this episode, we discussed the advantages of being an outsider, what makes up a star founder and the ingredients for success, the realities of running a startup, why so many startups fail and how to look for the signs, common traits of Jason's many billionaire friends and colleagues, startup deal terms and syndicates, and a whole lot more. It was a real thrill to learn about angel investing from one of the greats. So I hope you enjoy this wide-ranging discussion with the multifaceted Jason Calacanus.
Starting point is 00:01:03 You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires the most. We keep you informed and prepared for the unexpected. Welcome to The Investors Podcast. I'm your host, Trey Lockerbie, and today I'm super excited to have with me on the show, Jason Calacanis. Welcome.
Starting point is 00:01:35 I'm super pumped to be here. Well, I've been loving all the stuff you've been putting out, the all-end podcast especially, I think is just fantastic. And we recently had your bestie Chimoth on our show. And we were talking about his background a little bit and how he slowly realized his atypical background was an advantage or could be an advantage. And I know that when I was reading your book, you kind of described your humble upbringing in Brooklyn and feeling like an outsider because of it. And so I'm kind of curious, what was that like when you're first getting started and did the outsider feeling, Was it still there even after you sold wee blogs to AOL? So I have tried to cultivate my outsider status and maintain it.
Starting point is 00:02:19 It's a little hard to do as you become more successful in your friends, who you've been friends with for a while, also become super successful. Then all of a sudden people think you're Illuminati. So in a way, it's like I kind of look at it like the hip hop scene in New York. When I was growing up in the 90s, there was like this big hip hop scene. And I used to play basketball, the Chelsea peers with a lot of the hip hop guys. And, you know, they were just a group of guys doing business in the world. making art, and then all of a sudden, they became Jay Z and Diddy and DJ Clue and all these other
Starting point is 00:02:45 interesting cats. And, you know, it's kind of like that happened in the tech industry. We're all a bunch of outsiders. We're all a bunch of rebels. The 90s and the internet was like a pretty rebellious thing, actually. It was fighting against the establishment of dial-up, Delphi, CompuServe, Sprint, AT&T, AOL. They were all trying to control this new online experience and mitigate it for three, four, five dollars an hour, control the content, control your landing pages, and then this very disruptive thing called the internet came along and really changed everything about society and the world. And I was lucky enough to be born and in college when the precursor to the World Wide Web existed, which was ARPANET and Bitnet. And so, yeah, I've always liked to
Starting point is 00:03:26 feel like an outsider. And over time, you get old. I'm 51 now, which is really weird to say, because I feel like I'm 31. Like my energy level, my enthusiasm, I feel the same as when I was 25 or 35 or anything in between. But yeah, I still try to feel like an outsider. When I sold the companies, yeah, I felt like, wow, this is a big deal. I'm a millionaire now. I don't have to worry about money. And that was kind of mind-blowing as a kid from Brooklyn who grew up blue collar at best. And even still today out here, I guess a lot of people consider me like an insider's insiders because of my social circle and the investments I've made and the guests on the show. But I don't feel like I'm part of the Stanford computer science elite group. I still feel a little different. And I think, yeah, probably the same for Chumont. Saxon Freeberg probably are more actually part of that, right, having gone to elite schools and been part of that. So it's actually interesting. I never thought about it that way. But yeah, like you have two outsiders and then two insiders, basically. We just had a guest on the show who wrote a book, actually about the PayPal Mafia and David Sachs obviously featured in that. And they described
Starting point is 00:04:30 the culture there as highly functional, but like the debates were heavy and heated and frequent, right? And is that a culture you find pretty frequently in Silicon Valley? I mean, you're you came from Brooklyn, so you brought it your own kind of flavor of it. Yeah. I would say yes. I would say directionally correct. Yeah, I mean, I lived in New York, L.A. and San Francisco. In New York, if you go to a dinner party and you say something, you know, controversial or you make a statement, you might very well have somebody say, can you back that up or that's not right?
Starting point is 00:04:59 You know, like, people will get in people's grills about it. You know, you say, listen, I think this is the greatest artist of all time or I think this movie sucks. Somebody might be like, well, I think you're wrong. Then when I lived in L.A. is like, people are like, please do not make this on. comfortable. I do think the debate culture at PayPal was very real, knowing Rulhoff and Sacks are good friends of mine. I know Peter Thiel. I wouldn't say we're great friends. We haven't hung out socially all that much. But we know each other. We've had conversations. So I know all of these folks. And yeah, they like to debate. And I think if you are building companies, you're trying to change
Starting point is 00:05:30 the world. A fervent debate is necessary because it's kind of like you're going to the new world. It's like, do we go west or east? It's like, well, east is India. And you got to go around Cape Horn, that's pretty hard if you're leaving from Spain. And West, nobody's ever come back. So do we want to go the spice route and go around the Cape and we'll lose half the ships? Or do we want to go West and certainty of death in all likelihood? So I think that's why you see the people who run companies that are successful, whether it's Steve Jobs or Elon or Travis or, you know, pick the person. They tend to be great at debating stuff. And listening and taking in, you know, dissenting opinions. Actually, the dissent is kind of the most important part. You know, I've heard you
Starting point is 00:06:10 talk about startups and the way you talk about them is something I recognize as myself as a startup founder. And it's just, I know that you have this realistic perception of startup life because you've lived it. And I feel like you almost are there to kind of defend in a way what startups really are. You know, there's a lot of like, you know, people on the outside, they're like, well, why don't you just pay everyone equally? Let them work three days a week from somewhere else and give them help, you know, all these things. And you're like, you don't understand. I think there is a delusion that it's going to be easy. If it was easy, everybody would do it. And in peak markets, everybody does do it. As it gets easier, you see participation increases. So over the last couple years, we've been in a 13-year bull market since 2008 to
Starting point is 00:06:53 2020. We had this incredible 13-year run where a lot of young people have only experienced it going up into the right. Now, we've got a whole generation of people who are, say, 30-something years old, who've only known an up market. Now, I've been through three corrections, basically. 87, there was a little one in 94, 95, then there was the dot-com bust, and then 2008. So maybe 3.5 I've been through, and one of them was when I was just going to college. So I experienced them as an adult, but I was in 2.5 of them, like in the muck of those compression moments, and they're pretty brutal. And you do see when it's hard, less people try, and when it's easy, more people try. And so I do think that there's a certain number of people who are cut out for it. And again, this probably
Starting point is 00:07:35 is a little rough for people to hear. But if you don't want to work hard, if you don't want lead people, if you don't want to fight, if you don't want to deal with competition, if you don't want to go to war, if you don't want to be on a sports team, the reason these metaphor, sports teams and war keep coming up is because they're accurate and they're the most accurate to describe startups. Now, if you're describing a non-profit, if you're describing a GoFundMe project, if you're describing a Patreon project or art or a small business, maybe it isn't exactly a war. So I could understand why people are like, it doesn't have to be crazy or hard. It doesn't have to be manic. A lot of the people who say that are people who, on their first time out,
Starting point is 00:08:12 left on that ship and made it to the new world. I don't know if Christopher Columbus's, you know, a journey to America was his first time. But if it was theoretically, and he got there and it was a huge success, he'd be like, being an explorer is easy. And he wouldn't realize, not the 50 ships that tried before him were at the bottom of the ocean. Or they landed and, you know, caught in a fight and got murdered or eaten by animals or whatever. So it is a war. It is like a sports team. You have to cut people. These are hard things to deal with as the founder and the captain and the pilot.
Starting point is 00:08:45 And that is what's going on here. But anybody who's done it two or three times or has been a capital allocator or has been a journalist covering this or has been a board member or has worked at multiple startups knows it's a dogfight. And these companies almost universally have multiple pivots and or near death experiences in their first five or 10 years. And then even the ones that hit scale and feel like. they can never be knocked down, sometimes take a turn too fast, flip the car, and the whole thing
Starting point is 00:09:12 just is over. Or they just make a tactical mistake. And, you know, the company could be, you know, hobbled forever or maybe take a 10-year break. You know, Microsoft missed mobile. And it was a 10-year diversion. They've recovered, but that was a spinout. They flipped the car on that one. I want to talk about founders now that you brought it up, because you have this superpower of picking really great founders and through your angel investing career that we're going to talk a lot about. what you said just now kind of stood out to me. You were like, can they lead people? And something that I've kind of experienced for myself and seen in others is when you're founding a company,
Starting point is 00:09:46 I don't think leadership is really at the top of your mind, right? The idea, the company, the product, the marketing, the distribution. These are all the things at the top of your mind. And then at some point, you kind of flip and you have to become a great leader. You know, you have to learn a lot of skills that I don't think are quite natural to most. Are you looking for leaders early on? Or have you seen that evolve over time? And if so, what are the characteristics of that when you're looking and shopping for founders?
Starting point is 00:10:11 When you become a capital allocator, it really is great to be thoughtful and think through how you had the wins. Like, what did you see? And then maybe the anti-portfolio and maybe be able to do some forecasting or some critical thinking. So a lot of people who start are not leaders. They're just great players, right? And so they can run really fast and put the ball in the basket. You know, they're LeBron James. They're Michael Jordan.
Starting point is 00:10:34 Early in their careers, they're just savantes, right? they have a transcendent ability to do something, write code, market a product, package it, sell it, et cetera. And then what people realize is if you want to go fast, go alone, you want to go far, go together is this concept. And you can score 40 points as LeBron James and still lose the game. And Michael Jordan had a losing career. LeBron had a losing career. And then eventually you pair them with somebody, they make the team around them better. You know, there are certain people who are glue and who can really are leaders. And they inspire people to come on that journey. And that really is when you see if the person can be successful.
Starting point is 00:11:10 What got you here will not get you there is a conversation I have with almost every founder who's successful. And I say, listen, your product brilliance, your contrarian thinking, your inability to quit is what got you to this point. But your expectation of others and the absolute savageness you have on yourself, the standard you hold yourself to is so extreme and brutal. This preternatural insane drive you have and this criticism you have yourself cannot be unleashed on the people around you or else you will destroy them and they will not show up for work. So you got to make those people, you have to change how you treat them. You got to listen to them. You got to inspire them. You got to make them feel 12 feet tall. You got to ask them really good
Starting point is 00:11:53 questions. You got to demand excellence from them. You got to empower them. That's a different skill set. I can tell who is that broken person who has something to prove, that chip on their shoulder. and this is going to also sound contrarian. But if you show me a balanced person, I will show you a moderate outcome in startup land. If you're a balanced person and you've got equanimity and namaste, you feel great joy in your life, or are you going to work 78 hours a week to change the world
Starting point is 00:12:20 to kill your competitors and take everything personal and get this company over the finish line? I'm going to say no. I'm going to say in my experience no. Now, maybe my experience is wrong, but all the great founders I see from Steve Jobs, Travis, and on, they got something to prove. And they got an energy level that, to me,
Starting point is 00:12:39 is so easily discernible. And that's all I try to do. That's my secret power post investment. As I can just say to the founder, no bullshit, how's it going? What's keeping you up at night? I know you're grinding your teeth. I can see your jaw.
Starting point is 00:12:51 I can see that you haven't slept. Tell me everything. I hate to say it, but this is a safe space. You can tell me how you feel because I've been there. And I've been there with founders who are crying in the shower, calling me because they just puked and their families outside waiting for them to go to brunch and they're paralyzed because they've got two weeks of runway left. They're going to have to tell 40 people who are working for them that it's over. Can't raise money. And their entire identity and life is this startup and this title and this mission. And it's over. They failed the mission. Like, it can be pretty gnarly. But the great ones are like, yeah, I lost a limb. But I'm still alive. Get a robotic limb. Get back to work. I'll go on the next mission. I'll succeed on the next one.
Starting point is 00:13:32 That right there reminds me of this Charlie Munger quote where he said, all I want to know is where I'm going to die so that I don't go there. You know, what are the signs and common denominators of a failed startup? You will see founders, especially the young ones, be ashamed of their failure, not getting product market fit. Fancy word for consumers don't love the product. That's product market fit. Like, this is not a good hamburger.
Starting point is 00:13:55 I'm not coming back. And instead of making the burger better, they do everything but the burger. so they change the furniture in the restaurant, they changed the name of the store, and all they needed to do is just look at the burger and take a bite, and then make another burger and make it 10% better and do that 10 times. So pretty simple, I think, to solve that problem. Product market fit is just a matter of focus, right, and focusing on the product and iterating product velocity.
Starting point is 00:14:19 Product velocity requires that you have product people on your team who are really good. So if you have an average team and they're not focused, they may never get to product market fit because, again, back to this being a war, back to this being a competition, there could be somebody with better product people who are more focused. Or they could be not as good as you and more focused, right? That happens too. So you'll see somebody who's not creative at all like Zuckerberg and he has just tremendous success by just copying everybody else and being more focused and saying make it faster, make it simpler, copy more people's features. I mean, the guy never came up with his own idea.
Starting point is 00:14:52 Every feature on that site has been copied. There's literally not one innovation that Zuckerberg's ever made. He's made zero innovations and built one of the largest companies and most impactful companies of the generation. So it's a perfect example of somebody with no creativity, a memmic machine, a complete thief, you know, and he's making hits and had massive success. It's never too late. I've seen people run out of money and keep the company going. They tell everybody, can you take a salary deferral, sign this piece of paper, I'll give you your money back plus interest. If we get there, if not, we took a shot and we understand if you quit, or I'm cutting everybody's salary in half, or I'm going to give everybody a minimum wage for the next two months. And it's like a real crucible moment. But like I said, you know,
Starting point is 00:15:30 this generation has only known 13 years of up and to the right and each round being easier to raise than the next. And a lot of runway to not be focused. So I don't want to be like crazy old grandpa, like get off my lawn. But what we're seeing right now in the shakeout is a lot of founders realizing, oh, the last two rounds I raised super easy. I didn't have to prove anything. And now people want proof. And I have been really good at convincing people. through performance art, not actual performance. So when you raise your first round of funding, you're selling the promise of the company, but shortly thereafter, the product gets in marketing, you're selling the promise, not the promise, but the performance. And so all these theatrical
Starting point is 00:16:10 people who could make a great deck or network super well, they find themselves, S-O-L. They don't have any luck anymore. They're done. And that's the moment we're living in now. And I got a lot of founders who maybe have been given a lot of runway, and now the plane's got to get off the tarmac, and they may not have enough energy to get it off the ground. So that's actually what I'm dealing with at the moment, you know, when the market gets shaky like this. But you asked before about the successful ones,
Starting point is 00:16:39 and it turns out the crises makes the founder. Turns out the crucible, to my friend Ruloff from Sequoia, a peer and a mentor at once. You know, he always talks about the crucible moments for company. It's these crazy decision-making moments where the founder has to just, you know, go for it, right? You got to take that leap of faith. And, you know, if you look at Uber, if you look at, you know, any of the companies that had really hard times, it's like those hard times, that's battle testing a founder, right? That's the Jedi coming back from, you know, an impossible mission and losing a limb and then going on to the next company or the next mission.
Starting point is 00:17:13 So, you know, sometimes people have it backwards. You know, they think Robin Hood having a couple of challenges the last couple years, like, they're like, oh, well, that says something. This company has got problems. And it's like, right the opposite. These founders now had to deal with really hard things and it didn't kill them. And that's why that other colloquialism exists. Like, if it doesn't kill you and makes you stronger, like sometimes these phrases ring true because they're so true.
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Starting point is 00:21:52 Back to the show. You earn your stripes, so to speak. With that last point, how much do you weigh a second time founder over a first time founder just for that exact reason? A lot of schools of thought on this. One school of thought is, you know, the young founders, the inexperienced ones. you know, the Zuckerberg or the Bill Gates, quit college, go do this incredible thing. Larry and Sergey, Google, or Steve Jobs.
Starting point is 00:22:16 Like, there's just something about the audacity of a young person who doesn't have any experience in the world, being able to conceive of things that other people can't conceive of, or to have an energy level and something to prove that is really high. The truth is, it turns out the serial founders have a much higher success rate and have much higher returns in aggregate. Nobody's ever done the study. I would love to see it of those young folks who do hit it having outsized success if they stick with that company for multiple decades. So there could be two trends going on here. On average, the serial founder does not make the unforced errors. The crafty veteran knows how to get to the
Starting point is 00:22:54 free throw line, knows how to set a pick correctly, knows how to inbound the ball off of the defensive player's shoulder and take it back and dunk it like you see. And sometimes those highlight reels, they do something clever like that. Like that stuff is just could win the game. And the average game is won by just a handful of points, two or three points. And so not getting a technical or hitting a free throw can make all the difference in the world. And then there's the outlier success that occurs as well. So both things could be true. When you brought up Uber a minute ago, I wanted to talk about that as well because Uber has been one of your biggest home runs to date. And you have this quote in your book that I just actually absolutely love. I hadn't come across
Starting point is 00:23:33 it before. But you basically described someone asking how someone became rich and then responding with by selling too early. As I understand it, you're still holding your position in Uber. What is the thesis for holding that the stock is kind of below its IPO at this point? I was curious if you... bounced around, yeah. Yeah, you've bounced around. Are you just kind of letting house money ride at this point and seeing where it goes? I actually believe in the future of the on-demand economy and these great companies. And I think the transition to a new CEO and COVID, you know, these are two crucible moments. And I think they pass both of those crucible moments. And then getting to profitability, which was always like a very weird conversation, because having watched the company
Starting point is 00:24:13 up close, in the beginning, they were fabulously profitable because it was only Lincoln Town cars. Then when they went downstream to ride, sharing, obviously instead of making 10 or 20 bucks a ride, you know, you start making a dollar or two, but you have many more rides and consumption went crazy to the point of which people maybe were replacing their cars because Uber was so cheap, you know, parking somewhere might, we've all had this experience, like, hey, parking's going to be 40 bucks, and the Uber's going to be 15 each way. where the Uber is going to be 25 each way or 30 each way. It's $60, but you don't have to put gas in the car. You don't have an insurer of the car. So we're going to go full Uber. So all this was like so obvious to me. It was just math. And then you look at, I remember at some point I'd done the math. And I was like, oh, they lost a billion dollars. They did a billion dollars. They did a billion dollars. They're making $2 billion. I'm going to cost. This is inconsequential. They're obviously losing 50 cents a ride, but they could be making a dollar a ride. And I did it for like $0.54. And I did it for like, this is inconsequential. They're obviously losing 50 cents a ride, but they could be making a dollar a ride. And consumption wouldn't change.
Starting point is 00:25:08 And then if they did make it a dollar extra, a dollar 50 extra a ride, and they did two billion rides, they have $2 billion dollars more. And the $2 billion dollars more would equal this amount. And if they lost 10% of that, if 10% of the rides wouldn't accept a dollar 50 increase, they would have made $1.8 billion. So it's so obvious to me that they could turn that. And they hadn't because they were in a dog fight with Lyft or DoorDash or Postmates, which they bought. So, and Postmates losing a bunch of money per delivery right now. And I just looked at it and it's like, well, postmates at any point could just turn the dial. they're obviously building market share. So that's when I looked at it. I was like, okay, this is
Starting point is 00:25:39 so ingrained. It's so hard to get to 100 million, 200 million people using your product and paying for it that this will obviously figure this out. And then I don't know if you saw like the experiences tab now that they're testing where, okay, you're in a raw, you could order food to your house, you could take a ride to a restaurant. And while you're in the car to the restaurant or you're planning your day, you could buy tickets to a comedy show or make a reservation at a restaurant or do other experiences. So this concept of the super app, I think, was always Travis's plan and logistics everywhere, trucking, et cetera, which Uber Freight is doing particularly well, from what I understand, with Leor running it. So there was just all this massive opportunity,
Starting point is 00:26:15 and I think the massive opportunity is there. I don't see a world in which it's not 10 times bigger in 10 years, or at least five times bigger. And so, and I also think Airbnb, Uber, and DoorDash are the ultimate takeout candidates for Walmart, Amazon, Google, Apple, Facebook, Facebook. Facebook. Facebook, somebody will look at that collection and say, if Facebook was allowed to buy something right now, if Facebook bought any of those companies to combine their two or three billion people people with that? Oh my Lord, now they're really integrated into people's lives. You're going to a restaurant, taking Instagram pictures, ordering an Uber, but, you know, getting DoorDash or whatever. So I do think they're takeout candidates as well. But I also believe in taking chips off the table
Starting point is 00:26:52 as you go. So my best advice, you know, and this really depends on your net worth and how much inside information you have about a company. I don't have inside information about Uber anymore, but I did when it was private because it's legal when it's private, it's illegal when it's public. But my insights on those companies, I think, help me. Like, same thing with Robin Hood. I haven't sold any Robin Hood shares, and, you know, they had gone up to 30 or 40 and done down to 10. You know, I don't see a world in which Robin Hood doesn't have five or ten times as many members,
Starting point is 00:27:17 and those people are super sophisticated and they're young. So they could be getting their mortgages, their equity lines, 529 for college when they do have kids, you know, 401Ks. They're going to be doing everything financial inside of that app. 100%. Same with Square. I own some Square shares. I'm never going to sell those either because Jack's a genius and young people using Cash app and businesses using Square. I don't see them using it less. And I see more opportunities in the future. Uber, Airbnb, Robin Hood, all seem obvious now. But I mean, I can imagine when they pitch you for the first time, you're like,
Starting point is 00:27:51 okay, getting in someone else's car, staying at someone else's house or even Robin Hood. It's free trading. Like, you know, in your book, one other line I loved, was you said that the craziest, most outlandish ideas produce the biggest returns. I'm kind of curious, who has given you the craziest pitch that sticks out in your mind? It's been pretty crazy ideas out there, really weird ones. But if you just pause for a second and say, hmm, but what if it works? I always like to take that. And then the other rule, the cardinal rule I have is don't underestimate anyone, because everybody who starts in this business is awkward and has weird ideas and is unrefined. They're not polished. You know, Steve Jobs may have looked like a savant and a jevant.
Starting point is 00:28:29 genius when he was doing those pitches for the iPhone and the MacBook Air and the iPad and everything. Then if you watch his earlier pitches and you watch his earlier interviews, you know, you could see that raw energy, but certainly not the polish and the confidence. You did see confidence, but it was a different type, like a potential confidence, not a, I did this already confidence, and I'm sure on this one. So if the idea, if there's consensus on the idea, it probably should exist already. It could be an outlier idea that if it does work, could have outlined. results. You know, sometimes crazy is crazy and sometimes crazy is crazy like a fox.
Starting point is 00:29:05 I've heard this sentiment around angel investing in VC for that matter where they called it a negative art, which means that, you know, if you find one reason to pass, you should, because there's just so many opportunities, so many pitches coming at you. If you find one red flag, you're like, okay, I'm out. Is that how you view it? I mean, it sounds like you... No, that's stupid. I was going to say, it sounds like you put a lot more... Whoever had that advice? It's really dumb. We have in the investment company, you know, a dozen people helping me process all these investments, which is not easy when you have over 300. I say make a list of all the things that could go wrong. And then on the other side of your journal, list the things, but what if it goes right? But what if it works? Then you can
Starting point is 00:29:40 rip up the other side, because when you look at all the red flags, that's basically a roadmap of what you need to fix or avoid. So if I told you all the ways you could crash a car on your way to the, you know, Warriors game tonight at Chase Center, you're like, yeah, you could. You could, drive into the car in front of you and I could drive into the bay and I could go 150 miles an hour and I could get a, you know, a boulder could land on top of me. It's like, yeah, there's a million ways you could die on the way of the Chase Center. That's not what you focus on. You focus on staying in your lane and driving the speed limit. And if you want to be extra cautious, be a defensive driver and keep an extra space around you if you see somebody drifting from their lane, avoid
Starting point is 00:30:18 them. And look in your river of your mirror and look for people acting crazy behind you. In other words, like there's this saying in race car driving, like, don't look at the wall. Look at the road. If you look at the wall, you're going to drive into it. Stay on the road. Look at the road. You'll be fine. One thing you just said said out to me around the 300 or so companies that you now are invested in.
Starting point is 00:30:38 And you're looking at, I think, 30, 40 a year. It's the law of large numbers to a degree, right? Because you only need one of these to outperform to really make a buck. So I guess what's sitting with me is like how you optimize your time, because that's a lot to manage. And then you're running podcasts and you're doing research. You're talking about topical news on a daily basis. I mean, how are you optimizing your impact, you know, by joining the boards and these cap tables and having a say?
Starting point is 00:31:01 So I'm taking the route of mentoring a bunch of people around me. And I have people around me who are smart enough to say, hey, this is what you're really good at, do more of that. And this is stuff that you don't need to do. We have people in the organization who are better at that. And so I am ruthless about delegation. And I get more ruthless. As one example, I used to meet with every single company that applies.
Starting point is 00:31:22 to our accelerator. This is hundreds of companies per cohort and then I would do the last 50 and then I would do follow-up meetings for them. It was arduous. And then I would pick. And then over time, I just made simple rubrics, just heuristics of for that 100K check coming to our accelerator, I actually don't need to be involved in it. It's a very small check. The team I've trained can easily take the lessons I've learned and their own intuition to make those bets. And so I no longer pick those companies. I will watch a video of them pitching their company, maybe. I'll read our coverage of it, but I can be bionic in that way. So instead of me meeting with hundreds of companies, I can have my team do that. They can send me the ones that fit the criteria. They can tell me if they get that spidey sense.
Starting point is 00:32:07 And I can, I still take meetings, of course, but it does work a lot better if I radically delegate. Also, if we're going to debate the deal structure, if we're going to debate legal documents, do I need to do that? Probably not. I have some people on my team. And I say, here's the heuristics. Here's the rule set. This is our standard deal. I don't can vary at 10%, but let's stay in this zone and let me know. And if the founder really wants to debate it with me, the person says to them on my team, these are the things that I can approve. These are the things that we do as a firm. I've brought this request to Jason before, like, will you buy common shares? And he's never done it. And I probably brought it to him 10 times where a founder has asked,
Starting point is 00:32:45 will we accept common shares? And the answer is no. We have LPs. We told him we take preferred shares we can. Or will we waive our pro rata? No, we have LPs and we pitch them on our fund that we need to take our prorata in order to be a successful fund so that we can get more money so that we can keep investing in startup. So they can just say to the founder, Jason's in my experience going to very quickly say no, because this has happened a dozen times in the last two years. And you can of course contact Jason. Here's his mobile phone number, call them. And the person's like, yeah, you know, I don't want to bother Jason with that. So I think that radical delegation is really smart. And the two things that I can really be helpful on is hanging out with the founders that we've invested in,
Starting point is 00:33:22 meeting new founders who are elite and who have that Jedi, you know, when I sense the Jedi force power in them. And then doing my podcast, which helps me meet new startups and helps me promote the ones we've invested in or share them with my audience. And those two things are the highest leverage. So you've got to look at the highest leverage behaviors and then get rid of everything else. I'm glad you touched on a few of the terms that are kind of non-starters or require requisites for you. I'd like to kind of nerd out on that a little bit. In the book, you talked about pro rata rights and information rights all are obvious and even classes of shares, which I did have a question on, but I understand the preferred route.
Starting point is 00:34:01 I'm curious what you think about things like liquidation preferences nowadays and anti-dilution rights and certain things like that. Are you ever requiring things like that in a side letter? We don't do funky stuff like that because it's against our best interest in the long term. In the short term, I've seen East Coast VCs, small-minded VCs do weird stuff like this. And what happens is the next set of serious investors see it and you might scare them away. And part of what we do in Silicon Valley and we do in private company investing is we try to create a device where everybody's in it together. That device is the share price.
Starting point is 00:34:34 And you're the founder. You own 40% of the company. I'm an investor and I did the seed and I own seven. of the company, a Series A person owns 15%, and then a Series B person owns 10%, whatever it is, employees own 15%. You have this great aligning force. The shares were a dollar in the seed round. They're $4 in the Series A, they're $12 in the Series B. We all see our share price going up. We all know our employees know their strike price. And we can all just feel good about that. Now, preferred shares exist for a very specific reason for people who don't know. Preferred shares have, they're still one-to-one
Starting point is 00:35:06 with common, almost universally. And when a company IPOs or gets bought, all the share class has turned to common and everybody has an equal share. But until the exit happens, the preferred shares have some protective provisions. One of the protective provisions is so the founders just don't take the money and shut the company down. The assets of the company, if $5 million have been put in, if the company is only sold for $3 million, the investors get their money first. So they would become 60% whole and nobody else gets anything. In those cases, there might be something called a management carve out where you say, hey, a third of the money or 20% of the money will go to the people who go to the new company. But that would be like a disastrous sale. Nobody really wins.
Starting point is 00:35:43 But in a winning sale, you might have a situation where the founder or the board or a combination of them want to raise that a billion dollars. So somebody says, okay, I'll give you the billion dollar valuation. But if the company sells for 500 million, we'd like to get our 100 million back and at least get twice our money back. If we're going to put 100 million at risk, we'd like to get 200 million back. So now the company sells for 500 million. That person bought 10% for 100, but they get 200 million of the 500. So they got two times their money back. Participating preferred. Some people might call the liquidation preference.
Starting point is 00:36:13 Essentially, the easy way for you to think about this is, I'm guaranteed at least double my money. Now, the founder might say, that's fine with me. You paid a ridiculous price. You paid the billion dollar price. I wanted to hit unicorn status. And you do see that kind of funkiness happen. The other investors might sign off on that. Hey, we're going to put $100 million in the bank account.
Starting point is 00:36:29 Companies burning 20 a year. It gives us five years of runway. We got plenty of time to get to that billion dollar outcome. If we do sell for $500, sure, they got the $200. So they took 40% of the proceeds is $300 million left. The rest of the cap table then splits that pari-parsoe fancy word for based on their percentages. So there are some things like that. In a down market, a company might be struggling and they have a down round.
Starting point is 00:36:49 So they've raised in this theoretical billion dollar valuation. Now they can only raise that $400 million. Okay. So now you've got a real challenge because you've got to get people to buy into that. And that means you've got to sell more shares to raise less money. And it can start what's called the debt spiral in startups. And in a predatory environment, like we start off. after 2008 or certainly after 2000, somebody might say, listen, this company's going out of business.
Starting point is 00:37:11 I'll put 500K and give you a bridge loan. It's highly risky. The market's in turmoil. There's a war. There's a recession. Typically this happens during a recession. I'll give you the 500K, but I want a guaranteed 4x liquidation preference. I want four times my money back. So the company's value, you know, five million. I want two million back. And the founder might say, you know what? The chances of this working are like 10%. So the person should get four times their money. They should probably get 10 times their money. It's a very low chance of succeeding. So I'm going to bite the bullet and take that liquidation preference. But the problem is some people will try to put these kind of weird ratchets and concepts on when it's a good market.
Starting point is 00:37:44 And then the next person may just say, the cop table is too complicated. How do I unwind this? How do I unwind that? And so that's when you get the debt spiral. And that's what everybody's trying to avoid. You want to keep this dream alive that the price goes up and everybody's winning together. That doesn't mean that a company who takes a down round or has a funky round is going to fail, but it can cost pain down the road. You know, you're a big advocate for syndicates and or one of the, I think, original syndicates that have existed.
Starting point is 00:38:13 I was actually the first syndicate. The first syndicate. And the book is inspiring. And I know it's a couple years old now, but it's still, I went back and read it. And it's so inspiring to think about getting more into angel investing. I mean, obviously there's the accreditation piece and some other things. But with the syndicate, I'm curious, do you get any say in terms like that? Are you just, you know, leaning on the lead in the round to dictate things like that?
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Starting point is 00:41:37 is 7.8%. Past performance does not guarantee future results, current distribution rate as of 1231, 2025. Carefully consider the investment material before investing, including objectives, risks, charges, and expenses. This and other information can be found in the income fund's prospectus at fundrise.com slash income. This is a paid advertisement. All right. Back to the show. So what a syndicate is, is a group of people who invest in an LLC that that invest in a company. And there's a syndicate lead, in my case, me. And we were on Angelus for the first 30 deals. And then we started our own, The Syndicate.com. It's not particularly hard to start a syndicate. We actually invested in a company called Assure Fund Management with an A.
Starting point is 00:42:19 They were the back end for Angelus for a long time. There are back end. And they can set up for 15K as syndicate in legal documents. We close 68 deals in 2021 for $51 million. And so that's a pretty good pace. And so if you wanted to dabble in angel investing, you would have to go find deal flow. To go find deal flow means years of building a brand.
Starting point is 00:42:41 And doing 50 meetings to find one qualified company, at least 25. So a syndicate might say, I'm putting 50K into this company. Would you like to invest? Here's a deal memo. We happen to host a webinar with the founder. We take it pretty seriously, very seriously, I would say. We do diligence. We check the legal documents and we give access to the founder. Not all syndicates do this, by the way. There's no rules on what a syndicate does. Somebody could just put $50K into the company, do no diligence and then share it with you. It's up to you to do the diligence. In our case, we do diligence. You can do it yourself. But most of the time these rounds are oversubscribed. You can't get access to them as an accredited investor. And you would have to do
Starting point is 00:43:19 10 days of work, 100 hours, to find the one company. And then you would have to probably hit a minimum of 50K. So that's pretty much the minimum. With ours, the minimum's 4K per deal. And we have people who want to put one or 2K, and if we have room, we do that. I think the average person puts in 7K per deal, and our average deal is around 750. And that's usually a function of not how much interest we have. It's a function of two things. One, we are early stage investors. There might not be that amount of money in the round. So we get an allocation of $7.50, and then we have $1.5 million or $2 million in, then we have to pair back our investors and say, hey, you ask for 10K, we're going to give you six, yada, yada. Anyway, for the founder, they get
Starting point is 00:43:56 one item on their cap table. They don't have to have all these angel investors as individual items. The syndicate members can pick and choose which investments they want to do, and they can pick how much they put into each investment. So this is a massive, massive benefit to them. If they were in a fund, they would get a statement at the end of the year, like I do. I'm in 20 funds that are not mine and I think around that number. And they will send you a statement, here's what you invested. And you find out 10 years later how that bucket did as an index. Here, you get to pick and choose. You get to start your angel investing career. And you can put those angel investments on your angel's profile, your LinkedIn profile. You're an angel in this company. Now you put in 7K,
Starting point is 00:44:33 whatever. But it's a way for you instead of doing 150K check to do 12, 4K checks. This is a game that requires a lot of bets because most don't work out. I always ask, success. Angel investors, how many investments do you need in order to hit an outlier? An outlier, let's define as, you know, 25, 50, 100 to one return. So $1 equals $25, $50 or $100. Most angels will tell me something between 20 and 50. So that's what syndicates are. I like doing it because it's a lot of fun to have a large number of people rooting for a company. Well, you've had a big hand in and you've seen, you know, these founders become billionaires themselves. A lot of your friends have become billionaires right before your eyes. I'm curious about the traits that you notice amount the billionaires around. Is there a
Starting point is 00:45:16 common trait that you found between all of them that you've kind of singled out at this point? Well, there's really two ways to get there. One is to be an investor, capital allocator, and the other is to either found the company or be an early stage and be an early employee at the company. So you're either allocating capital or starting a company or being in the top 50, 100 investors at an outlier company. So on the capital allocator side, I think it's consistently placing bets over a long period of. time and holding the shares for a long period of time. You know, if you get $10 million in an exit and you sell your Facebook shares for $10 million, if you had held them, you would have had another
Starting point is 00:45:52 10x. And there's even bigger examples of that, like Google or whatever. There was somebody who was a fund manager who was in the same round as me who sold their Uber at $5 billion, I think. That was obviously a mistake. They missed the next 12 to 20x depending on when they sold. So those last couple of double-ups can be very material. That's something to keep in mind. That's why, you know, on the all-in pod, we talk about riding your winners. And I also don't care about being a billionaire, to be totally honest. So I have made some choices that are inefficient, like being a podcaster for half my day, where I could double the number of investments, but I enjoy it. And candidly, once you get past 10 or 20 million bucks, it actually does not matter. Like, the only things I can
Starting point is 00:46:36 think of that I would probably delight in would be owning the Knicks. I use the example of my book about like eating a hamburger. Like, I've had a hamburger with multiple billionaires. Pretty frequently I do that. Does the burger taste any differently to the four besties on All In? No, it's the same burger. I agree. I mean, there's certainly much more to life than money.
Starting point is 00:46:59 I think we use billionaire more as a shorthand for, you know, outlier or something like that. You mentioned the All In podcast on your show that these are all outliers. And I am just so impressed with the extensive knowledge and a wide variety of topics. you guys discuss, while also maintaining this respect and love for each other while disagreeing adamantly. If only you saw the moments between the two shows. There's been some blowout fights, actually. There's been some, you know, I don't want to get into how the sausage is made, but we
Starting point is 00:47:28 we've had some intense moments. I think that just adds to it. I mean, it's inspired me to find a similar friend group that can kind of level up the discussion in a way. I'm kind of curious that as we kind of part ways here, if you could end us with some principles that you've used to help cultivate such an inspiring group of friends and the network that you have? Yeah, I have for me, you know, growing up where I did, loyalty, being a good friend is critically important for survival. And, you know, it's just who you are. I
Starting point is 00:48:01 deliberately try to be the best friend to my friends that they have. And that can manifest itself in a lot of different ways, but, you know, it could be as simple as calling somebody and just saying, how are you doing? and putting yourself out there and to be relentlessly supportive. Other times it could be active. You know, you see me on CNBC defending Travis, you know, during the most intense moments of the Uber saga that are, you know, now in a TV show. So I'll put myself out there. I defended Robin Hood, in fact, on CNBC.
Starting point is 00:48:28 And so, you know, and my friends call that air cow, like, you know, air cover. You know, like if you're friends with JCal and you've got a tough moment in time, you know, he might go out there and help defend you. So I try to be a great friend. And it came from a good friend of my Fritz. We lived next door to each other in Brooklyn. And it was like a Friday or Saturday night. And he said, what are you doing?
Starting point is 00:48:50 And I was like, I'm a loser. I'm alone on Saturday night. He's like, are you friends? I'm like, yeah, I have a ton of friends. He's like, why don't you go hang out with your friends? I was like, well, nobody call me. He's like, call them. And I was like, oh, I don't know, really.
Starting point is 00:49:01 It's like when I'm 19 or 20 years old. I never really thought about that. Okay, yeah, good idea. I was like, well, you're my friend. What are you doing tonight? You want to go to the movies or get some dinner? He's like, yeah, let's go get some dinner and go to the movies. We went to dinner and got the movies.
Starting point is 00:49:12 We talked all night. We had a great time. And that was where it clicked for me. And so, you know, I know a lot of people who are very successful. And you'd be surprised on a Friday night or Saturday night, the most successful person you know or the 10 most successful people you know who you think are super happy, they might not have anything to do. And as you get older, your friend circle might contract a little bit or if you get really
Starting point is 00:49:32 famous or you get really rich, maybe it's harder to make friends. and, you know, you kind of have a smaller subset of like an inner circle. And so you can kind of, I think, really double down on building meaningful relationships. And if you look at life, I don't think anybody at the end, I'm sure I will not look at my life at the end and say, you know what? I went skiing with my friends too much. And, you know, I had too much fun with my friends laughing, playing poker, or taking my daughter skiing and teaching them how to ski.
Starting point is 00:49:59 And that was a waste of time. But I might look back and say, you know, I invested in 1,200 companies. I should invest it in 1,000. in and done another 100 days of skiing or play poker more. So there's a balance there. Well, before I let you go, I definitely want to make sure you can hand out to our audience. Everyone knows you, but can you hand off to your podcast, to your syndicate, anything else you want to share? I do a podcast called This Week in Startups Every Day with Molly Wood. Of course, the All In podcast. And I have something called The Syndicate.com. If you're an accredited investor and want to read the deal memos,
Starting point is 00:50:30 we do about two deals a week. And I'm Jason on Twitter.com slash Jason. And I have a another company I run that I'm CEO of called Inside.com, which you can go check out, which is a bunch of industry vertical specific newsletters. That's how I keep up to date and hopefully get really smart. One of the thing that I'm doing called Founder University. So if you're thinking about starting a company, but you don't know where to begin, I started a 12-week course called Founder. It's been pretty successful. And the All-In is going to do the All-In Summit, which you should join us for. We'll talk about it afterwards. May 15, 16, 17 in Miami. And yeah, that's it. I think that's everything I do.
Starting point is 00:51:03 Just that. Just that. I keep busy. You know, I like projects. I come up with ideas. For every founder university or syndicate, there's like four or five other crazy ideas I launched and shut down. I just, I like to try things. That's the other thing I learned from all these founders I work with. Like, if you think it's possible that something will work, well, give it a try, man. I was going to say, is this the Elon influence. You know, what I will say about Elon is he's one of the great people I've met in my life as a friend, incredibly hardworking and determined. And, you know, all this success that you see, is the result of not just his ability, which is very high, but a work ethic that is impressive
Starting point is 00:51:40 even to me. I'm a hard worker, but his ability to stay focused on a task, electric cars, 15 years, SpaceX, 15, 20 years, like these companies are in their second decade, and that is really the lesson of success is how long can you suffer through and never-ending series of challenges? And, you know, most people cannot do that for too long. And that's why entrepreneurs and successful people in society should be not villainized or demonized. They're very rare that somebody can keep that level of focus and determination to solve the world's biggest problems. And when they do hit it, we should be really happy and really thrilled that we have those people
Starting point is 00:52:22 in society because they're rare. And, you know, I'm lucky enough to have a lot of those friends. And, you know, the next time, like, you see six Teslas out of ten cars, in a parking lot and the air is cleaner and the ozone is not getting burned. You can thank Elon for that. All these car companies would not be doing what they're doing if Tesla had not been so successful. And I can tell you, Tesla would not be successful if he did not suffer and put that company on his back. And you want to talk about near-death experiences, he's outlined them. Like this is a, I was like a witness to it, you know, like having been there from when he made
Starting point is 00:52:54 the investment and had to take over a CEO, which he didn't want to do. I watched the whole thing happen. and like a lot of hard work and sleepless nights and weekends. And you see that over and over again. The fact that you can go order whatever food you want and having your house in 30, 40 minutes, or you can get a taxi from wherever and not have to drive drunk or leave your car behind and figure out how to get a cab and wait for two hours. Like, that's Travis, right? Like, he suffered over that company.
Starting point is 00:53:16 There's a lot of pain and suffering to create this delight and to solve the world's biggest problems. And we've got a lot of problems we've got to solve. But I am more optimistic now than I've ever been in my life for peace, for prosperity, for energy independence, for food, for transportation, for education, for opportunity, for democracy. Everything is trending so well in society. And it's because of entrepreneurs and scientists and scientists are entrepreneurial. I kind of put them in the same bucket, including my friend David Freeberg and capital allocators. When you hang out with those three
Starting point is 00:53:49 groups of people, I'll throw artists in there as well for creating joy in the world. There are people who build stuff in the world. And those people are rare. And they build stuff that we all benefit from. Whether it's the artist that makes us laugh or creates a piece of music that fills you with emotion or the scientist who creates that MRNA that gets society back on track and keeps people from dying from COVID, you know, or the capital allocator who puts the money behind Tesla and saves it from going extinct or the entrepreneurs who run these companies. And, you know, as a society, I have my concerns about democracy. If I'm being honest, that's the last one I mentioned because I think people take it for granted a little too much.
Starting point is 00:54:27 We need to have a strategy. And the strategy is going to be energy independence from science, capital allocation, and entrepreneurship. We must become energy independent. And in order to do that, we need technology, capital allocators and entrepreneurs to build nuclear, sustainable energy, everything. Batteries, new grids, new cars, solar, and most of all nuclear, which is, you know, we're making such amazing progress and we won't take the win. So anyway, it's top of mind for me. But democracy is something. that we really need to focus on. There was a tweet just today, I think, by Mark Andreson. It was kind of like prophetic. And I don't know, just really sit out to me. He basically said, this is the moment. Let's build nuclear. Let's frack.
Starting point is 00:55:10 Let's drill. Let's go. Basically, you know, I mean, this is not so sure about the fracking. Well, yeah, of course. And drilling like strategically. Strategically. Drill a little bit right now. I'm okay with it.
Starting point is 00:55:19 It's a time for nuclear for sure. The other ones I think we just, you know, certainly we need to be energy independent. Certainly Europe does. But I think nuclear, solar, batteries are the clear path. This idea of instant gratification that is consuming everybody, there's this Buffett quote I'm reminded of. He's got this quote that no one likes to get rich slowly. And I think that's consuming people. We're forgetting the power of compounding.
Starting point is 00:55:41 And you mentioned suffering for decades to build a company. And that's what it really takes to build something great. Like the progress that gets made. And so I always think in decades now when I look at startups, another kind of to your point about compounding interest, people don't get it. I actually teach people the rule of 72 in my accelerator. I'm like, okay, explain to me the rule of 72. I don't know what you're talking about. I'm like, divide your growth rate into the number 72, and that's how many periods it takes to double. And they're like, I don't understand. I'm like, if you're growing 10% a month in 7.2 months, you'll double. And they're like, no, if I'm growing 10% a month, I'll double in 10 months. I'm like, compounding. And then I say, well, what if you grew 10%
Starting point is 00:56:18 a week? They're like, well, then I would double in 7.2 weeks. I'm like, do it. Or try. See what happens. And, you know, like with battery technology, you're not going to do that. But with the number of rides in an Uber, you might in a market. You might actually double in 7.2 weeks. Actually, Uber did. So, you know, and consumer products certainly have Twitter, Facebook, et cetera. So, you know, compounding interest is really what it's about. In related news, it's very hard to make one feature of your product twice as good, but it's very easy to make 10 of your features 10% better. And if you take your product, whether it's a Tesla or an Uber or the app or com, you make 10 things 10% better, you make it loads 10% faster.
Starting point is 00:56:53 master. The logo is 10% better. The meditation is sound quality is 10% better. Everything gets 10% better. All of a sudden, like, people don't realize it, but the product's really nice. And, you know, I don't know if you ever watch this movie The Founder with Michael Keaton. It's incredible. Super underappreciated movie, especially for entrepreneurs. Ray Kroc was a broken person and some weird stuff, but his drive in this movie is worth watching. But that moment, the moment of the like motivational record he was listening to where they're talking about, like, hey, how many things? thousands of talented people, you know, have failed.
Starting point is 00:57:26 You know, it's not just talent. It's like the grit. It's amazing you bring up that moment. It's really fascinating because every entrepreneur I know has a moment like that where they're sitting there going, I could be somebody. I could be one of those people who does it. And it really is a mind switch from that's one in a million or that's one in a thousand or most people fail to, well, somebody's got to succeed.
Starting point is 00:57:50 So when I'm working with founders, I'm like, you probably, I'm going to give you this money. It's probably going to fail statistically. But if you do two or three companies, you're kind of succeed. The odds will be with you if you do three, four, five, certainly one of them is going to hit. So let's go on this journey together. And in fact, one of my great investments is Raul and Superhuman, which we put 500K into their first round, their seed round when he just had a deck, like a three or four slide deck. And that came because I had invested in his previously company, Reportive, because I liked this little toolbar he had made and I emailed info at Reportive and introduced myself to him and put a little bit of money into it.
Starting point is 00:58:22 And when he sold it to LinkedIn and I tripled my money, and I said, you know, just promise me when you do your next company, when you do your tour at LinkedIn, I'll be your first phone call and literally call me on a Sunday and said, hey, Jake Al. And I was like, where are you? He's like, I'm in San Francisco. I'm like, want to get bagels? He's like, sure. I was like, I can't wait to hear about your new company. Is how do you know I have a new company? I said, because you promised me you to call me. And it's two years after you sold. So you must have a new company. It's like, I do. I was like, okay. When are we going to meet? I'm like, where are you in the city? I can meet any time in the next three hours. He sat my house an hour and a half later. He said, what's the idea? He said,
Starting point is 00:58:55 oh, I'm going to take on Gmail. I said, okay, great. I love it. It's a big target. I said, how are you going to be Gmail? He's like, going to be faster. And it's going to be a dollar a day. I said, okay, you're going to take on Google with the largest server firms that they built from their own proprietary open source. Seems like a paradox, but they built their own servers. The largest data collection of servers in the world, you're going to beat them on speed. And they have unlimited engineers. He said, yeah. I said, how do you do that? He said, well, you know, here's the thing. They're building for sustainability for a billion people we're going to build for a million. I said, oh, okay, that makes total sense, right? You're building a Ferrari, not a Prius. Perfect.
Starting point is 00:59:29 He said, tell me this thing about like a dollar a day, $30 a month, $360 a year. Gmail's free. So you're going to get people to pay for something they get for free. He's like, yeah. He's like, how much time do you spend on email a day? I was like, two or three hours. He said, okay, if I can save you 10 minutes a day, what's that worth? I was like, well, I can tell you, it's 3,650 minutes a year, which is 60 hours. So 60 hours and each hour's worth $1,000 to me. I don't know. I pay it worth $60,000. So if you charge me 600, that would be 1%. You're charging me 50 basis points, like 1-200th of the value I'm going to get. He's like, exactly. I'm saying, I'm in. You want to talk about like a contrarian idea? I'm going to take on a free product, Gmail. Like,
Starting point is 01:00:11 I'm waiting for somebody to come and be like, I'm taking on Chrome. It's like, taking on a browser that's free built by Google. Let's go. Jay Cow, thank you so much for doing this. I really appreciate having you on the show. I've been loving the content you've been putting out lately, and thanks for being such a resource for everybody. And I hope we can do it again sometime.
Starting point is 01:00:27 Of course, of course. I appreciate it. All right, everybody. That's all we had for you this week. If you're loving the show, please don't forget to follow us on your favorite podcast app. And if you're looking to get in touch, you can always find me on Twitter at Trey Lockerbee.
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