24 March 2022

On today’s show, 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. He’s the author of Angel, where he lays out his playbook for turning $100k into over $100MM. You may also know Jason from the All In Podcast with Chamath Palihapitiya, David Sacks and David Friedberg or his other podcast This Week in Startups.

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  • 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!


Disclaimer: The transcript that follows has been generated using artificial intelligence. We strive to be as accurate as possible, but minor errors and slightly off timestamps may be present due to platform differences.

Trey Lockerbie (00:03):
On today’s show, we have Angel Investing legend, Jason Calacanis. Jason is an entrepreneur who sold his second business, Weblogs, 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, Robinhood, Calm, and 300 others, give or take. He’s the author of Angel, where he lays out his playbook for turning a hundred thousand into over a hundred million. And you may also know Jason from the All In Podcast with Chamath Palihapitiya, David Sacks, and David Friedberg. Or his other podcast, This Week in Startups.

Trey Lockerbie (00:35):
In this episode, we discuss 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 Calacanis.

Intro (01:07):
You are listening to The Investor’s 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.

Trey Lockerbie (01:27):
Welcome to The Investor’s Podcast. I’m your host, Trey Lockerbie. And today, I’m super excited to have with me on the show, Jason Calacanis. Welcome.

Jason Calacanis (01:35):
I’m super pumped to be here.

Trey Lockerbie (01:38):
Well, I’ve been loving all the stuff you’ve been putting out. The All In Podcast, especially, I think is just fantastic. And we recently had your bestie Chamath 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 described your humble upbringing in Brooklyn, and feeling like an outsider because of it. And so I’m curious, what was that like when you were first getting started? And the outsider feeling, was it still there even after you sold Weblogs to AOL?

Jason Calacanis (02:15):
So I have tried to cultivate my outsider status and maintain it. It’s a little hard to do as you become more successful, and 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, I look at it like the hip-hop scene in New York. When I was growing up in the ’90s, there was this big hip-hop scene. And I used to play basketball, the Chelsea Piers, with a lot of the hip-hop guys. And 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 interesting cats.

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Jason Calacanis (02:46):
And 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 a pretty rebellious thing, actually. It was fighting against the establishment of Dial-up, Delfi, CompuServe, Sprint, AT&T, AOL. They were all trying to control this new online experience and mitigate it for $3, $4, $5 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.

Jason Calacanis (03:23):
And so, yeah, I’ve always liked to 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. I 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.

Jason Calacanis (03:40):
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 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 insider 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 Chamath. Sacks and Friedberg probably are more actually part of that, having gone to elite schools and been part of that. So it’s actually interesting, I never thought about it that way. But yeah, you have two outsiders and then two insiders, basically.

Trey Lockerbie (04:23):
We just had a guest on the show who wrote a book, actually, about the PayPal mafia, and David Sacks, obviously, featured in that. And they described the culture there as highly functional, but the debates were heavy and heated and frequent. And is that a culture you find pretty frequently in Silicon Valley? You came from Brooklyn, so you brought it your own flavor of it.

Jason Calacanis (04:42):
Yeah. I would say, yes. I would say directionally, correct, yeah. I lived in New York, LA, and San Francisco. In New York, if you go to a dinner party and you say something controversial, or you make a statement, you might very well have somebody say, “Can you back that up?” Or, “That’s not right.” People won’t get in people grills about it. You say, “Listen, I think this is the greatest artist of all time.” Or, “I think this movie sucked.” Somebody might be like, “Well, I think you’re wrong,” and accept it. Then when I lived in LA, people are like, “Please do not make this uncomfortable.”

Jason Calacanis (05:11):
I do think the debate culture at PayPal was very real, knowing Roelof 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 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 were 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?”

Jason Calacanis (05:52):
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 pick the person, they tend to be great at debating stuff. And listening and taking in dissenting opinions. Actually, the dissent is kind of the most important part.

Trey Lockerbie (06:10):
I’ve heard you talk about startups, and the way you talk about them is something I recognize as myself, as a startup founder. And 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 defend, in a way, what startups really are. There’s a lot of mysticism, or people on the outside, they’re like, “Why don’t you just pay everyone equally? Let them work three days a week from somewhere else and give them the help,” all these things. And you’re like, “You don’t understand.”

Jason Calacanis (06:37):
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 of years, we’ve been in a 13 year bull market, since 2008 to 2020. We had this incredible 13 year run where a lot of young people have only experienced it going up and to 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, in the muck of those compression moments. And they’re pretty brutal.

Jason Calacanis (07:25):
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 is a little rough for people to hear. But if you don’t want to work hard, if you don’t want to 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 metaphors, sports teams and war, keep coming up is because they’re accurate. And they’re the most accurate to describe startups.

Jason Calacanis (07:52):
Now, if you’re describing a nonprofit, 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, left on that ship and made it to The New World. I don’t know if Christopher Columbus’s 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 are at the bottom of the ocean, or they landed and got in a fight and got murdered or eaten by animals or whatever.

Jason Calacanis (08:36):
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. 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 dog fight. 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 just is over. Or they just make a tactical mistake, and the company could be hobbled forever, or maybe take a 10 year break. Microsoft missed mobile and it was a 10 year diversion. They’ve recovered, but that was a spin out. They flipped the car on that one.

Trey Lockerbie (09:28):
I want to talk about founders, now that you brought it up, because you have this super power of picking really great founders, through your Angel Investing career, that we’re going to talk a lot about. But what you said just now stood out to me. You were like, “Can they lead people?” And something that I’ve experienced for myself, and seen in others, is when you’re founding a company, I don’t think leadership is really at the top of your mind. 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 flip and you have to become a great leader. 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?

Jason Calacanis (10:11):
When you become a capital allocator, it really is great to be thoughtful, and think through how you had the wins. 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. And so they can run really fast and put the ball in the basket. They’re LeBron James, they’re Michael Jordan. Early in their careers, they’re just savants. 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, if 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. There are certain people who are glue and who, really, are leaders. And they inspire people to come on that journey.

Jason Calacanis (11:07):
And that really is when you see if the person can be successful. 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 of yourself, cannot be unleashed on the people around you. Or else you will destroy them and they will not show up for work.”

Jason Calacanis (11:45):
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 questions. You got to demand excellence from them. You got to empower them. That’s a different skillset. I can tell who’s that broken person who has something to prove, that chip on their shoulder.

Jason Calacanis (12:02):
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, are you going to work 78 hours a week to change the world, 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, to Travis, and on, they got something to prove. And they got an energy level that, to me, is so easily discernible.

Jason Calacanis (12:42):
And that’s all I try to do. That’s my secret power, post investment, is 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. 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 because they just puked, and their family’s outside, waiting for them to go to brunch. And they’re paralyzed because they 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. 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.”

Trey Lockerbie (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.” What are the signs and common denominators of a failed startup?

Jason Calacanis (13:44):
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. 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 change the name of the store. And all they needed to do was 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.

Jason Calacanis (14:13):
Product market fit is just a matter of focus, and focusing on the product, and iterating product velocity. 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. That happens too.

Jason Calacanis (14:40):
So you’ll see somebody who’s not creative at all, like Zuckerberg. And he has this tremendous success by just copying everybody else and being more focused. And saying, “Make it faster, make it simpler, copy more people’s features.” The guy never came up with his own idea. 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 memetic machine, a complete thief, and he’s making hits and had massive success.

Jason Calacanis (15:11):
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.

Jason Calacanis (15:29):
But like I said, 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 not the promise, but the performance.

Jason Calacanis (16:09):
And so all these theatrical people, who could make a great deck, or network super well, they find themselves SOL. 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, when the market gets shaky like this.

Jason Calacanis (16:37):
But you asked before about the successful ones, and it turns out the crises makes the founder. Turns out the crucible, to my friend, Roelof from Sequoia, a peer and a mentor at once, he always talks about the crucible moments for companies. These crazy decision making moments where the founder has to just go for it. You got to take that leap of faith. And if you look at Uber, if you look at any of the companies that had really hard times, it’s those hard times, that’s battle testing a founder. That’s the Jedi coming back from an impossible mission, and losing a limb, and then going on to the next company or the next mission.

Jason Calacanis (17:13):
So sometimes people have it backwards. They think Robinhood having a couple of challenges the last couple years, they’re like, “Oh, well, that says something that this company’s got problems.” And it’s like, “Quite 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, “If it doesn’t kill you, it makes you stronger.” Sometimes these phrases ring true because they’re so true. And that is one of them.

Trey Lockerbie (17:43):
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?

Jason Calacanis (17:52):
A lot of schools have thought on this. And one school of thought is, the young founders, the inexperienced ones, the Zuckerberg or the Bill Gates, quit college, go do this incredible thing. Larry and Sergey, Google, or Steve Jobs. 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 outside success, if they stick with that company for multiple decades. So there could be two trends going on here.

Jason Calacanis (18:38):
On average, the serial founder does not make the unforced errors. The crafty veteran knows how to get to the free throw line, knows how to set a pick correctly. Knows how to inbound the ball off of the defensive player shoulder and take it back and dunk it like you see in, sometimes, those highlight reels. They do something clever like that. That stuff 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.

Trey Lockerbie (19:11):
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, I absolutely love. I hadn’t come across it before. But you basically described someone asking how someone became rich, and them 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 below its IPO at this point? I was curious if you-

Jason Calacanis (19:36):
It’s bounced around, yeah.

Trey Lockerbie (19:37):
Yeah, it’s bounced around. Are you just letting house money ride at this point and seeing where it goes?

Jason Calacanis (19:42):
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, these are two crucible moments. And I think they passed both of those crucible moments. And then getting to profitability, which was always a very weird conversation. Because having watched the company 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 start a dollar or two. But you have many more rides, and consumption went crazy. To the point at which, people, maybe, were replacing their cars because Uber was so cheap. 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.” Or the Uber’s 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 to insure the car. So we’re going to go full Uber.

Jason Calacanis (20:33):
So all this was so obvious to me, it was just math. And then you look at… I remember, at some point, I had done the math. And I was like, “Oh, they lost a billion dollars. They did two billion rides in the quarter.” I’m making this number up because I don’t have it at my fingertips. But I had done a calculation. They were losing something like 48 cents a ride, or 54 cents a ride. And I did it for three quarters, and I was looking at the number. I was 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.” And then if they did make it $1 extra, $1.50 extra, a ride and they did 2 billion rides, they’d have $2 billion more. And their $2 billion more would equal this amount. And if 10% of the rides wouldn’t accept a $1.50 increase, they would’ve made $1.8 billion.

Jason Calacanis (21:13):
So it was 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. And Postmate’s losing a bunch of money per delivery right now. And I just looked at it and I was 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 and I was like, “Okay, this is so ingrained. It’s so hard to get to 100 million, 200 million people using your product and paying for it, that they’ll obviously figure this out.”

Jason Calacanis (21:36):
And then, I don’t know if you saw, 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 this 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 Lior running it.

Jason Calacanis (22:02):
So there was just all this mass of opportunity. And I think the mass of opportunity’s 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 I also think Airbnb, Uber, and DoorDash are the ultimate takeout candidates for Walmart, Amazon, Google, Apple, 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 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, getting DoorDash, or whatever. So I do think their takeout candidates as well.

Jason Calacanis (22:40):
But I also believe in taking chips off the table as you go. So my best advice, 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, helped me. Same with Robinhood, I haven’t sold any Robinhood shares, and they had gone up to 30 or 40 and then down to 10. I don’t see a world in which Robinhood doesn’t have five or 10 times as many members. 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, 401(k)s. They’re going to be doing everything financial inside of that app, 100%. Same with Square, I own some Square shares. 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.

Trey Lockerbie (23:34):
Uber, Airbnb, Robinhood, all seem obvious now. But I can imagine, when they pitched you for the first time, you’re like, “Okay, getting in someone else’s car, staying at someone else’s house. Or even Robinhood, it’s free trading.” In your book, one other line I loved was, you said that, “The craziest, most outlandish ideas produce the biggest returns.” I’m curious, who has given you the craziest pitch, that sticks out in your mind?

Jason Calacanis (23:58):
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 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. Steve Jobs may have looked like a savant and a 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 can 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 there’s consensus on the idea, it probably should exist already. It could be an outlier idea that if it does work, could have outlier results. Sometimes crazy is crazy. And sometimes, crazy is crazy like a fox.

Trey Lockerbie (24:55):
I’ve heard this sentiment around Angel Investing, and VC for that matter, where they called it a negative art. Which means that, 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? It sounds like you-

Jason Calacanis (25:09):
No, that’s stupid.

Trey Lockerbie (25:10):
I was going to say, yeah, it sounds like you put a lot more-

Jason Calacanis (25:13):
That’s really dumb. Whoever had that advice, it’s really dumb. We have, in the investment company, 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 of things, but if it goes right? But what if it works?” And if it works, then you can 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.

Jason Calacanis (25:37):
So if I told you all the ways you could crash a car on your way to the Warriors game tonight at Chase Center, you’re like, “Yeah, you could drive into the car and front of you. And I could drive into the bay. And I could go 150 miles an hour. And a boulder land on top of me.” It’s like, “Yeah, there’s a million ways you could die on the way to 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 them. And look in your rearview mirror, and look for people acting crazy behind you. In other words, there’s this saying in race car driving like, “Don’t look at the wall, look at the road.” Because 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.

Trey Lockerbie (26:23):
One thing you just said stood out to me around the 300 or so companies that you now are invested in. And you’re looking at, I think, 30 or 40 a year. It’s the law of large numbers to a degree, because you only need one of these to outperform to really make a buck. So I guess what’s sitting with me is, how you optimize your time. Because that’s a lot to manage, and then you are running podcasts, and you’re doing research. You’re talking about topical news on a daily basis. How are you optimizing your impact, by joining the boards and these cap tables and having a say?

Jason Calacanis (26:51):
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 applied to our accelerator. This is hundreds of companies per cohort. And then I would do the last 50, and then I would do followup meetings with 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.”

Jason Calacanis (27:37):
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. And 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.

Jason Calacanis (28:09):
I have some people on my team and I say, “Here’s the heuristics. Here’s the rule set. This is our standard deal. And we could vary it 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, ‘Will we accept common shares?’ And the answer is no, we have LPs. We told them we’d 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 pro rata, in order to be a successful fund, so that we can get more money so that we can keep investing in startups.

Jason Calacanis (28:51):
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 him.” And the person’s like, “Yeah, I don’t want to bother Jason with that.” So I think that radical delegation is really smart.

Jason Calacanis (29:06):
And the two things that I can really be helpful on is hanging out with the founders that we’ve invested in, meeting new founders who are elite and who have that Jedi… 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 got to look at the highest leverage behaviors, and then get rid of everything else.

Trey Lockerbie (29:33):
I’m glad you touched on a few of the terms that are non-starters, or require requisites for you. I’d like to nerd out on that a little bit. That 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. 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?

Jason Calacanis (30:01):
We don’t do funky stuff like that because it’s against our best interests 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, 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. And you’re the founder. You own 40% of the company. I’m an investor. And I did the seed, and I own 7% 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 $1 in the seed round. They’re $4 in the Series A. And they’re $12 in the Series B. We all see our share price going up. The employees know their strike price. And we can all just feel good about that.

Jason Calacanis (30:50):
Now, preferred shares exist for a very specific reason. For people who don’t know, preferred shares, they’re still one-to-one with common, almost universally. And when a company IPOs or gets bought, all the share classes turn to common. And everybody 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’s 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 a disastrous sale, and nobody really wins.

Jason Calacanis (31:32):
But in a winning sale, you might have a situation where the founder, or the board, or a combination of them, want to raise it $1 billion. So somebody says, “Okay, I’ll give you the $1 billion 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 a $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 it liquidation preference. Essentially, the easy way for you to think about this is, I’m guaranteed at least double my money.

Jason Calacanis (32:06):
Now, the founder might say, “That’s fine with me. You paid a ridiculous price. You paid the $1 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 dollars in the bank account. Company’s burning 20 a year, it gives us five years of runway. We got plenty of time to get to that $1 billion dollar outcome.” If we do sell 500, sure they got the 200, so they took 40% of the proceeds. There’s 300 million left. The rest of the cap table then splits that, pari passu, fancy word for based on their percentages. So there are some things like that.

Jason Calacanis (32:35):
In a down market, a company might be struggling, and they have a down round. So they’ve raised in this theoretical $1 billion dollar valuation, now they can only raise that $400 million. So now, you got a real challenge because you got to get people to buy into that. And that means you 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 saw after 2008, or certainly after 2000, somebody might say, “Listen, this company’s going out of business. 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 of my money back. So the company’s valued at $5 million, I want $2 million back.”

Jason Calacanis (33:16):
And the founder might say, “You know what? The chances of this working are 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.”

Jason Calacanis (33:28):
But the problem is, some people will try to put these weird ratchets and concepts on, when it’s a good market. And then the next person may just say, “The cap table’s 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 cause pain down the road.

Trey Lockerbie (33:56):
You’re a big advocate for syndicates, and are one of the, I think, original syndicates that have existed.

Jason Calacanis (34:02):
I was actually the first syndicate on AngelList.

Trey Lockerbie (34:05):
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. 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 leaning on the lead in the round to dictate things like that, and you’re just a passive investor, if you’re going through a syndicate? Or what does that look like?

Jason Calacanis (34:27):
Yeah. So what a syndicate is, is it’s a group of people who invest in an LLC, that then invests in a company. And there’s a syndicate lead, in my case, me. And we were on AngelList for the first 30 deals. And then we started our own thesyndicate.com. It’s not particularly hard to start a syndicate. We actually invested in a company called Assure Fund Management, with an A. They were the backend for AngelList for a long time. They’re our backend. And they can set up for $15k a syndicate in legal documents. We closed 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. And doing 50 meetings to find one qualified company, at least 25.

Jason Calacanis (35:12):
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. And 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 10 days of work, 100 hours, to find the one company. And then you would have to probably hit a minimum of $50k. I’d say that’s pretty much the minimum.

Jason Calacanis (35:53):
With ours, the minimum’s $4k per deal. And we have people who want to put $1k or $2k in, 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 750 and then we have $1.5 million or $2 million in interest come in. Then we have to pare back our investors and say, “Hey, you asked for $10k, we’re going to give you six,” yada yada.

Jason Calacanis (36:21):
Anyway, for the founder, they get 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, I think around that number. And they will send you a statement, “Here’s what you invested in.” And you find out 10 years later, how that bucket did as an index.

Jason Calacanis (36:50):
Here, you get to pick and choose. You get to start your Angel Investing career. And you can put those Angel Investments on your AngelList profile, your LinkedIn profile, you’re an Angel in this company. And how you put in $7k or whatever. But it’s a way for you, instead of doing one $50k 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 successful Angel Investors, “How many investments do you need in order to hit an outlier?” An outlier, let’s define as, 25, 50, 100 to one return. So $1 equals $25, $50 or $100 dollars. 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.

Trey Lockerbie (37:31):
Well, you’ve had a big hand in, and you’ve seen 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 in the billionaires around. Is there a common trait that you’ve found between all of them that you’ve singled out at this point?

Jason Calacanis (37:47):
Well, there’s really two ways to get there. One is to be an investor, a capital allocator, and the other is to either found the company or 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. If you get $10 million in an exit, and you sell your Facebook shares for 10 million bucks, if you had held them, you would’ve had another 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.

Jason Calacanis (38:36):
So those last couple of double ups can be very material. That’s something to keep in mind. That’s why, 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. The only things I can think of that I would probably delight in, would be owning the Knicks. I use the example in my book about eating a hamburger. 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.

Trey Lockerbie (39:23):
I agree. There’s certainly much more to life than money. I think we use billionaire more as a shorthand for 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 wide variety of topics you guys discuss. While also, maintaining this respect and love for each other, while disagreeing adamantly.

Jason Calacanis (39:44):
If only you saw the moments between the two shows. There’s been some blowout fights, actually. There’s been some… I don’t want to get into how the sausage is made, but we’ve had some intense moments.

Trey Lockerbie (39:58):
I think that just adds to it. It’s inspired me to find a similar friend group that can level up the discussion in a way. I’m curious, as we 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?

Jason Calacanis (40:16):
Yeah. For me, growing up where I did, loyalty, being a good friend, is critically important for survival. And it’s just who you are. I 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 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 see me on CNBC defending Travis, during the most intense moments of the Uber saga that are now in a TV show. So I’ll put myself out there. I defended Robinhood, in fact, on CNBC. And my friends call that Air Cal, like air cover. Like, “If you’re friends with Jay Cal, and you got a tough moment in time, he might go out there and help defend you.”

Jason Calacanis (41:05):
So I try to be a great friend. And it came from a good friend of mine, Fritz. We lived next door to each other in Brooklyn. And it was a Friday or Saturday night. And he said, “What are you doing?” And I was like, “I’m a loser, I’m alone on Saturday night.” He’s like, “Don’t you have friends?” I’m like, “Yeah, I have a ton of friends.” He’s like, “Well, why don’t you go hang out with your friends?” I was like, “Well, nobody called me.” He’s like, “Call them.” And I was like, “Ah, I don’t know really.” This is when I’m 19 or 20 years old. I was like, “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 we go to the movies. And we talked all night and we had a great time. And that was where it clicked for me.

Jason Calacanis (41:41):
And so, I know a lot of people who are very successful. And you’d be surprised, on a Friday night or a 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 famous, or you get really rich, maybe it’s harder to make friends. And you have a smaller subset of an inner circle. And so you can, I think, really double down on building meaningful relationships.

Jason Calacanis (42:11):
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 I had too much fun with my friends, laughing, playing poker. Or taking my daughters skiing and teaching them how to ski. Man, that was a waste of time.” But I might look back and say, “I invested in 1,200 companies, maybe I should have invested in 1,000 and done another 100 days of skiing or played poker more.” So that’s a balance there.

Trey Lockerbie (42:37):
Well, before I let you go, I definitely want to make sure you can hand off to our audience. Everyone knows you, but can you hand off to your podcast, your syndicate, anything else you want to share?

Jason Calacanis (42:47):
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 thesyndicate.com. And if you’re an accredited investor and want to read the deal memos, we do about two deals a week. And I’m Jason on Twitter, twitter.com/Jason. And I have 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. Oh, I have one other 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.university. It’s been pretty successful. And the All In’s 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.

Trey Lockerbie (43:29):
Just that, just that.

Jason Calacanis (43:32):
I keep busy. I like projects. I come up with ideas. For every Founder University or syndicate, there’s four or five other crazy ideas I launched and shut down. I just like to try things. That’s the other thing I learned from all these founders I work with. If you think it’s possible that something will work, well, give it a try, man.

Trey Lockerbie (43:48):
I was going to say, is this the Elon influence?

Jason Calacanis (43:50):
Just try it. 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 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 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. These companies are in their second decade. And that is really the lesson of success is, how long can you suffer through a never-ending series of challenges? And 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 in society. Because they’re rare.

Jason Calacanis (44:50):
And I’m lucky enough to have a lot of those friends. And the next time you see six Teslas out of 10 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 have been so 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. I was like a witness to it, having been there from when he made the investment. And had to take over a CEO, which he didn’t want to do. I watched the whole thing happen. A lot of hard work, and sleepless nights and weekends.

Jason Calacanis (45:28):
And you see that over and over again. The fact that you can go order whatever food you want, and have in 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. That’s Travis. He’s suffered over that company. And there’s a lot of pain and suffering to create this delight, and to solve the world’s biggest problems. And we got a lot of problems we 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 put them in the same bucket, including my friend, David Friedberg.

Jason Calacanis (46:13):
And capital allocators. When you hang out with those three 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. Or the capital allocator who puts the money behind Tesla and saves it from going extinct. Or the entrepreneurs who run these companies.

Jason Calacanis (46:44):
And 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. 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 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.

Trey Lockerbie (47:27):
There was a tweet, just today, I think, by Marc Andreessen. It was prophetic and, I don’t know, it just really stood out to me. He basically said, “This is the moment, let’s build nuclear. Let’s frack. Let’s drill. Let’s go,” basically. This is-

Jason Calacanis (47:39):
I’m not so sure about the fracking.

Trey Lockerbie (47:40):
Well, yeah, of course, but I’m just-

Jason Calacanis (47:42):
And drilling strategically. If we have a drill a little bit right now, I’m okay with it. The time for nuclear, for sure. The other ones, I think, certainly, we need to be energy independent. Certainly, Europe does. But I think nuclear, solar batteries are the clear path.

Trey Lockerbie (47:56):
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. And you just mentioned suffering for decades to build a company. And that’s what it really takes to build something great.

Jason Calacanis (48:13):
Yeah. The progress that gets made… And so I always think in decades now, when I look at startups. Another 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.” And people are like, 2I 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% a week?” They’re like, “Well, then I would double in 7.2 weeks.” I’m like, “Do it, or try it, see what happens.”

Jason Calacanis (48:51):
And 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. And consumer products certainly have, Twitter, Facebook, et cetera. Compounding interest is really what it’s about.

Jason Calacanis (49:04):
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, and you make 10 things 10% better… It loads 10% faster. The logo is 10% better. The meditation sound quality’s 10% better. Everything gets 10% better. 10 things get 10% better. All of a sudden, people don’t realize it, but the product’s really nice. And I don’t know if you ever watched 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.

Trey Lockerbie (49:45):
But that moment, the moment of the motivational record he was listening to, where they’re talking about like, “Hey, how many thousands of talented people have failed? It’s not just talent, it’s the grit.”

Jason Calacanis (49:55):
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, “Ah, that’s one in a million, or that’s one in a thousand.” Most people fail to, “Well, somebody’s got to succeed.” So when I’m working with founders, I’m like, “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 going to succeed. The odds will be with you. If you do 3, 4, 5, certainly, one of them’s going to hit. So let’s go on this journey together.

Jason Calacanis (50:30):
And in fact, one of my great investments is Rahul in Superhuman, which we put $500k into their first round, their seed round, when he just had a deck, a three or four slide deck. And that came because I had invested in his previous company, Rapportive, because I liked this little toolbar he had made. And I emailed info@rapportive and introduced myself to him, and put a little bit of money into it. And when he sold it to LinkedIn and I tripled my money, and I said, “Just promise me, when you do your next company, when you do your tour at LinkedIn, I’ll be your first phone call.”

Jason Calacanis (50:58):
And literally, he called me on a Sunday and said, “Hey, Jay Cal.” And I was like, “Where are you?” He’s like, “I’m in San Francisco.” I’m like, “You want to get bagels?” He’s like, “Sure.” I was like, “I can’t wait to hear about your new company.” He goes, “How do you know I have a new company?” I said, “Because you promised me, you’d call me. And it’s two years after you sold. So you must have a new company.” He’s like, “I do.” I was like, “Okay.” He’s like, “When are we going to meet?” I’m like, “Where are you in the city? I can meet anytime in the next three hours.”

Jason Calacanis (51:20):
He sat in my house an hour and a half later. I said, “What’s the idea?” He said, “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 beat Gmail?” He’s like, “I’m going to be faster. And it’s going to be $1 a day.” I said, “Okay, you’re going to take on Google, with the largest server farms 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?” And he said, Well, 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. You’re building a Ferrari, not a Prius. Perfect.”

Jason Calacanis (51:56):
I said, “Tell me this thing about $1 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, it’s worth $60,000, so if you charge me $600, that’d be 1%. So you’re charging me 50 basis points, one 200th of the value I’m going to get.” He’s like, “Exactly.” I was like, “I’m in.” You want to talk about a contrarian idea. I’m going to take on a free product, Gmail. I’m waiting for somebody to come and be like, “I’m taking on Chrome.” And it’s like, “Taking on a browser that’s free, built by Google. Let’s go.”

Trey Lockerbie (52:44):
Jay Cal, 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.

Jason Calacanis (52:54):
Of course, of course. I appreciate it.

Trey Lockerbie (52:56):
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 @TreyLockerbie. And if you’re just starting out and want to learn how to invest in the stock market, go to theinvestorspodcast.com, or simply Google TIP Finance. And with that, we will see you again next time.

Outro (53:16):
Thank you for listening to TIP. Make sure to subscribe to Millennial Investing by The Investor’s Podcast Network, and learn how to achieve financial independence. To access our show notes, transcripts, or courses, go to theinvestorspodcast.com. This show is for entertainment purposes only. Before making any decision, consult a professional. This show is copyrighted by The Investor’s Podcast Network. Written permission must be granted before syndication or rebroadcasting.


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