Jason Calacanis | How Does Angel Investing Work? | Modern Wisdom 154

Jason Calacanis is an angel investor and podcaster. We’re constantly hearing stories of how people are making their millions and billions angel investing in Silicon Valley startups, but I have no idea how it all works. Thankfully I got hold of Jason, who was one of the first investors in Uber, Thumbtack, Calm and many more, to teach us everything there is to know about the industry. Get Surfshark VPN - https://surfshark.deals/MODERNWISDOM (Enter Promo Code MODERNWISDOM for 83% off & One Extra Month Free) Extra Stuff: Follow Jason on Twitter - https://twitter.com/jason Check out everything I recommend from books to products - https://www.amazon.co.uk/shop/modernwisdom #angelinvesting #siliconvalley #startups - Listen to all episodes online. Search "Modern Wisdom" on any Podcast App or click here: iTunes: https://apple.co/2MNqIgw Spotify: https://spoti.fi/2LSimPn Stitcher: https://www.stitcher.com/podcast/modern-wisdom - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: [email protected]

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  It would be like walking up to the betting window and be like, yeah, I'm gonna place a bet on this team. And you picked the wrong team than you intended. They give you the slip. Your team loses, you go to rip up the slip and you look like, oh, I made a mistake? Oh, I bet on the other team? Oh, I won?

• 0:17Chris Williamson?

  Fun fucking testing.

• 0:18Speaker 00

  Okay, great. Fantastic, right? Like, literally, that's the job of an investor. You just don't know which ones are gonna win. So you just basically treat everybody who's in your portfolio amazing. You try to just be as supportive as possible. Which is, you know, again, life is pretty simple. Just find the best people you can, invest in them, support the heck out of them. If it doesn't work out, and they did a good job, bet on them again.

• 0:49Chris Williamson?

  Jason Kalikannis in the building. How are you?

• 0:54Speaker 00

  What, what? How you doing?

• 0:55Chris Williamson?

  Fantastic.

• 0:56Speaker 00

  Thanks for having me on the pod.

• 0:57Chris Williamson?

  You are in the most beautiful studio that I think I've ever seen.

• 1:02Speaker 00

  Yeah, and you're in your bedroom.

• 1:04Chris Williamson?

  I am, that is true.

• 1:05Speaker 00

  With a lighthouse poster.

• 1:07Chris Williamson?

  With a what?

• 1:09Speaker 00

  With a lighthouse poster behind you.

• 1:10Chris Williamson?

  With a lighthouse poster, indeed, that is. But you know, we're all starting somewhere.

• 1:15Speaker 00

  With a wave crashing around it.

• 1:17Chris Williamson?

  It's very, it's chaos, right? What were we talking about just before we started? There's some chaos going on here.

• 1:22Speaker 00

  Chaos. Well, wait, where is that lighthouse?

• 1:25Chris Williamson?

  I'm not sure.

• 1:26Speaker 00

  Does it have some specific meaning?

• 1:28Chris Williamson?

  No, I'm not.

• 1:29Speaker 00

  What would Freud say about picking a lighthouse on the edge of

• 1:35Speaker 00

  human existence that's being pummeled by

• 1:40Speaker 00

  giant waves? What would that say about a man who puts that as the first thing he sees when he wakes up and the last thing he sees when he goes to bed?

• 1:47Chris Williamson?

  Can you tell that I'm-

• 1:48Speaker 00

  You a bit of a loner?

• 1:49Chris Williamson?

  Can you tell that I'm an only child, Jason?

• 1:52Speaker 00

  It does scream, I'm alone at the edge of existence. Yes.

• 1:56Chris Williamson?

  Can you tell that I'm

• 1:57Speaker 00

  But maybe you're opting into it. See, that's the thing about lighthouse operators. They're opting into it. Nobody's forcing there. It's not a jail. So there's a certain type of person who wants that solitude.

• 2:07Chris Williamson?

  Jason.

• 2:07Speaker 00

  Who wants that? That gig.

• 2:09Chris Williamson?

  Incredibly, incredibly perceptive, my friend.

• 2:14Speaker 00

  There you go. All right. Well, welcome to This Week in Freud. Okay, go ahead. For sure, man. Don't let me take it over in the first 30 seconds.

• 2:22Chris Williamson?

  That's fine. Do you find? So here's a question for you. I podcasting as a host, which you are, do you find it odd being on the other side of the mic sometimes? You slip into host mode?

• 2:32Speaker 00

  I do slip into host mode sometimes and I do start thinking like, no, this is the question you should ask. And you know, if you want me to answer that question, you asked me four questions, just the second one is the winner. That's what the audience actually wants to hear. Or why didn't you ask me this follow up question? Yes, that does go through my mind sometimes. It happens. It makes it very hard for me to listen to other podcasts. Because it becomes so obvious to me when the person who's doing, conducting the interview doesn't know what they're doing. And then it really makes it amazing when you listen to, you know, Howard Stern interviewing Hillary Clinton, or Joe Rogan interviewing Sam Harris, or Sam Harris interviewing anybody. You know, you start to realize, wow, some people are really great at this, right? And they all have different styles.

• 3:17Speaker 00

  And stylistically, you know, many different styles work. In some cases, it's very difficult for me when I know more than the subject. That was the thing I had to unlock as an interviewer. Sometimes I have somebody who's a guest and they know less about the topic we're talking about than I do. That doesn't often happen, but let's say it's angel investing or media, or something where I've spent, you know, a decade or two doing it. And they're a young founder. I, they're actually deferring to me and sometimes they might say, well, what do you think? And that's problematic. In fact, Evan Williams, who is very good at media, but I think, you know, we're, he's more successful than I am, having done Twitter and Medium and Blogger.

• 3:59Speaker 00

  But you know, I, I created better editorial brands at him, certainly with Engadget and the Speaking Startups, like singular editorial properties. So we have like long conversations. And when I interviewed him,

• 4:09Speaker 00

  Every time I'd ask a question, I'd say, "Well, what do you think? You did these other publications. You know, you did Silk and I reported. What do you think?" And I'm like, "Well, you're onstage in front of 2,000 people right now. I'm the interviewer." So, sometimes with people who are my friends or whatever, I'll just say, "Hey, listen, I might ask you a basic question that you know I know the answer to, or that you might be interested in my answer, but just humor me for the sake of the audience." And sometimes even interviewer, I'll say, "Hey, for the sake of the audience, can you explain what this is?" And I added that to my repertoire because every time I'd say, "What's, you know, a CPM? Explain CPM." They'd be like, "You don't know what CPM is? And you've been in the advertising business all time?" I was like, "No, I know, the audience."

• 4:52Speaker 00

  So then I have this way of coaching it and framing the question. Explain to the audience, or explain to somebody who doesn't know what CPM means. Cost per thousand, right? Anyway, you have to, you learn. I think somewhere after 200 or 300 of these like interviews, you'll get good at it. The problem is, most people in life... No, I mean, it's not a joke, either. I mean, I think a lot of people in life think like, "Well, I've done 10 podcast episodes, like, here we go. Where's my, you know, why are the ads not sold?" And it's like, "You might want to get to year three or four. You know, you might want to get 100, 200, 300 reps under your belt." Everybody thinks like, they go to the, you know, they shoot 100 three-pointers and that they're Steph Curry's. It's not exactly how it works.

• 5:34Speaker 00

  Maybe if you shoot like, you know, 1,000 a day for 100 days, you, you know, you might start to understand what shooting involves. You know, somewhere around the 100,000th.

• 5:46Chris Williamson?

  What makes a good podcaster, then?

• 5:48Speaker 00

  The best podcasters, in my estimation, are people who can't work for anybody else, and who don't want to work for anybody else, and who are fearless, and they have some level of respect from their audience. So if you look at Joe Rogan, if you look at Ben Shapiro, if you look at Bret Easton Ellis, if you look at the Red Scare, Dasha and Anna, if you look at Sam Harris, Leo Laporte, any of those folks, they are not working for anybody but themselves.

• 6:20Speaker 00

  You cannot aggregate them into a podcast company. God knows people have tried, Bill Simmons as well. They are singular voices who don't answer to anybody and so authentically connected with their audience that you know they're gonna say what they believe no matter what. And I think this goes to, you know, the influence Howard Stern had on the format of radio. Howard Stern was somebody considered a shock jock in the 80s and 90s in New York City and eventually went across the country here in America. And he would do shocking stuff, you know, would have strippers on the podcast, he would have, you know, a Ku Klux Klan member on the podcast. He was very outrageous. But then he kind of evolved and

• 7:03Speaker 00

  you started realizing, wow, he's so authentic and his interview style is so incredible that he gets people to share things that nobody else does. And they feel comfortable doing that. And that had, I think, a deep impact on me. Not the strippers and the Ku Klux Klan members, but the latter, which is, he's authentic, right? You know what he's saying is real. I think Charlie Rose also had that when he was on air. You know, you knew he was like actually reading the books or cared about the topics. He was an intellectual, a public intellectual who wanted to have these like really incredible discussions. Morley Safer, Oprah Winfrey. You know, there's a cohort of people who just got really good at interviewing people. And you can see that in podcasting. The reason podcasting is getting

• 7:43Speaker 00

  so popular right now is because the press and journalism and media is so broken. And that's leading to people wanting to, if you're a subject who was in the press a lot, like Sam Harris was in the press a lot, or Joe Rogan might be, or Leo Laporte might be, or Bill Simmons. You know, they were essentially throttled or mediated through the press. And when they got on a podcast as the host, now there's nobody editing them. Then you have their guests on, and then the guests are like, wait a second, you're gonna give me three hours to explain my point? Two hours? An hour? And I'm going to get misquoted by a journalist.

• 8:24Speaker 00

  And this is why journalism is really struggling right now is that the people who know the most are going direct to the audience. And journalists, by definition, only know 5, 10, 20% of the story. That's why they have to do research. That's why they have to hit the pavement. But because they don't control distribution anymore and they only have 10 or 20% knowledge of the situation, they can't compete with the people who are on the inside. They can't compete with people like me who, you know, invest in these companies. They don't have the knowledge base I have. A journalist can't. They're not doing it every day. Right? And I was a journalist. I was a founder and now I'm an investor and I'm still, you know, quasi-journalist doing my podcast. So it's a really fascinating time. And I think podcasting is a reaction to link baiting, SEO-driven content, content farming,

• 9:09Speaker 00

  and just the collapse of newspapers and magazines and those editorial formats, websites where people don't do fact checking and they write link baiting stories. People are tired of that nonsense and they want to go to the depth of a podcast where people feel that they're not going to be misquoted because I just gave you a six-minute answer to your question. As opposed to you gave me two lines in your story and just pick the ones that you think are the, you know, most interesting or, you know, most likely to get retweeted.

• 9:37Chris Williamson?

  The thing as well is that the ability to have time to play with ideas, right? To sandbox with ideas, to be subtle and nuanced and say something which isn't even quite formed. Whereas if you were to do an interview with a reporter and you play around with an idea which isn't quite formed and then that gets transcribed, that's precisely the loophole that they were looking for, right?

• 10:02Speaker 00

  I think so.

• 10:04Speaker 00

  I think that's exactly right.

• 10:06Chris Williamson?

  Cool. So I want to ask, everybody that's listening will have heard Silicon Valley, angel investing. But for me, as someone who likes to think that he is curious intellectually and learns about the world and does this podcast and we're on episode, this will be around about episode 150, so I might be about halfway to your bar of knowing, having an idea about what I'm doing.

• 10:30Speaker 00

  You think you'll get a proper microphone by episode 200?

• 10:34Chris Williamson?

  So right here.

• 10:35Speaker 00

  150 and using AirPods? What the heck's going on here?

• 10:38Chris Williamson?

  Right here.

• 10:39Speaker 00

  All right, all right. There, that's my boy.

• 10:42Chris Williamson?

  SM7B, I'm not fucking about, Jason.

• 10:46Speaker 00

  All right. Well, you know, you come on the podcast and you're in your bedroom and you got AirPods on. Or you not even have AirPods on. You got, you, you got cabled headphones on. But you do have the short SMB7. Is that right? SMB or SM7? That's the best microphone, by the way.

• 11:03Chris Williamson?

  SM7B, we're doing it. CloudLifter, OGNID14. We've got, the setup is here. Don't let it, don't let it fool you. And, but yeah, so Silicon Valley.

• 11:13Speaker 00

  Is your mom gonna come in with fish sticks?

• 11:17Speaker 00

  Is she coming in with fish sticks any minute now?

• 11:19Chris Williamson?

  That is, that's actually, well, because we're running about 15 minutes late, I've had to text her and let her know that she needs to push those back a tiny little bit.

• 11:26Speaker 00

  Push the fish sticks back a little bit?

• 11:27Chris Williamson?

  Yeah.

• 11:28Speaker 00

  Little bangers and mash coming? What do you got?

• 11:30Chris Williamson?

  Nice. That's some classic British food for you there.

• 11:33Speaker 00

  Any mushy peas there? Some chips?

• 11:35Chris Williamson?

  Tea.

• 11:35Speaker 00

  I like that fish and chips and the mushy.

• 11:36Chris Williamson?

  Yorkshire tea.

• 11:38Speaker 00

  Oh, I love a little tea. I'm having a little tea right now.

• 11:40Chris Williamson?

  Hey, I like it. We, did you come in, did you walk in with kombucha as well?

• 11:45Speaker 00

  No, I don't, I don't fuck with kombucha. I'm an adult.

• 11:49Speaker 00

  I'm a capitalist. We don't fuck with kombucha.

• 11:54Speaker 00

  Yeah, man, I'm not paying you $8 for some like fermented, like whatever. Come on.

• 11:59Chris Williamson?

  Something that someone else has already digested.

• 12:03Speaker 00

  Yeah, I don't, yeah, I'm not fucking with kombucha. Sorry.

• 12:06Chris Williamson?

  Got you. Right, so.

• 12:07Speaker 00

  That's quotable. I think that's quotable. Somebody put that on the, uh, the Reddit sub. Jake House not fucking with kombucha.

• 12:16Chris Williamson?

  Right.

• 12:17Speaker 00

  You get a Reddit sub of.

• 12:19Chris Williamson?

  Silicon Valley, right? Angel investing. It, it's a words that get thrown around a lot. I want to come to Floyd Mayweather, Angel Invest in Silicon Valley, and I want to learn how to throw a jab. I want to understand the structure of the industry. I don't know what seed extension is. I don't know what series A or series B or any of this bullshit. I want to know how the industry works. Can you, can you tell us how the industry works, Jason?

• 12:46Speaker 00

  Yes, I can. So there are companies being started all the time, right? There are mom and pop companies. There are pizzerias, there are movies and CDs created. And this is all entrepreneurship going on in the world, right? Somebody might start a design agency, somebody might start a PR agency, a dry cleaner, you get the idea. And these are all great businesses. They can employ people. Sometimes the owner can make a nice salary and be independent. Sometimes they can make even more than that. They can make a life for themselves, right? So that's all fine and well. What we do in Silicon Valley and in the venture capital industry is we look for the outlier companies, companies that can grow

• 13:29Speaker 00

  at a velocity that would be considered unrealistic, inhuman, bizarre to other people. And the best analogy I heard on this is that venture capital is like jet fuel. It's for rocket fuel. You wouldn't put rocket fuel like on a Vespa. Would not work out well. You're not trying to go mock whatever on those vehicles. So those vehicles are fine. They don't need a lot of money to start them. You can start a consulting firm for $0 today. You can just literally put up a free website and you can email a thousand people and say, here's what I do. And get three customers. The businesses we invest in, if you were to look at one like Uber

• 14:14Speaker 00

  or Robinhood or com.com, these are businesses that were intended to impact hundreds of millions of people, a billion people, large numbers of people. And that is a different type of business. And it requires a different type of capital and a different type of plan. Most of those businesses fail. And when they do fail, they fail hard. So. You have to also have a different expectation. If you're starting a consulting firm, you're really not going to fail. There's nothing really at stake, right? Like, what if I, we set up a website today and say, we're going to do a podcast consulting

• 14:55Speaker 00

  company, you know, C and J Podcast Consulting, and we're going to teach people how to do podcasts. Like, okay, if we get one customer a year, or 10, or 100, like, okay, I guess it's a success. It's more than zero. Whereas with a startup like Uber or Com, you know, you're, you're building something that is more complex and has a smaller chance of success. But if it does succeed, oh my Lord, it could change the fabric of society and humanity forever. And many companies have, like Google, Facebook, Uber, Airbnb. These things are changing society. And in order to do that, it's sort of an Olympic caliber sport. So that is the difference right now.

• 15:40Speaker 00

  You know, that's, that's the main difference in the type of companies we invest in. And so that's where most of the confusion comes in. People want to start a company that makes, you know, ginger beer or tea, or they're doing a company that has a noble purpose. And it's like, these do not qualify for the one in a thousand or one in 10,000 chance of an outlier. Therefore, you're not fundable by this industry. And that turns people off sometimes to the industry and they don't understand it. Or if I told you, you're going to start 10 businesses, six are going to zero, the seventh and eighth will return half the amount of money you put into them. The ninth will return two or three times what you put into it.

• 16:22Speaker 00

  And maybe if you get lucky, the 10th or the 20th or the 30th might return more than 30X. You put in a dollar, you get more than X. So it's a type of gambling and risk-taking that is very unique, very confusing from the outside. And even from the inside, the people who do this kind of gambling struggle with their own psychology and their own existence. So it's no doubt that it's confounding to everybody.

• 16:50Chris Williamson?

  Yes. To begin with, are tech stocks weathering when it goes due to scalability? Is it just the fact that that has the ability to really rocket off?

• 17:01Speaker 00

  Yeah, so I mean, if you look at public stocks, yeah, I mean, if you invested in Google, Netflix, or Amazon, you know, at their IPO, or anytime after the first five years of those companies, you'd be pretty happy today, I think. Facebook as well. And so, the companies are getting much larger today than they ever have, and I think they've become very resilient because they've been adding multiple business lines in a way that previous companies didn't. So, it used to be companies were one-trick ponies, they went public in year six, seven. Now you have companies staying private and going publics in year 10, 11, 12, 13, and they're much larger businesses, they're much stronger businesses, and then, once they get public, they get more ambitious, they start doing acquisitions, and they become

• 17:45Speaker 00

  super resilient. So, the resiliency of a company like Facebook, having bought WhatsApp, Oculus, and Instagram, three huge bets, or Google having bought Android, YouTube, much stronger businesses. And then, even in the classic businesses like Disney, having bought Pixar, Marvel, and Star Wars, you know, those companies now make them so much stronger that they're not reliant on just the Disney IP, you know, Snow White and Mickey Mouse, which, you know, those things could fall out of favor, but now they get this new life because they have all the Marvel characters, all the Pixar characters, and all the Star Wars characters, and all those worlds to just keep building and building and building.

• 18:26Speaker 00

  So, I think buying those kind of stocks, and I'm not a public stock picker, it feels like there's very little downside because the idea that Amazon or Google would go away anytime soon, or perhaps even in our lifetime, does not seem realistic. We did see Yahoo go out of business. So, previously, when they were one-trick ponies, like Yahoo was, or other companies, yeah, it might be more, it might be possible, like, you know, buying eBay or something. That's been a pretty resilient business, but, you know, they've got one business, really, and, you know, that does make it difficult.

• 19:06Chris Williamson?

  I get it. So, let's go back to the-

• 19:10Speaker 00

  We're investing in private companies, yeah.

• 19:12Chris Williamson?

  Yeah, yeah, let's go back to private. Where do you find these people? Are you walking down the street, you see some guy who's got a t-shirt on and says, "I own a startup"? Like, what happens?

• 19:22Speaker 00

  So the way I meet people is, you know, I have a podcast and amongst founders, I would be, you know, a celebrity on the scale of Lady Gaga or Michael Jordan.

• 19:36Chris Williamson?

  Have you got an outfit like Lady Gaga?

• 19:39Speaker 00

  Absolutely. I'm wearing a meat dress right now. Those of you listening, it's getting a little uncomfortable in the second half of the hour. You know, but outside of the industry, I'm a nobody, right? So when I lived in LA and I would go to industry parties, nobody would know who I was. And then when I'm in an industry party, you know, I might get asked to take 10 selfies in the tech business. And it really is a popularity contest amongst investors. Investors have brands and people want to be affiliated with different brands. So you might make an analogy of like creative artist agency or endeavor and the different agencies, William Morris Agency, whatever, in Hollywood. You get affiliated with an agency or you got affiliated as a musician with a record label.

• 20:23Speaker 00

  You know, you then become validated, you become anointed in a way, and it gives other people permission to engage with your startup or in the case of CIA and agencies or labels, music tours, whatever, movies. So a lot of what we do here is we anoint people and we fund them and then we tell them where the landmines are and we say, you know, let us know if you make it to the other side and how we can help. And, you know, it's, it really is basically like you're sending, you know, these founders into a war zone and you see who makes it to the other side. We see who, you know, the, the good news is it's not fatal, you know?

• 21:07Speaker 00

  And so if you fail and two out of three or three out of four startups fail, depending on, you know, how you measure it, might be even greater based on, you know, the number of experiments being run today by founders.

• 21:21Speaker 00

  You need only start three, four, or five companies to have a likelihood of success, right? So that's what I tell people when they, when their first company fails is that like, you know, Travis's third company was Uber. You know, Elon's third, one, two, three, a third or fourth, third and fourth companies were SpaceX and Tesla, right? So a lot of times people do their best work on that third time up at bat, fourth time up at bat. That actually seems to be a sweet spot, right? You're not like as nervous. Some people, Bill Gates, Jeff Bezos, Mark Zuckerberg, they hit the home run right out of the park. That's not common. It's memorable, so there's a survivorship bias to it. The fact that those companies have become big, or confirmation bias rather, not survivorship. Maybe it's both.

• 22:03Chris Williamson?

  It's uncommon amongst uncommon situations, right?

• 22:06Speaker 00

  Yeah. It is very uncommon for somebody and their first company to hit a giant outlier success. But because when it does happen, it's so memorable that it feels more common than it is, which I believe is the definition of confirmation bias or survivorship bias.

• 22:28Chris Williamson?

  Survival.

• 22:29Speaker 00

  Survivorship bias is like, okay, well, these people survived, therefore there was something, you, you, the fact that they survived, you read something into who will survive the next time, right? The, the problem with that was, the, the way they can't, they figured out survivorship bias was they looked at planes in World War II that had actually, where the bullet holes were when they landed. And they found the bullet holes, you know, were in all these different places and they were like, okay, well, this is what we need to fix or whatever. What they didn't realize is, those are the planes that made it back, got hit in the wing and didn't get hit in the cockpit or the engine. So it turns out that they weren't including in the sample where the bullets were on the

• 23:12Speaker 00

  planes that went down because they couldn't recover those planes because they blew up in the sky and crashed. Those ones got hit in the cockpit and the pilot got killed, or they got hit in the engine and the gas tank exploded, right? So you get this weird, you know, bias that is, you know, not, and that's one of the reasons why people who are in the VC industry are constantly trying to figure out the cognitive frameworks and biases and there's podcasts just about these things and there's people studying just these things. So that we as people placing the bets can try to figure out a model to unlock this. Like it's the fountain of youth or something, right? And that's a major problem for people is that the randomness that occurs here fools people, right?

• 23:56Speaker 00

  And then they start thinking, oh, well, I hit Uber, therefore I'm a great picker. And that's just not the case, right? Like, I don't think I'm a great picker. I think I have a great network and I have great relationships.

• 24:08Chris Williamson?

  Sounds like there's a lot of chaos going on.

• 24:11Speaker 00

  Yeah, I mean, one way to think about this job of venture capitalists or just investor in startups is 99% of my time is spent on the failed companies. So let me just say that again. You know, if you invest in, you know, 100 companies over your career and you look back on the time you spent, in all likelihood, you're going to have spent something in the range of 90% on the companies that failed. The companies that succeed, you go to the board meetings, they turn over the results and you go, well, that's more than we expected. And you're like-

• 24:47Chris Williamson?

  Everyone pats everyone else on the back, high fives.

• 24:50Speaker 00

  A bunch of high fives, yeah. I mean, and you know, I've had this in a number of times in my career where it's going up and to the right and the last thing I want to do is go, you know, hey, let's spend some time together screwing up your formula, right?

• 25:03Chris Williamson?

  Just you keep doing you. You keep on pushing whatever button you're pushing.

• 25:07Speaker 00

  Yeah. Yeah. And I mean, you could study it to figure out if you can accelerate it, you could study it to figure out if there are margin issues, competitive issues. There's a lot to do, even on the successful companies like- When your company's scaling, you need to hire a lot of people. You need to watch out for competitors. You need to build infrastructure. You need to have things in place that keep this very fast-moving rocket ship from blowing up as it gets to orbit. It's the ones that never even get the rockets to the launch pad that I spend a lot of time on. It's like, okay, is the rocket finished? Great, okay, are we gonna fire the rocket? Oh, there's no jet fuel in the rocket? Okay, great, okay. Oh, you don't have any astronauts either? Okay. Yeah, it's gonna be kinda hard to get to space without those two things. We're gonna need some jet fuel, we're gonna need some astronauts. Like, you know, we're gonna have to finish the rocket.

• 25:52Speaker 00

  Oh, the rocket's not done? Oh, okay. We gotta finish the rocket. If we've got any chance of getting to orbit. So, it's a chaotic job. The last week, just to give you a picture of my life with over 200 investments, the last week I've spent dealing with chaos at four companies. So, 2% of the company is just completely chaotic. And with these startups, they're almost inevitably running out of money, facing existential threats externally where Google's gonna make their product free, let's say. Or, you know, they're getting really well-funded competitors who then decide they're gonna give away $100 bills for $50 and take all the customers, you know?

• 26:36Speaker 00

  Which is what Lyft did with Uber and Uber did with other people. Like, they get into these crazy wars of discounting and, you know, it's pretty scary. So, yeah, I deal with a lot of chaos.

• 26:48Chris Williamson?

  So, how much, to step in there, sorry, Jason, how much of that is you coming in and massaging people and just saying, let's everyone chill out, let's bring a little bit of order to this chaos?

• 26:59Speaker 00

  Yeah, no, a big part of my job, that's why I liked your lighthouse poster so much, is, you know, when you look at that lighthouse, it's like, yeah, there's a giant wave, it's nature. Doesn't, you don't get the sense that that lighthouse is gonna get knocked over, right? And that's really my job, it's the job of the founder is, of any leader, is... To convince everybody that there is a plan and that we can succeed if we follow the plan and we stick together and we execute at the highest level possible, our chances, if we work together are greater than if we don't have a plan and we don't work together. And so a lot of what I will be talking to a founder about is, okay, what does success

• 27:43Speaker 00

  look like? What's the plan to get to success? Who do we need to be on the team to get to success? Okay. What are the other tactical issues going on? Oh, we're being sued by this person. Oh, we have to get out of this lease or oh my God, we've, you know, got these competitors. Okay, great. But let's focus on what's the goal, what's the plan, and who do we need to execute the plan to achieve the goal? And it's very hard to stay focused. You know, when there's bombs going on all over the place, it's very hard. And, you know, I spent some time working on an ambulance and it was always taken by the people who were in charge. My brother's a firefighter and lieutenant and, you know, when you watch

• 28:24Speaker 00

  those leaders in really chaotic situations, they just come in with a surgical precision and this level of calm where they're running into burning buildings or, you know, my first call on an ambulance was the night before Thanksgiving and maybe the late 80s, early 90s, and somebody had been stabbed right above their heart. And it was like, oh, this person could die. It's a coin toss situation. And just watching the calm at which people were able to triage these situations is always very impressive to me. And I always think about Samurai or Jedi in that regard, which is why there's a poster of Toshiro Mifune in the office. And, you know, if you look at Samurai's or Jedi Knights who were modeled

• 29:07Speaker 00

  off of Samurai, I think it's a very good metaphor for leadership, which is like, these are very powerful people who don't often take out the sword. They're going to figure out solutions. They're very focused and they're, they know how to block out what is not essential, right? So it's a great scene where Quijong Jim is fighting Darth Maul and these uh this wall gets like a laser wall gets blocking the two of them and Darth Maul is like pacing back and forth like a cheetah, you know, like in a cage. And Quijong Jim just kneels down, turns off the lightsaber and meditates and closes his eyes. And you know, really, that's like, I'm going to conserve my energy here and think about what the right decision is because those doors are going to open and it's going to be chaos.

• 29:52Speaker 00

  And if you look at a scene like the movie Gladiator, there's a scene where Maximus says, listen, whatever, anybody here in the army, great, come next to me, we're going to fight together. Whatever comes through those doors, we have a better chance of succeeding if we fight together as one. And he gives this big as one speech, you can look it up. Or there's another great scene in a movie called Black Hawk Down where the snipers say, listen, we got to go in and protect the pilots of that other Black Hawk, drop us in. And they said, listen, we don't know when we're going to have reinforcements. So if we're dropping you in, I need you to confirm with me that that's what you want and that you recognize that we don't know when we can get your reinforcements or if we can ever get reinforcements there and we're dropping you into this hostile territory

• 30:33Speaker 00

  where it's going to be the two snipers versus thousands of Somalians who are armed and are surrounding the helicopter. And you know, that's a, I use those metaphors because they, in each of those cases, people are working together and they're blocking out things that are not important and they're focused on what is important. And that really is what entrepreneurship and leadership is about, that ability to focus in, slow down, take that breath and say, okay, this is a dangerous situation, this is a critically dangerous situation, this is a, you know, they're going to drop us into this, you know, situation in Somalia and we're not going to get out in all likelihood, but we're going to take that chance anyway and we're just going to focus and let our training and our plan execute itself, you know, whatever happens.

• 31:18Speaker 00

  Now, those are all violent, crazy situations, but those are the metaphors I choose. I'm sure somebody else could come up with a much more peaceful one, but God, in my experience, it's a fucking war.

• 31:29Chris Williamson?

  I like yours. I like your ones.

• 31:31Speaker 00

  Running these companies is a fucking war. It really is. And that, and that's just the successful ones, you know, the ones that are not successful, you know, it's, you know, it's a war and chaos and.

• 31:47Chris Williamson?

  Whilst fighting the coronavirus.

• 31:49Speaker 00

  While fighting the coronavirus. Yeah, exactly. Like, those are, and those are things that are outside of your control. You know, imagine you're in the hardware business right now, which is hard enough. You're building a hardware startup, and you've got shipments coming from China, or you're supposed to have your hardware solution, you know, that clients paid for, and now it's, you know, lost in customs or something. Uh, there's a business disruption. Business disruption for, for Apple with hundreds of billions of dollars in the bank? No problem. Business disruption with somebody with six or 12 months of runway in the bank? Big problem.

• 32:21Chris Williamson?

  How much of what you've alluded to there, which is your ability to work out the controllables and the uncontrollables, bring a little bit of order to this chaos? How much of that is learned and how much of that is your constitution? And if it's learned and what elements are, would you be able to talk about a routine or any of the things that you do which tend to help you with that regard?

• 32:44Speaker 00

  Well, um, I would say, you know, some folks are the product of their environments, um, and that's their primary driver, and then other folks are very good at adding skills. Um, and, you know, I, I think you could probably do both. You know, Tim Ferriss, uh, the seeker, as I call him, you know, he seeks out knowledge and he learns it and he advances, um, and learns very quickly. That's kind of his thing. He just adapts and learns new skills very quickly. So it clearly can be done. Uh, but there is at its core, I do think, you know, uh, some situations that are high pressure that people grow up in that do define them.

• 33:25Speaker 00

  And so one theory I heard, I don't know if this is correct or has any basis, but it, it certainly is an interesting one to consider, is that a lot of the great founders, uh, who are good and operating in chaos and under stress, had a situation where one parent loved them very much and one parent maybe wasn't as available or was actively Cruel or mean, and that person then had to balance and learn to solve this problem every day of their life and their childhood, right?

• 33:56Chris Williamson?

  That's interesting.

• 33:56Speaker 00

  Two parents, you know, one who loved them and one who was chaotic or something, and they had to just make sense and navigate that. It does ring true to me. I mean, obviously, we see over and over again immigrants really overperform an index, you know, in terms of the percentage of them leading very large companies and their leadership ability. Something about immigrant parents and, you know, the work ethic that maybe people see in their parents when they work three jobs and they put in 60, 78 hours a week and they force their kids to study because they say, "I don't want you to have to work 90 hours a week." You know, there's something positive about that, which is, you know, why it's a little bit heartbreaking that we have this nationalism where we don't want to let in the people

• 34:39Speaker 00

  who are taking the greatest risk in the world, leaving one country to come to another to try to make a better life. It's like those people are, you know, under such incredible duress, just doing that, that they become exceptional citizens, I think, by and large, and become incredible for those countries that get to receive that gift, right? Like, if you look now in Silicon Valley, the number of Indian Americans who are leading companies out here is just extraordinary. And we had just a massive influx of Indians who suffered greatly, you know, in their journey here and to build a new life here, faced racism, faced, you know, having to work menial jobs

• 35:21Speaker 00

  to build stuff up and incredible work ethic and incredible focus on education. And now, Microsoft, Google, I mean, the number of Indian Americans running companies is just stunning and amazing. And now we want to not let them in to the country? It's bonkers, right? I mean, it's very sad for England, it's very sad for America.

• 35:42Chris Williamson?

  How about for you? How about you? Talk to me about your constitution. Talk to me about what it is that you're...

• 35:49Speaker 00

  Oh, me?

• 35:50Chris Williamson?

  Part of your practice as well. Talk to me about what makes, what sets you apart.

• 35:56Speaker 00

  Well, I definitely fall into the category of the or the archetype of like growing up in a difficult situation, Brooklyn in the seventies and eighties. Um, you know, my dad losing his bar when I was 18 years, 17 years old, uh, and just growing up in a bar and just seeing chaos all the time. I think, and then practicing martial arts for many years and running marathons. I think I just got a level of discipline and fortitude. Um, that, you know, I think some people, maybe they have a reaction the other way. They become, you know, they give up or whatever. Um, I, for whatever reason, just grew up a fighter and I, I mean, I still have that fighter mentality. Um, you know, they now, I'm super aware that the analogies I

• 36:38Speaker 00

  use, uh, you know, are these war and violent ones. Uh, or, you know, or non-violence in the case of the Jedi and Samurai, just violence is a last resort. So, you know, I, I am incredibly hardworking and dedicated and loyal and maybe, you know, to a fault. Um, at times, just not letting things go, right? So I have a hard time letting things go. Companies failing, you know, businesses failing, projects failing. I just have a never say die attitude, which is probably long-term not a great idea for returns. Being able to

• 37:19Speaker 00

  cut your losses and give up and move on and use that space to do another project is likely the better scenario as an investor and as an individual. Um, but you know, I, I just don't like giving up. I like to fight until the last, you know, arrow, the last bullet.

• 37:34Chris Williamson?

  You think you work on that moving forward? Do you think you'll maybe try and, try and, try and develop that a little bit moving forward? Or is it something that you're glad is a curse that you have to suffer for the strengths that it gives you?

• 37:48Speaker 00

  Yeah, I kind of like it. I'll be honest. I kind of like it. I like, you know, being against the odds, you know? Uh, I like the fear. I, I sleep better at night knowing I fought till the end, you know? And I feel like that's my job. Yeah. I mean, when I'm with the founder, I always tell the founder, You know, what do you want to do? You want to keep fighting or do you want to, you know, close this chapter of your life and move on to the next one? We will be here either way. If you want to keep fighting, I'll fight with you.

• 38:19Speaker 00

  If you want to shut the company down or sell it for parts to Google or Facebook and spend two or three years there licking your wounds and resting, investing and collecting a giant salary on the roof of Hooli while drinking cocktails or whatever. Fine, let's do it. And then we'll, we'll come back in two or three years and, and kick ass again. And so I kind of leave it up to the founder. That's the balance I found. My natural inclination is to fight, fight, fight and never give up. Because I've seen so many times that, you know, month 18 or month 30, a founder figures something out and the company goes supernova. And sometimes the idea is just not a great idea.

• 39:01Speaker 00

  And so you should, where the market conditions are just horrible and you're, and you're just fighting against something that you cannot beat. You know, like if you're fighting against like, you know, a tsunami, like it's, you can't swim your way out of a tsunami in all likelihood, right? And you probably want to retreat. So there's, there's a time for retreating. It's just not in my nature generally.

• 39:26Chris Williamson?

  I get it. I get it.

• 39:27Speaker 00

  And that, and I think it's, I think it's actually a limiting factor at times for me. I probably should cut my losses on a lot of things and just say, yeah, you know, it doesn't look like this business is going to work out. I wish you luck with it and we have to focus on the winners. I just have a very hard time doing that. I know VCs who do it really well. And I'm just amazed that they can just be like, yeah, that didn't work. We've committed as much capital as we want. We're going to get off the board and we wish you luck. Let us know if there's any way we can help. And I'm like, wow, okay.

• 39:57Chris Williamson?

  Super rational approach.

• 40:00Speaker 00

  It's a much more efficient approach, I think. And I see VCs do it all the time. They're just like, yeah, it's not a fit for us, you know? We're not going to keep going, but you know, we'll give up our board seat and yeah, if you want to buy us out for 10 cents on the dollar, whatever, you know, it's your company, you do what you want. But they kind of walk away from it.

• 40:18Chris Williamson?

  Yeah, it must be challenging. I would find it challenging to not become emotionally invested. You know, to not have that, that part of me that wants more than what the figures say, that has faith beyond what the balance sheet shows me, beyond what the, what the stats are. I don't know.

• 40:36Chris Williamson?

  I don't know whether that's personifying. I don't know whether that's trying to,

• 40:41Chris Williamson?

  trying to personify businesses almost as beings, you know, with personalities and stuff like that.

• 40:48Speaker 00

  Yeah, I mean, in order for another door to open, sometimes you got to close one. And sometimes you got to reinvent yourself. So it's, you know, I used to be a journalist and, you know, I think I took that as far as I wanted to take it. I still dabble by doing this podcast, et cetera, but it's not exactly, I don't do it for journalistic reasons exactly.

• 41:11Speaker 00

  And so sometimes you got to close the door on what chapter of a life in order to focus your energy on another. It's pretty much that simple. And for founders especially, because you can't do three or four companies at once, or two or three projects at once. It never really results in an outlier success, right? People look at what I'm doing. They're like, oh my God, you're doing so many things. And it's like, yeah, just, if you actually looked at what we're doing, it's all very strategic. It looks like there's a lot of activity, but it's really just two types of activity. One is providing a bunch of information to founders that help them. And two is investing in them. That's really, everything we do falls into those two buckets.

• 41:48Chris Williamson?

  So it looks from the outsider looking in like you're potentially spinning an awful lot of different plates. Whereas it's been streamlined into two very discreet areas, which allows you to then scale the volume that you're doing that.

• 42:03Speaker 00

  Correct. Yeah, I mean, we have one thing like podcasts and events and books, right? So like, oh, you wrote a book. Oh, you're doing a podcast. Oh, you're doing a lot of podcast episodes. Oh, you did a second podcast, Angel. Oh, and you're doing the launch festival and scale and Founder University and Angel University and Angel Summit. It's like, yeah, those are all one thing. That's just a way to meet people in the industry and let them, you know, share knowledge with each other. And we, as the hosts of the sharing of that knowledge, hopefully, people remember our names. So we can do number two, invest in their companies. That's it. It's literally two things. But, you know, if you looked at our Asana project

• 42:45Speaker 00

  board or our Notion or, you know, our customer support line, whatever, like, you would see a lot of different activities, but they all kind of fall into those two buckets. So it's sort of like, wow, Disney does a lot of things. It's like, yeah, they do Star Wars and they do Marvel and Marvel does Avengers plus Marvel does, you know, these other brands or whatever they do. You know, people outside the Avengers, they're doing Spider-Man and, you know, the X-Men as well, right? But then you look at all of it. It's like, yeah, they entertain people. Okay, do they do anything else? Well, they do the parks, but that's entertaining people. They do movies that entertain people. They do streaming. So it's entertain people. Okay,

• 43:26Speaker 00

  so they entertain people? What else do they do? They let you buy stuff that they entertained you with. Oh, okay. So I can buy like a Star Wars figure? Yep. You can buy, you can buy a Star Wars lightsaber. You could make one yourself. You can buy a Marvel T-shirt. You can buy a Marvel lunchbox. Okay, so their business is entertaining you and then selling you merchandise that was burned into your brain because you watched and you were entertained by it. Got it.

• 43:52Chris Williamson?

  It was burned so deeply that you forgot that they were doing it, forgot that they were doing something different.

• 43:57Speaker 00

  I mean, what other business do they have? You know, you look at and say the theme parks are different, or there's all these different themes in the theme park, right? They did Star Wars land, they do whatever land, this land, that land, Pixar Cars land, whatever. You know, they have Epcot Center, Disney World, Disneyland, whatever. It's all the same thing. They're entertaining you. You pay the money, they entertain you. And maybe you buy something on the way out. That's it. Any other business Disney is involved in?

• 44:22Chris Williamson?

  Is there something sort of symbolic or structural that people should be looking to, to apply for that, which is where you have a particular skill set within your life? How can I then scale that skill set so that it then dips into other areas? I'm allowed to then iterate on that, on that particular ability?

• 44:43Speaker 00

  It's good to understand what you're good at. That's for sure. I like to tell people what their superpower is, as I perceive it. And I, or I ask them like, do you think your superpower is this? And, you know, different superpowers can work for different things. Some people are engineers, like Elon's an engineer at his heart. Like he's, he's really a physicist and engineer who knows how to build stuff. And if you look at what he's building, like he's really good at metal. Like, a lot of what he does is like building parts and metal and shaping it so that it can go to space, or that electric car can be lighter and go further range. And a lot of the shit he learned at SpaceX went to Tesla and Tesla to SpaceX. Like, material science and engineering is what he does.

• 45:28Speaker 00

  And people will think like, oh, there's a lot more going on here. It's like, is there? Right? Like, he's, and he's, he's an engineer and he's a great engineer. And people, you know, look at him more like Steve Jobs or whatever. Steve Jobs wasn't an engineer, right? I think, I think Steve Jobs is a marketer, right? He knew like a packager, like he really understood how to package and market something to people, simplify it maybe. Like, maybe he's at his core, Steve Jobs was like, just a great designer of products, right?

• 45:56Speaker 00

  And, you know, a brand builder, right? Like, he built a brand and packaged stuff. He's really a packager, now that I think about it. Like, he made this package, Apple, it meant something, it evoked something, simple, clean, opening the box.

• 46:09Chris Williamson?

  Beyond the tech.

• 46:10Speaker 00

  Going into the store, using it, all the, yeah, all the experiences. So it's kind of like an experienced designer. Yeah, I just Corey's an experience designer. Actually, probably the best way to say it. He's an experience designer.

• 46:23Chris Williamson?

  I'd agree.

• 46:23Speaker 00

  Because the store is an experiencing, using your phone, using your laptop, opening up your phone, taking it out of the box. It's all an experience.

• 46:31Speaker 00

  And so, yeah, you need to know what you're good at. I'm a talker. Like, my skill set is talking. That's my superpower is talking. And so I do a podcast and then I talk to founders and I run an accelerator where you talk a lot about people's hopes and dreams and strategies to succeed. So talking is a good one.

• 46:49Chris Williamson?

  Precision with your speech is something that I think is a very, very under regarded superpower, something that I encourage a lot of the people that are listening to do if they're not having a conversation with a friend for 30 minutes every week, where they're undistracted and they're talking about something that they care about and that they're genuinely engaged in. I find the process of doing a podcast and recording, I find it therapeutic and sharpening and honing in terms of the skill and what it then enables me to do outside of that in a way that I never had before I did this and I wouldn't.

• 47:19Speaker 00

  Do you feel more energy when you finish the podcast than when you started?

• 47:25Chris Williamson?

  Yes.

• 47:27Speaker 00

  Right. So you're an extrovert, not an introvert. You come out of a discussion like this with more energy, more inspired than you do going into it. And people who are introverted would come out of this and feel exhausted and they would need to take a break and read a book or take a nap or be alone. And so that is really the energy of those two different archetypes of humans, introverts versus extroverts. And knowing that, like, some people, you interview them and they're just like, I, this was like exhausting for me, right? Other people, they're like, great, let's do hour two, let's do hour three, you know, they just want to keep talking. And so, you know, it's very important for you to understand what your skill set is, what your personality is, what you enjoy, and then lean into that.

• 48:10Speaker 00

  Because the truth is, when you're starting a company, you can always get other people to fill in. So if you're Elon and you're a great engineer, or you're Steve Jobs and you're a great, you know, experience designer, or you're a great talker and, you know, or you're a great sales executive, you can, you can acquire those other skills from other team members. You don't need to have them. So this idea that there's one type of founder, I get asked that all the time, how do you pick the founders? What founders succeed most often? And the founders that succeed most often are the ones who are self possessed and don't give up. It doesn't matter if they're introvert, extrovert, it doesn't matter if they're sales, marketing, product, developer, engineer, visionary, talker, leader, manager.

• 48:55Speaker 00

  All those different archetypes succeed all the time. There is no commonality, I don't think, other than people who are super self-possessed, and they're very focused, and they don't give up. So if you're going to look for traits, introvert, extrovert, what job they did previously, and how well they did that job, it's probably not as important as those other softer skills, which are actually the harder ones, which is, does this person really care about this idea? Are they going to quit? Will they give up? Or are they going to build a plan, get a team, and pursue the goal? And it really is that simple. What's the goal here?

• 49:40Speaker 00

  What's the plan? And who's going to execute the plan? And man, I can't tell you the number of times you ask that to a founder, and they don't have a plan, and they don't have a goal. And I tell everybody our goal here, when they come work at Launch, our investment company, launch.co, you can see our website, just a simple website. Anyway, what we do here at Launch is we invest in companies, and our goal is to be the best investors in Silicon Valley, or the best investors in the world, period. We want to be the best investors in the world. So we just work backwards to what does that mean? Well, we think it means supporting founders early. That's the tactic we're using, that's the plan. And the plan is to invest in 80, 90, 100 companies a year, and in 10 years have 1,000

• 50:23Speaker 00

  investments, and invest 10 times as much in the winners as we do in the ones that fail and go out of business. That's it. That's the plan. Let's execute on it. Podcast, big part of it. Podcast, we get to put our founders on the podcast, This Week in Startups. We get to put investors on the podcast, angelpodcast.com. We get to meet new founders on the podcast. I met the founder of com.com and invested in the company because he was on the podcast. And it's a tool. It's a tactic. It just happens to be a tool and tactic that is in my wheelhouse as the leader of the company, right? But I make it very clear for people, this is why we're here. And you know what? It's a lot of work to work with 100 companies a year. Because that means we got to meet thousands.

• 51:07Speaker 00

  And we have to sort through 10, over 10,000 to meet with a couple thousand. You know, we're going to meet with 2 or 3,000 companies this year after having gotten pitched by over 10,000, right? So just start thinking about those numbers. So if we meet 2, 3, 4,000 companies in order to get down to 100 investments, it's a lot of work. It's a lot of work.

• 51:27Chris Williamson?

  And you're searching for that potential payoff at the end, right? Which is that asymmetry is exactly why it's there.

• 51:34Speaker 00

  And nobody knows. And nobody, there's the punchline, nobody knows what's going to work. So, by the way, we're going to place a large number of bets, meet, we're going to place 100 bets after meeting thousands of people, after sorting through tens of thousands, and we don't actually know.

• 51:51Chris Williamson?

  And it might not work.

• 51:51Speaker 00

  Which one of the 100 every year is going to be the breakout. And in fact, if we all bet, if the 12 members of the team each picked two companies each, I doubt that we would, even picking 25 of them, I don't think the majority of people would pick the winner. I don't think, I thought Com.com would be the second best company in my portfolio. I did think Uber was going to be, you know, a very successful company. But I thought a billion or $2 billion company, not a $60 billion company. So I was off by 60, 30 to 60.

• 52:24Chris Williamson?

  Quite a bit, yeah.

• 52:25Speaker 00

  So even, even though I knew it was a winner, I didn't know the magnitude of it, you know? And Robinhood, like, stock trading app for millennials, like, I invested in that company and didn't think it was going to work. I thought the founders are incredible. I'm not sure their first idea is going to work, I think it'll probably be their second or third, and I was wrong. And delighted to be wrong.

• 52:45Chris Williamson?

  It's the best way, the best way to be wrong in history.

• 52:51Speaker 00

  Yeah, it's to place a bet and win. It would be like walking up to the betting window and be like, "Yeah, I'm gonna place a bet on this team." And you picked the wrong team than you intended. They give you the slip. Your team loses. You go to rip up the slip and you look like, "Oh, I made a mistake? Oh, I bet on the other team? Oh, I won."

• 53:10Chris Williamson?

  Fun fucking test.

• 53:11Speaker 00

  Okay, great. Fantastic, right. Like, literally, that's the job of an investor. You just don't know which ones are gonna win. So you just basically treat everybody who's in your portfolio amazing. You try to just be as supportive as possible, which is, you know, again, life is pretty simple. Just find the best people you can, invest in them, support the heck out of them. If it doesn't work out, and they did a good job, bet on them again.

• 53:37Chris Williamson?

  Come back, they'll do it again. I got two questions before we-

• 53:41Speaker 00

  Well, they'll definitely do another company again. They may fail again, but, you know, like I said, three out of four fail, then you only need to do four to get to a winner in all likelihood.

• 53:48Chris Williamson?

  I get it. I got two questions before we finish up, Jason. First one, going back to podcasting, someone who's been in the space for quite some time, 60 million plus plays, is that even more now, more than 60 million?

• 54:00Speaker 00

  Probably more, but whatever. I mean, we did 10, we've been doing it for 10 years and over 1,000 episodes. So it's still a boutique podcast. I mean, we're only talking about 200,000 people listening to every episode. It's no Joe Rogan. It's not millions of people listening to everyone. It's, you know, it's a boutique podcast about a very specific niche thing, but that niche thing, we're better than anybody at doing.

• 54:20Chris Williamson?

  So-

• 54:22Speaker 00

  I think that's what's important.

• 54:23Chris Williamson?

  Been in the space for a long time. Where do you see the podcasting space evolving over the coming years? What's next? More of the same?

• 54:30Speaker 00

  Well, I think the, I think the listening, the listenership's gonna, you know, double in the next year or so, because I think we're like right at this tipping point where it's starting to hit the public consciousness. And like with this election cycle, the fact that Bernie Sanders was on Joe Rogan, or-

• 54:49Speaker 00

  You know, that, you know, even presidential candidates are, and not just Andrew Yang, right, like not just like the 10th person in the race, but you know, the top person in the race is, are going on podcasts, or people who are writing really important books are now looking at the podcast as the better way to sell their book than going to the press. And consumers are realizing, reading journalists and publications is fine. And, you know, once in a while, there's going to be like a really important story, and that's great. But overall, if you really want to go deep into a subject, there's a podcast for it that's going to be better. And it'd be better to hear from the subject for an hour or two than to read the story where they were quoted once or twice.

• 55:34Speaker 00

  That, that's why journalists, the savvy ones, are getting so into podcasting. They're realizing they'll get more out of the same subjects in the same amount of time by recording it and releasing it whole. That's the big unlock. So when I had Dan Rose, formerly of Facebook and Amazon now, Kotu, he's the only person who's ever worked for Jeff Bezos and Mark Zuckerberg, and he did an incredible podcast. And, you know, he's probably would be very shy if the Wall Street Journal, New York Times, Washington Post, TechCrunch, Recode, or any other person called him because their guard would be up. And be like, okay, what's the story? Oh, you're doing an anti-Facebook story? Oh, you're doing an anti-Amazon story? Oh, you're doing an anti-Facebook and Amazon story?

• 56:13Speaker 00

  Oh, you're doing an anti, oh, Jeff Bezos gave away $10 billion to fight global warming, and nobody has ever put up a fraction of that? Oh, but he didn't give away all of his money, so let's criticize him because he only gave away 10%. It's like, literally, the guy just gave away the largest gift in the history of giving, except for Bill Gates and Warren Buffett. But I, I think it might still be the single largest gift ever. Puts him number three in philanthropy, I think, or four. But it's not enough. I think it's Gates.

• 56:46Speaker 00

  And literally yesterday, all the press was criticizing him. And, and the press is wondering why the top subjects don't trust him or don't want to work with him, or why Trump's rhetoric on fake news is so powerful. The reason why Trump is able to say fake news is not because the news is fake. It's because journalists haven't been doing a great job balancing out and be, and, and, you know, going straight down the middle with objective journalism. Because journalists have picked a side, they gave up objective journalism. And they went towards link baiting in order to save their publications, right? Because Fox showed if you pick a side, you win. So the New York Times is like, okay, we'll pick the left, MSNBC on the left, Fox on the right, Wall Street Journal on the right.

• 57:31Speaker 00

  So everybody's just picking a side and your subscriptions go up. So if you pick a side, your subscriptions go up. Anybody in the middle is toast. If you're going to go straight down the middle, people are just like, oh, okay. Well, this doesn't make me emotionally vested in what you're doing. You want to take down Trump? Great. You want to keep Trump in office and you want to troll the libs? Great. I'll give you money for those two things, but I'm not going to give you money for objective journalism right down the middle. And, you know, journalists have responded to that market condition and, you know, it's a, the proper decision in terms of keeping the lights on, it's the wrong decision in terms of building trust with subjects. The subjects just don't trust the press anymore. But, you know, I don't agree with Trump calling the press fake news. I don't think the news is fake.

• 58:16Speaker 00

  I think they're just have an agenda and they have a point of view and a perspective now, but they're still presenting it as objective, even though it's no longer objective. Like if all these press people are on Twitter dunking on Jeff Bezos for giving away $10 billion, and then they write about Bezos, it doesn't feel objective anymore. It feels like they're all anti-capitalist, anti, you know, there's a group of them that are just super anti-capitalist, super socialist, you know, and it's just depressing. Like I would rather see the, I get contacted by journalists, literally nine out of 10 times, it's some negative story. And one at 10 times, maybe they're on background and I can't tell if it's negative

• 58:58Speaker 00

  or not, but it used to be when I got contacted 10 times, a lot of journalists in the tech business would be like, hey, have you seen anything interesting?

• 59:05Chris Williamson?

  Uh huh.

• 59:05Speaker 00

  And I'd say, yeah, you know, I'm doing this company, Blockable, or we got this company Uber, or you should check out this company, Robinhood, they're really smart folks. And they would write a profile on them and they would talk about what they were doing and why they were doing it. It was super interesting. Like, that was really great because you were presenting to the audience, new stuff coming. The only criticism was maybe the tech press is a little too cheerleader-y, but now it's going the other way.

• 59:27Chris Williamson?

  Yeah, those advertorial type sort of things, yeah.

• 59:28Speaker 00

  Not even advertorial, I mean, I think the tech industry press were fans of technology. That's how it started.

• 59:36Chris Williamson?

  Yeah.

• 59:36Speaker 00

  Like, if you were writing about tech, you probably loved PCs in the 80s and software in the 90s and the internet in the late 90s into 2000s. You loved gadgets if you're doing a gadget. You just were a fan of the technology and what it could do, and you loved the people in the industry. And then the industry got so big that, you know, it needs to be criticized because there are bad things that have occurred. But we've lost that magic of like, hey, let's discover something new and write about it. They just don't, journalists don't do it anymore because it doesn't, nobody clicks on it. Like, you don't get clicks on Twitter for saying, Jason invested 100,000 in this new company that's going to try to change housing. Let me tell you about it. Like, that's not going to get as much as, you know, Bezos gave away only 10% of his money and he didn't guarantee how he's going to give it away or over what time period

• 1:00:21Speaker 00

  or who he's giving it to. And like, they'll find every reason to criticize him and how he gives away $10 billion. Instead of saying, wow, amazing, who would like to give $10 billion next? What an amazing gift. Because America's not spending on, you know, what countries are spending $10 billion fighting global warming? I don't know.

• 1:00:39Chris Williamson?

  Yeah.

• 1:00:39Speaker 00

  There's a great example. You know, we should be having him on, we should be having Bezos on TV, high-fiving him. And instead, they're going to be like, oh, you have too many drivers driving around causing pollution, driving, you know, Sprinter vans around, or you're killing the environment with cardboard. It's like, okay, yeah, there's a story about cardboard and sure, we can write that story, but can we just take a moment to... Let that sink in that he's decided to put $10 billion of his own money. It's a big number towards, you know, raising awareness for global warming and solving it.

• 1:01:12Chris Williamson?

  And the crazy thing between those two situations, the first one being you've done a thing, or this is something which is happening and Bezos putting up 10 billion is both of those things are news. Like that is news. It's a definition of news. A thing has happened which is potentially newsworthy. It's just that one of them has been spun a lot harder and been used as this crutch to push what some people would call an agenda. And I think what you've mentioned there about Trump, it's the fact that the, they say the best lies contain elements of truth, right? And that's why you're able to do-

• 1:01:45Speaker 00

  The devil mixes lies with truth. The devil mixes lies with truth.

• 1:01:49Chris Williamson?

  There it is.

• 1:01:49Speaker 00

  The Exorcist. William Peter Blatty. It's a really, really great book. If you want to read it, yeah. And Legion, the follow up. Really good books.

• 1:02:00Chris Williamson?

  I watched, I watched Legion. Is that the one where they're in a, they're in a like motel type cafe thing and then-

• 1:02:05Speaker 00

  Nursing home.

• 1:02:06Chris Williamson?

  All hell breaks loose.

• 1:02:07Speaker 00

  Lots of bad things happen. Anyway, the books are better because the books are really about Catholicism and God and pain and suffering. And why would a just God allow suffering and the devil and evil? So it's really through the lens of Catholicism, you know, a priest trying to come to terms with his own faith. And it just has a little bit of like this horrific edge to it with murder and why does murder and pain and suffering exist in the world? Like there's a scene in it where there's a, a group of people who have no, it's a little graphic, but it's a group of people who don't have the ability to feel pain. Like there's something wrong with their nervous system. So they don't feel

• 1:02:51Speaker 00

  pain. So if you were to put a cigarette out on their leg, or if a cigarette fell on their leg and burned them, they wouldn't feel it. And there's just a scene, I remember it was very evocative, of a little girl who was suffering that disease, who wanted to look out the window. She climbed on to a radiator and the radiator turned on when she was looking out the window and she got burned on her legs and didn't feel it. Why would God allow that to happen? Right? And that's actually, you know, why that movie is so powerful is because even though you don't get that from the movie explicitly, it's kind of this undertone where you're trying to figure out like the nature of evil. Why does evil exist in the world? Right? It's like one of those core- You know, mysteries of life, like, why, why, why do people do evil things?

• 1:03:36Speaker 00

  What is the point of it all? Why do people blow things up? Why is there terrorism? Why they're murderers, like serial killers, whatever?

• 1:03:45Chris Williamson?

  In a world that's got a God in it, it's a difficult, a difficult question to answer.

• 1:03:49Chris Williamson?

  Very difficult.

• 1:03:49Speaker 00

  Well, we got to God. It only took us an hour.

• 1:03:52Chris Williamson?

  Final question, final, final question, Jason. Do you have any cool tech on your radar at the moment?

• 1:03:58Speaker 00

  Cool tech on my radar? I am particularly interested in robotics outside of factories. I think it's a very, you know, interesting space that is going to

• 1:04:13Speaker 00

  get very big. I'm also very interested in education that is self-paced and occurs, you know, online or in small groups. But that is student-led kind of, you know, self-instr- what do they call it? There's a term for when it's student-led, but, you know, I like to look at the areas. I look at markets where technology hasn't had a huge impact. And for me, you know, robotics, people doing like manual labor that sucks is one. And that could be very interesting for humanity. And then another one is housing.

• 1:04:55Speaker 00

  And even housing plus robotics is kind of interesting to me, like robots building houses. Education, where the education system is super screwed up in the United States. I'd love to see more and more solutions for, you know, we're seeing these ISAs, income sharing agreements where people agree to share $30,000 worth of their salary over the next five years in exchange for you teaching them how to be a programmer or something like that. Or there are websites that'll teach you, you know, very niche websites, one to become a dancer, like stezy.co, we invested in S T E Z Y.co.

• 1:05:31Speaker 00

  And, you know, or brilliant.org, which teaches people math. This idea that there are going to be a vertical site that's just really good at teaching you one thing is fascinating to me because people go for these giant educations that cost $50,000 a year and they put themselves into a quarter million dollars in debt and then their first job out of school is 40 or 50K. So, you know, after taxes, if they're making $40,000 and they're 200 debt.

• 1:06:00Speaker 00

  They got a five to one ratio of, you know, after-tax income to their debt load. It's just never going to be paid off, right? Even if they lived with their parents and paid off $20,000 a year and lived off the other 20,000, it would take them 10 years to just get to zero. They'd be 31 years old before they were able to even consider having any kind of a life. It's bizarre. So, yeah, I just look at those big, broken markets, things that are hard. And just try to think as an investor, God, I can't wait for a founder to take on this one.

• 1:06:34Chris Williamson?

  Hmm.

• 1:06:35Speaker 00

  And blockables, block, B-L-O-K-B-L-E, blockable.com is doing modular housing, and I'm super excited about that. Cafe X is doing robotic coffee machines that will make coffee 24 hours a day in places where you can't get a good cup of coffee, give you food, all with like a robotic arm. And, you know, people are like, oh, that seems like overkill. It's like, yeah, it's overkill until you start making like a cold foam, you know, dirty chai, and you're getting espresso from here, and you're getting the chai from the tap, and then you're putting some cold foam on it, right? And then you put a donut on the side or a scone. Okay, so now the robotic arm's done four or five things, right? You start thinking every year the robotic arm does one or two more steps, right?

• 1:07:18Speaker 00

  Eventually, the robotic arm could be making a hamburger or a pizza or whatever it is, right? So there's, coffee is just, I think, the first area where you'll start to see robots be able to prepare a cup of tea or coffee and do it perfectly when, you know, when a human doesn't.

• 1:07:34Chris Williamson?

  I love the fact that coffee's the first frontier for robotics to get into. It's like we all require it. It's a human right to have coffee.

• 1:07:41Speaker 00

  You know, just robots outside of the factory. In a factory, it makes total sense, like move this over here, stamp it, move it down the line. It gets a little more complicated when Zoom is trying to make pizza, right? Like pizza is probably the 50th thing on the list you should do. Coffee is like the first, you know, or the first might be just, yeah, I think, I think coffee's a pretty good first.

• 1:08:04Chris Williamson?

  Coffee is definitely the first. We can agree on that, Jason.

• 1:08:07Speaker 00

  Well, it's the first time I, you know, I looked at every single robotics company and only one of them, Cafe X had done everything soup to nuts. Like they, there was no human intervention. And then when you look at the pizza, you looked at the burger, there was still a human who had to kind of keep an eye out the robotic arm and you had to have humans in the store. Once you, I mean, once you start putting humans in the store, it's like, well, okay, what's the point?

• 1:08:30Chris Williamson?

  Human could have done the thing, yeah.

• 1:08:34Speaker 00

  Yeah, I mean, then that doesn't mean there won't still be people, you know, just like cars may have replaced horses, like still not, still horses still get to exist, right? And we just may not have, you know, thousands of horses suffering in the middle of London or Newcastle. Is that, wait, you're in Newcastle?

• 1:08:52Chris Williamson?

  Correct, yeah, up north.

• 1:08:53Speaker 00

  By the, you buy the Spanish City?

• 1:08:57Chris Williamson?

  What's Spanish City?

• 1:08:57Speaker 00

  Spanish City, is that, the Spanish City, isn't that like, um, outside of Newcastle, there's a thing called Spanish City, which is a, um, Spanish City is like an amusement park?

• 1:09:08Chris Williamson?

  Are you thinking, are you thinking Newcastle, Australia?

• 1:09:11Speaker 00

  No, hold on a second, Spanish City?

• 1:09:14Chris Williamson?

  Spanish City? If I've lived in the northeast of England for 31 years and there's a Spanish City near me and I've never heard of it, I'm going to be really embarrassed.

• 1:09:26Speaker 00

  Spanish City is a dining, uh, dining and leisure center in Whitley Bay.

• 1:09:35Chris Williamson?

  Oh my god.

• 1:09:36Speaker 00

  Sunset town in North Tenneside. Is that near you or no?

• 1:09:40Chris Williamson?

  Whitley Bay is about 10 miles from where I am, but you've just picked, like, what is this? What is Spanish? Is it just a place, like a restaurant or something? Why do you know about this?

• 1:09:50Speaker 00

  Well, because it's in, um, a famous song called Tunnel of Love by a band called Dire Straits.

• 1:09:56Chris Williamson?

  Okay, yeah, yeah.

• 1:09:58Speaker 00

  Where Mark Knopfler spent a lot of time at the Spanish City. Um, and he wrote a famous line, "Like the Spanish City to me when we were kids." You can look it up.

• 1:10:07Chris Williamson?

  It's just some gaffe in Whitley Bay. It's some place. I'll go, next time I go for fish and chips on the seaside, I'll pop into Spanish City.

• 1:10:13Speaker 00

  And they actually buy the Spanish City, put the lyrics to that song Tunnel of Love. You know who Mark Knopfler and Dire Straits are, of course. Wait, now, when they say Jordy boy, where does a Jordy boy come from?

• 1:10:25Chris Williamson?

  Okay, so a Jordy is the colloquial term for people from Newcastle. So you have Jordies from Newcastle. That would be Brian Johnson from ACDC, Jordy. Yeah.

• 1:10:38Speaker 00

  Yeah, Mark Knopfler, considering stuff like a Jordy boy. You're a Jordy boy.

• 1:10:42Chris Williamson?

  Technically, technically, I'm a smoggy because I'm from Middlesbrough, which is about 40 miles south of here. And my dad would be a Macum because he's from Sunderland, which is, so you've got the three big cities, Newcastle, Middlesbrough, and Sunderland. It's all very, all very tight knit.

• 1:11:02Speaker 00

  Yeah.

• 1:11:03Chris Williamson?

  What do they call people from, what do they call people from Brooklyn?

• 1:11:07Speaker 00

  Ah, what do they call people from Brooklyn?

• 1:11:12Speaker 00

  Bridge and tunnel is a derogatory term from anybody who had to take the bridge or tunnel into Manhattan. So that could be Queens or Bronx or New Jersey even.

• 1:11:19Chris Williamson?

  Okay, yeah.

• 1:11:20Speaker 00

  No, if you're just from Brooklyn, you're from Brooklyn. It kind of stands for it.

• 1:11:24Chris Williamson?

  Well, yeah, I mean, I'm from, I'm from Middlesbrough, but you, let's get, let's come up with something. We need to do a rebrand. Let's get a new brand up.

• 1:11:31Speaker 00

  Well, no, there was, and there's a famous song called Sailing to Philadelphia that Mark Knopfler wrote. And it's about, it's actually one of the most beautiful songs ever written. And he, and he did the vocals with James Taylor, but it's about the people who built, who drew the Mason Dixon line, which was Charlie Mason and Jeremiah Dixon. And those were two English surveyors. And I believe Jeremiah Dixon was the Jordy boy. So he was a Jordy boy who did the Mason Dixon line in America.

• 1:12:06Chris Williamson?

  Good heritage. Great heritage, though.

• 1:12:08Speaker 00

  Yeah.

• 1:12:09Chris Williamson?

  Jason, we made it, man. We made it. Thank you very much.

• 1:12:11Speaker 00

  We did it. Made it to the end.

• 1:12:13Chris Williamson?

  Been an absolute pleasure.

• 1:12:14Speaker 00

  All right. Let me know when the pod comes out. I'm glad to be at episode 150. And let me know when you plan on leaving the lighthouse.

• 1:12:23Chris Williamson?

  You know, I used to have, I used to have, and I promise you, and I will, I can send you a photo to prove it. I used to have right there, that same size, Brooklyn Bridge.

• 1:12:33Speaker 00

  Really?

• 1:12:34Chris Williamson?

  Promise you.

• 1:12:35Speaker 00

  Why is that?

• 1:12:36Chris Williamson?

  Why did I change?

• 1:12:37Speaker 00

  You had an affinity? Uh, well, that's a good question, but why the Brooklyn Bridge didn't start with that?

• 1:12:42Chris Williamson?

  I liked it. The geometric pattern. So it's taken from the, um, it's taken from the bridge and you can see the slats running away from you and you can see all of the wires running up and across. And I just found it, I found it very mesmerizing. I found it very beautiful. Um, and then I-

• 1:12:57Speaker 00

  Have you walked across it yet?

• 1:12:59Chris Williamson?

  What was that?

• 1:13:01Speaker 00

  Have you walked across the Brooklyn Bridge?

• 1:13:02Chris Williamson?

  I haven't, no. I went to a stag do. We, you would call it a bachelor party. We call it a stag do. I went to a stag do in New York last year. Um, and I didn't get to spend any time-

• 1:13:14Speaker 00

  Go ahead and, uh-

• 1:13:14Chris Williamson?

  Outside of, uh, outside of-

• 1:13:16Speaker 00

  Go ahead and, go ahead and walk over the Brooklyn Bridge. A lot of people do it every day and, uh, it'll be part of history if you go do it. It's a pretty, it's a pretty amazing experience to walk across the Brooklyn Bridge. I used to ride my bike across the Brooklyn Bridge all the time.

• 1:13:27Chris Williamson?

  I want to stand in a spot where my photo was my photo, the photo that was there. I also want to find out, I, I can't find out where that lighthouse is. So one day a listener, a listener will tell me.

• 1:13:36Speaker 00

  No, it's very simple. You take a picture of that lighthouse and you just put it into Google reverse image search. You'll find it.

• 1:13:41Chris Williamson?

  There we go. That's why you get paid the big bucks.

• 1:13:43Speaker 00

  That's, perhaps, yeah. All right, man.

• 1:13:46Chris Williamson?

  Thank you.

• 1:13:47Speaker 00

  Great to be on the pod.

• 1:13:47Chris Williamson?

  Pleasure. Thank you.

• 1:13:48Speaker 00

  Cheers now. Bye.