Modern Wisdom - #154 - Jason Calacanis - How Does Angel Investing Work?

Episode Date: March 26, 2020

Jason Calacanis is an angel investor and podcaster. I'm constantly hearing stories of how people are making their millions and billions angel investing in Silicon Valley startups, but I have no idea h...ow 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 Jason's Company - https://launch.co/ Take a break from alcohol and upgrade your life - https://6monthssober.com/podcast Check out everything I recommend from books to products - https://www.amazon.co.uk/shop/modernwisdom - Get in touch. Join the discussion with me and other like minded listeners in the episode comments on the MW YouTube Channel or message me... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx YouTube: https://www.youtube.com/ModernWisdomPodcast Email: https://www.chriswillx.com/contact Learn more about your ad choices. Visit megaphone.fm/adchoices

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Starting point is 00:00:00 Oh yes, hello humans, welcome back to Modern Wisdom. My guest today is Jason Callacannis, the man behind the this week in Startups and Angel podcast, invested in Uber, Thumbtack, Well-Front, DataStacks, Robinhood, Carm and over 200 others. And I wanted to learn how Angel investing and Silicon Valley works.
Starting point is 00:00:24 Here on the news all the time, people making the millions out there in Silicon Valley, but I do not have a clue. I don't know what series A shares are. I don't know about seed capital or any of that stuff. So I wanted to ask him, said, Hey, Jason, teach me about angel investing. So today, that's exactly what you're going to get to learn. But for now, please welcome Jason Callican is in the building. How are you? What?
Starting point is 00:01:11 How are you doing? Funds for having me on the pot. You are in the most beautiful studio that I think I've ever seen. And you're in your bedroom with a lighthouse poster. With a what? With a lighthouse poster behind you. With a lighthouse poster indeed. That is, but you know, we're all starting somewhere. We're the wave crashing around it. It's very, it's chaos, right? What were we talking about just before we started? There's some chaos going on here. Chaos. Well, wait, where
Starting point is 00:01:40 is that lighthouse? I'm not sure. I'm not sure. Do you have some specific meeting? No, I'm not. What would Freud say about picking a lighthouse on the edge of human existence that's being pummeled by 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? Can you tell that I'm an-
Starting point is 00:02:04 You bit of a loner? Can you tell that I'm a- You bit of a loner? Can you tell that I'm an only child, Jason? It does scream I'm alone at the edge of existence, yes. Can you tell that I'm- But maybe you're opting into it. See, that's the thing about lighthouse operators. They're opting into it. Nobody's forcing there.
Starting point is 00:02:19 It's not a jail. So there's a certain type of person who wants that solid. Jason wants that gig. Incredibly perceptive, my friend. There you go. All right. Welcome to this week in Freud. Okay, go ahead.
Starting point is 00:02:34 For sure, man. Don't let me take it over in the first 30 seconds. That's fine. 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? I do slip into host mode sometimes, and I do start thinking like, no, this is the question
Starting point is 00:02:52 you should ask. If you want me to answer that question, you ask me four questions. The second one is the winner. That's what the audience wants to hear. Why don't you ask me this follow? 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
Starting point is 00:03:10 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 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 and stylistically, you know, many different styles work.
Starting point is 00:03:37 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 is 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 a decade or two doing it and they're a young founder.
Starting point is 00:04:00 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, but, you know, I created better editorial brands at him, certainly with Engage in the Speaking Startups, like singular editorial property. So we have like long conversations. So when I interviewed him, every time I asked my question,
Starting point is 00:04:26 I said, what do you think? You did these other publications. You know, you just look at our reporter, what do you think? Like, well, you're on stage 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
Starting point is 00:04:41 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 seat, what's the, what's a CPM explain CPM? They'd be like, you don't know what CPM is and you've been in the advertising business all times like no I know the audience
Starting point is 00:05:08 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 two three hundred of these like interviews you get good at it Promise 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,
Starting point is 00:05:35 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 a hundred, 200, 300 reps under your belt. Everybody thinks like they go to the, you know, they shoot a hundred, three pointers and that their stuff carries. It's not exactly how it works.
Starting point is 00:05:50 Maybe if you shoot like, you know, a thousand a day for a hundred days, you know, you might start to understand what shooting involves. What, somewhere around the 100,000th? What makes a good podcast to them? 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 Brett Eastern Alice if you look at the Red Scare
Starting point is 00:06:35 Dasha and Anna if you look at Ben Shapiro, if you look at Brett 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. 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 going to say what they believe no matter what. And I think this goes so you know the influence Howard Stern had on the the format of radio Howard Stern was somebody considered shock jock in the 80s and 90s in New York City
Starting point is 00:07:05 and eventually went across the country here in America and you do shocking stuff. You know, we'd have strippers on the podcast. He would have, you know, a Clue flux clan member on the podcast is very outrageous. But then he kind of evolved and 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 quick luck fan 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
Starting point is 00:07:44 books or cared about the topics. He was an intellectual, a public intellectual who wanted to have these like really incredible discussions, morally 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 so popular right now is because the press and journalism and media is so broken. podcasting is getting so popular right now is because the press and journalism and media is so broken.
Starting point is 00:08:09 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 going to give me three hours to explain my point, two hours and hour. And I'm going to get misquoted by a journalist. And this is why journalism is really struggling right now is that the people who know
Starting point is 00:08:46 the most are going direct to the audience. And journalists, by definition, only on no 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. Journalists 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
Starting point is 00:09:26 farming, and just the collapse of newspapers and magazines and those editorial formats, websites, 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 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 most interesting or most likely to get retweeted. The thing as well is that the ability to have time
Starting point is 00:09:58 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 an idea which isn't quite formed and then that gets transcribed, that's precisely the loophole that they were looking for, right? I think so. I think that's exactly right. 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
Starting point is 00:10:40 150. So I might be about halfway to your bar of knowing, having an idea about what I'm doing. You think you're gonna get a proper microphone by episode 200? So right here. 150 and using AirPods. What the heck's going on here? Right here. That is awesome. All right. All right. There. That's my boy. That's my boy. I'm not fucking about Jason. All right. Well, you know, you come on the podcast and you're in your bedroom and you got AirPods on.
Starting point is 00:11:08 Or you not even have AirPods on, you got, you got cable headphones on. But you do have the short SMB 7. Is that right? SMB or SM7? That's the best microphone, by the way. SM7B with the CloudLifter, Audi and ID 14. We've got, there the set up is here.
Starting point is 00:11:26 Don't let it fool you. But yeah, so Silicon Valley. Is your mom gonna come in with fish sticks? She coming in with fish sticks any minute now? That's actually, 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.
Starting point is 00:11:43 Push the fish sticks back a little bit Yeah, just a little bangers and match coming. What do you got nice? That's some classic Mochipis food for you there any mushy peas there some chips tea. I like that fish and cheese and the mushy tea Oh, I love a little tea. I'm having a little tea right now. Hey, I like it. We did you come in? Did you walk in with kombucha as well? No, I don't I don't fuck with kombucha. I'm an adult I'm a capitalist. We don't fuck with kombucha as well. No, I don't fuck with kombucha, I'm an adult. I'm a capitalist, we don't fuck with kombucha. Yeah, man, I'm not paying you $8 for something like fermented, like whatever, come on.
Starting point is 00:12:16 Something that someone else has already digested. Yeah, I'm not fucking with kombucha, sorry. Got you, right, so. That's quotable, I. That's quotable. I think that's quotable. Somebody put that on the reddit sub. Jake, I was not fucking with kombucha. Right.
Starting point is 00:12:32 Did you get a reddit sub? Silicon Valley, right? Angel investing. It's a word to 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 job. 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 tell us how the industry works,
Starting point is 00:13:01 Jason? Yes, I can. So there are companies being started all the time, right? There are mom and pop companies. There are pizza reas, there are movies and CDs created. The 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.
Starting point is 00:13:26 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
Starting point is 00:13:42 capital industry is we look for the outlier companies companies that can grow out of velocity that would be considered unrealistic in human bizarre to other people. And the best analogy I heard on this is that you know venture capital is like jet fuel. It's for a 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
Starting point is 00:14:23 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 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 You know 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 consulting firm You're really not going to fail. There's nothing really at stake, right?
Starting point is 00:15:09 If we set up a website today and say, we're going to do a podcast consulting company, C&J podcast consulting, and we're going to teach people how to do podcasts. Okay, if we get one customer a year or 10 or 100, I guess it's a success. It's more than zero. Whereas with a startup like Uber or Com, you know, 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,
Starting point is 00:15:46 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. You know, 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 wanna 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.
Starting point is 00:16:23 Therefore, you're not fundable by this industry, and that turns people off sometimes at the industry and they don't understand it. Or if I told you, you're gonna 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.
Starting point is 00:16:40 And maybe if you get lucky to 10th or the 20th or the 30th, might return more than 30x. You put in a dollar and more than the 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.
Starting point is 00:17:03 So it's no doubt that it's confounding to everybody. Yes, to begin with, are text stocks where the money goes due to scalability? Is it just the fact that that has the ability to really rock it off? Say it again. Text stocks seem to be where you're talking about here is the reason where most of us.
Starting point is 00:17:31 We talk about public ones. Pud? Or private ones. You talk about public or private. Public. 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.
Starting point is 00:17:50 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 where one trick ponies, they went public in year six, seven. Now you have companies staying private and going publics in your 10, 11, 12, 13 and they're much larger businesses, a much stronger businesses.
Starting point is 00:18:18 And then once they get public, they get more ambitious, they start doing acquisitions and they become super resilient. So the resiliency of a company like Facebook having what's app, 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,
Starting point is 00:18:52 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. 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.
Starting point is 00:19:24 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 buying eBay or something. That's been a pretty resilient business, but they've got one business really, and that does make it difficult.
Starting point is 00:19:43 I got it. So, let's go back to the private companies. We're in private companies. 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, are you on a start-up?
Starting point is 00:19:55 Like, what happens? 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. And then I'll have everybody else to like the lady Gaga. Absolutely. I'm wearing a new dress on it. I'm going to be listening.
Starting point is 00:20:20 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 us 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
Starting point is 00:20:50 agencies, William Morris Agency, whatever, in Hollywood. You get affiliated with an agency or you got affiliated as a musician with a record label. 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.
Starting point is 00:21:16 So a lot of what we do here is we annoy to 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 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 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 good news is it's not fatal.
Starting point is 00:21:43 You know, and so if you, and two out of three, or three out of four startups failed, depending on how you measure it, might be even greater based on the number of experiments being run today by founders. You need to only start three, four or five companies to have a likelihood of success. So that's what I tell people when their first company fails
Starting point is 00:22:04 is that Travis's third company was Uber, Elon's third or fourth companies were SpaceX and Tesla. 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. 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.
Starting point is 00:22:39 Maybe it's bummed. It's uncommon amongst uncommon situations, right? It is very uncommon for somebody in 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. Survivorship bias is like, okay, well, these people survived. Therefore, there was something,
Starting point is 00:23:09 the fact that they survived, you read something into who will survive the next time, right? The problem with that was, the way 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 whatever. What they didn't realize is those are the planes that made it back, got hit in the wing
Starting point is 00:23:39 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 pullets were on the planes that went down because they couldn't recover those planes because they blew up in the sky. 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 in this podcast 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,
Starting point is 00:24:24 right? And that's a major problem for people is that the randomness that occurs here fools people, right? And, 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. Sounds like there's a lot of chaos going on. Yeah, I mean, one way to think about this job of venture capitalists or just investor and 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, a hundred 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
Starting point is 00:25:20 you go, well, that's more than we expected. And you're like, everyone puts everyone everyone else on the back high five, a bunch of high fives. Yeah. I mean, and, you know, I've, I've had this in the number of times in my career where it's going up into the right. And the last thing I want to do is go, you know, hey, let's spend some time together, uh, screwing up your formula. Right? Like, just you doing you, you keep on pushing whatever button you're in. Yeah. Yeah. I mean, you could study it to figure out if you can accelerate it, you can study it to figure out if there are margin issues,
Starting point is 00:25:50 competitive issues. There's a lot to do even on the successful companies like when your company 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.
Starting point is 00:26:08 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. Are we going to fire the rocket? Oh, there's no jet fuel in the rocket. Okay, great. Oh, you don't have any astronauts, either.
Starting point is 00:26:21 Okay. It's going to be kind of hard to get to space without those two things. We're going to need some jet fuel. We're going to gonna be kind of 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. Oh, the rocket's not done? Oh, okay. We've gotta finish the rocket.
Starting point is 00:26:32 We've got any chance to get into 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 companies just completely chaotic. With these startups, they're almost inevitably running out of money, facing existential threats externally where Google is going to make their product free, let's say, or they're getting really well-funded competitors who then decide they're going to give away $100 bills for $50 and take all
Starting point is 00:27:10 the customers, which is lifted with Uber and Uber did with other people. They get into these crazy wars of discounting and it's pretty scary. So, yeah, I deal with a lot of chaos. So how much to step in there? Sorry, Jason, how much of that is like your post or so much? I'm massaging people. I'm just saying, let's everyone chill out,
Starting point is 00:27:32 let's bring a little bit of order to this chaos. Yeah, no, a big part of my job, that's why I like your lighthouse poster so much is, like, you know, when you look at that lighthouse, it's like, yeah, there's a giant wave of his nature. Doesn't, you don't get the sense that that lighthouse is going to get knocked over, right? And that's really my job.
Starting point is 00:27:49 And it's the job of the founder is, of any leader is to convince everybody that there's 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 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,
Starting point is 00:28:32 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 exude 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.
Starting point is 00:28:54 My brothers are firefighter and, uh, uh, uh, Lieutenant, and, you know, when you watch 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 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. So if this is a coin toss situation and just watching the calm at which people were able to triage these situations,
Starting point is 00:29:29 it's always very impressive to me. I always think about samurai or Jedi in that regard, which is why there's a poster of De Shire Mufune in the office. And, you know, if you look at Samurai's or Jedi Knights who were modeled 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
Starting point is 00:29:51 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 Quiggan Jim is fighting Darth Maul and these Qui-Gon Jim is fighting Darth Maul, and this laser wall gets blocking the two of them. And Darth Maul is pacing back and forth like a cheetah, like an accage. And Qui-Gon Jim just kneels down, turns off the lightsaber, and meditates and closes his eyes. And you're 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 going to open and it's going to be chaos. And if you look at a scene like the movie Gladiator, there's a scene where Maximus says,
Starting point is 00:30:32 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 us 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,
Starting point is 00:30:59 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 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 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 how 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.
Starting point is 00:31:30 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 they're gonna drop us into this situation in Somalia and we're not gonna get out in all likelihood, but we're gonna take that chance anyway and we're just gonna focus and let our training
Starting point is 00:31:50 and our plan execute itself, whatever happens. 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 more. I like yours. I like your ones. I like your ones. Running these race companies is a fucking war. It really is. And that's just a successful ones.
Starting point is 00:32:14 You know, the ones that are not successful, you know, it's, you know, it's a war and chaos and while fighting the coronavirus. It's a war and chaos and while fighting the coronavirus. 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. Are you supposed to have your hardware solution? You know, that client's paid for and now it's,
Starting point is 00:32:43 you know, lost in customs or something. There's a business disruption, business disruption 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. How much of what you've alluded to there, which is your ability to work out the controllables
Starting point is 00:33:04 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? Well, I would say, you know, some folks are the product of their environments, and that's their primary driver, and that other folks are very good at adding skills. And I think you could probably do both. You know, Tim Ferris, the seeker, as I call him, you know, he seeks out knowledge and he
Starting point is 00:33:43 learns it and he advances and learns very quickly. That's kind of his thing. He just adapts and learns new skills very quickly. So it's clearly could be done. But there is at its core, I do think, you know, some situations that are high pressure, that people grow up in that do define them. And so one theory I heard, I don't know if this is correct or has any basis, but it certainly
Starting point is 00:34:09 is an interesting one to consider, is that a lot of the great founders who are good in 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? It's interesting to 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 overperforming index I mean, obviously, we see over and over again, immigrants really overperform in index, in terms of the percentage of them
Starting point is 00:34:47 leading very large companies and their leadership ability, something about immigrant parents and 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 forced 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
Starting point is 00:35:11 bit heartbreaking that we have this nationalism where we don't want to let in the people 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 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.
Starting point is 00:35:47 And we had just a massive influx of Indians who suffered greatly in their journey here and to build a new life here, face racism, face having to work menial jobs to build stuff up and an 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.
Starting point is 00:36:20 How about for you? How about you? Talk to me about your constitution. Talk to me about what it is that you're part of your practice as well. Talk to me about what sets you apart. I definitely fall into the category of the or the archetype of like growing up in a difficult situation, Brooklyn in the 70s and 80s. You know, my dad losing his bar when I was 18 or 17 years old
Starting point is 00:36:46 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. That, I think some people maybe they have a reaction the other way, they become, they give up, but whatever. I, for whatever reason just grew up a fighter, and I, I mean, I still have that fighter mentality,
Starting point is 00:37:12 they now, I'm super aware that the analogies I use, you know, are these war and violent ones. Or, you know, or nonviolence in the case of the Jedi and Samurai just violences less resort. So, I am incredibly hardworking and dedicated and loyal and maybe to a fault at times, just not letting things go. 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
Starting point is 00:37:53 returns. Being able to 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. But, you know, I just don't like giving up. I like to fight until the last, you know, arrow, the last bullet. I think you work on that moving forward. You think you'll maybe 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? Yeah, I kind of like it. I'll be honest.
Starting point is 00:38:26 I kind of like it. I like, you know, being against the odds. I like the fear. 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 wanna do? You wanna keep fighting?
Starting point is 00:38:47 Or do you wanna, you know, close this chapter of your life and move on to the next one? We will be here either way. If you wanna keep fighting, I'll fight with you. If you wanna 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
Starting point is 00:39:07 roof of Hulu while drinking cocktails and whatever Fine, let's do it And then we'll we'll come back in two or three years and kick ass again And so I kind of leave it up to the founder. That's the balance I found my natural Your 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 in the company goes supernova and sometimes the idea is just not a great idea and So you should or the market conditions are just horrible and you're and you're just fighting against something that you cannot beat.
Starting point is 00:39:45 You know, like if you're fighting against like, you know, a tsunami, like, it's, can't swim your way out of a tsunami in all likelihood, right? And you probably want to retreat. So there's a time for retreating. It's just not in my nature, generally. I get it. I get it. And I think it's actually a limiting factor at times for me. And you probably should cut my losses on a lot of things and just say, yeah, you know, it doesn't look like this business is gonna work out. I wish you luck with it.
Starting point is 00:40:16 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 luck. Let us know if there's any way we can help. And I'm like, wow, okay. Super rational approach. Just it's a much more efficient approach, I think. And I see VCs do it all the time. They're just
Starting point is 00:40:41 like, yeah, it's not a fit for us, you know. We're not going to keep going, but 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, what your company, you do what you want, but they kind of walk away from it. Yeah, it must be challenging. I would find it challenging to not become emotionally invested, you know, to not have that part of me that wants more than what the figures say that has faith beyond what the balance sheet shows me beyond wants more than what the figures say, that has faith beyond what the balance sheet shows me beyond what the stats are.
Starting point is 00:41:10 I don't know. I don't know whether that's signifying, I don't know whether that's trying to try to personify businesses almost as beings, with personalities and stuff like that. 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, etc. But it's not exactly, I don't do it for journalistic reasons exactly.
Starting point is 00:41:45 And so sometimes you got to close the door on much happier of a life in order to by doing this podcast, et cetera, but it's not exactly, I don't do it for journalistic reasons exactly. And so sometimes you gotta close the door on much happier of a life and 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,
Starting point is 00:42:04 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. So it looks from the outside, looking in like you're potentially spinning an awful lot of different plates. Whereas it's making stream, streamlined into two very discrete areas, which allows you to then scale the volume that you're doing that up. Correct. Yeah, I mean, we have one thing like podcast and events and books, right?
Starting point is 00:42:45 So like, oh, you wrote a book. Oh, you're doing a podcast. Oh, you're doing a lot of podcasts 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. And 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
Starting point is 00:43:04 with each other. to meet people in the industry and let them 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 if you looked at our Asana project board
Starting point is 00:43:22 or our notion or our customer support line, whatever. You would see a lot of different activity, but they all 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, they do Marvel and Marvel does Avengers, plus Marvel does these other brands or whatever they do. People outside the Avengers, they're doing Spider-Man and
Starting point is 00:43:46 the X-Men as well. 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 they do, streaming service, entertain people. Okay, so they entertain people. What else do they do? They let. Okay, so they entertain people. What else they do? They let you buy stuff that they entertain you with. Oh, okay, so I can buy like a Star Wars figure. Yep, you can buy Star Wars lightsaber. You could make one yourself.
Starting point is 00:44:14 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. It was burned so deeply that you forgot that they were doing it, forgot that they were doing something different. I mean, what other business do they have? You know, you look at and say that the imparks are different, or there's all these different
Starting point is 00:44:38 themes in the theme park, right? They did Star Wars Land, they do whatever land, this land, that land, Pixar, cars land, whatever. They have Epcot Center, Disney World, Disney Land, whatever. It's all the same thing. They're entertaining you. You pay the money, they entertain you. And you maybe buy something on the way out. That's it. Any other business Disney is involved in? Is there something sort of symbolic or structural that people should be looking 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
Starting point is 00:45:16 ability. 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. Or I ask them, do you think your superpower is this? Different superpowers can work for different things. Some people are engineers. Elon's an engineer at his heart. He's really a physicist and engineer who knows how to build stuff. If you look at what he's building, like he's really good at metal.
Starting point is 00:45:47 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 tested at SpaceX. Like material science and engineering is what he does. And people will think like, oh, there's a lot more going on here. It's like, is there, right?
Starting point is 00:46:09 Like 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 was in an engineer, right? And I think Steve Jobs is a marketer, right? He knew like a packageer. 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,
Starting point is 00:46:27 just a great designer of products, right? And you know, a brand builder, right? He built a brand and package stuff. He's really a packageer. And now that I think about it, like he made this package Apple and meant something. It evoked something, simple, clean, opening the box. Beyond the store.
Starting point is 00:46:47 Beyond the store. Using it. Yeah, all the experiences, it's kind of like an experience designer. Yeah, I just call it an experience designer. Actually, it would probably be the best way to say it. He's an experience designer. I agree. Because the store is an experience saying using your phone, using your laptop, opening up
Starting point is 00:47:03 your phone, taking it out of the box, it's all an experience. And so yeah, you need to know what you're good at, or I'm a talker. Like my skill set is talking. That's my super power 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. Precision with your speech is something that I think is a very, very under regarded superpower,
Starting point is 00:47:30 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
Starting point is 00:47:51 to do outside of that in a way that I never had before I did this. And I would do. Do you feel more energy when you finish the podcast than when you started? Yes. 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.
Starting point is 00:48:12 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, intermerents or sectroverts. 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, they're like, great, let's do our two, let's do our three, you know, they just want to keep talking.
Starting point is 00:48:40 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. 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, experienced designer, or you're a great talker and, you know, or you're great sales executive, you can acquire those other skills from other team members. You don't need to have them.
Starting point is 00:49:07 So this idea that there's one type of founder, I get to ask 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 extra, it doesn't matter if they're sales, marketing, product,
Starting point is 00:49:23 developer, engineer, visionary, talker, you know, leader, manager. 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, you know, what job they did previously and how well they did that job, it's probably not as important as those other software skills, which are actually the harder ones, which is, this person really care about this idea. Are they going to quit?
Starting point is 00:50:06 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? What's the plan? And who's going to execute the plan? And man, I can't tell you the number of times you know, you'll 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 or an investment company, launch.co, you can see our website, just simple website. Anyway, what we do here at launch is we invest in
Starting point is 00:50:38 companies and our goal is to be the best investors in Silicon Valley. The best investors in the world, period. We want to be the best investors in Silicon Valley. 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.
Starting point is 00:50:58 And in 10 years have a thousand 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. Podcasts, big part of it.
Starting point is 00:51:12 Podcasts, we get to put our founders on the podcast this weekend startups. We get to put investors on the podcast, angel podcast.com. We get to meet new founders on the podcast. I met the founder of calm.com and invested in the company because he was on the podcast and It's a tool. You know, it's a tactic It's 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 like this is why we're here and you know what? It's a lot of work to work with a hundred companies a year because that means we got to meet
Starting point is 00:51:42 thousands and we have to sort through ten 10,000 to meet with a couple of thousand. You know, we're going to meet with two or three thousand companies this year after having gotten pitched by over 10,000, right? So just to start thinking about those numbers. So if we meet two, three, four thousand companies in order to get down to a hundred investments, it's a lot of work. It's a lot of work. And you search for that. One in 50 people people potential pay off at the end, right?
Starting point is 00:52:07 Which is that a symmetry exactly why it's there. And nobody knows and nobody there's the punchline nobody knows what's gonna work. So by the way, we're going to place a large number of bets meet the we're gonna place a hundred bets after meeting thousands of people after sorting through tens of thousands. We're going to place 100 bets after meeting thousands of people after sorting through tens of thousands. And we don't actually know which one of the hundred 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 calm.com would be the second best
Starting point is 00:52:48 company in my portfolio. I did think Uber wasn't gonna be a very successful company, but I thought a billion or two billion dollar company, not a 60 billion dollar company. So I was off by 60, 30 to 60 out of it. So even though I knew it was a winner, I didn't know the magnitude of it, you know? And Robinhood, like, stock trading out from millennials,
Starting point is 00:53:08 like I invested in that company and didn't think it was gonna work. I thought the founders are incredible. I'm not sure their first idea is gonna work. I think it'll probably be their second or third and I was wrong. And delighted to be wrong. This is the best way to be wrong in history.
Starting point is 00:53:25 Yeah, it's the place of bat and win. It would be like walking up to the batting window and be like, I'm going to place a bat on this team. And you pick the wrong team than you intended. They give you the slip. Your team loses, you go to rip up the slip and you look that, oh, I made a mistake. Oh, I bat on the other team. Oh, I won. Fun fucking test. Your team loses. You go to rip up the slip and you look that I made a mistake. I bet on the other team. I won.
Starting point is 00:53:47 Fun fucking test. Okay, great. Fantastic. Literally, that's the job of an investor. You just don't know which ones are going to win. You just basically treat everybody who's in your portfolio amazing. You try to just be as supportive as possible. Again, life is pretty simple. You 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, and bad on them again, come back.
Starting point is 00:54:14 They'll do it again because I got two questions before we'll definitely do another company again. They may fail again, but you know, like I said, three out of four failed. Then you only need to do four to get to a winery and we'll like we had. I get it. I got two questions before we finish up. Jason, first one. Yeah. Going back to podcasting.
Starting point is 00:54:30 Someone who's been in the space for quite sometimes 60 million plus plays. Is that even more now? 160 million? Probably more, but whatever. I mean, we did 10, we've been doing it for 10 years and over a thousand episodes. So it's still a boutique podcast.
Starting point is 00:54:43 I mean, we're only talking about 200,000 people listening to every episode. It's no Joe Rogan, not millions of people listening to everyone. It's a boutique podcast about a very specific niche thing. But that niche thing were better than anybody had doing. So I think that's what's important. Been in space for a long time.
Starting point is 00:55:00 Where do you see the podcasting space evolving over the coming years? What's next? More of the same? for a long time, where do you see the podcasting space evolving over the coming years? What's next? More of the same? Well, I think the listening, the listenership is going to, 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
Starting point is 00:55:20 Sanders was on Joe Rogan or, you know, that, you know, even presidential candidates are 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 podcast 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
Starting point is 00:56:02 going to be better. And it'd be better to hear from the subject for an hour or two, then to read the story where they were quoted once or twice. 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 a Facebook and Amazon now, a co-to, he's the only person who's ever worked for Jeff Bezos and Mark Zuckerberg and he did an incredible podcast. And, you know, it probably would be very shy if the
Starting point is 00:56:35 Wall Street Journal of New York Times, Washington Post, TechCrunch, Recode or any other person call him because their guard would be up. And they go, okay, what's the story? Oh, you're doing an anti-Facebook story. Oh, you're, 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. Oh, you're doing an anti. Oh, Jeff Bay says, gave away $10 billion to fight global warming and nobody has ever put up a fraction of that.
Starting point is 00:56:59 Oh, but he didn't give away all of his money. So let's criticize him because he only gave away 10%. I was like, literally, the guy just gave away the largest gift in the history of giving except for Bill Gates and Warren Buffett. But I think it might still be the single largest gift ever. Put some number three in philanthropy, I think, or four. But it's not enough. I think it's Gates. And literally yesterday, all the press was criticizing him. And the press is wondering why the top subjects don't trust them or don't want to work with them, or why Trump's rhetoric on fake news is so powerful. The reason why Trump is able to say fake news
Starting point is 00:57:38 is not because the news is fake. It's because journalists haven't been doing a great job balancing out and going straight down the middle with objective journalism because journalists have picked aside 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 MF-SembyC on the left Fox on the right Wall7BC on the left, Fox on the right, Wall Street Journal on the right. So everybody's just picking a side and your subscriptions go up. So if you pick a side, your subscriptions go up. Anybody
Starting point is 00:58:14 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 wanna keep in Trump in office and you wanna troll the libs? Great. I'll give you money for those two things, but I'm not gonna give you money
Starting point is 00:58:32 for objective journalism right down the middle. And journalists have responded to that market condition and it's 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. That, you know, I don't agree with Trump calling the press fake news. I don't think the news is fake.
Starting point is 00:58:52 I think they're just having 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.
Starting point is 00:59:14 It feels like they're all anti-capitalist, there's a group of them that are just super anti-capitalist, super socialist, it's just depressing. Like, I would rather see that, 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 or not.
Starting point is 00:59:35 But it used to be when I got contacted 10 times, a lot of journalists in the tech business would be like, hey, has it, have you seen anything interesting? 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.
Starting point is 00:59:48 And they were right 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 cheerleadery, but now- Yeah, like those auditorial The other way. Yeah. Not even an advertorial. I mean, I think the tech industry press
Starting point is 01:00:09 were fans of technology. That's how it started. 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 guy, you just were a fan of the technology. And what it could do, and you loved the people in the 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.
Starting point is 01:00:32 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 Jason invested 100,000 in this new company that's going to try to change housing. Let me tell you about it. 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 or who he's giving it to and they'll find every reason to criticize him and how he gives away $10 billion. Just sort 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
Starting point is 01:01:13 $10 billion fighting global warming. I don't know. This is a great example. You know, we should be having a month, we should be having Bezos on TV, high-fiving him, and instead they're going to be like, oh like oh well 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 could write that story, but do we 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.
Starting point is 01:01:47 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, 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 they say the best lies
Starting point is 01:02:17 contain elements of truth, right? And that's why you're able to do. The devil mixes lies with truth. The devil mixes lies with truth. The devil mixes lies with truth. There it is. The exorcist. William Peter Blattie. It's a really great book.
Starting point is 01:02:32 If you wanna read it, yeah. Then Legion the follow up. Really good books. I watch Legion. Is that the one where they're in a, they're in a motel type cafe thing and they're all hell breaks loose. Lots of bad things happen.
Starting point is 01:02:44 Anyway, the books are better because the books are really about Catholicism and God and pain and suffering and why would adjust God allow suffering and the devil and evil. So it's really through the lens of Catholicism, a priest trying to come to terms with his own faith and it just has a little bit of like this horrific 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
Starting point is 01:03:17 A group of people who have no Little graphic, but so group of people who don't have the ability to feel pain Like to something wrong with their nervous of people who don't have the ability to feel pain, like to something wrong with their nervous system, so they don't feel 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, is very evocative of a little girl who's suffering that disease who wanted to look at the window.
Starting point is 01:03:37 She clamped on to a radiator. In the radiator, turned on when she was looking at 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 try and 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 do people do evil things? What is the point of it all? Why do people blow things up?
Starting point is 01:04:15 Why is there terrorism? Why they're murderers? Like serial killers, whatever. In the world that's God in it, it's a difficult question you want to say. Very difficult. Well, we got to God, it, it's a difficult question to answer. Very difficult. Well, we got to God, it only took us an hour. Final question.
Starting point is 01:04:30 Final question, Jason. Yeah. Do you have any cool tech on your radar at the moment? Cool tech on my radar. I am particularly interested in robotics outside of factories. I think it's a very interesting space that is going to get very big. I'm also very interested in education that is self-paced
Starting point is 01:04:56 and occurs online or in small groups. But that is student-led kind of, self-instraught, what do they call it? There's a term for when it's student-led, but I like to look at the areas, I look at markets where technology hasn't had a huge impact, and for me, robotics people doing like manual labor that sucks is one. And that could be very interesting for humanity. And then another one is housing. 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,
Starting point is 01:05:47 income sharing agreements where people agree to share $30,000 worth of 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 stz.co. We invested in STE stz.co.
Starting point is 01:06:08 And, you know, or brilliant.org, which teaches people math, this idea that they're gonna 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
Starting point is 01:06:26 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 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, I lived off the other $20,000 they 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 So yeah, I just look at those big broken markets, things that are hard,
Starting point is 01:07:06 and just try to think as an investor, God, I can't wait for a founder to take on this one. And blockable, B-L-O-K-A-B-L-E, blockable.com is doing modular housing, and I'm super excited about that. CafeX 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,
Starting point is 01:07:25 give you food all with like a robotic arm and you know people 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? Eventually the robotic arm could be making a hamburger
Starting point is 01:07:59 or a pizza or whatever it is, right? So there's coffees, just I think the first area where you'll start to see robots be able to pair a cup of tea or coffee and do it perfectly when a human doesn't. Other of the fact that coffee is the first frontier for robotics to get into, is that we all require it. It's a human right to have coffee. 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
Starting point is 01:08:29 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 mean, I think coffee is a pretty good first. Coffee is definitely the first to agree on that Jason. Well, it's the first time I, you know, I looked at is a pretty good first. Coffee is definitely the first to be integrated on that Jason. Well, it's the first time I looked at every single robotics company and only one of them Kaffeex had done everything soup to nuts. Like 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 at the robotic arm and you had to have humans in the store.
Starting point is 01:09:04 Once you, I mean, once you start putting humans in the store, it's like, wow, okay, what's the point? You even could have done the thing, yeah. Yeah, I mean, then that doesn't mean there won't still be people, you know, just like cars may have replaced horses, like, just don't not, 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 made? Wait, you're in Newcastle? Correct, yeah. Oh, no, no. By the sp- by the Spanish city. What's Spanish city? Spanish city is that the Spanish city is not like a outside of Newcastle is a thing called Spanish city, which is a Spanish
Starting point is 01:09:43 city is like a amusement park. Are you thinking Newcastle Australia? No, hold on a second, Spanish city. What's that? 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,
Starting point is 01:09:59 I'm gonna be really embarrassed. Spanish city is a dining and leisure center in Whitley Bay. Oh my goodness. I'm not in town in North Tennessee. Is that near you or no? Whitley Bay is about 10 miles from where I am, but you've just picked like, what is this? What is spun? Is it just a place like a restaurant or something? Why do you know about this? Well, because it's in a famous song called Tunnel of Love by a band called Dyer Straits,
Starting point is 01:10:34 okay, yeah, yeah. It will wear a mark-knife which spent a lot of time at the Spanish city. And he wrote a famous line, like the Spanish city to me when we were kids. You can look it up. It's just some gaff in Whitley Bay. It's someplace. I'll go next time I go for fish and chips on the seaside.
Starting point is 01:10:49 I'll pop into some. 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, what does a Jordy boy come from? Okay. So a Jordy is the colloquial term for people from Newcastle.
Starting point is 01:11:08 So you have Jordies from Newcastle. That would be Brian Johnson from ACDC, Jordy. Yeah. Yeah, Mark, I've got to say something like a Jordy. You don't have to. You're a Jordy boy. Technically, technically, I'm a smoggy because I'm from Middlesbrough,
Starting point is 01:11:23 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, very tight-knit. Um, yeah. What do they call people from Brooklyn? I was like, I can't really remember. What do they call people from Brooklyn? I want to call people from Brooklyn.
Starting point is 01:11:54 Richard 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. Okay. Yeah. Now if you're just from Brooklyn, you're from Brooklyn. Kind of stands for 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 stands for. Yeah, I'm from Middlesbrough, but let's come up with something. We need to do a rebrand. Let's get a new brand. Well, no, there's a famous song called Sailing to Philadelphia that Mark Notha wrote.
Starting point is 01:12:14 And it's about, it's actually one of the most beautiful songs ever written. 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. Good heritage. Great heritage, sir. Yeah. Jason, we made it, man. We made it.
Starting point is 01:12:49 Thank you very much. We did it. Made it to the end. Absolutely. All right. Well, let me know when the pod comes out. I'm glad to be an episode 150. And let me know when you plan on leaving the lighthouse.
Starting point is 01:12:59 You know, I used to have. I used to have and I promise you, and I can send you a photo to prove it. I used to have right there that same size Brooklyn Bridge. Really? Promise you. Why is that? Why did I change? Do you have an affinity?
Starting point is 01:13:15 Well, that's a good question, but why the Brooklyn Bridge to the start with that? I liked it. The geometric pattern, so 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 very mesmerizing, I found it very beautiful. And then I... Have you walked across it yet? What was that?
Starting point is 01:13:38 Have you walked across the Brooklyn Bridge? I haven't... No, I went to a stag do. You would call it a bachelor party. We call it a stag do. You would call it a bachelor party, we call it a stag do, or into a stag do in New York last year. And I didn't get to spend any time outside of... Go ahead and walk over the Brooklyn Bridge. A lot of people do it every day.
Starting point is 01:13:58 And it'll be part of history if you go do it. It's a pretty amazing experience to walk across the Brooklyn Bridge. I used to ride my bike across the book and bridge all the time. I want to stand in the spot where my photo was my photo, the photo that was there. I also want to find out, I can't find out where that lighthouse is. So one day, a listener, a listener will tell me,
Starting point is 01:14:14 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. There we go. That's why you get paid the big books. That's, perhaps, yeah. All right, man.
Starting point is 01:14:24 Thank you. ...grat be on the farm.

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