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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: modernwisdompodcast@gmail.com

Jason CalacanisguestChris Williamsonhost
Mar 26, 20201h 14mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:49

    Investor mindset: bet broadly, support founders, and re-bet on great people

    1. JC

      ... it would be like walking up to the, to the betting window and being like, "I, I, yeah, I'm gonna place a bet on this team," and, uh, you, you pick the wrong team-

    2. CW

      Mm-hmm. Mm-hmm.

    3. JC

      ... than you intended. They give you the slip. Your team loses, you go to rip up the slip and you look that y- "Oh, I made a mistake? Oh, I bet on the other team? Oh, I won?"

    4. CW

      Fun-fucking-tastic.

    5. JC

      "Oh, okay. Great."

    6. CW

      (laughs)

    7. JC

      "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. Um, which is, you know... Again, it's like 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, then bet on them again.

  2. 0:49 – 2:22

    Studio banter and the “lighthouse poster” as a chaos metaphor

    1. CW

      Jason Calacanis in the building. How are you?

    2. JC

      What what?

    3. CW

      How you doing? Fantastic.

    4. JC

      Thanks for having me on the pod.

    5. CW

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

    6. JC

      Yeah. And you're in your, and you're in your bedroom.

    7. CW

      I am. That is true.

    8. JC

      With a lighthouse poster.

    9. CW

      With a what? (laughs)

    10. JC

      With a lighthouse poster behind you. I see it.

    11. CW

      With a lighthouse poster indeed, that is.

    12. JC

      Yeah.

    13. CW

      But you know, we're all s- we're all starting somewhere.

    14. JC

      With a wave crashing around it.

    15. CW

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

    16. JC

      Chaos. Well, wait. W- where is that lighthouse?

    17. CW

      I'm not sure. I'm not sure.

    18. JC

      Does it have some specific meaning?

    19. CW

      (laughs) No, no, I'm not...

    20. JC

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

    21. CW

      Can you tell that I'm an-

    22. JC

      You a bit of a loner?

    23. CW

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

    24. JC

      It, it does scream, "I'm alone at the edge of existence," yes.

    25. CW

      Can you tell that I'm th-

    26. JC

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

    27. CW

      Jason, you-

    28. JC

      Who wants that, that gig.

    29. CW

      Incredibly, uh, incredibly perceptive, my friend.

    30. JC

      There you go. All right. Well, welcome to this week in Freud.

  3. 2:22 – 5:46

    Being a podcast host vs a guest: interview instincts and audience-first framing

    1. CW

      That's fine. Do you fi- 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. JC

      Uh, I do slip into host mode sometimes, and I do start thinking like, "No, this is the question you should ask." And-

    3. CW

      (laughs)

    4. JC

      ... 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.

    5. CW

      (laughs)

    6. JC

      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, you start to realize, wow, some people are really great at this, right? And they ha- all have different styles, 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?"

    7. CW

      (laughs)

    8. JC

      A- and that's problematic. I, 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, I, I created better editorial brands than him certainly with Engadget and This Week in Startups, like singular editorial properties. So, we have like long conversations, and when I interviewed him, every time I'd ask him a question, he said, "Well, what do you think? You did, you did these other publications. You know, you did Silicon iReporter. What do you think?" (laughs) And I'm 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 that you know I know the answer to, or that you might be interested in my answer, but, uh, just humor me for the sake of the audience." And, and sometimes even interview I'll say, "Hey, for the sake of the audience, can you explain what this is?" And I, I added that to my repertoire because every time I'd say, "What's, you know, uh, a C- 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 this time?" I was like, "No, I know the audience." 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, uh, you have to, you learn. I think somewhere after two or three hundred of these, like, interviews, you'll get good at it.

    9. CW

      (laughs)

    10. JC

      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 ten podcast episodes. Like, here we go. Where's my..."

    11. CW

      (clears throat)

    12. JC

      "... you know. Wh- why, why are the ads not sold?" And it's like, mm, 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, they shoot 100 three-pointers and that they're Steph Curry. It's just not exactly how it works. 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 episode.

  4. 5:46 – 12:19

    What makes a great podcaster—and why podcasting is booming

    1. CW

      What, what makes a good pod- podcaster then?

    2. JC

      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, um, 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, um, Sam Harris, uh, 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, uh, 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 to, you know, the influence Howard Stern had on th- the, the format of radio. Howard Stern was somebody who was considered a shock jock in the '80s and '90s in New York City and, uh, eventually went across the country here in America. And he would do shocking stuff, you know. He would have strippers on the podcast, he would have, uh, you know, a Ku Klux Klan member on the podcast. It was very outrageous. Um, 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 a, I think a, 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, uh, 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. Morally Safer, Oprah Winfrey. You know, there's a cohort of people who just got really good at interviewing people and, and you can see that in podcasts. And the reason podcasting is getting 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, y- 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, an 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 the most are going direct to the audience, and journalists, by definition, only own, 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. 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 really a fascinating time, um, and I think podcasting is a reaction to link baiting, SEO-driven content, content farming, 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."

    3. CW

      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, and say something which y- 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, the loophole that they were looking for, right?

    4. JC

      Um, I think so. I think that's exactly right.

    5. CW

      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, 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, uh, bar of, of knowing, having an idea about what I'm doing, um-

    6. JC

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

    7. CW

      (laughs) So right here-

    8. JC

      After 150 and using AirPods, what the heck is going on here?

    9. CW

      Right here, that is an SM-

    10. JC

      All right, all right. There, that's my boy. That's my boy, the Shure SM7.

    11. CW

      SM7B. I'm not fucking, I'm not fucking about, Jason.

    12. JC

      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 (laughs) you got cabled headphones on, but you do have the Shure SMB7.

    13. CW

      Mm, I am-

    14. JC

      Is that right? SMB or SM7?

    15. CW

      SM7.

    16. JC

      That's the best microphone, by the way.

    17. CW

      SM7B. We're doing it.

    18. JC

      SM.

    19. CW

      Cloudlifter Audient iD14. We've got e- the setup is here. Don't let it-

    20. JC

      All right.

    21. CW

      Don't let it fool you. And, but yeah, so Silicon Valley.

    22. JC

      Is your mom gonna come in with fish sticks?

    23. CW

      (laughs)

    24. JC

      Is she coming in with fish sticks any minute now?

    25. CW

      Uh, that is-

    26. JC

      Tell them.

    27. CW

      ... 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.

    28. JC

      Push the fish sticks back a little bit?

    29. CW

      Yeah, just a-

    30. JC

      Little bangers and mash coming? What do you got? What's on the menu?

  5. 12:19 – 16:50

    Angel investing 101: venture capital is “rocket fuel” for outliers

    1. CW

      Silicon Valley, right? Angel investing. It, it's, uh, 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?

    2. JC

      Um, yes, I can. So, uh, there are companies being started all the time, right? There are mom and pop companies, uh, there are pizzerias, 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. And these are all great businesses, they can employ people, sometimes the owner can make a, a, a nice salary, uh, and be independent. Sometimes they can make even more than that. They can make a life for themselves, right? Uh, 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 at a velocity that would be considered unrealistic, inhuman, bizarre, uh, to other people. And the best analogy I heard on this is that, you know, venture capital is like jet fuel. It's for t- or rocket fuel. Y- you wouldn't put rocket fuel, like, on a, a Vespa. (laughs) Uh, it would not work out well. Like, you're not trying to go mock whatever, um, y- you know, on those, uh, 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, you know, get three customers. The, the businesses we invest in, uh, you know, if you were to look at one like Uber or Robin Hood, um, or com.com, these were businesses that were intended to impact hundreds of millions of people, a billion people.

    3. CW

      Wow.

    4. JC

      You know, large numbers of people. And, uh, 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 a consulting firm, you're really not gonna fail. There's nothing really at stake, right? Like, what if ... If I, we set up a website today and say, "We're gonna do a podcast consulting company, you know, C&J Podcast Consulting, and we're gonna 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 Calm, you know, you're, you're building something that is more complex, um, 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. Uh, 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. Um, uh, so that is the difference right now. Y- 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 wanna start a company that makes, you know, ginger beer or tea, uh, or they're doing a company that has a noble purpose. And it's like, these do not qualify for the one in 1,000 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, 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, 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 30X. So it's a type of gambling and risk-taking that is very unique, very confusing from the outside, and even from the inside, um, the people who do this kind of gambling struggle with their own psychology and their own existence. So, it- it's no doubt that it's confounding to everybody.

  6. 16:50 – 19:12

    Why tech (and platform companies) dominate: scalability and resilience via expansion

    1. CW

      Yes. To begin with, are tech stocks where the money goes due to scalability? Is it just a fact that that has the ability to really rock it off?

    2. JC

      Yeah. So I mean, if you look at public stocks, yeah, I mean, if you invested in Google, Netflix, or Amazon (laughs) you know, at their IPO or any time after the first five years of those companies, you'd be pretty happy today, I think. Uh, Facebook as well. And so, the, the companies are getting much larger today than they ever have, and I think they've become, um, very, um, 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, 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 super resilient. So the resiliency of a company like Facebook having bought WhatsApp, Oculus, and Instagram, three huge bets, or Google having bought Android, um, YouTube, much stronger businesses. And then even in the classic businesses like Disney having bought Pixar, Marvel, uh, 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, and (laughs) Mickey Mouse.

    3. CW

      Mm-hmm. Mm-hmm.

    4. JC

      Uh, 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. So-... uh, I- I think buying those kind of stocks, um, and I'm not a s- public stock picker, it feels like there's very little downside because the idea that Amazon or Google would go away, uh, any time soon or perhaps even in our lifetime s- does not seem realistic. Um, we did see Yahoo go out of business. So previously when they were one-trick ponies like Yahoo was, uh, 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- they've got one business really and, you know, that- that does make it, um, difficult.

    5. CW

      I get it. So-

    6. JC

      Or more challenging.

    7. CW

      ... let's go back to the-

    8. JC

      But we're investing in private companies.

    9. CW

      ... the private.

    10. JC

      Yeah.

  7. 19:12 – 24:09

    Deal flow and investor branding: how founders get “anointed”

    1. CW

      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 that says, "I own a startup." Like what happens?

    2. JC

      So the way I meet people, um, is, you know, I have a podcast and amongst founders I would be, you know, a celebrity on the scale of Lady Gaga, uh, or Michael Jordan. And then there's everybody else in the world-

    3. CW

      Have you gone out- have you gone out and felt like that, Lady Gaga?

    4. JC

      Absolutely. Um, I'm wearing a new dress right now.

    5. CW

      (laughs)

    6. JC

      Um, for those of you listening, it's, uh, getting a little uncomfortable in the second half of the hour. Uh, 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, uh, you know, I might get asked to take ten selfies in the tech business. And it really is a popularity contest amongst, uh, investors. Investors have brands and people want to be affiliated with different brands, so you- you might make an analogy of, like, Creative Artists 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, um, you know, you, uh, 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 CAA and agencies or labels, music, tours, whatever, uh, 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, "Uh, let us know if you make it to the other side (laughs) and how we can help."

    7. CW

      (laughs)

    8. JC

      And you know, it- it's- it really is basically like you're sending, you know, um, these founders into a war zone and you see who makes it to the other side, we see who- who, you know ... The- the good news is, it's not fatal, you know? 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, um, might be even greater based on, you know, the number of experiments being run today by founders, you need only start three, four, 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' third company was Uber, you know, Elon's third, one, two, three, yeah, third or fourth c- 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. Y- some people, Bill Gates, Jeff Bezos, Mark Zuckerberg, they hit the home run right out of the park. Uh, that's not common. It's memorable, so there's a survivorship bias to it, the fact that those companies have become big.

    9. CW

      Mm-hmm.

    10. JC

      Or confirmation bias rather, uh, not survivorship. Or maybe it's both.

    11. CW

      (laughs) It's uncommon-

    12. JC

      Confirmation.

    13. CW

      ... amongst uncommon situations, right?

    14. JC

      Yeah. Um, it is very uncommon for somebody on 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. Right?

    15. CW

      Survivorship.

    16. JC

      So survivorship bias is like okay, well these people survived, therefore there was something y- y- y- you- you- the fact that they survived, you- you read something into who will survive the next time, right? The- the problem with that was the- the way they ca- 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. And what they didn't realize (laughs) is those are the planes that made it back-

    17. CW

      (laughs)

    18. JC

      ... got hit in the wing and didn't get hit in the cockpit or the engine. So it turns out the- they weren't including in the sample where the bullets were on the planes that went down because they couldn't recover those planes because they blew up in the sky and crashed.

    19. CW

      (laughs)

    20. JC

      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- 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, right? Uh, and- and that's a major problem for people is that, that the randomness that occurs here fools people, right? Um, and- and then they start thinking, "Oh, well, I hit Uber, therefore I'm a great picker." And- and that's just not the case, right? (laughs) Like I don't think I'm a great picker; I think I have a great network and I have great relationships-

    21. CW

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

  8. 24:09 – 26:59

    Chaos is the job: spending most time on failing companies and existential threats

    1. JC

      ... uh, with people. Yeah, I mean, one way to think about this job of venture capitalist or just investor in startups is, um, 99% of my time is spent on the failed companies. So let me just say that again. (laughs) 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 gonna 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." A- and (laughs) you're like-

    2. CW

      Everyone pats everyone else on the back, high fives.

    3. JC

      It's a bunch of high fives, yeah. I mean, and, and, you know, I've s- 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, uh, screwing up your formula," right? Like-

    4. CW

      Mm-hmm. Just, "You keep doing you. You keep on pushing whatever button you're pushing."

    5. JC

      Yeah. Yeah, and 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, com- comp- competitive issues. There's a lot to do, even on the successful companies. Like, when your company's scaling, you need to hire a lotta 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, you know, gets to orbit. Um, it's the ones that never even, you know, get the rockets to the launchpad, you know, m- 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 into space without those two things. We're gonna need some jet fuel and we're gonna need some astronauts. Like, you know, I'm gonna have to finish the rocket. Oh, the rocket's not done? Oh, okay. Well, we gotta finish the rocket, um, if we got any chance to get into orbit." So it's- it's a chaotic job. Like, the last week, just to give you a picture of my life with over 200 investments, the last week I've spent dealing with, you know, chaos at four companies. So 2% of the company is just completely chaotic, um, you know, and with these startups, they're almost inevitably running out of money, facing, uh, existential threats externally where Google's gonna make their product free, let's say. Uh, or- or, you know, they're getting really well-funded competitors who then decide they're gonna give away $100 bills for 50 bucks and take all the customers (laughs) , you know, uh, which is what Lyft did with Uber and Uber did with other people. Like, they get into these crazy, you know, wars of discounting and, uh, you know, it's pretty scary. So yeah, I deal with a lot of chaos, and I think that's why-

    6. CW

      So how much, to step in there, sorry Jason, how much of that is you coming in and ma-

    7. JC

      ... that's why I liked your poster so much.

    8. CW

      ... and massaging people, and just saying, "Let's everyone chill out. Let's bring a little bit of order to this chaos"?

  9. 26:59 – 32:22

    Leadership under pressure: lighthouse steadiness, emergency services calm, and war metaphors

    1. JC

      A lot. 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 as nature, doesn't- you don't get the sense that that lighthouse is gonna get knocked over, right? K- and that's really my job, is the job of the founder is, of any leader, is, uh, to convince everybody, um, that there's a plan, and that we can succeed if we follow the plan, uh, 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, we have to get out of this lease. Or, oh my God, we've, you know, got these competitors. Okay, great. But let, 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, uh, all over the place, it's very hard. And, uh, you know, I spent some time working on an ambulance, and I was always taken by the, the people who were in charge. Uh, my brother's a firefighter, uh, and, uh, a 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, you know, uh, my first call on an ambulance was the night before Thanksgiving, uh, in 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, this is a coin toss situation. And just watching the calm at which people were able to triage these situations was always very impressive to me. I always think about samurai or Jedi in that regard, uh, which is why there's a poster of Toshiro Mifune, uh, in the office. Um, and, you know, if you look at samurais or- or Jedi knights, uh, 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 v- don't often take out the sword. They're gonna figure out solutions, they're very focused, and they're- they know how to block out what is not essential, right? So there's a great scene where Qui-Gon Jinn is fighting Darth Maul, and these, uh, this wall gets, uh, 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, uh, Qui-Gon Jinn just kneels down, turns off the lightsaber, and meditates and closes his eyes. A- and, you know, really, that's like, "I'm gonna conserve my energy here and think about what the right decision is, because those doors are gonna open and it's gonna be chaos." And if you d- if you look at a scene, uh, like the movie Gladiator, there's a scene where Maximus says, "Listen, whatever- anybody here in the army, great. Come (laughs) come next to me, we're gonna 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 gotta go in and protect the pilots of that other Black Hawk, uh, drop us in." And they said, "Listen, we- we don't know when we're gonna 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 you reinforcements or if we can ever get reinforcements there and we're dropping you into this hostile territory, where it's gonna 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, um, because they ... In each of those cases people are working together, um, a- and they're blocking out things that are not important and they're focused on what is important. A- 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 gonna take that chance anyway and we're just gonna focus and let our training and our plan execute itself, you know, whatever happens." Now, those are all violent, crazy situations, um, but those are the metaphors I choose. I'm sure somebody else could come up with a, a much more peaceful one, but, God, in my experience, it's a fucking war.

    2. CW

      I like yours. I like your words.

    3. JC

      Running these companies-

    4. CW

      I like your ones.

    5. JC

      Running these various companies is a fucking war. It really is. And, and that, and that's just the successful ones, you know? (laughs) The ones that are not successful-

    6. CW

      (laughs)

    7. JC

      ... you know, it, it's, uh, you know, it's a war and chaos and-

    8. CW

      Whilst fighting the coronavirus.

    9. JC

      (laughs) 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 where you're supposed to have your hardware solution, you know, that client's paid for, and now it's, you know, lost in customs or something. Uh, there's a business disruption. Business disruption for A- 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.

  10. 32:22 – 37:37

    Nature vs nurture in handling chaos: childhood adversity, immigrants, and Jason’s own background

    1. CW

      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, then 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?

    2. JC

      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 folk- folks are very good at adding skills. Um, a- and, you know, I, I think you can 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, uh, 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, it certainly is an interesting one to consider, is that a lot of the great founders, uh, 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, uh, cruel or mean. And that person then had to balance and learn to solve this problem every day of their life in their childhood, right?

    3. CW

      That's interesting.

    4. JC

      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, um, you know, in terms of the percentage of them leading very large companies, uh, in their leadership ability. Something about, uh, immigrant parents and, you know, the, the, 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." Um, you know, there, 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 wanna 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, um, under such incredible duress, um, just doing that, that they become exceptional citizens, I think, by and large, a- and become incredible for those countries that get to receive that gift, right? Like, if you look now in Silicon Valley, um, the number of Indian-Americans, uh, who are leading companies out here is just extraordinary. Um, and we had just a massive influx of Indians, uh, who suffered greatly, you know, in, in their journey here a- and to build a new life here, faced racism, faced, you know, uh, having to work menial jobs to build stuff up, and, an incredible work ethic, an incredible, uh, focus on education. And now Microsoft, Google ... I mean, the, the number of Indian-Americans running companies is just stunning, uh, and amazing. And now we wanna 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. Just, you know, nationalism.

    5. CW

      How about for you? How about you? Talk, let ... T- talk to me about your constitution. Talk to me about what it is that you're ... Or y-

    6. JC

      Oh, me.

    7. CW

      Part, part of your practice as well.

    8. JC

      (sighs) ohh.

    9. CW

      Talk to me about what, what makes-

    10. JC

      yeah.

    11. CW

      ... what sets you apart.

    12. JC

      Well, 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. Um, you know, my dad losing his bar when I was 18 years ... 17 years old, uh, and, and just growing up in a bar and, and just seeing chaos all the time, I, 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, that now ... I'm super aware that the analogies I use, uh, you know, are these war and violent ones. (laughs) Uh, or, you know, or non-violence in the case of the Jedi and Samurai, just violence as 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, I just have a never say die attitude, which is probably long term not a great idea, uh, for returns. Uh, 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. 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, you know (laughs) . I, I like to fight it to the end.

  11. 37:37 – 40:49

    When to fight vs when to quit: emotional attachment, cutting losses, and founder-led decisions

    1. CW

      Do you think you'll 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, a curse that you have to suffer for the strengths that it gives you?

    2. JC

      Yeah, I kinda like it. I'll be honest. I kinda like it. I like, you know, being against the odds, uh, you know. Uh, I, I like the feel ... I, I sleep better at night knowing I fought till the end, you know?

    3. CW

      For those that are out there.

    4. JC

      And I just, 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 wanna, uh, 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 roof of Hooli while drinking cocktails and whatever, fine, let's do it. Um, and then we'll, we'll come back in two or three years and, and kick ass again." Eh, and so I kinda leave it up to the founder. That's the balance I've found. I, my natural, you know, inclination is to fight, fight, fight and never give up, uh, 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, 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. You know, like if you're fighting against, like, you know, a, a tsunami, like (laughs) it's, you can't swim your way out of a tsunami in all likelihood, right? You'd probably want to retreat. So there's, there's a time for retreating. Um, I, it's just not in my nature generally.

    5. CW

      I get it. I get it.

    6. JC

      Uh, uh, 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 gonna work out. I wish you luck with it, and we have to focus on the winners."

    7. CW

      (laughs)

    8. JC

      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. Um, we've committed as much capital as we want. We're gonna 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."

    9. CW

      Super rational approach.

    10. JC

      Just ... It's, it's a much more efficient approach, I think. I, I, and I see VCs do it all the time. They're just like, "Yeah, it's not a fit for us, you know. Um, we're not gonna keep going, but you know, we'll, we'll give up our board seat, and yeah, if you wanna buy us out for 10 cents on the dollar, whatever. You know, it's your company, you do what you want." But they, (laughs) they kinda walk away from it.

    11. CW

      (laughs)

    12. JC

      Um ...

    13. CW

      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, 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. I don't know whether that's-

    14. JC

      Yeah.

    15. CW

      ... personifying, I don't know whether that's trying to, um, trying to per- personify businesses almost as, as beings, you know, with personalities and stuff like that.

  12. 40:49 – 53:48

    Two-bucket strategy and founder traits: superpowers, focus, and the portfolio math

    1. JC

      Yeah. I mean, uh, in order for another door to open, sometimes you gotta close one, um, and sometimes you gotta reinvent yourself. So it's, uh, you know, I used to be a journalist and, you know, I think I took that as far as I wanted to take it. Um, I still dabble by doing this podcast, et cetera, but it's not exactly, I don't do it for journalistic reasons exactly. Um, and so sometimes you gotta close the door on one chapter of your life in order to focus your energy on another. It's pretty much that simple. Uh, and, and for founders especially because you, you, 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? Uh, people look at what I'm doing and 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.

    2. CW

      Mm-hmm. So it looks from the outside looking in like you're potentially spinning an awful lot of different plates, whereas it's been-

    3. JC

      Sure, it's making startups.

    4. CW

      It's been stream, streamlined into two very discrete areas, which allows you to then scale the volume that you're doing that at.

    5. JC

      Correct. Yeah, I mean, we have one thing, like podcasts and events and books, right? So they're 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 Skale and Founder University and Angel University and Angel Summit?" It's like, yeah, those are all one thing.

    6. CW

      Mm-hmm.

    7. JC

      That's just a way to meet people in the industry and let them, you know, share knowledge with each other. Um, and we as the hosts of the sharing of that knowledge, hopefully, uh, people remember our names so we can do number two, invest in their companies.

    8. CW

      Ah.

    9. JC

      That's it. It's literally two things. But y- you know, if you looked at our Asana project board or our Notion or, you know, our customer support line, whatever, like you would see a lot of different activity-

    10. CW

      (laughs) Yeah.

    11. JC

      ... 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. Uh, you know, people outside the Avengers, they're doing Spider-Man and, you know, um, 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.

    12. CW

      (laughs)

    13. JC

      They do streaming service to entertain people. Okay, 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 a- you can buy a Star Wars light saber. 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.

    14. CW

      It was burned so deeply-

    15. JC

      And yeah, we're still getting them.

    16. CW

      ... that you forgot that they were doing it, forgot that they were doing something different.

    17. JC

      I mean, what- what other business do they have? You know, you look at it and say the theme parks are different, where 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. And 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 you maybe you buy something on the way out. That's it.

    18. CW

      Pfft.

    19. JC

      Any other business Disney is involved in, I don't know.

    20. CW

      Is there something sort of sym- 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?

    21. JC

      It's good to understand what you're good at, that's for sure. Um, I, 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 could 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.

    22. CW

      Mm-hmm.

    23. JC

      And people will think like, "Oh, there's a lot more going on here." It's like, is there? Right? Like, he's an e- he's a- 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 thi- I think Steve Jobs was a marketer, right? He knew how... Like a packager, like he really understood how to package and market something to people. Simplify it, maybe. Like maybe he's a, at his core, Steve Jobs was like just a great designer, um, of products, right? Uh, 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.

    24. CW

      Mm-hmm.

    25. JC

      It was simple, clean, opening the box-

    26. CW

      Beyond the tech.

    27. JC

      ... going into the store, using it. All the... Yeah, all the experiences. So y- he's kind of like an experience designer. Um, yeah, at his core he's an experience designer. Actually, that'd probably be the best way to say it. He's an experience designer.

    28. CW

      I'd agree.

    29. JC

      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. And so yeah, you need to know what you're good at, right? I'm a talker. Like my skill set is talking. That's my superpower, is talking. And, uh, 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 tra- and strategies to succeed. So talking is a good one.

    30. CW

      Precision with your speech is something that I think is uh, uh, a very, very under-regarded superpower. It's 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 in sharpening and honing in terms of the skill and, 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-

  13. 53:48 – 1:03:55

    Podcasting’s next phase and the media trust collapse: candidates, books, and “agenda-driven” news

    1. CW

      I get it. Uh, I got two questions before we finish up, Jason. First one-

    2. JC

      Yep.

    3. CW

      Going back to podcasting. Someone who's been in the space-

    4. JC

      Yeah.

    5. CW

      ... for quite some time. 60 million-plus plays? Is that even more now, more than 60 million?

    6. JC

      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. I mean, we're, we're only talking about 200,000 people listening to every episode. It's no Joe Rogan.

    7. CW

      Mm-hmm.

    8. JC

      It's not millions or, of people listening to everyone. It's, you know, it's a boutique podcast about a very specific niche thing.

    9. CW

      Mm-hmm.

    10. JC

      But it, that niche thing, we're better than anybody at doing.

    11. CW

      Mm-hmm. Um, so-

    12. JC

      I think that's what's important.

    13. CW

      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?

    14. JC

      Well, I think the, I think the listening, the listenership's gonna, you know, double in the next year or so, 'cause 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, um, or, you know, uh, that, you know, even presidential candidates are, and not just Andrew Yang, right? Like, not just like the tenth person in the race, but-

    15. CW

      Uh-huh.

    16. JC

      ... you know, the top person in the race-

    17. CW

      Uh-huh, uh-huh.

    18. JC

      ... um, 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, um, and, you know, once in a while there's gonna 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 gonna 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. 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 at CO2, um, 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 and New York Times, Washington Post, TechCrunch, Recode, or any other pe- person called him because their guard would be up. And he'd 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?"

    19. CW

      (laughs)

    20. JC

      "Oh, you're doing an anti, uh, 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-"

    21. CW

      Everyone's unhappy.

    22. JC

      "... let's criticize him because he only gave away 10%." Right, 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. Um, puts him number three in philanthropy, I think, um, or four, um, which is-

    23. CW

      But it's not enough.

    24. JC

      ... I think it's Gates. A- 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, uh, balancing out and being, 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 are like, "Okay, we'll pick the left, MSNBC 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 in the middle is toast. If you're gonna 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 wanna 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 for objective journalism right down the middle." And, you know, journalists have responded to that market condition and, you know, it's a, 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. Um, that a- you know, I don't agree with Trump calling the press fake news. I don't think the news is fake. 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, I, it doesn't feel objective anymore.

    25. CW

      Mm-hmm. Mm-hmm.

    26. JC

      It feels like they're all anti-capitalist, anti... You know, they, there's a group of them that are just super anti-capitalist, super socialist, you know, and it, it's just depressing. Like, I would rather see them... Eh, I get contacted by journalists, literally nine out of 10 times it's some negative story, and one out of 10 times maybe they're on background and I can't tell if it's negative 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, is, have you seen anything interesting?"

    27. CW

      Mm-hmm.

    28. JC

      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 Robin Hood, 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, the only criticism was maybe the tech press is a little too cheerleadery, but-

    29. CW

      Yeah, like those advertorial type sort of things.

    30. JC

      ... now it's gone the other way.

  14. 1:03:55 – 1:08:34

    What Jason is watching next: robotics beyond factories, housing innovation, and alternative education models

    1. CW

      Do you have any cool tech on your radar at the moment?

    2. JC

      Cool tech on my radar. Um, I am, uh, particularly interested in robotics outside of factories. I think it's a very, um, you know, interesting space that is going to, um, get very big. Um, I'm also very interested in education that is self-paced and occurs, you know, online, uh, or in small groups. Uh, but that is, uh, student-led kind of, you know, um, self-instruc- uh, what do they call it? Um, there's a term for when it's student led, but, um, I, you know, I, I like to look at the areas ... I, 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. Um, and then another one is housing, and even housing plus robotics is kind of interesting to me, like robots building houses.

    3. CW

      Mm.

    4. JC

      Um, 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, uh, 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, uh, or there are websites that'll teach you, you know, very niche websites, one to become a dancer, like steezy.co. We invested in S-T-E-E-Z-Y.co. Um, a- and, you know, or brilliant.org, which teaches people math. This idea that they're going to be a vertical site that's just really good at teaching you one thing, uh, 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 in 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 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. Um, so yeah, I, I just look at those big, broken markets, things that are hard, um, and just try to think as an investor, "God, I can't wait for a founder to take on this one."

    5. CW

      Mm.

    6. JC

      And Blokable's, Blok, B-L-O-K-A-B-L-E, blokable.com is doing modular housing and I'm super excited about that. Café Ex 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 doughnut 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 or pizza or whatever it is, right? So there, 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, and do it perfectly when it, you know, when a human doesn't.

    7. CW

      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, a human right to have coffee.

    8. JC

      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.

    9. CW

      (laughs)

    10. JC

      Coffee is like the first, you know, or the first might be just ... Yeah, I think, I think coffee is a pretty good first, actually.

    11. CW

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

    12. JC

      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 or 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 y- I mean, once you start putting humans in the store, it's like, "Well, okay, what's the point?" Right?

    13. CW

      A human coulda done the thing, yeah.

  15. 1:08:34 – 1:14:08

    Wrap-up banter: Newcastle geography, Dire Straits references, and the Brooklyn Bridge

    1. JC

      Yeah, I mean, it di- and that doesn't mean there won't still be people, you know, just like cars may have replaced horses, like they're 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. Does that mean ... Wait, you're in Newcastle?

    2. CW

      Correct, yeah. Up north.

    3. JC

      By the Spa- You by the Spanish City?

    4. CW

      What Spanish City?

    5. JC

      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 a amusement park. It has like a, like a-

    6. CW

      Are you thinking, are you thinking Newcastle, Australia?

    7. JC

      No. Hold on a second. Spanish City. One second.

    8. CW

      Spanish City?

    9. JC

      Oops.

    10. CW

      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 gonna be really embarrassed.

    11. JC

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

    12. CW

      (laughs) Oh my god.

    13. JC

      It's a town in North Tyneside. Is that near you or no?

    14. CW

      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?

    15. JC

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

    16. CW

      Okay. Yeah, yeah.

    17. JC

      Um, 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.

    18. CW

      It's just some gaff 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.

    19. JC

      And they actually, by the Spanish City, put the lyrics to that song, Tunnel of Love. You know who Mark Knopfler and Dire Straits are, of course.

    20. CW

      Mm-hmm.

    21. JC

      Wait, now when, when they say Geordie boy, where does a Geordie boy come from?

    22. CW

      Okay. So a Geordie is the colloquial term for people from Newcastle. So you have Geordies from Newcastle. That would be, uh-

    23. JC

      Correct.

    24. CW

      ... Brian Jo- Brian Johnson from AC/DC, Geordie. Yeah.

    25. JC

      Yeah.

    26. CW

      You-

    27. JC

      Mark Knopfler-

    28. CW

      You-

    29. JC

      ... uh, considers himself like a Geordie man.

    30. CW

      Then you, you'd have-

Episode duration: 1:14:05

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