Interviewing Jason Calacanis - "I will be the greatest investor in the history of Silicon Valley."

Interviewing Jason Calacanis - "I will be the greatest investor in the history of Silicon Valley."

Authored by Zhill Olonan • 
August 6, 2018
“This idea that people have no agency and no ability to change their life...it's patently false in the age of free education that's available globally to everybody.”Jason Calacanis - Episode 78

Angel investing, which is backing and investing in companies at the earliest stages, is a high-risk, high-reward game.

Jason Calacanis, who was one of the first investors for billion dollar startups Uber and Robinhood, came from a difficult beginning. As a scrappy kid from Brooklyn who lost out on a $20 million buyout offer for Silicon Alley Reporter when the dotcom bubble burst, Jason refused to give up and made his fortune as an angel investor. Still not satisfied, Jason is setting his sights even higher to impact the world at scale. Within the episode, he tells host Geoffrey Woo that he is aiming to become the greatest investor in the history of Silicon Valley.

In this discussion, you'll discover:

  • How and why Jason plans to become the greatest investor in Silicon Valley
  • The impact of social media and identity politics on conversation and discourse
  • Techniques for developing a self-aware, self-improving mindset

Listen now on iTunes and Youtube.

You can check out Jason Calacanis on his show: This Week In Startups.

I want people to understand that I am confident that if I invest in your company, we're going to do great things together, and that I can be a game changing investor. If you are the greatest of all time and you aspire to be the greatest of all time you will attract the greatest. And so, people see the work ethic I put in, and they see the goals I set.Jason Calacanis - Episode 78

Transcription

Geoff: I'm excited to talk to my friend Jason Calacanis. Jason, great to have you on the program. I know I was in your hot seat last week.

Jason: Yes. 

Geoff: So great to have you in our studio.

Jason: It is my pleasure, thanks for having me.

Geoff: So a lot of people consider you the G.O.A.T. angel, the greatest of all time angel investor.

Jason: It is half true.

Geoff: So what's the edge? I mean there's a lot of credible people in the area, what do you think is your unique edge here?

Jason: It's a good question. I will say that there are three or four angel investors who did really well. Bill Lee, Chris Sacca, Ron Conway ahead of me, but they don't angel invest anymore.

Geoff: Right.

Jason: So since some of those have retired, I think Ron Conway and Sacca are no longer investing, and then Bill Lee has Craft Ventures and Mark Andreessen has Andreessen Horowitz, so those two don't angel invest, they put in three, four, five million dollars, so it's sort of like being Kevin Durrant when Lebron James leaves the game he'll be number one by default and or the Greek Freak after that when Kevin Durrant goes, so. 

I bring that up because I want to let people know that I'm serious about what I do as an angel investor. So I will say I'm the G.O.A.T angel investor or I will be the greatest of all time. The reason I say that is because it's marketing, it's aspirational, and it lets my team know exactly what I'm focused on and why their jobs are super important. So some people think it's a little cocky or arrogant, which is great, that's what I'm going for. 

The reason I say that is because it's marketing, it's aspirational, and it lets my team know exactly what I'm focused on and why their jobs are super important. So some people think it's a little cocky or arrogant, which is great, that's what I'm going for.

I want people to understand that I am confident that if I invest in your company, we're going to do great things together, and that I can be a game changing investor. Because if you are the greatest of all time and you aspire to be the greatest of all time you will attract the greatest. And so, people see the work ethic I put in, and they see the goals I set.

I've changed my goal, it's obvious that I'm one of the top angel investors of all time and I think it's obvious to anybody paying attention that I will be the greatest of all time hands down, because Paul Graham, he stopped working three or four years ago at Y Combinator, so there's an argument to be made that he's truly the G.O.A.T, because I don't, I mean they're up to 1500 or 2000 investments over there.

But the truth is, I think he stopped maybe when they hit 500 or 750, and then he's been in Europe for the last couple years hiding out and enjoying his money. But the truth is, if you put all their investments together, I think it equals 70 to 80 billion dollars in market cap, those companies. You put all mine together, it equals 70 to 80 billion dollars. 

So if you put my track record against Y Combinator, and institution that's deployed maybe 20 times the amount of capital. I've done as well as them with five percent of the capital. I've done as well with 150 investments as they've done with 1500. So just in terms of efficiency, I'm a machine.

Geoff: Which is interesting because I think that you clearly have the infrastructure around you, you have the book, the podcast, conference and the newsletter.

Jason: I'm building it, yeah. And the university, founder of that university. 

Geoff: Yeah, but you would see that a lot of these angels that you mention will build up, turn into venture capitalists, growth investors.

Jason: Sure.

Geoff: Start taking outside money.

Jason: Yup, and we have outside money too with our syndicate Jason's, syndiacte.com.

Geoff: So why have you chosen the focus, is that a particular strategy, you just are like focused on-

Jason: Yes. 

Geoff: -that early, early stage?

Jason: Yeah, it's a strategy. 

Geoff: Okay. And which is kind of interesting because I think that a lot of investors tend to just acquire assets under management. Why have you avoided that?

Jason: Right. It's a strategy because there's two ways you can generate amazing wealth and power in Silicon Valley. It's a small handful. One, you could be a founder and that will get you the most power and the most notability, the most fame, and the most money.

Right. It's a strategy because there's two ways you can generate amazing wealth and power in Silicon Valley. It's a small handful. One, you could be a founder and that will get you the most power and the most notability, the most fame, and the most money.

But you have to hit it a bullseye. You have to build Facebook, Google, Tesla, Airbnb, Dropbox, Uber, Robinhood, I mean, it's a one in a thousand or one in five thousand chance that you're going to do that, become a unicorn.

So that is the most power, the most wealth and the most fame and victory and high fives. After that, being the person who sources the company, the first person, has the most power. They don't have the opportunity to make the most money. 

The people who are the later stage, so Sequoia's growth, Masayoshi Son's growth fund with SoftBank, Yuri Milner, the people who have multi billion dollar funds, cash on cash they will make the most money. Because if Mark Andreessen puts a billion dollars into Skype and sells it for twice as much, he gets-

Geoff: A billion dollars. 

Jason: 20%, no, not a billion, but he gets 20 or probably 30% carry, 30% of the billion dollar gain.

Geoff: Right. 

Jason: So he makes $300 million. For me to make $300 million, I've got to hit like two or three Ubers. So my job is much harder, however, being the person who sources the deals, finding Henry from you know, Café X, in Hong Kong when he was in school, or finding Blockable when they had just left Amazon to go make this modular housing company, that's what I do. 

I find the diamonds in the rough and I bring them through my incubator, syndicate them, build a position of between six percent and 30 percent of the company and then I hand them off like a point guard to you know, a short list of venture capitalists who I believe are the G.O.A.T's in their category. So Roelof Botha, Chamath Palihapitiya, David Sacks, Bill Gurley, these are the people that I, when I bring the ball up the court, I give them the alley-oop. 

And so if you look at Uber, I did the seed, Bill Gurley did the Series A, and there's a long list of companies where I incubate them, brilliant.org, which is been an incredible company I handed off to Chamath, and Social Capital, they've done amazing things with it. Café X, David Sacks from Craft Ventures, formally of Yammer and PayPal, he's taken that one on and he's now done the Series A with me. Just this week, so I view my job as being the point guard, and I like having massive impact and sourcing the deals and being the first money in.

I was the second investor in Thumbtack after Marco's parents, third investor in Uber, early in Robinhood, WellFront, Desktop Metal and Datastacks, those six unicorns, and then calm.com, you look at that company, they came on my podcast, nobody would invest in Alex, just except for Michael Acton Smith who now is the co-CEO, but it was, he was having a very hard time, nobody wanted to invest in a meditation app, we put $378,000 in for eight percent, people wrote Cora posts, you can look them up, will Jason lose $400,000 investing in Calm? 

That company reportedly, it's in the press, closed money at a $250 million dollar evaluation, and they've doubled their revenue since they closed that. There's a rumor going around in the press that they're making $70 to $80 million dollars a year. 

Geoff: Cool. How about that IRR?

Jason: And I invested when they had $10,000 a year in revenue. And I had my own thesis of why meditation and mindfulness would work, and I have my own thesis on why Alex, too, the co-founder and CEO, who really was working on it full time, was a team of one, I had my own thesis on why he would be a unicorn CEO and people didn't believe in him I think. 

They didn't see what I saw. I saw the raw talent. I saw this person was one of the great product minds of our generation, up there with Elon and Steve Jobs. So other people didn't see it.

Geoff: Right, so what is that sixth sense? I think I mean, when we talk about angel investors, you're often seeing things that are, $10,000 a month, right, like it's barely anything. 

Jason: $10,000 a year.

Geoff: $10,000 a year, okay even smaller. So. 

Jason: $10 a year for the app I think.

Geoff: How do you read people? What's that sixth sense, is it from poker? I know you're a big poker guy.

Jason: Yeah a lot of it's from poker signaling, I've learned, both are very similar, you can tell when people are telling the truth, you can tell when people are lying to themselves, you can tell when they're lying to you. These are different things. Like people can delude themselves, or they can outright lie to you and that's fraud. 

So those are two very different things, I like a delusional person, I like a person who's lying to themselves, to a certain extent I'm lying to myself saying, my new mission is not to be the greatest angel investor of all time, I want to be the greatest investor in the history of Silicon Valley. Which there's probably 50 people in front of me now.

But I'm putting it out there right now on this podcast for the first time, I will be the greatest investor, not angel, not venture, investor. In the history of Silicon Valley, because I'm not going to stop.

But I'm putting it out there right now on this podcast for the first time, I will be the greatest investor, not angel, not venture, investor. In the history of Silicon Valley, because I'm not going to stop.

Geoff: What's the benchmark for you? Like what does that mean? IRR?

Jason: It is now. Well no, I would, that's a great question. It's certainly, you have to have the returns. I think the number of unicorns that I invest in the first round were, let's say the number of unicorns I invest in at under $30 million dollars and under.

Geoff: Right.

Jason: Because I could put ten more unicorns on my angel list page, or my portfolio page by just buying secondary shares. So if you want to go buy, I mean and I know a very famous angel investor, I won't say who, but they literally put Twitter, Facebook, Tumblr and a bunch of other stuff on their angel's page and they're just like yeah, I bought $10,000 in secondary shares in second market and I put them as angel investments. 

Geoff: Right.

Jason: If you look at the six companies, seven companies I mentioned, six unicorns and Calm which I think will be a unicorn, I invested in all those companies for a combined value of under $100 million. All seven. The average valuation of those companies, the median valuation would have been five million. The median would be five million. So I'm not fucking around, like I will be the greatest investor in the history of Silicon Valley.

Geoff: Yeah.

Jason: And that means I have to be, you know, that means Sequoia, Doug Leone, Michael Moritz, Roelof Botha, these are like heavyweights.

Geoff: Yeah.

Jason: That's like me saying, I'm a rookie in the NBA, I'm Kobe Bryant and I'm going to be better than Jordan. That's like a big statement that I'm making today. But that's what I'm going to try to do. And if I fail, okay fine I'll go from number 100 to number 50. 

Geoff: Right.

Jason: It won't be that bad.

Geoff: Yeah. 

Jason: I'll be in the top 50. 

Geoff: Yeah.

Jason: But I'm going for the number one slot because I'm 47 and I'm going to do this for another ten, 20, 30 years, completely conceivable I hit another six unicorns every six years or a unicorn a year for the next 20. I'll have 26 unicorns. Who has 26 unicorns? Not many.

Geoff: Yeah, what's the diff? Like how do you get there from, like what's the difference between you, greatest of all time, investor period, and today, Jason today? Does that mean more people on your team?

Jason: Well I'm going to have to build massive, I need to do many more investments.

Geoff: Okay.

Jason: Have massive infrastructure. And I need to put larger dollar amounts to work and I need to be on the board at these companies. All of which I've set up to do now. 

Geoff: Okay.

Jason: So I'm building the infrastructure, building the team, building the compensation package for those teams. I all ready have the network, I all ready have the platform. That doesn't need to get much bigger. 

Geoff: Right.

Jason: And I need to go international which I've started to do, you may have seen Launch Festival was in Sydney this year.

Geoff: Right. 

Jason: It will be in Sydney next year. We'll have some other announcements. My book just got translated into Japanese.

Geoff: Yeah, I saw that.

Jason: Last week.

Geoff: Yeah.

Jason: So I'll be going to Japan on a book tour. It's going to be translated into seven other languages, so it will be in nine languages. And I'm starting work at the end of the summer on my next book and the first book just had it's one year anniversary and has over a thousand five star reviews on Amazon and Audible. So it's a highly rated book. And I wrote it myself, like I didn't have a ghostwriter.

Geoff: No ghostwriter. 

Jason: Like some other famous people here in Silicon Valley.

Geoff: Yeah. 

Jason: Who have books that have done really well.

Geoff: Yeah. 

Jason: But that's the secret, they had ghostwriters and they bought 25,000 copies of their own books through a marketing agency to be a best seller. I didn't do any of that bullshit.

Geoff: Yeah if it works, it's gotta mean, that's kind of like the-

Jason: It's called cheating.

Geoff: Or like Campton Creek or some of these other companies that kind of juice their own wheels. One thing I think is refreshing with your style is that you actually have swagger. I feel like, maybe this is, you know, I've been in Silicon Valley, I guess including my years at Stanford, for a decade. 

So haven't been around the rodeo for that long, but it seems that like even in the last nine, ten years or so, it feels that more and more people are being more cautious and I feel like you've been one of the rare folks who have been quite outspoken with your opinions and putting yourself out there.

Jason: Yeah.

Geoff: And also putting, you're saying hey, I want to be the greatest investor in Silicon Valley, that's like a big target. I feel like more people should aspire towards that kind of swagger. I mean, what do you think is the difference, has the environment changed? What do you think are the big drivers?

Jason: No, I think people are full of shit, number one. 

Geoff: Okay.

Jason: So there's a lot of people running around town saying it's not about the money. But of course they have all the money. You know, it's like really convenient to say it's not about the money when you have a billion dollars and a jet and five houses right? Oh it's not about the money, it's like, well you have the money, so. 

You know, I grew up lower middle class, my dad was a bartender, my mom was a nurse, they lost everything when I was 17 years old. When my dad got behind on his taxes and almost went to jail when the feds came and literally the feds came with raid jackets and shotguns and took his bar. But I'm an outsider, you know, I don't think people really wanted me in this business, there are people who actively fought against me, high profile names in this business who tried to subvert my ascendance. 

So I'm a kid from Brooklyn who people didn't want to have, or a group of people really didn't want to become an insider, and then thanks to Uber, you know the other investments are great but that's the one that really set me apart, obviously. So thank you Travis, I'll always be loyal to Travis and Garrett Camp for that. That got my fly wool started in Sequoia, making me the first Sequoia scout, that was what gave me the ability to then do the Uber investment, Thumbtack investment, DataSacks investment and a bunch of other famous investments.

So you know, I've been very blessed to have a supporter in Sequoia, supporter in the founders of the early companies, but I got here by being candid. By being blunt. And there was time when people took me aside and was like, you know, you're kind of inside the tent now, you're an insider, you don't need to swing your elbows around and fight for every rebound. 

And you know, when I was a kid I was the type of kid who would jump into the middle between two six foot people or when I was five five, and just rip the rebound right out of their hands because I would just sit there in a basketball game and I would say okay, the ball's coming off the rim, he's going to get the rebound, and when he goes and brings the ball down to his waist I'm going to run around the left hand side and I'm just going to swat it and then I'll steal it.

And I would just do it over and over again, because I knew I was at a disadvantaged trying to rebound heads up against people taller than me. But I knew they were going to have to bring the ball down to their waist, which is what they always do which is so stupid, and then I'd just rip the ball right out of their hands. So I had to be scrappy, it was the only way I was going to get there. 

But I knew they were going to have to bring the ball down to their waist, which is what they always do which is so stupid, and then I'd just rip the ball right out of their hands. So I had to be scrappy, it was the only way I was going to get there.

So I am a little more cautious about what I say, because it can be misinterpreted, you know, people, Gawker, I'm in, said I was a racist because I said I believe that anybody can aspire to do great things and get there. And they're like, that's racist. I'm like, I'm sorry wait a second, I thought that was the American dream?

Geoff: Yeah, that is.

Jason: And they're like, no it's racist because you're a white guy saying it. And I was like okay, well listen, identity politics aside, you're an Asian guy, I'm a white guy, okay, everybody's got an opinion but if we have to frame every discussion through an identity politics? I think it's just super unfair to everybody that their opinion is being contextualized based on who they are. 

Now that doesn't mean that you can't take into account a person's individual experience, but you can't also not give people their own experience. My experience was, I fought my way into the industry, so for you to tell me I didn't fight my way into the industry, and that I'm an insider, and that everything was given to me, well that's counter to my entire life's experience. It'd be like me sitting across from you, and being like oh, you're Asian so you're good at math? 

It's like, well no, I might have sucked at math but is the reason you're successful, did you go to Harvard in the Ivy league? Did you go to school after, you know like, there's this bizarre meme that has spread in the last decade, especially because of social media, that we have to judge everybody by the color of their skin and what they say in context to that as opposed to their personal experience.

Geoff: Right.

Jason: But that doesn't mean there's not injustice in the world and there are abhorrent things that are happening and it's really scary, like this racism and Trump and Ku Klux Klan, and there's good people on either side, but in the dialogue I think we have to have room for listening to people's opinions before we start judging them based on who they are.

Either way, whether it's a white guy, a black guy, an Asian guy, a woman, a trans person, let's just have a calm discussion about what the person's intent was. And my intent was look, all the world's information is now online. I there is any skill, name me any three skills that you need in your startup.

Geoff: Understanding of biology.

Jason: Okay. 

Geoff: Understanding human performance in elite athletes and military.

Jason: Okay. 

Geoff: And supply chain, how do you manufacture at scale. 

Jason: Perfect. If I went on Google, I mean sorry, YouTube.

Geoff: Right.

Jason: Coursera, EdX, Amazon, Audible, do you think I would find any books on those or courses on those topics? 

Geoff: Yeah, you'd get a good intro, like for sure. 

Jason: Great.

Geoff: Absolutely.

Jason: Yeah. And how many people do you interview for those jobs who have not taken those free courses on Coursera, EdX, Khan Academy, et cetera?

Geoff: The majority of them, right?

Jason: The majority.

Geoff: Right. 

Jason: So the majority of people have, staring them in the face, courses from MIT and Stanford, that are now available for free and they don't take them, why? We have to ask ourselves this fundamental question, because when, how old are you? 

Geoff: 29.

Jason: Okay, so you remember a time before the internet? Or maybe?

Geoff: Yes, vaguely.

Jason: Vaguely. 

Geoff: When I was in elementary school.

Jason: Right before the internet. 

Geoff: Like when Google was just coming out and it was like, whoa. 

Jason: And you had to get information from?

Geoff: Library, books. 

Jason: The library.

Geoff: Yeah.

Jason: You had to go to the library, we had a lot, and your library may or may not have the books.

Geoff: Right. 

Jason: And certainly whatever the most important courses were, there were no books. Now, on your phone, high speed video, you can take a course on machine learning and AI, you could take 20 courses on machine learning and AI.

Oh, what if I'm not good at math or I'm not really, okay, well you can take it and get 20% of the knowledge, but if not, you can go to Khan Academy or brilliant.org and you can do whatever math that you didn't get in high school or college. Oh well I'm even worse than that, I can't even read. Okay, well now you can go, you know, a step before that. 

So this idea that people have no agency, right, because we're talking about performance, people have no agency and no ability to change their lot in life, is patently false in the age of free education available globally to everybody.

Geoff: Right. 

Jason: If I want to learn how to play guitar, I can download one of five apps and start doing it. I don't have to hire a guitar teacher. It's a hundred dollars a year for Yousician. I started playing guitar, I'm up to like level seven league guitar, I bought a new electric guitar and every week I try to put an hour or two into that.

Geoff: Nice. 

Jason: I wanted to learn how to play tennis. I literally just put, how to hit a tennis ball, I watched four videos, all of a sudden my friend came over and we were hitting the tennis balls around and he's like, wow, how long you've been playing? I was like, three days. I literally just watched a YouTube video. All of the answers are out there.

Now I'm not the person to say this in today's identity politics driven world because I'm a white male of privilege who's made a shit ton of money and is very successful, and wrote a book with the subtitle, how I turned a hundred thousand into a hundred million, I get it. 

But this is the undeniable truth. Tim Ferris is out there, figuring out performance and telling people every week on his podcast and in his books, here's how to win.

Geoff: Right.

Jason: But people don't read it. Gary Vanderchuck is out there, here's how to dominate social media, here's how to do marketing, some people are not watching it. And then we have to ask ourselves, well if all the information is there, then why are people not consuming it.

And then we have to ask ourselves, well if all the information is there, then why are people not consuming it.

And if there are more job openings than people looking for jobs, which just happened for the first time in the history of our country. More job openings than people looking for jobs. What is the disconnect? Well I did research on it. The disconnect is geography and education and skills, obviously.

Geoff: How about a cultural? 

Jason: Well now you're going to touch the third rail. 

Geoff: Right. 

Jason: So you explain to me culturally or why maybe this isn't happening, because that's the thing we can't have that discussion.

Geoff: Yeah we can't have that discussion.

Jason: We can't have it. You can't have it as an Asian because people are so racist against Asians.

Geoff: Yeah.

Jason: That you might say something insane like, well, what about motivation? What about the motivation to take the AI course?

Geoff: Yeah well I think that-

Jason: You want to say it don't you? But you're scared to say it.

Geoff: No I mean I think, I think Asians are interesting right, you have, we're this like weird minority that sometimes gets bucketed into white and then other cases get bucketed into African American, black or latino.

Jason: Yeah. 

Geoff: And it's just like, we're this weird, yeah, third rail, that's like unmentioned by the traditional political discussion. 

Jason: And Asians are subject to horrible racism consistently and it's allowed and accepted in society. Asians get beat up constantly. Do you know how, I mean, is this true or not true?

Geoff: Yeah I think I agree with you. 

Jason: Yeah.

Geoff: Yeah.

Jason: And I know, there's just a great podcast, Still Processing, which is done by Jenna Wortham and another gentlemen from The New York Times, it's one of my top three favorite podcasts, I try to listen to podcasts that are by people who are as different from me as possible.

Geoff: Mm-hmm (affirmative).

Jason: So I listen to Ben Shapiro.

Geoff: Yeah.

Jason: Who is a Jewish.

Geoff: Conservative.

Jason: Conservative, you know, has very strong opinions that I don't agree with but he's very intelligent and I like to hear the other side's perspective.

Geoff: Yeah.

Jason: And then I listen to Jenna Wortham and I'm sorry to the guy who's on the podcast with her, but I believe they're both gay, I know they're both African American and they both live in New York, in Brooklyn where I grew up and they clue me into hey, here's what a black lesbian living in Brooklyn deals with, and how she thinks about Beyonce or cultural appropriation, all this stuff, or the childish gambino video. This is stuff that I can't, being a white guy from Brooklyn who now lives out here, process. 

Geoff: Right.

Jason: They did a two, and that's why it's a great name for a podcast, Still Processing, they did two episodes on racism directed at Asian people, and this is something close to my heart because my wife is Korean. So I have three daughters, who are all Hapa, half Asian half white, you know, and so it's amazing to me the racism my wife faces.

Like my wife will be being treated horribly by, in a service type situation, and then I walk up and they're like oh, sir, oh no, of course, whatever you want. Yes of course, we'll upgrade you, we'll do this, we'll do that, oh late checkout of course. My wife asks for a late checkout-

Geoff: They ignore her?

Jason: They ignore her, they, no, that's not the policy. I walk in and I'm like, hi, I need a late checkout, five o'clock. They're like oh, let me see if I can do that for you sir. We can only do four. I'm like all right, well I'm a gold member, I'm platinum, you know how often I stay here? And I've got 20 employees and they stay here, I mean can't you just give me one more hour? I spend three thousand dollars on this hotel this week. 

And they're like oh yes of course sir we'll do that. If my wife tried that they would be like, you know, five foot Asian woman, they would just not give it to her, give her that kind of respect. 

Anyway, long story short, we're now getting to the point where we have to really start thinking about the two factors that I think are holding a large group of people back. One is obviously motivation and the two is, knowing that this possibility exists.

We're now getting to the point where we have to really start thinking about the two factors that I think are holding a large group of people back. One is obviously motivation and the two is, knowing that this possibility exists.

Geoff: Yeah.

Jason: And I think that's kind of the biggest problem, it's one I've been working on with my team. A lot of times people don't believe they could be CEO. They don't believe that they could start a company. There was a time when Asian Americans and Indian Americans, in Silicon Valley, and this wasn't too long ago, this was maybe ten years ago, didn't believe that they could be CEO's. 

They believed they could be CTO, they could be the VP of Engineering, they could be the number two slot, the number three slot, but my Indian friends would call it the curry ceiling, I'm sure you've heard that.

Geoff: Yeah. Or the bamboo ceiling. 

Jason: And Asian Americans, what's that?

Geoff: The bamboo ceiling, for Asians.

Jason: The bamboo ceiling, like and now, I think because you had over the last 30 years so many senior positions held by Asian Americans and Indian Americans, that it became clear that there was no difference, and then Sundar is running Google and Satti is running Microsoft. It's so obvious, the examples had to be there. 

So now you look at African American women, Latino women, people of color, trans people, like they're not represented. Even in those second or third positions. And so, that's what we've been working on in our company, is trying to move upstream to where people are considering starting companies or maybe working on a project and engage and embrace and provide education and advice in that area. 

So we started something called founder.university, and it's our little hack, we moved upstream, we said hey, if you've got a product you're working on, that's launched or not launched but you know, you're in beta, come to founder university for three days, spend three days with me, and I'm there for all three days, and we do it six times a year, so it's 18 days of my year and we do it for underrepresented founders and female founders three out of the six times, exclusively. 

And we found all the female founders. And we're starting to find the Latino and African American founders. So all these people who are saying, you can't find them, well they're looking in the wrong spot. Yeah, you can't find them with a Series B yet, there aren't a bunch in the Series B, but there's a ton in the seed stage. 

So move upstream a little bit and look in that area and I think you'll be pleasantly surprised that there are massive overachievers. Right now I'd say like three or four of the most promising companies we have that are over performing are led by women. 

Geoff: Nice. And I hope you make a lot of money off of them, or as they grow.

Jason: Well I mean, I am very focused on returns. 

Geoff: Yeah.

Jason: You know like, returns give me, and not just because I need more money, I don't really care about money, I'm, you know, we're sitting here in the same black tee shirts, wearing the same sneakers and the same jeans and I've got a cheaper watch than you. Money, who cares?

Geoff: Right. 

Jason: If we go have a hamburger after this, it tastes the same.

Geoff: Right.

Jason: If me and Mark Cuban and Elon Musk have a hamburger, it tastes the same. Doesn't matter how much money you have, right, it's the same hamburger. And that's what I always tell people. Like there is an absolute fear of running out of money, so when they do the studies they show people under-

Geoff: Like 70K a year.

Jason: 70K a year, wouldn't be for San Francisco, but for the country, once you get past 70K, you start to have the fear and the anxiety, and the paralysis that comes from being poor which I lived with, my parents were poor the whole time and it was tension constantly. 

Geoff: Yeah.

Jason: I mean every fight was over money, there was no fighting about anything but money. If there was going to be a fight it'd be over oh my god, are we going to make X purchase or Y purchase and X was the rent and Y was tuition. You know, it was, so I understand and I feel people who are going through that level. 

And that's another thing we have to do is we have to find a way for people to have enough space for them to take risk. So I've been really looking at trying to find startups, now that we've identified for motivation and performance, people need to know that the opportunity exists, they need to see that other people like them can do it and they're not going to be stopped and they cannot be stopped.

And we need to create a little bit of room for them to be able to engage in this. Which could be something as simply as, there's a school called Lombada school, and I just had the founder, Austin on my podcast, and he's giving free tuition. And then he takes a portion of the salary afterwards if they get a job. And now he found the impediment for certain groups of people was, housing. 

So now he's providing free housing, I think he puts the cost of the housing into the education and get it back, and then taking time off from work. So that means you have to put these things on the weekends or nights or whatever. 

So I feel like the world is trending towards such a beautiful place, but obviously when you watch the media or Twitter it's just people raging at each other. 

Geoff: Yeah.

Jason: But if you read Steve Pinker's books, Our Better Angels, and Enlightenment Now, we're really starting to trend towards poverty going away in our lifetime, like I'm talking about extreme poverty. And we're seeing extreme opportunity open up. 

When I was coming up the idea that a kid from Brooklyn like me could take a course at MIT was laughable, with my 71 three year average. I would never be able to take that course. Now that course is being taken by ten or 20,000 people per semester. There are 500 people taking it at MIT and whatever, 50 times that taking it online. 

Geoff: Right.

Jason: The world's getting better. 

Geoff: Yeah, no I think that's interesting and I hope that, it really sounds like you see money as a way to influence the world around you which I think is a great help.

Jason: Well money and power. 

Geoff: Yeah. You need both. 

Jason: You know I've given a lot of thought to my own psychology over the years, so people who are listening to this are probably like, oh, fuck Calacanis, you know, he said something obnoxious ten or 20 years ago.

Well people evolve. And part of my evolution over the years is realizing that in the victim Olympics and in the suffering Olympics that I may not be the last person. You know? Like I might actually be two thirds of the way down and there might be a third of people who had it harder than me.

Geoff: Yeah.

Jason: And it took a while for me to realize that because I had the experience of having to fight and fight to make rent in my $325 apartment. I had to fight to pay my tuition, it took me five years at school.

I had to fight to get into investments even later. I had to fight to get my magazine up and running on my credit card. I just, everything felt like a fight to me. For decades. 

Geoff: So when people try to boil you down as identity politics, you're just kind of like, screw you.

Jason: I mean listen, if people want to, like when Gawker said I was a racist. And now this stuff is still on the internet, and then people are still like look, Jason's a racist because Gawker said it. 

I'm like, well Gawker also like did all these other horrible things, like take a pause for a second. If you believe I'm a racist because I believe that opportunity exists that has never existed before, well then we're just intellectually-

Geoff: You're not, you're talking past each other. 

Jason: We're intellectually talking past each other.

Geoff: Yeah.

Jason: Now, if you say I can't relate to the experience of an African American woman who grew up in a certain city, I can, at this point in my life, I can say yes, 100%. I might have in my earlier years be like, well you can't understand what I did, you know? But now it's like, it's pretty obvious people have had it harder than me because I've seen it up close and personal, like yes people have it harder than me, I am not the hardest case. 

Although I did feel that way, I had a chip on my shoulder, felt like I had it really hard. Because it was hard, you know, like my dad almost went to jail, we lost all, you know he was in, he was literally had a six figure lien against him from the government.

It was pretty terrorizing as a 17 year old to go through that. But I think we have to like stop talking through each other, stop doing the identity politics, and start looking into people's hearts and their intent. Let people evolve, let people grow, let people collaborate together, right?

But I think we have to like stop talking through each other, stop doing the identity politics, and start looking into people's hearts and their intent. Let people evolve, let people grow, let people collaborate together, right?

Geoff: And have long form conversations, I think that's why Ben Shapiro, Jordan Peterson, these intellectual folks are getting such attraction.

Jason: Yeah, well of course.

Geoff: I think people are seeking actual depth and nuance to conversations that you just can't have anymore. 

Jason: I mean, an Asian American and a white guy talking about the experience of African Americans or poor people, like if we tried this on Twitter, all nuance would be lost, right?

Geoff: Who the hell are you guys talking about this?

Jason: But if you hear me say, I think I've evolved my position, I've created a product that helps me identify underrepresented founders, it's actually increased the number of underrepresented founders we invest in, and I've learned a lot listening to Jenna Wortham's podcast, and yeah there are probably some leaks in my logic that I wasn't aware of, but you'd be like, oh wow, Jason's a human being, he's not like a cardboard cutout of some Silicon Valley douche.

Geoff: Right.

Jason: I mean I might be a little douchey time to time, I own four Teslas, that's kind of, that might be a little douchey to own four, it's unnecessary, I'm only buying one more, the next Roadster, I'm not buying the semi.

Geoff: Okay.

Jason: But I take my position very seriously.

Geoff: One thing I wanted to bring up and I think this is more in line with some of the athletes or military people on this program is, it sounds like you have a very focused, or at least in the athletic context, when we talk to athletes, who have a very self aware approach to improve themselves. 

Jason: Yeah. 

Geoff: And it sounds like you've evolved yourself over the years. So what are the key things that you do to self evaluate, self reflect and manipulate yourself? 

Jason: Sure. Being self aware is super important.

Geoff: Yeah. 

Jason: There's a lot of different ways to get there. I mean some people go to therapy, some people have close friends how they have blunt conversations with, some people take psychedelics, I mean, people do all kinds of different things to try to be self aware. I have surrounded myself with people who tell me the truth and who I tell the truth to. And have candid discussions with.

And I'm very lucky that these are some of the most successful people in the world. So I can sit at my poker game with Phil Hellmuth, the greatest poker player in the world, and he can evaluate me as a poker player but also as a human in my game, and I've evaluated Phil. And Phil and I have had a cantankerous relationship at times, but we also have a very loving relationship where we put our arms around each other and say we love each other as two grown men, and we do. I love Phil Hellmuth like he's one of my favorite people. 

But we've also had just crazy fights and arguments and madness. So, if you can surround yourself with truth tellers. Chamath is going through a rough time right now, social capital, and he's also been on top of the world. I've gone through rough patches where he's given me advice. Our friend Dave Goldberg who passed away tragically three years ago, two and a half years ago, he was always like this great voice of reason who would pull me aside and say like yeah, you're right about this, you might be wrong in the way you're delivering it. 

He was like this great truth teller to Chamath to myself, to Phil. So I think if you surround yourself with truth tellers and people who are honest and candid with you, they'll tell you the leaks in your game. Because in poker, we will pull each other aside if we're friends and say you know, I watched you, how you played that hand, it was pretty obvious what you had and here's how you might play differently in the future, right? Well you can also do that in life. 

You have to ask people to be candid with you. I've done that with my team, I've asked my team to be candid with me, I'm candid with them. And you have to, I use the word candid which I got from Ed Catmull in a really good book called Creativity, where he didn't ask people to be honest with him about why Toy Story 2 sucks or doesn't, let's be candid about this plot point or this character. When you say be honest, his position was, at Pixar, you're saying you're not being honest so now start being honest. When he says being candid, he'd say, you're being honest, but now I want you to be even more raw in your feedback. 

So I think asking people to be candid with you is just this magical gift. And then also I have haters because I'm so active on Twitter and other places, and people are like, will get in the comments on YouTube and be like, you're talking over the guest, let the guest finish. Or you're talking, whatever.

And I'm like yeah, you know, that is a habit of mine, I talk a little too much or whatever, could be a leak in my game. Sometimes it works really well in an interview like in this case where you're interviewing me, sometimes if I'm talking over a guest who has something to say, it could hurt the interview. So I love my haters. In fact, internally call them jaters with a J. 

Geoff: Okay. 

Jason: And we all just, the jaters make you better.

Geoff: Yeah. 

Jason: Because typically, when somebody's criticizing me anonymously on Twitter or on YouTube-

Geoff: They're brutally honest. 

Jason: They're like, you fat fuck, you talk with a lisp, and you're losing your hair and you look like you haven't slept and I think you're talking over the guest a little bit too much, let them finish. Oh by the way, did I mention you're a fat fucking piece of shit? Blah, blah, blah, blah, blah. It's usually like this sandwich of like, hate, hate, hate, hate, hate, some very valid insightful criticism, and then hate, hate, hate. 

And what you have to do is have a thick skin and say okay this is an anonymous troll who's in their mom's basement eating fish sticks who maybe is a little jealous of where you got in life, whatever. Or they're just a hater, or they're just a troll having fun, or it's one of your friends breaking your balls and chops with you know, like at a poker table, but anyway, just let all the personal hate go away and just look at that cornerstone.

So when Gawker said oh you're a racist, I was like, why are they saying that? I don't get it. And then I talked to some of my friends who are in certain groups and they said well, here might be why they're saying that. You come across as clueless because you actually think you had it as hard as other people. And I was like, oh. Is that actually the reason?

And my wife was like, yeah that's the reason. You think that you had it hardest. Do you think there's anybody who had it harder than you? So when my wife did that, in my book, I talk about how hard I had it, and I wanted to share my story, and then I put, she said yeah, but you don't mention the other people. And I said well it's my book. Harper Collins pay me, for my book. They're not paying for other people's stories.

She's like yeah, but remember we talked about being clueless and maybe not thinking. And I rewrote that chapter at the end of the chapter I said listen, and I said it in my own words, but my wife read it and gave me some really good edits on it and I said, as much as I feel I'm an outsider, I'm paraphrasing myself, I recognize that there are people who didn't have a dad who bought them a thousand dollar computer.

And there are people who didn't have two parents and owned their home, barely. And there are people who maybe, who had this more difficult or that more difficult and that for those people I salute them and I'm rooting for them, right. 

And I understand that even though I felt it was really hard, objectively, it wasn't. And, because you know what? I look at these trust fund kids, and they would say stuff to me like, yeah my dad is like really on my ass and if I don't go to like get my law degree-

Geoff: He's not going to release the money.

Jason: I'm not going to get my trust fund, he's not going to release it. And I wanted to choke these kids when I was in college. I was like, you have a trust fund? What is that?

Geoff: Those kids are soft, yeah.

Jason: They're like well, I get like, I mean it's not like a big deal, I get like three thousand a month. You get three thousand a month, what do you have to do? Like I'm making three thousand a month like fixing laser printers under desks. Like what do you have to do for three thousand dollars?

No, nothing, I just get three thousand a month because it's a million dollar thing and there's 50 thousand in interest so they just give me the interest, or have the interest I get in a payment every quarter and then there's a trust I have to ask, and if I want to do it, but he really wants me to be a lawyer and I was like, go to law school. For free? You can go to law, he'll pay for it? Do it. Your mom and dad will pay for law school?

I hated those kids. Now I look at it and I have some sympathy or them. I'm like oh, your dad used money and your parents used money to manipulate you to have your adult life be what they wanted it to be, not what you wanted it to be, and you had to sacrifice those years.

Like I can actually have sympathy for a trust fund kid now. Which I could never have sympathy for a trust fund kid I wanted to punch those kids in the face. I was so jealous of them, right. Or Asian Americans, like this whole tiger mom concept which people, did you have parents who were super pro education, who just pushed you harder?

Geoff: Yeah I think that's in the Chinese culture. 

Jason: Yeah.

Geoff: But I think-

Jason: But do you resent them for it or do you laud them for it? Because I wish I had parents who pushed me harder. And then I talk to my wife and people in our family and then people in our extended circle, and I'm exposed to just a lot more Asian American culture and it leads to a lot of depression and anxiety in Asian Americans that people don't actually give them credit for.

Geoff: Right.

Jason: Do you have anxiety and did you suffer from anxiety and stress from the pressure put on to you by having a tiger mom or dad?

Geoff: I think that's a good question.

Jason: Well answer it candidly.

Geoff: I think I was fairly rebellious.

Jason: Okay.

Geoff: So I think I just kind of like, I remember just getting into big fights, in sort of middle school, early high school, where I think the lessons were just embedded in me where it became instead of an extrinsic, I guess focus on achievement, it became very intrinsic and then kind of like the noise of getting badgered was annoying. So I think it worked long term.

Jason: Right.

Geoff: In terms of having aspirations of a strong work ethic, valuing my education, but it was definitely tumultuous in terms of I guess more American independence, free spirit, what I think is good about American culture.

Jason: But they based their love for you-

Geoff: Yeah.

Jason: -on your engagement in academics.

Geoff: Absolutely.

Jason: And you felt that.

Geoff: Yeah. 

Jason: So you felt you would get less love from your parents, if you were not as academically inclined, and you would get more love if you had more engagement in academics. Correct or no?

Geoff: I mean I think there was pressure, but I don't think was based on rescinding or giving love.

Jason: Okay.

Geoff: I think it was made very clear, I think my parents were always very supportive. 

Jason: Ah.

Geoff: But clearly there was a push. 

Jason: Because I've heard that sometimes like love, you're not going to be part of this family or we do not love you if you do not excel. 

Geoff: No I've had Korean friends who would get the belt on, get whacked.

Jason: They would literally get hit.

Geoff: Yeah.

Jason: And this is in the '90s.

Geoff: Yeah.

Jason: This is not in the '60s or '50s.

Geoff: Right. 

Jason: We're talking about in the '90s they would be whipped with a belt.

Geoff: Yeah, kids would come in-

Jason: If they did not get perfect math scores or reading scores.

Geoff: Yeah, I'd be like whoa, my parents are pretty hardcore but not that hardcore.

Jason: Yeah. Yeah. So it's interesting, everybody has different experiences.

Geoff: Yeah.

Jason: And I think that's one of the things that podcasting-

Geoff: Have you read Thomas Seoul's Black RedNecks, White Liberals?

Jason: No. 

Geoff: It's an interesting sketch on culture and how different minority groups have evolved in culture.

Jason: Yeah. I've tried to educate myself.

Geoff: Yeah.

Jason: I read Hillbilly eulogy and try to listen to media and read books that just are not going to be in my natural wheelhouse.

Geoff: Yeah.

Jason: Like, Charlemagne The Gods book, from the Breakfast Club, and I listen to The Breakfast Club once in a while you know, like the interviews and stuff. Just try to expand my consciousness beyond, you know.

Geoff: Do you think that's one of your edges? It seems that you put yourself out there for critique and like put yourself out in their culture and I think that helps you learn fast on other people perhaps. 

You think that's part of the edge? I mean it sounds like you can imagine that you have your rich friends who are just like I'm rich now I want to be on my yacht, I want to be with only my rich friends.

Jason: You know people do tell me to shut up.

Geoff: Right? They just instantly lay it out, and I think that probably gets them complacent, weak. Where I think you maintain an edge.

Jason: I think it does make you weak, yeah for sure. I mean I like to keep writing I like to keep having my opinion, and for better or worse, because I've examined my own psychology, and a lot of my psychology and my motivation came from being poor and not having power and living in a harsh environment where being poor and weak and not powerful was pointed out to you and was a risk when you grew up in Brooklyn.

I mean I like to keep writing I like to keep having my opinion, and for better or worse, because I've examined my own psychology, and a lot of my psychology and my motivation came from being poor and not having power and living in a harsh environment where being poor and weak and not powerful was pointed out to you and was a risk when you grew up in Brooklyn.

Geoff: Right. 

Jason: This literally was the pastime was to sit there and-

Geoff: And bust each other's balls.

Jason: Bust each other's chops, and whatever was the thing that was the most sensitive to a kid in Brooklyn, was the thing that all the other kids would key on. So there was a couple got divorced on our block. And that's all we did for a year was make fun of the kids whose parents got divorced. I look back on it and think-

Geoff: Damn that's real.

Jason: We were insane, evil little creatures. But it was equal opportunity because they would look and say, your dad's an alcoholic, your dad, your mom's fat, your parents are getting divorced, you're poor, you're wearing your brothers sneakers with holes in them.

Geoff: So you had like thick skin growing up. 

Jason: I mean, a thick skin would be an understatement. You had to psychologically be prepared to be interrogated. So if you got your haircut, we'd be like oh, you got your haircut? Oh where'd you get it done? And you'd be like oh I went to Astro Place, we're like okay good because we're going to go there and kick that guys ass after, I'm not going to let him do that to your hair like that. We'll go beat the shit out of that guy for doing that to you.

It was literally every step along the way. So I think when people are like Gawker, calls me a racist, I'm like, I don't care.

Geoff: Yeah.

Jason: That's some loser kid at Gawker wants to say this bullshit, like I for better or worse am immune to criticism and that has led to blind spots for me, it has also leads to the fact that I just keep forging ahead with a samurai armor on me that stuff bounces off of.

Geoff: Yeah.

Jason: But of course, anybody with that samurai armor, you have to take the armor off sometime.

Geoff: Right.

Jason: And you have to be able to have a downtime where you feel loved and safe. And so I have my family and I have my friends, I can take my armor off, I can be safe. And I think Phil Hellmuth and I also have both of that thing, we both have to be on guard.

Geoff: Right. 

Jason: You know, he's the world's greatest poker player, he's getting attacked constantly at the poker table.

Geoff: Right. 

Jason: And then sometimes he wants to take his armor off and feel safe and yeah, he's a samurai warrior but the armor is heavy.

Geoff: Yeah.

Jason: And being a founder of a company or a high profile person you have to have this armor up all the time and then with social media it's become a hundred X.

Geoff: Yeah.

Jason: You know Elon's trying to save the world from climate change and global warming.

Geoff: Yeah I've been seeing this Tesla stuff on Twitter.

Jason: And they're attacking him.

Geoff: What do you think of all this?

Jason: And it's just like, I think Twitter is, I didn't invest in Twitter, it was a $50 million dollar, $25-$50 million dollar mistake. And the reason I didn't want to invest in Twitter was because I thought it was going to be a cacophony of idiots. Because you didn't write blog posts, because I was a snob, because I am a good writer, I'm a great writer. 

And I was like, if you want to write, and you want me to read what you have to say, write three paragraphs, do a blog post, 500 words, I'll read it. But if you want to write a sentence or two, and a couple fragments? No. I don't care what your opinion is.

Geoff: Right.

Jason: Write a thought out piece. Write a thousand words. I'll read that, because I came from the blogging era that Twitter replaced.

Geoff: Right.

Jason: Or largely replaced. Blogging went away because Twitter was just so instantaneous.

Geoff: You're still super active on Twitter.

Jason: I am, and I'm announcing today that I'm giving it up.

Geoff: No you're not.

Jason: For the next 30 days.

Geoff: Really?

Jason: I am, I'm dead serious. I'm deleting it from my phone because-

Geoff: Whoa. 

Jason: It's becoming such a distraction for me, and I want to write the next book and I deleted it off my phone for six months and I wrote the last book. So I want to get the next book done, it's been a year since the last one came out, I want to spend this year doing it so I have a book come out every other year or something, and I have like two great books in me that I want to write and I've been writing notes on both, and I'm going to make a decisions by the end of the summer which one I'm going to go with.

Geoff: So you really put your money to, where your mouths at in terms of morality or ethics. I mean I was on Wikipedia I was like, yeah, like Jason pulled all of Facebook, like you sold all your Facebook shares because you weren't happy with what they were-

Jason: Yeah, I don't want to own Facebook. I kind of feel like that company's amoral. I feel like every decision they make is in the best interest of reducing friction to make more money, not in thinking about our society. 

So like, Twitter was like, you know what Milo Yiannopoulos, you're a troll. You're ruining the system for everybody, this is a private place, you're banned for life.

Geoff: Right.

Jason: We can't have you on here causing a mob of people to attack celebrities who are the core of the service. We're just going to make a decision. And then you look at Zuckerberg and it's like yeah, info wars and Holocaust deniers and yeah they're misguided and I'm going to kind of steer them in the right direction and we can work with them. 

It's like, you have not been paying attention. The only way to work with a Nazi is to kill a Nazi. Right? Like this is the level of insanity we've become in our society is where people are like yeah we need to be tolerant of Nazis. No, you need to punch a Nazi.

Geoff: Right. 

Jason: You know? Like if somebody wants to come up and spew some Nazi bullshit to me, it's going down. Period. I'm not having it. Like we have to go back to that America, where if people really want to be racist pieces of garbage and they want to espouse Nazi nonsense, not on my platform. 

So if you want to have info wars, and you want to say the Sandy Hook parents were in on a conspiracy to murder their own children, you know that's just a bridge too far. I mean I understand Zuckerberg's point, I am for free speech. But I am also for people who want to say racist, Nazi, crazy stuff, they don't have to be on your platform, this is not a big brave decision.

Geoff: Right.

Jason: You know? Like yes the Ku Klux Klan, the ACLU will fight for them to march down main street, okay, good, we know where they are. That doesn't mean The New York Times has to give the Ku Klux Klan an ad.

Geoff: Equal platform.

Jason: And an equal platform. It's The New York Time's platform. And Zuckerberg's a coward and he only cares about money, and he only cares about the share price and he's always thought this way. 

And if you think that his position has changed over the years, it hasn't. He said, these idiots are giving me their information, they're stupid fuckers. Like that's the transcript of his IM, you ever see it?

Geoff: Yeah.

Jason: That was his position as a child. 

Geoff: Yeah.

Jason: And that is his position as a man child. He hasn't evolved. I don't believe he's evolved. I mean if he wants to sit down and have a cup of coffee with me, I'll sit with him and see for myself if he's evolved. I don't believe his behavior shows an evolution in any way.

And that is his position as a man child. He hasn't evolved. I don't believe he's evolved. I mean if he wants to sit down and have a cup of coffee with me, I'll sit with him and see for myself if he's evolved. I don't believe his behavior shows an evolution in any way.

He allowed the Russians to buy racist ads on his platform in rubles. That, in all likelihood, led to some number of people not coming out to vote in the election. He did this be he doesn't want to review ads, and he doesn't want to eliminate ads in the system, he wants to make money.

Geoff: Right. 

Jason: If you put an ad in with a link to an affiliate network on Amazon, or a dating site, you will not get it through. Why? Because that affects their bottom line. 

Geoff: You're taking money off the platform, yeah. 

Jason: Taking money off the platform.

Geoff: Yeah. 

Jason: But if you put racist ads up against Hillary Clinton to try to get African Americans and swing states to not come out for Hillary? He'll let that go through. That tells you everything you need to know. He does not care. And if you look at what he did with groups, are you a member of any groups on Facebook?

Geoff: Yeah. We have one of the largest intermittent fasting groups, We Fast, yeah.

Jason: Perfect. Have you been added to groups? When you go to the group page, that you didn't add yourself to?

Geoff: Yeah, people do, like our-

Jason: People have added you to groups. 

Geoff: Yeah, yeah, yeah. 

Jason: The number one reason group systems did not flourish was because you had to convince people to join them.

Geoff: Mm-hmm (affirmative).

Jason: So somebody at Facebook came up with the killer idea. Put a box on the top right where you put in people's email addresses-

Geoff: Invite friends, yeah.

Jason: -and their names, and then you invite them.

Geoff: Yeah.

Jason: But you're not inviting them to join, because that's friction. You're joining them.

Geoff: Right. 

Jason: You're making the decision for them.

Geoff: Right. 

Jason: Well Zuckerberg did this, and a group of gay men who were in college, this is a story you can search for on Google and you'll find it very easily on Google News, were added to a gay men's choir in their college. It then posted that on their walls, their parents saw it.

Geoff: Outed everyone.

Jason: Their parents didn't know their kids were gay.

Geoff: Yeah.

Jason: Can you imagine the pain and suffering Zuckerberg caused in that instance? That's what he does over and over again. He looks at that, and his response to that was, well maybe you should have different friends. That's Zuckerberg's bizarre approach. 

Now either he's clueless socially, which is a group of people believe he is clueless on a social basis. Or you can believe that he is for removing friction and is obsessed with the growth of his company and move fast and break things. 

So in the evidence pile, and just on a logic game theory, breaking this down, either he's socially inept or he's obsessed with growth to the point of not caring about the ramifications. Or-

Geoff: But I think he's realizing that he's going to get bucketed here and he's going to get regulated.

Jason: Yeah.

Geoff: So I think in his self preservation, I think he seems to be doing the right lip service at least.

Jason: It's always been lip service, he says it every time.

Geoff: Okay.

Jason: And nothing changes. And nothing will change. Nothing will change.

Geoff: But I think his self preservation instinct will carry him through.

Jason: I think, I think he's numb.

Geoff: Like I think he's smart, right? You don't think, you think he's still going to be amoral or just run the platform?

Jason: I think the amoral way of running the platform means you win. And I think for someone like him it's a video game of how big can it get, and how do I get everybody on the planet on my platform. It's a giant video game and he is heads down. There is-

Geoff: Potential risk, when governments like okay, we're going to start banning you?

Jason: Maybe. But if you look, he got pulled in front of all these courts.

Geoff: Right.

Jason: And what happened?

Geoff: He talked through his way, I mean the players are-

Jason: I mean what's the ramification been? 

Geoff: Nothing.

Jason: What's happened since that time? 

Geoff: I mean stock has gone up.

Jason: The stock has gone up.

Geoff: Yeah. 

Jason: So if the scoreboard is the stock and the usage of the product, he keeps winning, he's going to keep the same behavior.

Geoff: Yeah. 

Jason: I think he learned the wrong lesson, which is he can dodge bullets. He's learned that he's, he's like Neo in the Matrix, he can literally slow down time, dodge the bullets, and get right back up. He's learned the wrong message. The only way this stops is if the EU or another country bans Facebook. Or levels fines that would be so large that they would be a deterrent, but I mean the biggest fines were five billion for just now.

Geoff: Google.

Jason: for Google.

Geoff: Right.

Jason: For the Android. And then two billion before that for shopping. So seven billion for a 700, 800, 900 billion dollar company is laughable. 

Geoff: Right.

Jason: They are laughing. They're like, for the love of God, let's preserve this system where you fine us a fraction.

Geoff: And they'll litigate it for a bunch more years anyway.

Jason: Exactly.

Geoff: Yeah.

Jason: Just, please create this system where I get charged a fraction.

Geoff: Yeah.

Jason: And its not that I dislike Zuckerberg personally, I mean I don't want to make it too personal and I did at one point say, he had an Asperger like approach to product design and I realize, I felt bad about that because I'm not a psychologist, this is like when you're sort of talking about evolving, like I thought that was a leak in my game, I would make things a little too personal. 

And I've tried to refine my way of presenting myself to not make it personal. Unless it's about me, I'll be very personal about myself, but I try to make it not too personal. I was watching Saturday Night Live, I don't know if you saw the skit where they had him on the Weekend Update, on the news? 

Geoff: Didn't catch that.

Jason: They literally made him into somebody suffering from like, clinical Asperger.

Geoff: Right.

Jason: Where he's like, make eye contact, laugh, ha-ha-ha, now? Continued eye contact. Connect with the person. Like they were literally treating him as if he was on the spectrum to a level of disfunction. Which I thought was actually cruel and unnecessary. 

I think he's going to have to live with himself and all the money in the world, if you have to go to bed at night and think, God I'm the most hated person on the planet and wake up that way, it's not worth it.

Geoff: Right.

Jason: It's not worth it. And I think Bill Gates-

Geoff: But do you think he thinks like that? 

Jason: Well I think-

Geoff: I mean I don't like, do you think, like what do you think is in Trump's head, like when he goes to bed? Right, like I think some of these people-

Jason: Well that's a whole different ball of wax. I mean.

Geoff: Right, but I think some of these people are just very much in their own universe.

Jason: I think you're, yeah, like there's sociopathic behavior, which you know, I wouldn't even begin to know how to diagnose Donald Trump. How much of it's an actually and how much of it is just derangement.

Geoff: He's Neo. 

Jason: How much of it is corrupt.

Geoff: Yeah.

Jason: I mean it's very hard to understand that one. But for Zuckerberg I can tell you it's very similar to Bill Gates I think. Where Bill Gates was, remember when Bill Gates was hated because Microsoft was a monopoly and taking over the world?

Geoff: Yeah, I remember growing up seeing that. 

Jason: And it was very personal, it was very vindictive, people were really like his competitors, they really attacked him and he, they have that deposition tape where he's getting upset and he comes across very poorly. 

And then I think it kind of crushed his entrepreneurial spirit and he left Microsoft, they did like the goodbye video with him with his box, leaving, and then he went and took all his money and now he's going to solve malaria and other diseases.

Geoff: Toilets and yeah.

Jason: And he's literally going to get rid of poverty in the world. 

Geoff: Yeah. 

Jason: So I think a lot of that motivation came from being so hated in the public sphere.

Geoff: Right.

Jason: So I think that for Zuckerberg, he really needs to take that big pile of cash he has and go put it to use and make up for the chaos he's caused in the world.

Geoff: Yeah.

Jason: Like if I was him, I would literally start giving away billions of dollars as quickly as possible to make people feel good about it, like this, I think he did the hospital here?

Geoff: Right.

Jason: The Zuckerberg Chan hospital? 

Geoff: Yeah.

Jason: And then I think Benioff also did it.

Geoff: Right.

Jason: We went there when we were having our babies, it's an incredible place. So I give him, I judge him and I think we should judge people.

Geoff: With their actions. 

Jason: I mean this idea like don't judge people, I judge people on their actions. I think his actions as a corporate executive have been terrible, horrible, except for shareholders, and I think his wife's donations to charity which I think she leads have been exceptional, so I mean more Chan less Zuck. 

Geoff: Yeah, giving credit where credit's due. 

Jason: Yeah. 

Geoff: So I want to move on to some audience questions.

Jason: Oh boy.

Geoff: So Christine asks, well I don't think these are too tough.

Jason: Here we go.

Geoff: She asks like a Peter Thiel kind of question, so what do you believe that no one else believes? 

Jason: I believe anybody can accomplish anything. 

I believe anybody can accomplish anything.

Geoff: And no one else believes that?

Jason: I think few people believe that. I believe America's the greatest country in the world.

Geoff: Okay.

Jason: I still believe it, I don't think that people believe that. I believe that the world is getting better. Not worse. I think there's a small cohort of people who believe that, I think most people do not. 

Geoff: Mm-hmm (affirmative). Okay. Fair enough, yeah.

Jason: I believe people change.

Geoff: Yeah. 

Jason: I don't know if most people believe that.

Geoff: Hopefully Zuckerberg can change.

Jason: Yeah. 

Geoff: Yeah.

Jason: If Zuckerberg's listening, which he's not.

Geoff: Yeah.

Jason: I believe you can change. Get yourself a group of friends who are candid with you.

Geoff: Yeah.

Jason: I don't think he has, I don't think he maintains friendships with the people who are candid with him. So the people like Sean Parker, Chamath, Dave Morin.

Geoff: His original, right.

Jason: Who are critical, his original team, who are critical of him, I don't think he's friends with them. I think he's friends with the sycophants. You know, and the people who tell him he's right. And that he's a God. Listen I appreciate what he's built, any entrepreneur who can build something that big deserves some level of kudos.

Geoff: Right.

Jason: It's not people are like oh you're jealous, I'm like, I'm rich. I'm not jealous at all.

Geoff: Right.

Jason: I've got a lot of friends, I maintain friendships for decades. I'm literally having my first employee from New York in 2000, no I'm sorry, in '91 or '92 bringing his family by my house for a barbecue tomorrow, and we haven't seen each other in 20 years. 

I literally maintain friendships for decades and have like incredible good will. I'm not jealous about him I just don't like the way he runs the business. Two different things.

Geoff: Right. 

Jason: So I'd say, I believe anybody as being capable of anything is the thing that most people don't believe and that is absolutely true.

Geoff: What do you think of, I mean, as wearing off of the bearishness perhaps of America, I mean I think, I'm curious how you size up China and how their system of capitalism is comparing against America. 

This is something I've been thinking about recently where in America, you have our best entrepreneurs, like Basos or Elon Musk getting sort of hated on. Or you have you know the President sort of hitting on it. 

Jason: It's a pendulum. Yeah.

Geoff: But in China, they're basically backing like these, like their winners are getting backed by government subsides and government monopoly, you know.

Jason: Yeah because the government there is smart, they realize that the competition isn't between the citizens of China.

Geoff: It's with the globe.

Jason: It's between the countries.

Geoff: Yeah.

Jason: And so here we're in fighting, which is what Putin has basically done this huge campaign to do is to turn us against each other.

Geoff: Yeah.

Jason: And they've turned us against each other on the two issues that will never be resolved, guns and abortion. Literally our whole country is fighting over these two key issues that could be solved very simply. Let the states decide. Make them not federal issues.

We're never going to resolve them. So if you want to make California a gun free or a gun registration lite zone, where everybody can own one gun and only these types of guns, fine. And then if you want to own a bunch of guns, move to the state next door. 

Geoff: Right.

Jason: And in Nevada if they want it to be a free for all, fine. But if you cross the borders you got to behave and if the number of weeks when a pregnancy can be terminated is up for massive debate, we can have different states have, and they do, can have different rules around that.

Geoff: Right.

Jason: And then we can get back to focusing on America winning. And what that looks like. But you know, you have to remember, China is just developing it's middle class, if you're a journalist, and you criticize anyone you'll wind up in jail. If you want to practice a religion and criticize your local government, you will be murdered.

Geoff: Right.

Jason: So we are a much better country than them. People can sit here and criticize the President, they can make a big blow up baby doll of the President in London and do that, capitalism is important, it's not as important as democracy. 

Capitalism is a great add on to democracy, and you have to really know how to nurture it, but communism plus capitalism is not the ideal. What you want is compassionate capitalism combined with democracy.

Geoff: So my fear is that if you have government start backing like just game changing technology, like-

Jason: AI.

Geoff: General AI.

Jason: Yeah. Good luck.

Geoff: Or you just have.

Jason: Good luck.

Geoff: We'll see that experiment happen.

Jason: Putting a gun to people's head and saying, do work. It's not as good as the intrinsic. So to your point before about intrinsic vs. extrinsic, like yeah you can beat people into doing things and there have been Olympics that have been won my communist countries that will beat their own Olympians. Like they would torture Olympians if they didn't win in certain countries. All right, that's not, that's not a long term strategy. 

Geoff: Yeah, I mean that's an experiment to be run in the next 10, 20 years. 

Jason: That's short term. You know, external motivation is short term, internal is long term, America's got an internal motivation where people here feel they can change the world. This is why it's important for all citizens in America to feel that way. 

You know, external motivation is short term, internal is long term, America's got an internal motivation where people here feel they can change the world. This is why it's important for all citizens in America to feel that way.

The Latino girl growing up in L.A., African American, lesbian in Brooklyn, any, everybody should feel they can change the world here. And that's the big tragedy I think has to be resolved here is that not everybody feels that they can live the American dream because they're getting pulled over for driving while black. 

Or I don't know if you saw the video today of somebody selling gourmet lemonade, in the Mission, and somebody called the cops on them for-

Geoff: Like the Permit Patty types.

Jason: The Permit Patty things, and it's like, who are these moronic idiots who are like, if a little girl wants to do a lemonade stand and sell bottles of water and learn capitalism, let's go.

Geoff: Yeah.

Jason: Rock n' roll. They don't have a permit? Really? Girl Scout cookies are going to need permits? Selling lemonade stands going to need a permit?

Geoff: Yes.

Jason: And you, who has the time for this? What bitter, anger, self loathing do you have in your soul that you're going to stop people from having a barbecue? You're just sad that nobody invited you to a barbecue. That's what you, when I look at those Peppermint Patty's, Permit Patty people I'm just like, oh don't you get it? They're not experiencing love in their life.

Geoff: Right.

Jason: Nope, they have no friends, nobody invited them to a barbecue. They just want to sit down and laugh and have fun at the barbecue. Well that's what America's supposed to be about.

Geoff: Yeah. 

Jason: When Permit Patty shows up, you know, we need to say to Permit Patty, like oh, did you want to join the barbecue? Why don't you go pick up some lemonade and we'll get the burgers and somebody else will get the charcoal and let's all have a barbecue together.

Geoff: Yeah that's the strength of America.

Jason: That's what America's about.

Geoff: Yeah.

Jason: That's what we need.

Geoff: Yeah. 

Jason: It's people who are different, celebrating and being Americans together. I think actually that's going to be the end game. I think we're going to get out of this Trump era, this Russian collusion, all this madness, and at some point people are just going to be like, you know what? Fighting over guns and abortion and all this stuff is just exhausting.

Geoff: Yeah.

Jason: And they'll just delete Twitter, they delete the social media stuff, Facebook. And they just go have, in my ideal world, a picnic. You know, if we're all sitting around having a picnic, we can discuss this issues.

Geoff: Yeah.

Jason: But reaching across the aisle and, they had the kid Ben Shapiro on Politically Incorrect, no, what's the? 

Geoff: Bill Maher?

Jason: Bill Maher. It used to be Politically Incorrect, I don't know, I think it's the Bill Maher show.

Geoff: Yeah, yeah, yeah.

Jason: Whatever it is now on HBO. And they were trying to goat him into like a Twitter like fight.

Geoff: Right they were trying to troll him basically.

Jason: Yeah and they were trying to make it seem like they had really divergent opinions. It wasn't that divergent. And that's what you find is, you take somebody like Ben Shapiro and then you take my friend Sam Harris, and then you put the two circles on top of each other, one's an atheist, one's like a devout Jew and they're really not that different.

Geoff: Right. 

Jason: Like yeah, one believes in religion, one believes religions like a virus, but other than that, they can have a civil discussion. Why can't we have civil discussions anymore? Why do we have to paint everybody as being on one side or the other? Most people are right down the middle. Right? Most people are reasonable.

Geoff: Right. 

Jason: You know people in the south are not anti-gay to the extent people want to paint them out to be. Rednecks, like they have gay people in their family. They're totally accepting of it in the majority of cases. 

There are some people who are bonkers and need to join the 21st century but the majority of people are not anti-gay in the south. There are some who are, but it's not the majority. But we paint them as all one Redneck group, that's anti. 

Geoff: Yeah. Yeah I mean I think that's a strength of America, where I think we have the best culture in terms of just getting the best of everyone in the world in being here. I know that we're tight on time here.

Jason: Yeah.

Geoff: So we had a couple other audience questions, but I think we'll have to leave it for next time.

Jason: Part two?

Geoff: Yeah, part two.

Jason: Part two. Give me one more question. I'll do one more.

Geoff: Yeah. I mean I think that-

Jason: Which one's your favorite question? 

Geoff: Well.

Jason: That we didn't get to. 

Geoff: I mean I think it's like, what's next on you, so you have a master plan of you're going to be the best investor period. 30 year trajectory, rest of 2018, 2019 look for you, what can we look out for? 

Jason: What can we look out for?

Geoff: We know there's a book. 

Jason: I'm going to do another book. But read Angel, or listen to it, especially if you're a founder, a lot of founders thought oh, it's a book for angel investors and it is, but it's also a way to reverse engineer your funding and understand how investors pick which businesses to fund and which ones not to fund, so it's definitely worth reading as an entrepreneur. 

Our incubator is accelerating in the number of classes so I'm looking for companies in the Goldilocks zone. Goldilocks zone for us, you haven't done your Series A yet, but you have a product in market with some traction. So, not too hot, not too cold. And then the big thing that's happened recently is Jasonsyndicate.com has 2500 members, the last deal we did, we were able to do I think 2.2 or 2.4 million dollars. 

So that makes us like a Series A investor, so now we're co-leading Series A's with Series A firms, not just angel investing. We have an incubator, we do seed rounds, but we're also going to be doing more and more co-leading of Series A's.

Geoff: So loading up, yeah.

Jason: Which is something new. And the reason this is possible is, Trump did something right, or he didn't stop something right that started before him is probably more accurate. Which is-

Geoff: A plus right, the Reggae Plus, or the reggae TV.

Jason: Well not, put aside Reggae Plus.

Geoff: Okay. 

Jason: The number of syndicate members in a ten million dollar or smaller deal, went from 99 in this LLC structure called an SPV, special purchase vehicle, to 250. That means instead of just having 99 people investing Café X or Blockable and filling up and doing a 500K or a million dollar round, now we can go 250. So if 250 people put 5K in each, it's all of a sudden $1.25 million. Right?

Geoff: Yeah. 

Jason: And so that's changing everything and then you may have read the SEC is going to change, or they're going to add to the accredited investor definition. So there'll be a credit investors who make $200,000 plus a year.

Geoff: Like a million in assets?

Jason: A million in assets outside of their home.

Geoff: Yeah.

Jason: Or a million in assets outside their home, and they're going to come up with essentially what is sophisticated, which means either through life experience or education, you don't meet the financial criteria but you meet those.

So it could be maybe a Master's in Business or you worked as an accountant, or you took a course on financial literacy. Because right now, the trust fund kid we talked about earlier, would be accredited.

Geoff: Right but he has no experience. He's all money.

Jason: And an Economics professor teaching MBA students in a city that paid under $200,000 a year would be unaccredited.

Geoff: Right. 

Jason: That makes no sense, that the trust fund kid, or the lottery ticket winner is more sophisticated than the professor or somebody who took a course. So that's going to be, I think that's passed as law I believe, that's my understanding, and that, I could be wrong, now the SEC has to figure out how to deploy that intelligently, and the SEC really has to take their time and do this right, but I hope they do it quickly, or I hope they do it as efficiently as possible I should say, not quickly. Because they're up against people doing, ICO's that make no logical sense.

Geoff: Like crypto things and other topics we could dive into.

Jason: Yeah they're doing ICO's where people are sending money to wallets, not even bank accounts to people they don't know in places in the world where they could be ISIS or North Korea, who knows?

Geoff: The places have been slowing down now, like all the-

Jason: Oh it's been stopped.

Geoff: Yeah.

Jason: Because people are being arrested.

Geoff: Right.

Jason: Because they're selling Chuck E. Cheese tokens.

Geoff: To unaccredited investors.

Jason: To unaccredited investors and saying it's not a security,.

Geoff: Raising like $200 million dollars.

Jason: And the person buying it is saying, I'm buying it because I want it to go up in value and I want to get a thousand to one.

Geoff: Right. 

Jason: So if the person buying it believes it's a security and you believe it's a utility, the SEC will side with what the person buying it thinks, not what you believe. So that's been worked out I think now people are scared to death. Doing these ICO's is more expensive and more risky than just going with a credited investor. So if you're a founder, don't be stupid.

Geoff: I'll have to add one last question. So I think because of our human performance audience here, we've talked a little bit about keto, ketosis, fasting.

Jason: Yeah.

Geoff: What's your protocol that you do personally? I know that I see you post big tomahawk steaks every now and then. You got to get-

Jason: It's something, it's the one piece of my life I have to solve this year.

Geoff: Okay.

Jason: Because I was a marathon runner, 63 black belt in TaeKwonDo, and was working out like a maniac through my late 30s.

Geoff: Yeah.

Jason: But then in my 40s I had kids and stopped. And I went from 165 pounds to 213 at the peak. So a massive 50 pound swing almost. 

Geoff: Yeah.

Jason: Which is crazy. And now I've lost half of that, but I still have half to go. I've been experimenting with a little bit of the intermittent fasting, that seems to work well for me. Ketosis and just the Atkins diet, low carb diet works really well for me, and I just built a home gym. 

So I'm trying to make it more of a routine. I wake up I work out. In all honesty and candidly, it's like the one part of my personal life I just have not been able to get under control.

So I'm trying to make it more of a routine. I wake up I work out. In all honesty and candidly, it's like the one part of my personal life I just have not been able to get under control.

I got my gambling under control, my addictive personality, I channeled that into investing, it's like a much healthier, or playing poker where I'm you know, become a very good player. 

Not great but very good, and I only play in games where I'm not the worst. I'm in the top half of the players.

Geoff: I mean if you're in a regular game with Phil Hellmuth you've got some good reason.

Jason: Well I'm always behind him but you know, I'll always be a loser to him, but in my personal poker game I'm right in the middle of the pack I would say. I no longer play in games where I'm the eighth or ninth best player, I only play if I'm the fifth or sixth best player at the table so at least I have a equal money chance of winning.

I just won't put myself in those situations anymore. I used to. So yeah, it's one thing I've got to get going, that's why I've been drinking your product. Which tastes horrible but it's incredibly effective. 

Geoff: Okay. There you go.

Jason: Yeah, you have to get the flavor set up. But I think people like it not tasting good. It makes it more like, it makes it feel like it works. 

Geoff: Yeah.

Jason: If I dump it into a Perrier would it still work or no?

Geoff: It works.

Jason: Okay. 

Geoff: So people have been mixing with cold brew coffee.

Jason: Oh perfect. 

Geoff: There's been like a little community where people are tapering around.

Jason: Yeah that's what you got to do. You got to get the price down. When is this going to be like five bucks a bottle?

Geoff: Working on it. Working on it. Working on it.

Jason: How long? Two years? Five bucks a bottle is what it needs to hit. 

Geoff: So, yeah I would just get-

Jason: It has to be the cost of two Gatorade's. 

Geoff: Yeah so we're looking at, so we did a three metric ton run. And we're looking to do a 30 metric ton run very shortly. 

Jason: And that will get you down.

Geoff: That will get us down at least by around half.

Jason: Perfect.

Geoff: So that's what we're working on.

Jason: Oh so if you just keep doing larger and larger quantities it will go down.

Geoff: Yeah, theoretical yield is a little bit more expensive than sugar. So.

Jason: So what you need to do then is just have people do a pre-order and do like and Elon Musk style model three Kickstarter.

Geoff: Kind of yeah, I mean.

Jason: If you say buy a years worth, give us five thousand dollars, or give us two thousand dollars, you might get a hundred people to do it. 

Geoff: All right, do you want to be number one? 

Jason: No. Not till you get the flavor right. No maybe, I mean maybe I should. I have been working on trying to understand this better. You are the expert, I'm the neophyte, but.

Geoff: All right.

Jason: This was something you can teach me.

Geoff: Yeah, lets talk about it offline.

Jason: All right.

Geoff: Thanks so much Jason.

Jason: My pleasure.

We want to hear from you.

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