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SPEAKER_01
So here's your transition report.

SPEAKER_03
What we are the Simpsons LA for 10 years and spent 10 years with my wife there. I got married, started a family, and that's about the last six years here in the Valley because I wanted to see if I could become the best angel investor of all time, which was like sort of a goal or one of the best, right? And so I moved up here for the deal flow and I started the accelerator, put 20 companies through the accelerator, seven companies at a time. So 140 have gone through in the last five years or so.

And it's been wonderful. And then the pandemic hit. No founders want to come here anymore.

San Francisco was getting more and more expensive. So probably two out of three startups we were investing in weren't here anymore. A funny thing happened.

We didn't want to stop doing the accelerator in the pandemic. So we moved the class online. When we moved it online two or three times as many people wanted to come to the accelerator.

And so that was a very interesting moment of reflection for me. Then I thought I refused to have anybody on the podcast unless it was in person because I thought my superpower Sam was to be able to look people in the eyes and decide if I should invest in them or to look them in the eyes and be able to figure out what the next question was on the podcast. Now a hundred percent of people have awesome setups are totally accustomed to zoom and don't want to come to San Francisco either to be on the podcast or to come to our accelerator.

I have been investigating potentially moving to Austin.

SPEAKER_01
Well, I heard a funny story and I thought it was baller. I don't want you to be embarrassed. Okay, here we go.

You were talking to someone and he's like, yeah, I'm looking for a house here. And someone's like, well, you know, if I see something, I'll send it to you. What's your budget? And you said something like, oh, there is no budget.

SPEAKER_03
Well, I mean, relatively speaking, the houses in San Francisco, they're not in the penance, the wider peninsula. They're not comparable in price. I mean, in San Francisco, everything's 1500 to $2,500 square foot and Austin, it's 600 to a thousand.

I thought it was a baller move.

SPEAKER_01
I thought it was a baller move. Everyone says like this and that and then the person told me a story. He just said it in such a good way.

He goes, oh, there is no budget. Anything I want. And I was like, that's a baller answer.

That's a great answer. And I just thought it was cool. Oh, there you go.

SPEAKER_03
Yeah. I've just been researching, you know, I've been to South by a bunch of times since like the late nineties. I went to the second South by Southwest interactive before they even had a, before they were even using the convention center.

I don't think the convention center was built. It was just all at that, whatever that weird hotel was. On six street is where they used to host it.

And there'd be 50 people, you know, per talk. And maybe there were 200 people there for a South by Southwest interactive in 99. 2000 time period.

It was very small. And so I love the town. And yeah, I would be up for the adventure possibly.

I'm looking at it. I'm investigating it and we'll see what happens.

SPEAKER_01
So Jason, you started a media company 10. How long ago was that?

SPEAKER_03
Well, most people don't know that I started in the magazine business in the 90s. So I'd started a magazine called cyber surfer, which was about online services and CD-ROMs. Then the internet happened and I started Silicon Alley reporter, which was about tech companies in New York.

I grew that to a $12 million business a year with a hundred employees or so. And then the dot com crash happened. I lost everything.

So that company for a couple of years salary to Dow Jones, which then bought me out of my contract after two weeks, which is very weird. Yeah. Then I started Weblogs Inc. Engadget auto blog sold that 18 months or so after starting it for 30 million bucks.

That was considered an amazing feat or accomplishment at the time. Then sort of Mahalo, which became inside and started Angel Investing. This is a co-scout and it all started going in that sort of certain direction and really as a journalist and a publisher, you ask questions and you try to get to truth, or at least you used to.

Now you kind of, we could talk about late stage journalism, but back in the day, original journalism, you were supposed to be independent and just ask really honest, fair questions, get the answer, double check that your facts were correct and publish a story and not put a link baiting headline on it. So that's where I cut my teeth. And after doing that for a while, I realized it really is the same thing as interviewing somebody and meeting with somebody about an investment.

You're asked basically the same questions. What are you working on? Who are your customers? What's your business model? What's the roadmap like? Where will this business be in 10 years? Those are all questions that an investor might ask. Those are all questions journalists used to ask, right? So journalism, you know, Omalik went into investing, Michael Moritz from Sequoia famously was a journalist who went and a writer who went into investing.

And there's a, you know, MGC, just Alexis, there's a bunch of people who started in journalism and then went into venture and investing. It's just a perfect parallel career path.

SPEAKER_01
And before we get into talking about, I want to ask you about Robin Hood. I want to ask you about some startup ideas. And Sean has a question about this list that you used to made.

But before last question, before we get into all that, you're a gambler. Oh, yeah. Do you think over the last 10 years have you lost or won gambling?

SPEAKER_03
Probably not even with losses in the beginning and then wins and losses later on. Over time, I went from playing very low stakes. And so the first five years of my career, probably the total amount that would be what would be the equivalent of what's on the table now.

So it's, you know, I used to play in $1, $2 games and now I play in $100, $200 games. So it's a hundred X, right? Literally in terms of Nolan, Lemon Holden and the blind. So I think it's sort of like the new golf.

So instead of having a golf club membership, I play poker. And I think it's how I became besties with a large number of high profile people and it's worked out well.

SPEAKER_01
What is the biggest hand you've been part of?

SPEAKER_03
That's a great question. I've been in some six figure hands a couple of times in my life. The worst that ever happened to me was I was playing in Los Angeles in a game and I lost seven hands in which I was the favorite, clear favorite, like 60, 70, 80% favorite in six of them.

And then in one, I was even, you know, almost like 51, 49. And to lose seven in a row where you are the, you know, favorite, even if it was just 50, 50, you know, you can do the odds of that, you know, 50, 50, 25, 12, 6, 3, 1.5, whatever basis points, 0.

6 basis points. It's like one out of 300 games that would have to happen or something. And I lost like 70 grand that night and was infuriating.

And then I came back the next night and won 170 grand. So I had this incredible swing. So 175, it's pretty big.

I stopped playing in those big games because I didn't like the way it felt to me to either win or lose. And I felt like I was getting close to an addiction that was unhealthy. And so I kind of pumped the brakes on it.

I was invited to all those Molly games, if you remember those. And at that time I was playing in $1, $2, $3. $1, $2, $2, $5, $5, $10 games.

And Molly would text me and call me and say, like, oh, Leo is here. Oh, you know, this very famous person's here. They want to see you.

And I was like, they want to see me lose 50 grand. Like, no, thanks. So I passed on going to all those games and I just played in the smaller $500 buying games, $1,000 buying games.

And I do it for the social. It really is not going to be any comparable amount of money that I would make in startup investing. Therefore, I would rather get the rush of gambling through startups and investing in them than in poker, because I feel like I'm better at startups than poker.

I mean, I know I'm top five angel investor of all time. And in poker, I'm not even in the top 5 million or whatever, you know, in all likelihood.

SPEAKER_01
All right. Well, Sean, Sean is back here. Apparently he has some technical difficulties.

He had a joint on his phone. Sean, you there?

SPEAKER_02
Yeah, I'm here. I don't know if you guys can hear me all right, but Jason, as soon as you join, my internet died, but I said, no, I will not miss the pod that everybody's been waiting for. Jason, I don't know if you've heard this, but there's a great tweet that was about our podcast and it said, my two favorite podcasts this year.

It goes, my first million, which is millionaires talking millionaire shit. And all in billionaires talking billionaire shit. And I was like, that's the description of our podcast.

SPEAKER_03
To be clear, I'm not a billionaire.

SPEAKER_02
Yeah, but you know, nobody's really working on it. Exactly. There's a great book that me and Sam like to read.

It was about how I got rich or how to get rich, how to get rich.

SPEAKER_01
It's so embarrassing to say it. You know the author, Jason. It's Felix Dennis.

You know Felix Dennis? Yeah, he's a publisher.

SPEAKER_02
He created Maxim magazine and some other things, but he says in there, he's like, you know, if you can count your money, you're not rich. He's like the richest people have no idea how much money they really have at any given time. He's like, so if you're counting your money, you're not there yet.

SPEAKER_03
I didn't even know this book existed. Is it good? It's the best. I remember this guy.

He was a mad man.

SPEAKER_01
It's a horrible title and he named it that kind of as a joke. He's kind of a shithead in a good way. Like he seems like a wonderful human being, but he loves poking fun.

But his writing is rhythmic and beautiful.

SPEAKER_03
I'm going to check it out. I mean, people said that about the title of my book because I put like exactly, you know, what I turned into what on the cover of the book.

SPEAKER_01
He's really good. And he was a poet. He wrote books and a businessman, very eclectic person.

SPEAKER_03
No, there's no audio version of this. Correct. He wrote in 2009 before the audio revolution.

I just added the paper.

SPEAKER_01
He died soon after. It adds to the the allure a little bit. But I want to, can I ask you about Robin Hood? So Robin Hood went down last week.

Everyone knows what's going on. Well, it didn't go down.

SPEAKER_03
The situation went down.

SPEAKER_01
The situation went down.

SPEAKER_03
I thought you meant the service went down. I was like, I didn't hear about that.

SPEAKER_01
Are you an angel investor in Robin Hood? I'm an angel investor.

SPEAKER_03
Yeah, I met them before. It's a pretty funny story. And I met them before they launched the product in a bar.

Paradoxically enough, I was speaking at Adeo Resi's founder Institute and he likes this dive bar in Palo Alto called Antonio's Nut House. And he asked me to go there. And Adeo's roommate in college was a guy named Elon, who had a rocket ship company and electric car company.

And he's like, meet me over here. Elon's going to come over for a drink. So the three of us are having a drink there and Vlad and his partner came up and said, Hey, you're Jason Calacanis and you're Elon Musk.

And he said, yeah. And he said, I said, tell me about your startup. And Vlad goes, how do you know I have a startup? I said, you recognize me.

We're in Palo Alto. Like what? I mean, it's not going to be a script. I mean, we're not like, we're not at the Chateau Marmont.

You know, I'm not Steven Spielberg. So go ahead and give me the pitch. And he said, Oh, I want my idea is I'm a quant.

And I said, what's a quant? He said, you don't know what a quant is quantitative analysis. I said, I kind of know, but explain to me what you do. And he said, well, you know, we try to make algorithms.

And I was like, don't tell me this is another thing where you're making an algorithm and selling access to the algorithm instead of just printing money. He's like, no, no, no, that would be stupid. But if we had the algorithm, we just use it.

He said, we're going to get millennials to trade stocks. And I said, you know, millennials are kind of from what I understand. And I've read their commitment phobic, right? And he's like, yeah, so they're living with their parents trying to pay off college debt and you want them to buy stocks.

And he's like, yeah, I was like, you realize there's been no retail investor since 2008 when the whole thing collapsed. He goes, that's the opportunity. I said, oh, that's a good pitch.

Actually, that's a big opportunity. If you did succeed in getting this next generation to a new industry to embrace buying stocks, my God, what would that look like? That'd be incredible. And I said, hit me with the business model.

He said, well, we're going to make it free. I said, so your idea is to go after a group of people who are on their parents, Netflix accounts to save money, get them to trade stocks, and your business model is free. He's like, yep, I was like, I'm in.

So I invested and he really, you know, they really wanted to create this revolution. And so that's the great paradox or irony of this situation is that they wanted to enable this revolution. That's why they named the company Robinhood.

That's why they made it free to trade. That's why they created a mobile app, not a big desktop Bloomberg app. They wanted to make it more accessible and mission accomplished.

There are some rules to the road. And I don't think anybody ever anticipated millions of people deciding on the same day that they would suddenly take up stock trading and all by the same stock, you know, like this is a black swan of black swan events. Like it really is an edge case.

And if you look at the reporting, they could have been shut off from trading based on what I've read. I don't have inside information about any of this situation, but I think they could have been shut off and trust me, nothing, there's nothing they want to do more than get more users and empower them to trade. That's what they're here for.

SPEAKER_01
I mean, they want to how much did you invest in them back then?

SPEAKER_03
I think I put in 50 K or 100 K, which is my typical bet back then.

SPEAKER_01
It's going to turn out to be pretty very, very, very lucrative deal.

SPEAKER_03
Yeah, I mean, when you hit on one of these, the Uber investment wound up being, I mean, at its peak, maybe 4,000 X, 5,000 X, depending on when, you know, you choose to sell it. And I sell on, I think around half my position. So I'm still long Uber, you know, I think in the next five to 10 years, the company will be significantly larger, especially since they got this food business style.

SPEAKER_01
And just for the quick math, 5,000 X times 25,000. Is 50,000 is 250 million.

SPEAKER_03
I put 25 K into Uber, so it'd be more like 125 million or something like that. At the time I wrote the book, the first three or four investments I had made in that 25 K range were over 100 million. It worked out pretty well.

I don't know what exactly the valuation is or the multiple is right now for calm or Robin Hood. But generally, if you hit something as an angel investor and you're investing in a five to $25 million company, and it becomes worth $5 billion or $25 million, you can do the math, you know, with dilution, you would basically cut it in half and with dilution, you might make 100 to 500 X.

SPEAKER_02
You did Uber as a scout, right?

SPEAKER_03
Yeah, I was a Sequoia scout, right?

SPEAKER_02
Would you say, because I think, you know, there's no argument investing track record pretty fucking amazing entrepreneurial track record more like singles and doubles. Do you think that's more like, is that just the variance of entrepreneurship startups hard to, you know, go or do you feel like actually you're a better investor than entrepreneur?

SPEAKER_03
Building media companies is really a fool's errand. You know, they're just really hard to build ad based businesses. Even the biggest ones, you know, they get to a billion dollar valuation like Vox or something like that.

They're losing money. They're challenged, you know, on their best day, right? Like if you're building media businesses, you're, you must really love it, right? They're just hard to scale. And unfortunately, that's what I love to do as an entrepreneur.

Back in the day, Weblogs Inc becoming worth $30 million after 18 months. You know, if I kept that going, it probably would have become a, you know, $300 million exit if I worked on it for another whatever 10 years. There's no doubt I could have done that.

I'm sure I could build businesses worth a billion dollars, but you know, I don't think I'm Elon or any of those type of folks. So I've definitely done better as an angel investor. That's for sure.

But a lot of this is about timing. Back when I was an entrepreneur, the market for a business would be 20, 30 million homes that had high speed internet. That was kind of the market.

Now you look at the market, we've got two billion people with high speed smartphones in their pockets. So just do the math on that. It is a hundred X.

The desktop market that we used to address and they have built in credit cards. The number of credit cards people had on the internet was in low millions. And I was an entrepreneur.

Now you've got, you know, whatever every iOS device, right? Has a credit card associated with it and some percentage of the Android devices. And those are with people all the time. So people used to be in probably in front of their desktop for a couple of hours a day.

Now they're on their phone from the moment they wake up, they look at their phone and the moment they go to bed, they look at their phone, right? So we've not only a hundred X the market size in my mind, we've probably 10 X or five X the usage. So it might be a 500 X swing. And then the number of people with credit cards, you know, ready to go and app store payments and all this kind of stuff or their wallet like or their wallet like already in their browser ready to buy.

I mean, it's a totally different world.

SPEAKER_00
All right, everyone.

SPEAKER_01
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SPEAKER_03
That's why you see something like com.com just go or, you know, clubhouse just go from zero to 10 million users or zero to 10 million. And wrapping you very, very quickly.

And then also the ad networks are so sophisticated now. We didn't have that. Back in the day, you had to wait for things to spread word of mouth.

And maybe you buy billboards or bus ads, traditional ads. It wasn't like this infrastructure of I'm gonna go and have my ad buyer go on Facebook or Twitter and Google search and figure out the channels and figure out the cat and all these tools to help you do that and creatives. It just that infrastructure wasn't there.

So it's just a different world. But certainly all history will show me as a better investor than entrepreneur for sure.

SPEAKER_01
You made a comment about, you said, I'm not an Elon. I don't know what your relationship is with him, but assuming you are or we're close, you host a podcast with Chamath who's like all the rage right now. Presumably you hang out with a lot more pretty wild, crazy, incredibly successful people like that.

What are those attributes that you're referring to when you said they are something?

SPEAKER_03
You need to have a singular focus and you have to be willing to give up everything for that.

SPEAKER_02
And I asked the question a little differently. I want to do it person by person. What's their superpower? Give me Elon.

What's his superpower?

SPEAKER_03
People forget, he's a world-class engineer. And so I think people forget that because he's also so good at Twitter. But he is a world-class engineer.

He's a great marketer. I think he added the marketing skill later. So he's very good at both of those things now.

Great communicator obviously. But I think singular focus and fearlessness would be what the superpower is. I mean, he can really focus on something and he's fearless in his approach.

If you look at the public record of what he's talked about with Tesla, how many times that company was on the brink and how many times he was all in. I'm not saying all in, he was gonna lose half his money. He had already lost all of his money into those businesses and he was hanging on based upon according to what he said publicly alone in the financial crisis during the Tesla dark phase.

That's his superpower, Tramoth. He's really smart, he's a really smart analyst and strategist. Also hard working and increasingly becoming a great communicator, as you can see.

SPEAKER_02
What about you? What's your superpower?

SPEAKER_03
I think I am incredibly good at figuring out who's gonna be a winner in life. And then I'm extremely good at being an advocate and friend for people. Probably on the margins, good at media, hosting a podcast, writing, etc.

But I'm probably best as a mentor friend, supporter of people and helping them work through stuff. I mean, I think that's why I probably have a lot of really close friends. And I think why the all in podcast actually works is because I have a deep personal relationship with Chamath and Saks.

Increasingly freeberg, but to be honest, I was much deeper friends with David Saks and Chamath. But being close friends is I think what makes that podcast, what has made that podcast in 19 episodes become the number one tech podcast. And the number this morning, somebody texted me and they're like, do you know you're the number 11 podcast? I'm like, no, we're the number one podcast in tech.

He said, no, you're number 11 overall. And I was like, what? And so yeah, in iTunes apparently we're number 11 today, overall, which is really mind blowing when you think about it.

SPEAKER_01
I actually want to hear the answer to a question Sean had about this list. So an idea that we've discussed a lot on this podcast is lists. So there's many examples of this.

One example is a little bit different, but the JD Power Award, JD Power. Sure, yeah. Another one is Gartner.

Like these businesses that are based on this idea of create, like we are an authority and we're going to name what's best.

SPEAKER_03
Consumer reports. Yeah. Wire cutter, 30 under 30, Midas touch list, all this stuff.

SPEAKER_01
Yeah. Well, you did something similar. You want to take it, Sean?

SPEAKER_02
Yeah, well basically, all right. So the context here is a lot of our audience is people who are about to do their first startup or a lot of our college students. There is of course, you know, people who are more established, but for a lot of people, they love the ideas we bring up where you needed nothing.

It's like, I call it the cake batter startup. It's just add hustle. You didn't need to be a programmer.

You didn't need to be a brilliant engineer. You didn't need tons of money to get started. We talked once about lists as, you know, one way to gain influence in any bubble, any, whether in Hollywood, you're in New York, you're in San Francisco, is you just make the list.

It could be kind of a fucking arbitrary list, to be honest with you, but you, by becoming the kingmaker, by being the one who ranks who's who, everybody sort of needs to open up access to you in a way. And you become a central player. And I, I used the example.

Now, I actually don't know exactly what you did, but I heard you say this once, because I've been listening to your podcast for a long time. I had heard you say once about the Silicon Alley 100 or something like that. You went from kind of nobody in that scene to deciding who are the power players by making this list.

And all of a sudden you kind of became a somebody because you made that list. Is that fair or am I exaggerated?

SPEAKER_03
Yeah, I mean, I had started this as exactly fair. I started Silicon Alley reporter and I said, let's do our top 100 internet people, but at the time in 1996, we could only find 60 people in total who were working in the internet industry. So then I asked the 60, do you know anybody else? And they, my team said, let's just make the top 10 or top 25.

I said, no, it's gotta be 100. And so we literally for, you know, number 60 to number 100 had a teacher, an accountant, an HR, like a head hunter, a lawyer, we just filled it in. But then I specifically was like, okay, DoubleClick is the biggest company, but Esther Dyson's been here the longest and she did PC Forum and she's like kind of a legend in New York.

Let's put Esther Dyson as number one and DoubleClick as number two. The two Kevin's Kevin Ryan and Kevin O'Connor from DoubleClick back in the day. And they were kind of the Google of Silicon Alley in New York is what they were referred to as.

We just did that to tweak them. And we put people on the list that were wild cards. We call them wild cards specifically, just to tweak people.

They're like, where do you put the wild cards? How do you compare them? Because, you know, we have the valuations of companies. We have number of employees. We have how much revenue, how high profile they are, how well known they are.

So you could kind of say like, well, Uber is bigger than Postmates and Postmates is bigger than this company. And you could, if you were doing it today, come up with some really valid metrics. And I was just like, okay, just pick a random number.

Just literally put Doug Rushkoff anywhere. Like put him as number 12. Who cares? Just to tweak people.

And that's why when people are like, oh, I really want to be in the 30 under 30 or 40 under 40, I'm like, you do realize like it's a bunch of like journalists in a room trying to figure out how to get people to debate it. Just like on sports radio, somebody's like, oh, you know, I don't have LeBron on my Mount Rushmore, or I don't have Kobe on my Mount Rushmore. Oh my God, how do you not have Kobe on your Mount Rushmore? You know, like people go crazy.

So, you know, it worked. And then I ranked it, which, you know, most people would just say, just, you know, make the hundred. And there was one argument, like let's put the top 10 and then we'll put everybody else alphabetical.

And I was like, nope, we're going to rank every single one. And we're going to sit here and put people into three buckets. Then we'll put them into four buckets.

I'll put them into five buckets. And we just sat there, you know, at the big conference room table and everybody's one pager that would be in the magazine. And we gave two pages to the top 10 and then one page to everybody else.

And I did that for five, six, seven years. And it really tweaked people. And then everything became, my whole life became PR people lobbing me like, hey, we were 27, we should really, you know, there's an argument for us to be 15.

These seven companies between us and there, you know, we, those companies aren't even business anymore, blah, blah, blah. So it was pretty hilarious. And it just forced people to pay attention to us.

SPEAKER_02
We got to find the most prideful and sensitive group. And then we got to do it.

SPEAKER_01
One of the secrets behind, like, so there's this great book called made to stick, which I love Dan and Chip professors at Stanford. And they, well, my favorite story is about a news publisher in South Carolina who had a local newspaper that everyone else, I mean, obviously local newspapers were going out of business. This guy was thriving.

It was a small ass town and someone says, what's your secret? He goes, I'm going to tell you in three words, ready? Names, names, names. If I'd print the phone book, if I could, my whole philosophy is to mention as many names as possible, because if you see someone you know, or you are mentioned in something, you are always going to share it. And so I've stolen this concept constantly and I've created all types of content.

And you always want to name as many people as possible because that gets the most amount of shares and creates what Jason's describing. It's like a secret or not a secret, but it's a very powerful weapon. Yeah, it works.

SPEAKER_03
It does work. People like to read about themselves. And I think what you're seeing in journalism today is like a sort of breakdown of like maybe overusing that device.

Kind of what Gawker did and BuzzFeed did at that seminal moment, they both really tried to hack SEO and social. And it was much easier to do what they called process journalism, which you know, TechCrunch dabbled in as well, which is you get a tip to your tip line, you just print it. And then you say, is this true? And it was like, that really is what TechCrunch was doing and Gawker were doing in the early days.

So much so that in order to get them off the scent of what I was doing with Mahalo, I had already, I had bought the domain name Kokua as well, which means to help or to guide in the Hawaiian language or sort of Aloha, Mahalo, Kokua are the three important words. I was able to get two of the three. And we emailed them from fake Yahoo accounts and said, I just interview with Jason Calacanis.

He talked about himself for 56 minutes of the hour. And then he asked me about myself for four minutes. He's doing a podcast network in New York, LA and San Francisco.

He's building studios that are street level and Gawker printed it verbatim. They got it from multiple sources when we sent it to him from one fake Yahoo account. And then I published that Yahoo email.

We basically proved how easy it was to sort of spoof them and how low their bar was. But that's kind of what people do now. Like, I don't know if you guys have had this experience where somebody quotes you or mentions you and your Google alert goes off and you're like, I never talked to this person.

They're like, yeah, no, we didn't have time to talk to you. And it's like, really? You had time to put me in your story, quote me, but you didn't have time to email me. And my email is my Twitter handle and my DMs are open.

Really? OK, fair enough.

SPEAKER_02
We sold our company last year and somebody tipped off TechCrunch or whoever. And they published that, hey, we got bought and they said we got bought for 25 million. And it was actually a little less than that.

And so they reached out to Twitch or Amazon for comment. And they were like, they don't comment. So they didn't say anything.

And they asked me and I was like, hey, if you were lazy enough or you just printed this wrong number that's higher than the real number, I'm also not going to correct you. I'm not going to get myself in trouble by giving you the real number. But man, these guys will just print anything.

That's crazy.

SPEAKER_01
Well, what's crazy is that with Sean's deal, and I'm not saying it was greater or lower or whatever. That's irrelevant. But the headline said a rumored this.

And then when it's linked to a reference, it will say Sean's company, which sold for it becomes a rumor and then a fact. And it is pretty wild. And that was on TechCrunch.

SPEAKER_03
Yeah. I mean, late stage journalism is a trip. It's really weird.

It's gotten super weird. I mean, the amount of stuff that is like this really crazy device, which is whatever was printed in other blog posts is fact. Therefore, I'm going to write in my article, Chimamah Polyhop, like the San Francisco Gate, some former Gawker writer, a sports writer over there.

And then they did a takedown piece of Chimamah. And then he links to 20 other stories. And I know these stories are not true, but they basically then frame them a certain way, and they don't do any fact checking.

It's weird. Late stage journalism is really weird. I mean, I think that's why you see so many people going direct.

And last night, I was tweeting back and forth with the founder of the information. And she was lamenting how Mark Andreessen had blocked everybody who was a journalist. Therefore, when he starts a room on clubhouse, the journalist can't get in.

And they were like lamenting how bad that is. And it's like, well, you attacked Mark Andreessen relentlessly for years. He felt it was unfair.

And now he just goes direct. He doesn't need journalists. And journalists stopped writing about me once my podcast or my two podcasts became the number one and number 11 tech podcasts, because I have more reach than them.

They don't want to write about me because they're competing with me. You know, Vox and The Verge and whoever, TechCrunch, they're competing with me for audience. They don't want to link to me.

They don't want to talk about me. So I think what we're going to have happen is Andreessen Harvest is going to have their media arm. Chamath, myself, Sacks will have our media arm.

Other people have their media arms. You know, obviously Elon has his Twitter. He goes direct.

People are just going to go direct. They're going to rat around the press. And the press is kind of flailing now.

Like why is everybody routing around us? It's like, well, because you're not doing fact checking and you're writing link baiting headlines and people feel they're being treated unfairly. So they're going to rat around you. And so it's a really interesting opportunity slash moment in time.

It's very entertaining.

SPEAKER_01
What's the CEO of Robin Hood, Vlad? Yeah, you know him. You're early there. So you definitely want them to win.

You want them to succeed. If you were him, how would you have handled this past two weeks or 10 days or whatever?

SPEAKER_03
Yeah, whatever. Wednesday, I think Wednesday to Monday.

SPEAKER_01
It seems like whatever.

SPEAKER_03
Two months. It's been like less than a week. It's literally Wednesday to now.

Well, I think the blog post they put out on Friday was great where they explained what they're required to do with their clearing houses. And I think that's where they stumbled. They should have just said like, listen, we want you to trade.

We have to have more money in our accounts in order to have more traders on our platform. And we have covenants that we have to abide by in order to stay solvent. Therefore we will not be at we're going to start a waiting list and we're not going to allow people to trade until, you know, maybe a week from now and no new trades and we're going to raise more money so that we have a bigger work chest here to keep this going.

And Vlad knows, you know, he the communication was self optimal on Wednesday and it got better on Thursday, Friday. And I think it's gotten much better today. Still not perfect.

Not every founder is like perfect at managing the press. And I think Robin Hood has largely been a hero and hasn't had to face many challenges just like Uber didn't for a long time. And then Uber did, right? So where Facebook didn't have to deal with any of this and then Facebook did, you'll see this pattern where a startup hits scale and then things are so big that when they bump into something or they trip and fall, it can leave a dent.

It can leave some collateral damage and the stakes get higher. Obviously Airbnb had that when everybody was like, oh yeah, somebody's going to throw a party in some Airbnb and trash the place. And sure enough, I don't know if you remember that seminal moment when, you know, there was a meth party in somebody's apartment, they went through all our pictures and desecrated her apartment.

It was horrible. And it was like, you really rented your apartment with all your stuff in it to somebody and like 20 meth heads came and destroyed the place and they wound up compensating the woman and people now are like, oh, hotel rooms get trashed by rock stars and there's drug parties and you know, holiday ends on Sunset Boulevard. If I rent out this space, that's something that could happen to me.

How do I stop parties from happening? I had an Airbnb for a while and we had a whole thing where you couldn't do parties in it. And then one morning I wake up and I look at my phone, there's 20 notifications from 12 to 5 a.m. and it's the drop cam at the gate and the drop cam is going off and there's all these like Uber's and Lyfts showing up and the person threw a party there after we explicitly told them not to and they did $5,000 in damage and it all got paid for or whatever, but you know, it's a risky run. It's a risky run.

So long way of saying this happens to every company if they hit scale, whether it's autopilot with Teslas, Twitter fell well, clubhouse last night.

SPEAKER_02
When Twitter went down for like six months straight, it was like, oh, I can't tweet. When Robin Hood went down, it was like, oh, shit, you know, I can't, it ended the pump, which was unfortunate, you know.

SPEAKER_03
Well, I mean, people could have gone on other platforms if people were more super motivated, they could have just gone down the line of the other platforms and continued to pump the stock. But I think you pointed something out there, which is this is an artificial behavior going on. This isn't people buying and selling stocks.

This was a war. And so people were trying to figure out how to hack the system, essentially on both sides of the trade and actually feel bad for GameStop. Like what happens to GameStop, their employees and existing shareholders when this thing

SPEAKER_02
is getting whipped around like this, they paid off like $400 million of debt and so did AMC basically save the fences. No, they did. They converted all their debt.

And when did they do that today? No, they did it last week when it was all happening, but AMC did it first and then GameStop also did it where they paid out. They didn't issue new shares, I don't believe, but they used, what did they do? They did some kind of conversion where they, they were able to take, because they both had like $500 million of debt and really no pathway to pay it off. So this was like Santa Claus dropped off.

SPEAKER_03
AMC did what they call like an at market raise or something.

SPEAKER_02
Yeah. They used it fast, right? They had like a basically 24 to 48 hour window to do something and they did well. So I think that was good for them.

But yeah, you know, they were getting ragdolled for kind of no reason here. So this podcast is usually not about like what's going on in media and politics and stuff like that. What we do is we sit down and we bring something, we say, dude, I had to move last week and you know, it's a pain in the ass, blah, blah, blah.

Why doesn't somebody create this or have you seen this? This is a cool idea. What if you applied it to this other space? And so we are very much a brainstorm. That's why the podcast has gotten somewhat popular because, you know, most podcasts are just kind of interviews.

And so I don't know if somebody prepped you. If your handlers have told you what this podcast is. I don't know if you brought any ideas to the table.

SPEAKER_03
No, I've got a million ideas. I'm good at brainstorming. It's literally brainstorming is what I do for a living.

Perfect.

SPEAKER_02
So hit us with a couple. Hit us with a couple. You don't have to go too in depth.

You can go kind of rapid firing. If something's juicy, we'll jump on it. But tell us some ideas that you see some opportunities that either you would do if you had time or you think other people should go do.

SPEAKER_03
Okay, ideas that I would like to do or other people should do. I think the Slack communities that are paid are very interesting. I know you have won a trends.

SPEAKER_01
Not a Slack community, Facebook community. I think Slack communities are horrible.

SPEAKER_03
Okay. Well, I think paid communities. I thought you had started on Slack, right?

SPEAKER_01
No, we always did Facebook and people shit on us. I think if you're going to say paid communities are great, I totally agree. I think everyone, a lot of people go to Slack and I think it's the worst platform for a community.

Why? It's too, maybe ephemeral. Is that the right word? People say do you get lost on Facebook, but there's Facebook threads in our community that literally has 300 replies on Slack. It's like Facebook is a podcast and Slack is clubhouse.

It's too fast.

SPEAKER_03
It's too fast. Yeah. I agree with that. That's probably true.

I haven't figured out which platform is the best for this. We have a Slack community for this week and startups that's got a couple of thousand people each week use it. It's free.

We're actually hiring a community manager to figure this out. We have an investment in a comic called Soul Savvy, S-O-L-E-S-A-V-Y.com.

SPEAKER_01
Yeah, I almost did that too.

SPEAKER_03
Yeah. They are doing phenomenal. I think they charge $30 or $40 a month to be part of that community.

I think the top 10,000 people in every topic want to be part of a community and pay $100 a year, $20 a month or something like that to be part of it. I also think the same about newsletters and teaching and education. I'm really taken by ISIS as well.

We have a couple of three investments now, I think, in the income sharing space. I think that that's going to change education. I'm particularly interested in that.

Consumer subscriptions are the big one that I think are going to be phenomenal because we've had Com, STEEZY for dance, Brilliant for math, Musician, Tonebase for music.

SPEAKER_01
Let's talk about communities real quick. Then we're going to go on to income share agreements because Sean loves that. Let me tell you what I think about communities, which is, I agree.

I think they're going to be huge. I think that there's way more room for them. The problem is not a question of which platform is to host these communities as best.

It's which is the least worse, which is the least bad because everyone complains about Facebook, but I've been hosting communities for 10 years. It's hands down the best because it has the most liquidity. People are there.

Their attention is already there. It's way easy to comment. Every other platform I think to host a community is way of a distant second to Facebook and Facebook is not even that good.

It's only good because people are there.

SPEAKER_03
Yeah, that's what I like about Slack is that I have all my slacks open. I have one for launch, one for inside, one for launches founders, one for my syndicate, one for my house. I've got all these different Slack communities.

When I add one more there, it's just in the left hand navigation. I found people really like that. I've got an Austin community where I have two Austin communities that are Slack communities on part of now.

A community manager, community that I'm a member of, it's definitely interesting as a concept.

SPEAKER_02
Yeah, somebody who needs to do the sub-stack for paid communities where you give somebody a very quick splash page where you describe the community, you let them take payments, and then it says, great, here's where the community lives. You actually don't try to build the community part. Let them put it in Slack or Facebook or Discord or wherever they want to put it.

But just the paywalling, you should make that, this is a dead simple, easy to share and easy to paywall basically. That's what sub-stack really did. I think somebody should do that for paid communities.

SPEAKER_03
Sub-stack is actually giving, they had them on the podcast and they told me they weren't giving advances to writers, but then I read they are giving advances. I don't know if they changed their minds or they did on the slide, but my understanding is that one of the reasons they got people over was they gave them whatever, guaranteed minimums or something, which is pretty smart, I think, actually.

SPEAKER_01
By the way, sub-stack, I'm actually not terribly bullish on it all. Why? Because the fee is way too high. I think the fee is way too high.

SPEAKER_03
What is the fee? 10%, 20%? Yeah, 10%. 10%. I think if you're under 100K, who cares? But if you get to a million, giving them 100,000 for MailChimp software and Stripe, makes no sense. You could literally hire three full-time customer support reps from home, or two, for 50K each or three for 35K each, whatever, and have a staff working for you.

SPEAKER_01
That leads into the next problem with them, which is, I imagine they would make most of your money off the big shots, but if you're a big shot, you're going to want to bail and do your own thing. And if you're not a big shot, can you sustain writing a newsletter every week or every day or every month for two or three years? I think most people are going to know.

SPEAKER_03
No. Having done 1,200 podcasts, I can tell you the answer is no. Most people don't have the stamina for it.

You have to love it. You have to intrinsically love it. Trust me, on Inside, where we got up to, I think, 30 newsletters at the peak, the burnout issue was real, and we got down to, I think, now we're down to 12 newsletters.

We've been trying to really have multiple people on each newsletter so that they get higher quality and it's more sustainable. And it just, people do burnout. It is a grind.

SPEAKER_02
I had a personal newsletter for three months that was paid, and I burned out in three months. And it made substantial money. I was making 50K a month, and I was just like, fuck this.

I don't want to do this anymore. I was probably like one of the top five sub-stack earners, but I just didn't want to keep doing it.

SPEAKER_03
It was too much. Yeah. We'll see where they take it. I mean, it's off to a great start, so I give them a lot of credit.

I mean, all those businesses where you take a percentage are really problematic. It's sort of like the ad rep business. There used to be this concept that you would never hire an ad, a sales team, you would just hire a rep firm.

And what would happen is, there were all these rep firms in the early days of the internet, like in the double click days in the 90s, and they would rep the New York Post online for their ads. And then if you, and you would take 30%, if you succeeded and made your clients successful, they would look and say, okay, you made us $3 million, you took 900K. We could hire five salespeople for 100K each and give them 500K and commissions that plan.

Why are we doing this with you? And so your reward for succeeding was losing your best customers. The reward for Patreon succeeding is they lose that customer to a stripe or ghost or, you know, there's all these like tools that charge you a flat rate to do subscription. So you had someone like Sam Harris, who is the largest person by far on Patreon from what I understand.

And then he just laughed and moved it to his own side and I'm personal friends with Sam and actually convinced him to do his podcast. We were at dinner and I told him, like, you're really built for this. I mean, the problem is, if you do it, you'll never write another book, which both things have turned out to be true.

And he, um, he just moved it over to his own platform and he gave up all those folks. So owning your audience is so critical. This is why I think clubhouse is going to be awesome in one way to get new audience.

And I've been, you know, I've done three rooms now that I started and I got to, I'm at 10 or 15,000 followers, I think, but then I'm just constantly driving them to follow me on other platforms, subscribe to the podcast and sign up for my email so that I can build a long-term relationship with them. And then capiche.fm, which you know, Austin, I think, has got his own version of clubhouse.

It's slightly different, but it's very different, but you get to own your email addresses and phone numbers of your followers in your group. And that's going to be the big win is like, imagine if you own one of your, you know, owned all the members of your clubhouse, right? Like you guys own the members of your Facebook in a weird way, even though Facebook doesn't give you access to it, you actually have their contact information in order to add them, right? You can't get into it unless you add them.

SPEAKER_01
What industries interest you about the income share agreement?

SPEAKER_03
Interest sharing agreements are very powerful because they shift the burden of getting a benefit from the education to the person providing the education as opposed to the student. So when you go to college, they give you the education, they take your money. And then there's this like little tiny office somewhere called like careers where they have a couple of binders of jobs and like somebody like you come in and they point you to the binders, like that's pretty much as sophisticated as from my understanding, like Lambda and a lot of these places spend as much time teaching as much time placing students as they do teaching.

And so we have a company called on Delta, which teaches just growth. So if you want to be a growth marketing manager, you go there, I think it might be 10 K for their course, you know, which would be like half or a third of one year of college. And then they only take that money.

If you get a job over 40 or 50 K, I think just like Lambda and they only take it up to 15 K or something. I'm just making up the numbers here. So I really like that idea of people in society being able to not take the risk.

So I'm thinking about taking Founder University, which is our two day free course, which was a way for us to get deal flow and meet founders and making it like a 12 week course. I'm trying to hire somebody to run that for me and then charging $12,000 or $6,000, but making it nice. So hey, if you pay us, great.

If you want to pay for it up front, or we don't need to make that money. But if you do get a job as a founder, sure, great. Pass back because so many people want us to create that product, but I don't have the time for it, but if you have a budget, then you could actually hire a sustainable staff.

And education has to change. I don't know. What do you like about it, John?

SPEAKER_02
Well, I mess in Lambda school and it was because early on I was like, oh, shit, the incentives are aligned. Now the school has to get you a high-ranked job, which is the reason people go to school. So I think that that was just obvious to me.

And even though at the time they had like, I don't know, 80 students total ever lifetime, it was pretty clear that the completion rates were super high. The placement rate were super high, like orders of magnitude above what MOOCs did and even like the success rates of colleges. And so that I liked.

And then I was like, okay, this is great, but it's not winner-take-all. And so I just invested in like a Lambda for Brazil and like a Lambda for just investing in a whole bunch of that because that same model just seems to work like Awari, which is Lambda school for Brazil. And they're crushing it.

Lambda is never going to go and figure out how to like hit the Portuguese speaking market well and do it better than somebody who's there who just took Lambda and said, I can do Lambda better than you can do Brazil. And so I just liked that model. And I think I'm going to make a bunch of money investing in those.

And I think that fundamentally it makes more sense to me because I went to Duke, I paid a shitload of money for that. It's exactly what you're talking about, you know, like nobody there ever even talked about getting a job. I was pre-med and they didn't even ever say like, by the way, here's what a doctor does.

Or you want to meet a doctor?

SPEAKER_01
Sean, you're pre-med at Duke? That's hilarious.

SPEAKER_02
I did not know that. I took the MCATs and everything. I was ready to go.

Oh my gosh. I was ready to go for a 10-year like kind of post college commitment. I had this crazy idea for the sushi restaurant.

I was like, I'm going to do that instead. Luckily I was saved by sushi, right? But the point is like when I went there, what was cool was the stamp. Like, oh, it's kind of just like the filter.

It's like, if you're smart enough to get into Duke, I think you're pretty smart. Everything thereafter, the education itself and the way they help you with your career is like, God awful. That's why I was like, all right, I'm going to make this my mission.

I'm going to start a university someday. And so that's like, that's been a personal mission of mine since then. So that's why I like ISAs because I think it's a tool to create a university that actually makes sense in the modern world.

SPEAKER_03
There's a bunch of platforms now too that are becoming like the Amazon web services of the space like MeritOS. And what they're going to do is just like you don't have to rack servers anymore when you start your startup. Imagine you start a course and you're like, how do I get this infrastructure? How do I do the legal work? How do I collect the money? How do I enforce these and make sure they're fair or whatever? And you'll just be able to use something like MeritOS and have it work.

SPEAKER_02
So I think a better, I looked at those guys, the ISAs as a service, I think that's cool, but there's realities. There's not that many successful schools that you're going to be able to sell to, right?

SPEAKER_03
So I think it's going to be all, I disagree with you, Sean. I think what's going to happen is people are actually going to create courses for everything and then they're either going to fall into like a teachable, very affordable $500 to $2,000 or they're going to be so long and you know, intense that they're going to go with ISAs and they're going to need somebody to just do that back end for them. I think Lambda actually uses MeritOS and on Delta, I think uses MeritOS as well because why bother, you know, administrating all the stuff that somebody just better at? Like it would be like me doing what a sure fund management does for our SPVs.

Like, do I really want to be in the business of like doing the legal paperwork and filings and collecting the wires or would I rather just give every time we do one of these 12 K in fees to a sure fund management and be done with it, right? It's a much better life.

SPEAKER_02
I think the better model is the clear bank for ISAs. So the biggest problem all these guys have is cash flow, right? You sell an ISA, but you're not going to get paid until they have to get educated for a

SPEAKER_03
year or two and then they have to get a job. There are people who are setting up like hundred billion people setting up hundred million dollar funds just to give it to whoever, right? Because they're going to get a decent rate of return and it would probably be uncorrelated with the stock market and you know, you're not going to make a profit off of treasury bills or bonds, right? So these will be higher, 70%, I don't know. You got to be careful with the clear bank kind of stuff because a lot of those places will be like it's an AK fee and then I'm like, well, what's the annual interest rate? And they're like, we don't have interest in this like, okay, if the AK fee on 200 K is 4% and it's every 60 days and it's 4% times 6, but it's compounding.

So what does that actually equal like 35% or something? Like it's like double credit card rates when you annualize it. So you have to be very careful. You might be leaving a lot of money on the table.

SPEAKER_01
So paid communities, paid communities.

SPEAKER_03
ISA is big. What else? I think travel is going to have, you know, just talking about the pandemic. I believe travel is going to be a huge revolution.

SPEAKER_01
Anything specifically?

SPEAKER_03
It's hard to know which aspect will be the biggest, but there's going to be like, there's the YOLO travel kind of situation, but then there's this nomadic lifestyle. And I think one of the unlocks people had was from the pause, everybody paused and said, do I need to be here? Are my kids doing good in school or is your baby sitting? Right? Like you basically evaluate everything. Do I love this job? Do I love what I do? Do I love my spouse? Do I love this life? Like there's a lot of divorces, a lot of people leaving cities, divorcing cities, a lot of people divorcing schools and saying, you know what, my kids in this school, but they're not actually doing great.

And I tried something else and it's better. And so I think all of that. So I would put education in that as well.

And I think that now that people have seen from remote school that the education portion of the six hours of the day is like two hours. And then two hours is probably socialization and two hours is probably electives and gym and more babysitting, I guess is, you know, how one parent told me, like, I never realized how much of my child day was babysitting versus learning because I sit with them for an hour and a half a day and I get through all the learning. And then the learning is typically here's 10 minutes of an explanation, go work on your own for 40 minutes.

Here's 10 minutes work for 40 minutes. Here's 10 minutes work for 30 minutes because you have 20 people in a classroom. And I think that's going to change.

Micro schools, distance learning, all this stuff is on the table now.

SPEAKER_01
You tried to set up a micro school.

SPEAKER_03
I basically did. I knew the teachers unions would resist going back to work because they're very powerful. They're also probably in the high risk group in some cases over 50 or over 60.

And so I just assumed we would not be going back to school in the fall in the spring. I started the search for a teacher. I got barbecued online because people were like, oh, rich guy wants to steal a teacher because I said, like, Hey, does anybody know who the best fifth grade teacher is elementary teacher? I want to start a micro school because I just did the math like teacher salaries in our country is 50 to 45 to 80 K depending on what city you're in.

Private school is 30 to 60 K depending on what city you're in. So two parents in private school equals a teacher because there's so much overhead. So if you just do the math, you can basically hire a teacher and have two students and you're at break even in three, you would be basically at a profit or a cost savings.

And you would have a one to two or one to three teacher ratio. So that's what we did. We didn't actually get to the point where we had other students in our micro school.

We just hired a full time teacher for our one daughter who was 11. And that's a very privileged thing to do, but it's probably just slightly more than going to private school. And it's been amazing.

It's the best year our daughter has ever had. And I'm thinking about setting up a school for next year, maybe we couldn't get it together because most parents wanted to send their kids back to school. And I didn't want her to go back to the classroom because I thought it's just too high risk.

She's going to get COVID and bring it home. And so and I didn't think the teachers would be coming back. And so yeah, I took a different view of it.

SPEAKER_02
I think you're totally spot on that the pause made everybody question all the all the things we just did robotically and kind of habitually. Do I need to live here? I think that was like that spot on. And if you're an entrepreneur, you're looking for these ships and looking for these cracks.

You're looking for the new platforms and looking for the behavior changes. Because like when things get shaken up, that's where the startup gets to move and create something new where where the incumbent hasn't quite reacted to that shift.

SPEAKER_03
It's just like college in the Isis, I think K through 12 school needs to be addressed. The amount of money that's actually going into the classroom versus administrators is really weird. I'm not an expert on it, but there's something very weird going on.

And the people who are suffering the most from it, I think are the people who need the education the most. I would much rather see people who are on the lower end of the economic spectrum be able to take vouchers of 10 to $15,000 each, which is what we spend on the average child. I guarantee you that five parents in a community could hire a teacher and do a better job than going to a public school of 30.

I think overall the parents would be so much more engaged if they had that opportunity. But the second you say vouchers, you're like, that works against poor people. And it's like, or it works for poor people.

This whole idea that like poor people are dumb and they can't organize is so just infuriating to me. Every time I say like, education is free online, like there's so much of an opportunity, we were like, no, poor people are dumb, and they don't they're not motivated and poor people are not able to get it together enough to learn online. And I'm like, really? Are you sure? And like poor people don't have internet.

I'm like, are you looking at these statistics like anybody in the economic spectrum who doesn't own a smartphone, like they may own a smartphone from three years ago, but everybody's got a smartphone like who doesn't have a smartphone. People are just incredibly biased against poor people that they're dumb and they don't have connectivity and they can't self organize. Do you think giving six parents $12,000 each and 72 K that they would not what do you guys think would they do a better job than going to the worst school in California or the bottom 10% of schools? No way if they hired their own teacher.

It's a no brainer. But I mean, you say vouchers and all of a sudden you're like some evil Republican, whatever, you know, free market radical, it's not radical. Why not give parents the opportunity to run their own schools? I think there would be a huge unlock for America and we create competition for the public schools.

If parents could opt out of public school and get 10 15 K and then start their own schools, that'd be amazing.

SPEAKER_01
So before we like end the show, you made a bet with Scott Galloway, right?

SPEAKER_03
I did. Can't remember. We've gotten to it, but I don't think we could ever construct the bet because.

SPEAKER_01
Well, okay, you made a figurative. It was like, I would bet you these companies, I forget the ones are going to be worth more than X.

SPEAKER_03
Yeah, it was like Uber, Tesla. He said Uber and Tesla were going to zero. Sure. I remember correctly, but JC Penney was going to be the number one company. No, Macy's.

Macy's, I'm sorry. Macy's was going to be bigger than Amazon. I think he's probably getting paid by Macy's.

I think he probably got like a high paid speaking gig or something.

SPEAKER_01
What bets would you are you wanting to make right now?

SPEAKER_03
Beating Scott Galloway in any kind of business venture is like, I'm trying to think of an analogy that's not completely offensive. But I mean, it literally would be like Dramon Green beating me in a game of one on one is me beating Professor Galloway in any business endeavor or podcasting endeavor. Like it would literally be the same as me versus Dramon.

SPEAKER_01
So what bet now? I mean, that's not like that bet that you made that figurative bet. It's not that outrageous. I mean, many, many, many, it's not that unpopular.

Many people would have said the same thing. Here's the way to say it.

SPEAKER_02
Is there something that other people are really bullish on that you or bearish on that you take the counter side of it?

SPEAKER_03
Everybody thinks X and I think Y on cryptocurrency. I think, you know, we have not seen a single use case beyond speculation and hope. That makes me very nervous, you know, even about Bitcoin.

And there's a lot to love about Bitcoin. I was covering Bitcoin when it was under a dollar. I have exposure Bitcoin at $200 and $800 a coin.

So I've done fabulously. And I should say when I say I mean my wife, because you heard me talking about it and her siblings were into crypto and she just bought a bunch of Bitcoin. So we've made large amounts of money off of crypto because my wife is so smart.

And I actually probably had 20 or so coins I got were in at one of the I have about like 20 coins at a dollar each or something back in the day. And they got stolen when one of those exchanges went belly up, like the whole exchange went away and they took everybody's coins. It was pretty funny.

If it was 10 or 20 coins, it was probably 300 to 600,000. I mean, there are people who have 100 bitcoins or 1000 bitcoins on a USB drive and forgot their password. But I think what's going to happen with Bitcoin, a distinct possibility is that a better technology comes out that actually does something other than storage of money and other than money transfer and other than and it's, you know, Bitcoin is not incredible at money transfer.

It's not, it's still kind of expensive. And if that happens and that gets, you know, the sort of Reddit mania or populace viral mania, you could see people just using their Bitcoin to buy those other currencies or that other currency that so I would be very careful of you on Bitcoin to at a low price and you don't have other money. Like take some profit and buy a house.

If you don't own a house, I met people at the height of the crypto, the last crypto bubble, which I think was three Christmases ago and it was 20 K. And I just said on stage, listen, if you bought this shit for 100 bucks and you're worth $5 million right now, just sell a million dollars and buy your condo sell 2 million and buy a house and then let the other 3 million ride. I get being a gambler, but you know, you have to pair your positions and get some diversification at some point.

So I think people being bullish on I still think Bitcoin zero or Bitcoin under a thousand is a distinct possibility. Now would that happen overnight? No, I think it would be a slow ride as people realized a theory or whatever the next one is is the better one, right? And then people are buying XRP in the middle of this SEC investigation and that's a total fraud. I mean, when you read the complaint from the SEC, it's like, oh my God, these guys were trying to buy their way onto exchanges, giving like a million dollars in cash and they were trying to create according to the claim, they were trying to create accounts that made it look like people were long.

So they were trying to find accounts that they owned that were selling XRP to then suddenly flip to being buyers and timing that with being on Coinbase or whatever exchange they were trying to buy their way onto. I mean, it was crazy manipulation going on, I think based on reading. Did you guys read the SEC XRP claim?

SPEAKER_02
It's one of the shadiest things that's still just out there, you know, still running.

SPEAKER_03
It's crazy. They sold the two folks in charge, so $650 million in XRP to people who are buying it specifically to speculate. They've never used it as a utility ever, the overwhelming majority of those people.

They were strictly buying it and so that makes it an equity. And so that would be like you and I just selling our stock certificates for, you know, my podcast or something on the street to people. That's why we have the SEC.

That's why we have rules is so that people don't get screwed. And these guys were doing according to the complaint, complete market manipulation and insider trading basically.

SPEAKER_02
I had a friend who a couple of years ago was organizing a hostile takeover of the XRP chain because basically everybody in crypto knows XRP is just kind of bullshit. He was like, look, there's basically, it was, I think, worth $10 billion at market cap at that time, maybe a little bit more. It was $20 billion market cap at that time.

He went to investors who already agreed, like XRP, there's really no value and no utility and it's kind of a scam. He raised like $60, $70 million to take a giant short position. And in crypto, $60, $70 million could do a lot of damage.

And then also had a campaign where any XRP holder, so he was going to short it massively, which caused the price to just tank. And then as it was tanking, it was going to launch a public campaign that says, look, here's all the sort of dumb things that XRP has done and why it is not a legitimate project. I will give you the opportunity now to trade in your XRP for 10 to one ratio to this other coin and we're not going to do any of those things.

And you can get to a legitimate project at a multiplier if you go now. And if you wait two days, it'll go down to five to one, then it'll go down to one to one. So trade it in now, which would cause what you saw with GameStop, that's what was going to happen.

And unfortunately, one of the investors that he was talking to leaked it to the press. They found out about it and then they were able to massively collateralize against a potential short attack and they took like $400 million and sold so that they would be able to defend, which was crazy. But it was going to go down.

SPEAKER_03
I'm not long crypto, but I do think there's some interesting underlying technology there. It's just really strange that all this money's poured into Bitcoin and other cryptocurrencies and there really are very few use cases for it.

SPEAKER_02
You're saying that the store of values at $10 trillion use case, right?

SPEAKER_03
Yeah. If you look at the internet, there's more than one killer app on the internet. Crypto was positioned as this is the new internet.

Everything is going to change. And exactly one thing has changed store of value. That is the only thing that has changed speculation and store of value.

There's nothing else crypto has put a dent in. I mean, during those white paper days with ICOs, people were telling me like it's over for Uber and Airbnb. It's all going to be on the blockchain.

It's going to be immutable records of each ride and your coins are going to pay for the ride. And but they already have a database at Airbnb. Like, why would a public blockchain be better for that? And they're like, because it's immutable.

And I'm like, what does that even mean? Like you can't change it. Like, is that a benefit? Not changing the database? That's not a benefit.

SPEAKER_01
That's a cost. You want a lot of your stuff to be centralized.

SPEAKER_03
Yes, decentralized. It makes no sense. Like decentralized makes sense.

If you want to trade the risk of decentralization, which is massive. If you want to trade that risk, you know, in exchange for not having a central overlord, I get it. Like for bit torrent or for freedom of speech or something, it could make sense.

But I still remain very skeptical that nothing, no use case really has come out of this, aside from speculation and money sort, which are valid. That's what I'm short in the world. I'm long startups.

I'm really long, non-accredited investors participating in private markets. I think that's going to be the big revolution of the next decade. The SEC has been working on accreditation laws and republic seed invest and all these equity crowd financing sites have shown that there's an appetite and obviously game stop and Robin heard of shown there's an appetite and crypto and the ICO craze showed there was an appetite amongst the 96% of Americans were not accredited to participate.

I'm hoping that we can have a test where people can take a test, you know, 20, 30, 40 questions and show they're sophisticated. They may not be accredited with money in the bank, but they may be sophisticated. In fact, the people who are writing the sophistication laws or the accreditation laws at the SEC in all likelihood do not make enough money to be accredited.

The average economics professor or MBA professor doesn't make enough money to be accredited every year. Those are amongst the most sophisticated people in the world when it comes to finance as the

SPEAKER_01
user of seed invest. It's not there yet. Not there yet.

I don't think so. No, we raise money on seed invest. I think I'm long crypto.

SPEAKER_03
You broke up, Sean, but we got you your long crypto, even though there's no use case and you're short investing in companies that have a million use cases and customers got it.

SPEAKER_01
I raise money on seed. So you do too, right?

SPEAKER_03
We did seed invest. Yeah, it worked fine for insight.

SPEAKER_01
I think it's okay. I don't like giving updates. I don't like sharing private information a lot publicly.

SPEAKER_03
Yeah, you shouldn't do it if that's the case.

SPEAKER_01
I guess that's not a problem with seed invest. It's a problem with just the rules that come along with it. It's not their rules.

That's just the SEC. But I think there's still a long way to go.

SPEAKER_03
It's going to take time, but I like the idea of people putting a hundred bucks in. If you didn't have to do as much reporting, it'd be better. They should basically say, if anybody puts in under $1,000, you don't have to do reporting or anything.

You're capped at whatever dollar amount. You capped at a million dollars a year in raising. So you can raise $1,000 from 1,000 people one time a year.

So then if you did do something for Gazy for four years or five years straight, the biggest the hole would be would be four or five million as opposed to crypto where you have holes that are billions of dollars, right?

SPEAKER_01
No, I'm on board. Well, Jason, thank you. This is awesome.

We're going to publish this in a few days, two days, I think. We appreciate you coming. We'll have to do it again.

We're big fans of the All In podcast and how many downloads do you have prep? So do you know?

SPEAKER_03
I don't know. I mean, the YouTube video, you know, it's really hard to get information on podcasting and like how many downloads you have to this day because all the pod catchers download the stuff in the background and then a bunch of people are putting CDNs in front of your file. So like you don't know, you know, what's being front run and cashed.

But the YouTube video had 140,000 views in the first 48 hours. So I'm guessing it's got to be a half million or something like that. I mean, I think that's what the top podcast gets.

We were number 11 today, which is bonkers overall. And this week and start up spin perennial top 20 in tech, you know, top 10 sometimes on the video side, it's always top 10 on the audio side. It's the top 20.

SPEAKER_01
I'm looking at your videos now. Now we have a target. You've got a target on your back and we're going to we're going to see what we can do.

177,000 views in two days. It is pretty good.

SPEAKER_03
That's pretty wild. I mean, in 19 episodes, we became the 11th podcast in the world, I guess. You know, I don't know how accurate the iTunes is.

SPEAKER_01
I wouldn't look at it that way. I was like, like, you've been doing it for 10 years. It's a 10 year overnight success.

SPEAKER_03
That's very nice of you to say. Yes. This week in startups was a niche podcast where we only talk about startups. And this is a podcast where we talk about Trump, the stock market, censorship and whatever the top five topics in the world are.

So you know, if you have a narrow aperture, you know, you can get a very distinct endemic audience like you have for your pockets or I have for this week in startups. And then if you go general, like Ben Shapiro or Joe Rogan or all in podcast, you can get many, many, many, many, many more folks if it clicks. This one happens to have clicked.

And I think when you look at the pandemic, we're all going to look at the pandemic and say, what did we get out of the pandemic? Like, what did we try to do? And I did maybe five or six different little projects and two of them have really stuck all in, you know, like I said, has become one of the top podcast in the world. And then remote demo day, we have invested in, we basically have seven companies present for three minutes to our syndicate and it's just led to a whole new level of deal flow. And we just did our largest deal ever on our syndicate for $3.

3 or $4 million, which is a million dollars more than the previous record. And that's all because of remote demo day because we got companies that were a little bit further in their life into our wheelhouse and our syndicate grew. That was the other thing that grew tremendously is our syndicate grew double during the pandemic.

So a lot of people online looking for things to do. So you got to look at this pandemic and say, what did you get out of it? Because the number of shots and arms right now is 1.5 million a day and 130, 40 million people I think are on the other side of COVID in the United States because they've had it or they have the shot now, like 30 million people have had the shot.

So we're going to probably get 2 million people a day and we only need another 70 million people a day on the other side to hit 200 million, which would be when herd immunity hits. So we might be 30 days out from hospitalizations and deaths just plummeting and hospitalizations are plummeting and deaths are flat. So this could be an amazing turnaround.

I believe that by the summer, everything's back to normal. People are saying the fall. I think April, May, there's going to be so many vaccines available that they're going to be anybody's going to be able to walk up seven days a week to any pharmacy in April or May and get a vaccine if they want it.

That's what I think is going to happen.

SPEAKER_01
Well, that's going to be a good day when that does happen.

SPEAKER_03
You know anybody who's gotten the vaccine?

SPEAKER_01
Yeah, do doctor friends.

SPEAKER_03
Okay, this is the test. How many people do you personally know like you've had lunch with or a conversation with? How many people do you personally know? Not friend of a friend, but your friend, somebody you've had a conversation with family, God forbid, that's died from COVID. I have one.

My mom's best friend. One. Okay, you have one.

SPEAKER_02
Sean. No deaths that I personally know and two people who I know have the vaccine, my father and my mother-in-law.

SPEAKER_03
Perfect. I know 15 people now have had the vaccine personally and I know one person who's died. How about you, Sam?

SPEAKER_01
I've know two people that have gotten the vaccine, a doctor couple, and then my family has gotten COVID. I haven't. And I have one death, a family friend.

SPEAKER_03
I think that's what we're going to see is I think over the next 30, 60 days, you're going to know 50 people who've had the vaccine and you're only going to know one person who's died from it. And the first 75,000 people who were in the trials, none of them have died. And I think only one got hospitalized and nobody has been in the hospital for more than 30 days.

So this vaccine has, is a miracle of science and has been underhyped. Underhyped. So that's why I think I'm looking for travel investments.

If anybody hears this and they've got a travel related investment, I think now is the perfect time to start ramping up and thinking about that Jason at Calacanis.com, Jason on Twitter, Jason on Instagram.

SPEAKER_01
At Jason, Jason Calacanis.com. And what was the third one?

SPEAKER_03
Well, Calacanis.com. I'm at Jason on Twitter, at Jason on Instagram, Jason on Tumblr.

SPEAKER_01
No one uses that. Okay. Thanks, man.

SPEAKER_00
And I'll shoot this to you when it's live.