My First Million - #150 - Jason Calacanis Joins The Brainstorm To Talk Robinhood, Gambling and the Opportunities He's Investing In
Episode Date: February 3, 2021Shaan Puri (@ShaanVP), Sam Parr (@theSamParr), and Jason Calacanis (@jason) discuss: - The reason Jason gambles and how much he has made over the years - How Jason made the transition from being a jou...rnalist to being an investor - How Jason became an investor in Robinhood - Why Substack and tech media may be doomed - The big opportunities in paid communities - Why Jason predicts ISAs and travel startups are going to boom Thank you to Lemon.io for sponsoring today's episode! They are offering a 15% discount for the first 6 weeks of work for all MFM fans. Go to Lemon.io/mfm to claim the offer! Have you joined our private FB group yet? It's a page where people share each others million dollar ideas or what they're already working on: https://www.facebook.com/groups/ourfirstmillion. Editing thanks to Jonathan Gallegos (@jjonthan) See acast.com/privacy for privacy and opt-out information.
Transcript
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I feel like I can rule the world.
I know I could be what I want to.
I put my all in it like no days off.
On a road, let's travel, never looking back.
Jason, how are you?
Great.
So Jason's here on My First Million.
We're going to talk about ideas and stuff,
and Sean's going to pop in in a second.
But I heard you might be moving here to Austin.
Is that true?
It's definitely being considered.
I'll just tell you just straight up my thinking on it.
I spent 30 years in New York and, you know, was amazing, 20 years in Brooklyn, just over 10 years in Manhattan.
And then I moved to L.A. for 10 years and spent 10 years with my wife there, I got married, started a family.
And then spent 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 it 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 100% 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.
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.
Well, I mean, relatively speaking, the houses in San Francisco,
they're not in the wider peninsula.
They're not comparable in price, right?
I mean, in San Francisco, everything's $1,500 to $2,500 square foot.
And Austin, it's $600 to $1,000.
I thought it was a ball and move.
Everyone says like this and that.
And then the person told me his 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.
Yeah.
I've just been researching.
You know, I've been to South by a bunch of times since like the 90, late 90s.
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 6th 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.
What happens? So Jason, you started a media company, 10, how long ago was that?
Well, most people don't know that I started in the magazine business in the 90s. So I started a
magazine called CyberSurfer, 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 100 employees or so. And then the dot-com crash happened.
I lost everything. Sold that company for a couple of years' salary to Dow Jones, which then
bought me out of my contract after two weeks, which was very weird.
Yeah, then I started Weblogs, Inc. Engadgett AutoBlog, 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 started a Mahala, which became inside and started an angel investing us as a Coy Scout, and it all started going in that sort of certain direction. 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.
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 realize 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 an investor might ask.
Those were all questions journalists used to ask, right?
So journalism, you know, O'Malley 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, M.G. Siegel or 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.
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 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?
Probably net 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 bet 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, $200.
$100 game. So it's $100, right? Literally in terms of no limit hold them in 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. What is the biggest hand you've been part of? 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 percent favorite in six of them, and then in one I was even,
almost like 51, 49.
And to lose seven in a row where you are the 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 it 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, $2, $5, $5, $10 games.
And Molly would text me and call me and say, like, oh, Leo's here.
Oh, you know, this 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 am.
I'm top five angel investor of all time, and in poker,
I'm not even in the top five million or whatever, you know, in all likelihood.
All right.
Well, Sean is back here.
Apparently he had some technical difficulties.
He had to join on his phone.
Sean, you there?
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 podcasts.
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 perfect description of our podcast.
To be clear, I'm not a billionaire.
Yeah, but, you know, nobody's really a billionaire.
Exactly.
There's a great book that me and Sam like to read, what it was about how I got rich or how to get rich.
How to Get Rich.
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.
He Great Max 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.
I didn't even know this book existed.
Is it good?
It's the best.
I remember this guy.
He was a madman.
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 seemed like a wonderful human being, but he loves poking fun.
but his writing is rhythmic and beautiful.
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.
He's really good, and he was a poet.
He wrote books and a businessman, very eclectic person.
No, there's no audio version of this.
Correct.
He wrote in 2009 before the audio revolution.
I just added the paper.
He died soon after.
It adds to 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.
The situation went down.
Oh, the situation went down.
I thought you meant the service went down.
I was like, I didn't hear about that.
Are you an angel investor in Robin Hood?
I'm an angel investor, 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, 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.
I mean, it's not going to be a script.
I mean, 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, well, my idea is I'm a quant.
And I said, what's a quant?
He said, you don't know what a quant it 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, they're
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 investors 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 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 said, 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 Robin Hood. 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 buy 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, there's nothing they want to do more
than get more users and empower them to trade. That's what they're here for. I mean,
they want to grow. How much did you invest in them back then? I think I put in 50K or 100K,
which is my typical bet back then. It's going to turn out to be pretty, very, very, very lucrative
deal. 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 on Uber, you know, I think in the next
five to 10 years, a company would be significantly larger, especially since they got this
food business dialed in. And just for the quick math, 5,000 X times, or 5,000 is 50,000 is 250 million.
I put 25K 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 25K 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 Com or Robin Hood. But generally, if you hit something as an angel investor and you're
investing in a $5 to $25 million company and it becomes worth $5 billion or $25 billion, 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.
You did Uber as a scout, right?
Yeah, I was a Sequoia Scout, right.
Would you say, because I think, you know, there's no argument.
Investing track record is pretty fucking amazing.
Entrepreneurals track record, more like singles and doubles.
Do you think that's more like, is that just a variance of entrepreneurship,
startups, it's hard to, you know, go, or do you feel like actually you're a better
investor than entrepreneur?
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 on their best day, right?
Like if you're building media businesses, 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 on
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 2 billion people with high-speed smartphones
in their pockets.
So just do the math on that.
It is a 100-X, the desktop market that would.
we used to address and have built in credit cards. The number of credit cards people had on the
internet was in low millions when 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 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
100xed the market size in my mind. We've probably 10xed or 5x the usage. So it might be a 500x 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 already in their browser ready to buy. I mean,
it's a totally different world. That's why you see something like com.com or, you know,
clubhouse, just go from zero to 10 million users or zero to 10 million in revenue 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'd buy billboards or bus ads,
traditional ads. It wasn't like this infrastructure of, I'm going to go and have my ad buyer go
on Facebook or Twitter and Google search and figure out the channels and figure out the cac and
all these tools to help you do that in 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. 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 were close, you host a podcast with Chmoth,
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? You need to have a singular focus.
and you have to be willing to give up everything for that.
And I ask the question a little differently.
I want to do it person by person.
What's their superpower?
Give me, Elon, what's his superpower?
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, you know,
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 like all in, like he was going to lose half his money.
Like 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 days.
That's his superpower.
Chamath.
He's really smart.
This is a really smart analyst and strategist.
also hardworking and, you know, increasingly becoming a great communicator, as you can see.
What about you? What's your superpower? I think I am incredibly good at figuring out who's going to 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, you know, 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 Chimov and Sacks, you know, increasingly Freiburg.
But to be honest, I was much deeper friends with David Sacks and Chimoth.
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.
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, you know, the JD Power Award, you know, J.D. Power.
Sure.
Yeah.
Another one is Gartner.
Like these businesses that are based.
on this idea of, like, we are an authority and we're going to name what's best.
Consumer reports.
Yeah.
Wirecutter, 30 under 30, Midas Touch List, all this stuff, yeah.
Well, you did something similar.
You want to take it, Sean?
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 them are college students.
There's, of course, you know, people who are more established, but for a lot of people,
they love the ideas we bring up, or you needed nothing.
It's like, I call it the cake batter startups where it's just add,
muscle. 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, whether you're in Hollywood, you're in New York, you're in San Francisco, is you just make the
list. It can 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 use the example. And I actually don't know what 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 Allie 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?
Yeah, I mean, I had started this is 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 my team said, let's just make the
top 10 or top 25. I said, no, it's got to be 100. And so we literally, for number 60 to number
100, had a teacher, an accountant, an HR, like a headhunter, 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 Double Click as number two, the two cabins, Kevin Ryan and
Kevin O'Connor from Double Click 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 wildcards.
We call them wild cards specifically just to tweak people.
They're like, where do you put the wild cards?
How do you compare with 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, with a 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,
lobbying 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, 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.
We got to find the most prideful and sensitive group, and then we got to do it.
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, 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.
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 bought the domain named KokuA as well, which means to help or to guide in the
Hawaiian language, it was sort of Aloha, Mahalo, Kakula, 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 interviewed with Jason Kalakanis. 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, L.A. 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 talk 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?
Okay.
Fair enough.
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 where 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 like giving you the real number, but like, man, these guys will just print anything.
That's crazy. Well, what's crazy is that with Sean's deal, and I'm not saying it was greater
or lower, whatever, that's irrelevant. But the headlines.
said a rumored this and then when it's linked to a reference it'll say Sean's company
which sold for it like becomes a rumor and then a fact and it is pretty wild and that was on
tech crunch 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 there's like this really crazy device which is whatever
was printed in other blog post is fact therefore I'm going to write in my article
Polly Hop, like the San Francisco Gate, some former Gawker writer, is a sports writer over there,
and then he did a takedown piece of Chamath. And then he, like, links to 20 other stories.
And I know these stories are not true, but, you know, they basically then frame them a certain way,
and they don't do any fact-checking. It's just, 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 and Dresen had blocked everybody who's a journalist, therefore when he starts a room on clubhouse,
the journalists can't get in.
And they were like lamenting how bad that is.
And it's like, well, you attacked Mark and Driesen 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, you know,
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 tech crunch 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
Andresen harris is going to have their media arm chumov 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 rot around you.
And so it's a really interesting opportunity slash moment in time. It's very entertaining.
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? Yeah, whatever, Wednesday, I think Wednesday to Monday.
It seems like two months. It's been like less than a week. It's literally Wednesday to now.
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
war chest here to keep this going.
And Vlad knows, you know, the communication was suboptimal on Wednesday, and it got better
on Thursday, Friday, and I think it's gotten much better today.
And it's 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 or 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
and they went through all her pictures and desecrated her apartment.
It was horrible.
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 inns 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.
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 can's
going off. And there's all these like ubers and lifts 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.
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.
Well, I mean, people could have gone on other platforms.
If people were 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 I actually feel bad for GameStop.
Like what happens to GameStop their employees and existing shareholders when this thing is getting whipped around like this?
They paid off like $400 million of debt.
And so did AMC.
They haven't raised any money, right?
No, they did.
They converted all their debt.
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 down a bunch of debt, if I'm not wrong.
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 were able to, because they both had like $500 million
of debt and really no pathway to pay it off.
And so this was like Santa Claus dropped off a special gift for them.
What they call like an at market raise or something?
Yeah.
They acted 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.
ragdalled 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 brainstormed something.
We say, dude, I had to move last week and you know what'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, you know, if your handlers have told you
what this podcast is. I don't know if you brought any ideas at table.
No, I've got a million ideas. I'm good at brainstorming.
Literally brainstorming is what I do for a living.
Perfect.
So hit us with a couple.
You don't have to go too in depth.
You can go kind of rapid fire.
And 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.
Okay.
Ideas that I would like to do are other people should do.
I think the Slack communities that are paid are very interesting.
I know you have one of trends.
Not a Slack community, Facebook community.
I think Slack communities are horrible.
Okay.
Well, I think paid communities, I thought you had started on Slack, right?
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, is maybe ephemeral.
Is that the right word?
Like, people say do you get lost on Facebook, but there's Facebook threads in our community
that literally has 300 of applies on Slack.
It's like Facebook is a podcast and Slack is Clubhouse.
It's like it's too fast.
It's too fast.
Yeah, yeah.
So I agree with that.
That's probably true.
I haven't figured out which platform is the best for this.
You know, we have a Slack community for this week in startups.
That's got a couple thousand people each week use it.
It's free.
I mean, I'm actually hiring a community manager figure this out.
We have an investment in a company called SolS-S-S-A-V-Y.com.
Yeah, I almost did that too.
Yeah.
And they are doing phenomenal.
I think they charge $30 or $40 a month to be part of that.
community. So I think the top 10,000 people in every topic want to be part of a community and pay
$100 a year or $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 IIS 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.
So I'm particularly interested in that. And consumer subscriptions are the big one that I think are
going to be phenomenal because we've had calm, steasy for dance, brilliant for math,
musician, tone base for music.
Let's talk about communities real quick.
And then we're going to go into income share agreements because Sean loves that.
But 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.
You know, people are there.
Your attention's already there.
It's way easy to comment.
Every other platform, I think, to host a community is way of a distance second to Facebook.
And Facebook's not even that good.
It's only good because people are there.
Yeah, that's what I like about Slack is that I have all my Slack's 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.
And so when I add one more there,
it's just in the left-hand navigation.
And so I found people really like that.
And I've got an Austin community where I have two Austin communities
that are Slack communities I'm part of now,
a community manager community that I'm a member of.
It's definitely interesting as a concept.
Yeah, somebody needs to do the substack for paid communities
where you give somebody a very quick splash page
where you're like, 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 Substack really did.
Well, and I think somebody should do that for paid communities.
Substack is actually giving, you know, 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.
So I don't know if they changed our minds or they did it 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.
By the way, substack, I'm actually not terribly bullish on it all.
Why?
The fees way too high.
I think the fees way too high.
What is the fee?
10%.
20%?
Yeah, 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, you know, or two for 50K each or three for 35K each or whatever and have a staff working for you.
And 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.
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 intrinsically love it. Trust me, at inside where we got up to, I think, 30 newsletters at the peak, the burnout issue is real. And we got down to, I think, now we're down to 12 newsletters and 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 burn out. It is a grind.
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 substack earners,
but I just didn't want to keep doing it.
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.
We'll see.
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, like, 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 client 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 in 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 left 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 them like,
you're really built for this.
I mean, the problem is if you do it,
you'll never write another book.
both things have turned out to be true.
And 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 platform,
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 a 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 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 answer.
add them, right? You can't get into it unless you add them. What industries interest to you about
the income share agreement? 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 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 it is.
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 10K 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 $40 or $1.4.
50k, I think, just like Lambda. And they only take it up to 15K 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 be 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, pay us 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, right?
And, you know, education has to change.
I don't know.
What do you like about it, John?
Well, I invest in a 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-pay 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, I'm 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's 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 like 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 ever say like, by the way, here's what a doctor does.
or you want to meet a doctor.
Sean, you were a pre-med at Duke?
That's hilarious.
I did not know that.
I took the MCATs and everything.
I was ready to go.
Oh my gosh.
Before I signed up for a 10-year, like, kind of post-college commitment,
I had this crazy idea for this 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,
gone 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 ISA is because I think it's a tool to create a university that actually
makes sense in the modern world.
There's a bunch of platforms now, too, that are becoming like the Amazon Web Services of the
space, like Maritas.
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?
do I enforce these and make sure they're fair or whatever?
And you'll just be able to use something like Maritas and have it work.
So I think a better, because I looked at those guys, the ISAs as a service, I think that's cool,
but there's reality is there's not that many successful schools that you're going to be able to sell to,
right?
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 Isis
and they're going to need somebody to just do that back in from.
I think Lambda actually uses Maritas and on Delta, I think, uses Maritas as well.
Because why bother, you know, administrating all this stuff is somebody just better at?
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 12K in fees to,
assure fund management and be done with it, right? It's a much better life. 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 year or two and then
they have to get a job. There are people who are setting up like 100 billion, people setting up
$100 million 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 Clearbank 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 200K 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.
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.
So paid communities.
Pay communities.
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.
Anything specifically?
It's hard to know which aspect would 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 it
babysitting? 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. Actually, 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's 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.
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.
You tried to set up a micro school.
I basically did.
I knew that 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.
school in the fall in the spring. I started the search for a teacher. I got barbecued online because
people are 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 80K, depending on what city
you're in. Private school is 30 to 60K, 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 and 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 microschool.
We just hired a full-time teacher for our one daughter, who was 11.
And, you know, 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, right?
And so, and I didn't think the teachers would be coming back.
And so, yeah, I took a different view of it.
I think you're totally spot on that the pause made everybody question all the things we just did robotically and kind of habitually.
Do I need to live here?
I think that was like that's spot on.
And if you're an entrepreneur, you're looking for these ships.
They're looking for these cracks.
You're looking for the new platforms.
You're looking for the behavior changes.
It's like when things get shaken up, that's where the startup gets to move and create something new, where the incumbent hasn't quite reacted to that ship.
It's just like college and the Ices, 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 $10,000 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.
And every time I say, like, education is free online.
Like there's so much of an opportunity.
People are 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 in 72K 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 that would be a huge unlock for America.
And it would create competition for the public schools.
If parents could opt out of public school and get 10, 15K and then start their own schools,
that would be amazing.
Before we like end the show, you made a bet with Scott Galloway, right?
I did.
I can't remember.
We got into it, but I don't think we could ever construct the bet because...
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.
Yeah, it was like Uber, Tesla.
He said Uber and Tesla were going to zero.
Sure.
I remember correctly.
But J.C. Penny 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.
What bets would you, are you wanting to make right now?
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 Draymond 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 Drayman.
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, it's not that unpopular. Many people would have said the same thing. Here's a way to say it. Is there something that other people are really bullish on that you or bearish on that you take the counter side of it? Everybody thinks X and I think why? 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 to Bitcoin at $200,800 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 for crypto because my wife is so smart. And I actually probably had 20 or so
coins I got, were in one of the, I bought 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.
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 1,000 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, you know, Bitcoin's not incredible at money transfer.
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.
So I would be very careful of you own 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 is three
Christmases ago, and it was 20K, and I just said on stage, listen, if you bought this shit for
$100 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 $1,000 is a distinct possibility. Now, would that happen overnight?
No, I think it would be a slow ride as people realized.
Ethereum 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?
It's one of the shadiest things that's still just out there,
you know, still running.
It's crazy.
They sold the two folks in charge
sold $650 million in XRP
to people who were 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 inequity.
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 so that people don't get screwed.
And these guys were doing, according to the complaint, complete market manipulation and insider
trading, basically.
I had a friend who a couple 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, or maybe a little
bit more. It was 20 billion market cap at that time. He went to investors who everybody
agreed like XRP, there's really no value and no utility and it's, you know, it's kind of a scam.
He raised like $60, 70 million to take a giant short position. And in crypto, $60 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 would cause 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 a 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.
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 a $400 million that sold so that they would be able to defend, which was crazy.
But it was going to go down.
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.
You're saying that, but store of values at $10 trillion use case, right?
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 is 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. But they already have a database at Airbnb. Like,
why would a public blockchain be better for that? 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. That's a cost. You want a lot of your stuff to be centralized.
Yes. Decentralized. It makes no sense. Decentralize 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 BitTorrent 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 store, 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, GameStop and Robin Hood have 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 user of Seed Invest, it's not there yet.
Not there yet?
I don't think so.
No.
We raised money on seed invests.
I think I'm long crypto.
You broke up, Sean, but we got you.
You're 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.
I raised money on seed vests.
You did too, right?
We did seed invest.
Yeah, it worked fine for inside.
I think it's okay.
I don't like giving updates.
I don't like sharing private information a lot publicly.
Yeah, you shouldn't do it if that's the case.
I guess that's not a problem with.
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. It's going to take time. But I like the
idea of people putting 100 bucks in. If you didn't have to do as much reporting, it'd be better.
Like they should basically say if anybody puts in under $1,000, you don't have to do the
reporting or anything. And you know, 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 Fugazi, you know, 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? 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 prepsode? Do you know?
I don't know. I mean, the YouTube video, you know, it's really hard to get information on podcast.
and like how many downloads you have to this day
because all the podcatchers download the stuff in the background
and then a bunch of people are putting CDNs in front of your files
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 got we were number 11 today
which is bonkers overall and this week in startup spin
and 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.
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 see what we can do.
Yeah, 177,000 views in two days.
It is pretty good.
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 iTunes is.
I wouldn't look at it that way.
I was looking at it like you've been doing it for 10 years.
It's a 10-year overnight success.
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 can get a very distinct endemic audience
like you have for your podcast or I have for This Week in Startups.
And then if you go general, like Ben Shapiro or Joe Rogan or All In Podcasts, you can get
many, 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 podcasts 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 a 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, it doubled 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 in 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've had 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 debts 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.
Well, that's going to be a good day when that does happen.
Do you know anybody who's gotten the vaccine?
Yeah.
Do you doctor friends?
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.
One.
My mom's best friend.
One.
Okay, you have one.
Sean?
No deaths that I personally know and two people who I know have the vaccine, my father and mom,
mother-in-law.
Perfect.
I know 15 people now have had the vaccine personally, and I know one person who's died.
How about you, Sam?
I know two people that I've gotten the vaccine, a doctor couple, and then my family has gotten
COVID.
and one death, a family friend.
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 is a miracle of science and has been under-hyped.
Under-hyped.
So that's why I think I'm looking for traveling,
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 calacanus.com, Jason on Twitter, Jason on Instagram, Jason at calacanus.com. I'm at Jason on Twitter, at Jason on Instagram. Jason on Tumblr.
No one uses that. Okay. Thanks, man. We'll talk soon and we'll shoot this to you when it's live.
