Lex Fridman Podcast - #161 - Jason Calacanis Startups, Angel Investing, Capitalism, and Friendship

The following is a conversation with Jason Calacanis,

who’s an entrepreneur, investor, author of Angel,

How to Invest in Technology Startups,

and as many people may know, he’s a fun, brilliant,

long time podcast host of This Week in Startups,

and co host of the All In podcast

with Chamath Palihapitiya, David Sachs, and David Friedberg,

who all happen to be poker buddies

and self proclaimed besties.

The result is always a great listen

due to both the love and the heated disagreements.

Quick mention of our sponsors,

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and Rev Speech Detect Service.

Click the sponsor links to get a discount

and to support this podcast.

As a side note, let me say that I’ve been learning a lot

about real world finance in the past few months.

To give you a bit of context on the side,

I’ve studied trading from an algorithmic trading perspective

as a machine learning and a game theory problem

off and on for a few years in undergrad and grad school.

I found the distributed complex system aspect of finance

and economics in general fascinating,

but now I find even more fascinating

the human side of the whole thing,

ideas of greed, power, freedom, and truth.

Wall Street bets, Robin Hood, and the whole beautiful mess

around this topic allows us to have great conversations

about human nature and the systems that underlie

the rise and fall of civilizations.

If you enjoy this thing, subscribe on YouTube,

review it on Apple Podcast, follow on Spotify,

support on Patreon, connect with me on Twitter

at Lex Friedman.

And now, here’s my conversation with Jason Kolokanis.

I have a million things to talk to you about,

but we do happen to be living through

what I would think of as a historic event

in terms of its impact, in terms of almost philosophically

thinking about the role of people

and how they can fight power

with this whole Wall Street bets and GameStop situation.

I was wondering, you’ve covered in your amazing

all in podcast, you guys have been having

fascinating battles over this whole situation.

I was wondering if you could tell maybe

from your perspective, as it’s unrolling

the saga of Wall Street bets and GameStop,

what are some interesting insights

that you have about this whole set of events?

In full disclosure, I was an angel investor

in Robin Hood before they launched.

And when I met the founder, Vlad, and his partner,

you know, they pitched me at a bar,

not too far from where we are right now in Palo Alto,

called Antonio’s Nut House.

And my friend Adeo, it’s a really good story,

my friend Adeo had asked me to speak

at his founder’s institute, which is kind of like

an accelerator for people who were thinking

about starting a company.

And so I gave a talk, and then he said,

hey, let’s go to Antonio’s Nut House

and we’ll meet Elon for a drink.

And so Elon met us for a drink there.

And it’s the divest of dive bars.

Like you’ll take a beer and it will…

I love the image of all of this.

You hang out with Elon at a crappy bar.

Yeah, I mean, it is the worst bar in the peninsula.

Like just garbage on the floor, and like cheap beer,

and warm beer, and like you’ll pick up your pint glass

and be lipstick on it.

It’s brutal.


Not your lipstick.

You understand, somebody else’s lipstick.

And so we’re sitting there and Vlad walks up

with his partner and he says, you’re Jason Calacanis.

And I said, tell me about your startup.

He said, how do you know I have a startup?

I said, you recognize me.

And I mean, that’s the only way.

And he goes, is that Elon Musk?

And I said, yes, Elon, come say hi.

And he came over and said, hi.

I said, tell me what you do.

He said, well, I’m a quant.

I said, what’s that?

And he said, quantitative analysis.

And I was like, oh yeah, yeah, I know about that.

That’s like you guys make algorithms

and then try to beat the market, right?

He’s like, yeah.

I was like, so you’re gonna pitch me on a startup

and you’re gonna sell your algorithm to other people.

And if it was so good, why wouldn’t you just use it yourself

and print money?

He’s like, yeah, yeah, no, no, that’s not our business.

Our business is we’re gonna create an app

to get millennials to trade stocks.

And he said, hmm, you do realize

there’s no retail investors anymore.

Like the dot com crash plus the 2008 financial crisis

eliminated any individual’s belief

in participating in the stock market.

And he said, that’s the opportunity.

I said, okay, I like it.

Tell me more.

He said, well, we’re gonna get these millennials to trade.

I said, the same ones who live in their mom’s basements

and take Uber and Lyft and are on their parents,

have no money, got screwed and went 250K into debt

for school and now can’t get a job.

Those people?

And he’s like, yeah.

I’m like, okay, they have no interest in their future,

but they’re gonna trade stocks.

He said, yeah, that’s the opportunity.

I was like, how are you gonna make money?

And he said, well, that’s the best part.

It’s gonna be free.

And I said, so your idea is to get a group of people

who have no interest in saving for their future

to trade and your business model is free.

And he said, yes.

I said, I’m in.

Because in almost all cases, the crazy outlandish ideas

that nobody believes in are the ones

that have the greatest returns.

I mean, Uber, I introduced to about 25 investors

and three of us said yes.

So a full 12% of the community who saw that deal

decided to do it.

So your sense about this idea being good

had to do with the fact that this guy was just crazy

and ambitious and bold thinking,

or was it that there was something here

in allowing a much larger magnitude of people

to be able to be investors?

Yeah, the way to do really well as an angel investor

or just in technology or in life

is to not say what could go wrong,

but to say what could go right.

And then to just imagine for a moment,

if it does work, what would the world look like?

And so when Elon was investing in Tesla

and some other guys were running it

and he was trying to save the company,

it wasn’t, is this gonna work?

It was almost positively not gonna work.

And he knew that, but if it does work,

what does the world look like?

And so that’s really what you’re looking for

is not the chances of success,

but if it does succeed, what would that look like?

And that’s what the world needs more people doing.

And so when you looked at Robinhood, it was like,

well, if he does succeed, what would the world look like?

And now we’ve seen what it looks like.

You have a generation who are so financially sophisticated

that they know how to do puts and calls

and shorts and research at a level

that dominated the hedge fund industry.

So let’s pause for a second.

These traders sitting there on a subreddit

in a discord server are able to do analysis and research

and then act in unison to say,

we’re going to beat in the Robinhood sense,

this group of sophisticated insiders

who have more access and more access to capital,

but we will figure out how to solve this problem.

And most things don’t work.

It’s like the Wikipedia.

There’s no way the Wikipedia would ever work, except it did.

You’re like, how is this ever gonna work?

You’re not paying anybody,

but it’s both the largest corpus of an encyclopedia ever.

So I think Robinhood actually succeeded.

And then what we saw was this system

and a lot of the systems in our society,

whether it’s the political system,

the constitution of the United States,

education, higher education, which you’re involved in,

and then even the financial system,

we have not stress tested and stress tested it,

and we don’t actually know all the edge cases

and how it works.

So Trump was able to just really put this crazy stress test.

Is the democracy going to hold?

Are we gonna break this two or three,

200 someone year old experiment?

And then we looked at the financial markets

and it turns out there were more people shorting the stock

than stocks and shares were available.

I don’t know how that’s possible.

And then I’m trying to uncover,

where can I see a list of people who have shorted the stock?

And it’s like, you can’t,

but we can tell you sort of how many every two weeks

or maybe twice a week, we can create a report.

Maybe we know.

I was surprised that nobody knows

the list of people who were shorted

and you guys are trying to figure that out.

Yeah, there’s no transparency on a lot of these systems.

And if you call to try to short a stock,

it’s almost like they’ll tell you on the phone,

let me see, I think I might know a guy

who has shares to loan out.

So it’s like, am I calling to try to find

like a 73 Mustang Grande in gold?

You’re gonna call around, it’s like,

shouldn’t this be like on a ledger somewhere

and be completely transparent?

So now we’re seeing those things.

And I think the investigations will make it super clear.

But of course, in a vacuum without information,

there are so many investors in these startups

that conflicts can start to appear.

And then you know how it is with people

in conspiracy theories, the mind starts to wander, right?

And so in some cases, there is actually a conspiracy.

And then in other cases, people’s mind will fill in like,

oh my God, there’s some grand conspiracy here.

I can tell you Robinhood’s only goal

is to get more people to trade stocks

and to democratize it even more.

And they apparently were on the brink of seizing as an entity

if they didn’t get more money to cover all these trades.

I mean, they were on the brink

and they raised $3.5 billion or something like that

in a week.

Yeah, so in some sense, Robinhood enabled this very,

like the magic of this distributed system

of WallStreetBets, right?

You said Wikipedia, which is another,

which is probably one of my favorite websites

and one of my favorite examples of like a distributed system

somehow coming together in a way,

just like you said at that crappy bar,

I would have guessed it would never work.

But if it does work, it changes everything and it did.

And Robinhood in that same way probably enabled

or was one of the major enablers of WallStreetBets

of giving power, like empowering young kids to learn

about how this whole messy financial system works

and take on the big elite centralized players.

Yes, and it’s very easy.

When these companies get big,

one thing that’s changed is the footprint of these startups

and the velocity at which they grow.

So something like Airbnb is another perfect example

of something that should really not work in practice,

but it does.

Like I’m gonna rent my couch or my extra room to somebody

like a serial killer,

or I’m gonna stay in somebody’s house,

like a serial killer’s house.

And it’s like, it really sounds scary,

but it actually works and it has not destroyed

the hotel business.

It has added.

So the best startups induce a market to exist.

If you look at Uber or Airbnb, people replace their cars

and Uber was not competing ultimately with taxis.

They were competing with car ownership,

public transportation, walking, or just not going out.

And then you look at Airbnb,

a lot of people who stay in an Airbnb

would not be taking a trip to Kyoto,

if not for the fact that they could get a $75 beautiful room

with great reviews in Kyoto for three weeks.

It inspires people and it manifests the market

because the product is so transcendent, right?

And I think that’s one of the things that Robinhood did.

You can’t learn how to do this options trading

and puts and calls and all this sophistication stuff,

unless you actually do it.

It’s just too hard to learn except in practice,

just like poker.

If you wanna learn how to play poker or guitar

or tennis or skiing, like you can talk about it.

You can watch YouTube videos,

but at a certain point, you gotta get on the mountain.

At a certain point, you gotta put some chips in the pot

and it’s gonna be painful.

Like poker is gonna be painful.

You’re gonna lose a lot of money

and that’s why you should play at the small tables first.

And even in trading, like you look at people

who are doing this crazy trading and GameStop,

a company that’s worth maybe a couple of billion dollars,

but certainly not tens of billions of dollars.

Of course, the people who are throwing their money in last

are gonna lose it.

I think everybody knew that.

And so it was a momentum play

and they’re betting against the hedge funds.

So I think it’s good for people to learn

and become financially literate

and just always understand the concept of the risk of ruin.

The good news is for a young person,

the risk of ruin might be like they lose $5,000 or something

and then they have to build their stack back up.

But that’s really the only thing I am concerned about

is there are people who will play poker or blackjack

or sports betting or whatever it is and lose control.

Just like there might be people who try alcohol

and lose control.

But we can’t build a system based upon limiting

the average person’s behavior based upon somebody

who can’t control their ability to drink.

Two glasses of wine instead of 20.

How does this whole thing end?

Probably in tears.

For who?


Who’s crying?

Is everybody crying?


Who’s crying when?

So I think there were some of the hedge funds

that were crying initially.

That maybe some of the Wall Street Bets people

who bought last would be crying.

And then eventually there’s probably another set

of hedge funds or even the Wall Street Bets mob

and that army, some of them might’ve broke ranks

and then shorted the stock.

So nobody knows.

So everybody has to be aware of what’s happening

in the game.

So if Wall Street Bets said, hey, let’s squeeze

these hedge funds because they have too much short interest.

Let’s all buy the stock.

Then some of them might’ve said, okay,

you know, it’s at two or $300.

Maybe I’ll join the short movement now that they’ve covered.

And they could have shorted their been like double agent.

So people have to understand like this stuff is gnarly

and it’s a free for all.

I mean, it is a literal free for all.

There’s a kind of morality,

like a big statement that Wall Street Bets made

in terms of like the elites can’t just push us around.

They can’t bully around.

But at the same time, you know,

they’re also interested in making money, right?

What’s your sense?

You said that some of the people in the Wall Street Bets

might’ve broken off and shorted the stock.

Are they more interested?

There was an emergent like morality that emerged

and said like, we’re not gonna put up

with the centralized elites,

but is that going to continue?

Are they going to fight the power structures

that are bad for society?

Or are they going to now like,

I mean, are they ultimately going to introduce more chaos

that’s going to damage the economy and damage the world?

Or are they going to continue being the good guys

and fighting the evils that manipulate the market?

What’s your sense?

You know, it really feels like the Dark Knight series

of films where like some people

just want to see the world burn.

I think there is a contingent of people

who just literally want to see chaos.

Like, you know that contingent on some of these forums

who just want to create chaos, right?

So there’s certainly that chaos contingent,

but I think overall what the arc will show

is a group of people getting massively educated.

You see it in crypto as well.

There was like a three year period

where all of these failed entrepreneurs who I knew

who couldn’t build companies were then coming back to me

after their companies has failed or after they gave up

or couldn’t clear market raising money

with the venture capital community

and they were doing ICOs.

And I was like, I met you before, right?

And they’re like, yeah, yeah, yeah.

No, I’m doing an ICO now.

I’m like, okay, where’s your company at?

And they’re like, here’s a white paper.

And I was like, this white paper with spelling errors in it

that says you’re going to destroy Airbnb

because everybody’s apartment

is gonna be on an immutable ledger.

Like, wouldn’t that be better in a regular database

that was private and not public?

Like, why does it need to be on an immutable ledger?

It can’t change.

I’m like, not changing the database is a feature?

That does not seem like a good feature.

And they couldn’t explain it.

They’re like, well, just people are interested in ICOs.

And there was that ICO mania.

And what it showed was there’s a global appetite for risk.

People want to try new things.

This is one of the great things about the human spirit

is one of the great things about capitalism.

And one of the things that concerns me most

about where we’re at in society

is the sort of socialism, communism,

entrepreneurship is bad, technology is bad,

and polarization of wealth,

and people getting rich is a bad thing.

When I grew up, I’m 50 now,

but when I was a Gen Xer growing up,

we kind of maybe too much idolized Bill Gates

and people who were doing interesting things in the world.

And we thought capitalism was a force for good.

I still believe capitalism is a force for good

because when a group of people build a product or service

that changes the world and it gets globally distributed,

whether it’s Tesla or SpaceX or Google or Airbnb

or Uber or Robinhood,

everybody gets to benefit from that product or service

having to compete.

And if you look at the places where there’s no competition

like public education or less established colleges

and something like that,

less competition for accreditation degrees,

like things tend to get a little weird, don’t they?

And people tend to be protected and that’s not good.

You need competition.

Doesn’t mean that people shouldn’t have global healthcare.

It doesn’t mean that we shouldn’t have a safety net,

but we need to keep capitalism vibrant,

especially because China has now coopted capitalism

and created their own version of capitalism,

which is communism with capitalism.

It’s like this weird operating system

like we still want to keep communism

so we can take any of your gains at any time,

but we’d like you to be entrepreneurial.

And then you have somebody like the founder of Alibaba,

Jack Ma, who disappears for a couple of weeks.

Who’s that?

No, I’m just kidding.

Who’s Jack Ma?

I was like, he kind of disappears for a couple of weeks

and then he comes back and he’s really sorry

about the things he said and then he disappears again.

And like, we have to be very careful.

You know, we have to be very careful if China wins

capitalism, this is going to be an existential threat

for humanity.

The Chinese are no joke.

I mean, they are seriously focused

and they are picking the winners.

It’s a very weird system because it is in fact,

I don’t know what you call it.

Like communism and capitalism is such a overloaded terms,

but they do encourage entrepreneurship,

but they, and they do a good job of it.

Oh, yes.

But then they’re like, they’re like the surveillance thing

and they’re controlling things in a way.

It’s weird because it seems to work really well for them

in the short term.

Yes, it’s definitely got short term benefits.

So the question is like, how that gets distorted

and it becomes worse and worse and worse,

which it potentially might be.

And I think on, you know, the entrepreneurial spirit,

which you have a podcast all centered

around the entrepreneurial spirit,

is one of the magical things that makes this country great.

I don’t know if money is deeply tied into that.

I do get bothered by people, you know,

treating the word billionaires if it’s a bad word.

But in general, like all the hard things,

all the difficult things we’re going through in this country,

it seems like the way out is going to be

making the entrepreneur the hero of society

of like letting that young kid with a big dream

and the guts to take the big risks

and build something totally new,

giving them a chance and whatever that involves.

I don’t think it’s about taxes.

I don’t think it’s about like regulation, all that stuff.

It’s about us and just public discourse saying

that kid, that guy, that girl, they’re bad asses.

Like encourage them to do it.

We have to have people buy in

to the fact that they have that opportunity.

And I think one of the problems in society is

there’s a group of people who actually don’t believe

that they can succeed or they don’t believe

even more perniciously that other people can.

And that’s the group of people that I think are highly vocal

but a small group of people,

which are generally people of incredible privilege,

rich parents, white city dwellers, liberals.

They kind of look and say,

poor people cannot change it a lot.

And they’re battling in their minds

to protect poor people.

But they have this very weird

patriarchal kind of approach to it,

which is they think that they’re not capable

of changing their lot in life.

And they’re like, it’s not possible.

And then once in a while, I’ll tweet something where I say,

it’s really incredible that every piece of knowledge

you could possibly want is now available for free on YouTube.

And every course from MIT and Harvard and Stanford

is available on edX or Coursera.

And all that information is there freely available.

And you can take the lectures.

This is amazing.

And then people will be like,

yeah, but people don’t have access to it.

I’m like, they do.

It’s free.

Here’s the link.

And they’re like, yeah, but they don’t have internet.

And I’m like, here’s the chart

of internet penetration in America.

And they’re like, well, poor people don’t have internet.

And I’m like, really?

Find me any downtrodden person without a smartphone

with a high speed connection

that capitalism provided for $12 a month or $15 a month.

It’s very hard to find that.

And we have it so well in this country

and there’s so much opportunity,

but people don’t believe it.

And that’s actually one of the problems.

See, the average American still watches

four or five hours of television a day.

And often I meet people and they’re like,

I need a technical co founder.

But all I need is a million dollars.

And I’m like, okay, well, what is your skill?

And they don’t have a skill.

And I’m like, well, are you a designer?


Are you a product manager?


Are you a developer?


Are you a sales executive?


Do you have an idea?

Well, as my friend, Sam Harris,

I think your friend as well says like,

everybody has like a million ideas an hour.

Like you don’t really get credit for those.

Even when you’re asleep, your idea is spewing ideas.

Like zero credit for your ideas.

It’s all about execution.

And we’re seeing.

You have to believe that you yourself

can be the core of that execution.

You yourself can build the thing in every,

no matter what your circumstances are.

I mean, we could talk about like structural racism

and all those kinds of things that push things down.

But from the individual perspective,

when you just like are coaching

or giving advice to an individual,

you can literally change the world.

I mean, Wall Street Bets is an indication of that

in the financial space that you yourself can have,

can change the world.

That’s why this country is amazing.

Still the best country in the world, right?

I mean, it still is amazing the opportunity

provided to people.

All this educational experience is online.

And the ability, what I tell young people

who are looking for advice, I say,

the skill you need to refine

is the ability to learn new skills.

Like if you become good at learning a new skill,

and Tim Ferriss, a friend of mine has really pioneered this,

he can get to 60 or 70% of like the knowledge

in a skill in some incredibly short period of time.

And I’m not saying he’s gonna become a virtuoso drummer

or a great basketball player,

but Tim and I were on vacation together

in like a group vacation in Italy

and there was a basketball court.

And I said, let’s go shoot some hoops.

I’d never shot before.

And I was like, okay, come on, I’ll teach you.

And Tim is fabulously uncoordinated.

People don’t know this.

Like he tried to dribble a basketball and do a layup

and it looked like he had a blindfold on.

I mean, you’ve never seen something less elegant

than Tim Ferriss doing a layup in basketball.

And then he watched me do it three or four times

and I watched him study me.

And listen, I’ve been playing basketball in Brooklyn

since I was a kid.

I got a couple of moves and he was just taking notes

and taking notes and taking notes.

And by the end of a couple of hours of doing this,

I could just watch him checking his form

and figuring it out.

That’s every skill in the world now.

And what I tell people is like, I’m like,

did you watch Game of Thrones?

And they’re like, yeah.

Watch Breaking Bad?

Like, yeah, I’m like, okay, that’s about 400 hours.

How about you don’t watch the next two

and you put that 400 hours into learning

how to be a graphic designer, a UX person,

a developer, whatever it is and learn how to add skills.

That’s what I did my whole life.

I was a kid from Brooklyn, went to school at night,

but I was very quick to get to maybe 50%

of the knowledge base of graphic design

or being a writer or being a sales executive,

whatever it was, a developer even.

And I was just good enough to not have people

be able to bullshit me like when I hired them.

And that was a big unlock.

When you know enough that people can’t snow you,

that’s a really good one.

And look at yourself.

You figured out how to set up an entire podcast,

people don’t know this,

but you don’t have a team around you.

I have a team of like five, six people working on my podcast.

With even knowing enough about to set this up,

you would then be able to hire a team.


And you’ll be able to call them on their bullshit

if they’re not doing a good job.

And that’s really important.

And I don’t know that much about this whole thing,

but I know enough to be able to then see

who knows their stuff and not.

You’re absolutely right.

And the process of learning how to learn

is essential there because I did martial arts,

jiu jitsu and so on.

And it’s so funny to watch.

I did Taekwondo, yeah.

Taekwondo is awesome.

It’s funny that there’s some people

that do an activity for years,

because just sort of elaborate on something

you were saying about hours.

It’s not always the amount of hours,

it’s the quality that you put in.

Deliberate practice versus just doing some behavior.

I mean, literally I’ve been playing chess

and trying to get that going again

after watching Queen’s Gambit and I got chess.com.

And I realized I was just playing

and I’m not getting better.

And then I was like, oh wait,

there’s a little analysis feature here in chess.com

where it will show you your blunders and mistakes.

And I’m like, oh, I’m spending no time

reviewing my losses in chess

and I just wanna play the next game.

I should really review these losses

and figure out what mistakes I made.

And when I started doing that,

I was like, oh, I’m getting better.

So some deliberate practice really works.

And if you wanna take it all the way,

Magnus Carlsen, shout out to the guy,

he has an app, but there’s a few other coaching apps

where you focus on the end game,

you focus drilling a particular,

you basically don’t play the game at all.

You just focus on drilling the different aspects.

The openings, the end game, the end game, yeah.

And there’s different kinds of puzzles.

So you can really make it into a deliberate practice.

Not to make this episode sponsored by chess.com,

but they literally have puzzles.

So I was like, oh, and it’s $100 a year for this product.

And I just thought to myself, this is capitalism.

They don’t need to charge you $100 an hour for a lesson.

They can charge you $100

and they’ve created the ability for you to play chess

24 hours a day against opponents

who are perfectly matched against you based on your rating.

And they analyze every game and they have puzzles

and they have tutorials and they’ve got everything else.

It’s like, just think about how much value

is being provided to society because of capitalism

and because competition.

If you want things to get better

and you wanna step up your game,

just make it slightly competitive.

It is one of these things in human existence

that is so powerful.

I don’t know, did you see the Michael Jordan documentary,

The Last Dance?

Like half of it, I’m still working through it.

He’s so competitive and petty.

It’s so inspiring that all he cares about is just winning

to the level of which he literally,

there’s like this running meme, I took that personally

and I took that person.

I don’t know if you’ve seen the images of him

sitting smoking a cigar,

looking at like an iPad or a video clip

and it’s like, I took that personally.

And you can make a super cut

of every time he took something personally,

he literally takes everything personally

to give himself that competitive motivation to win.

That’s capitalism.

And when people are competing,

man, look at what Elon did to the space of cars.

Like every, they were literally laughing at him

in the first 10 years.

Electric cars, ha ha, that company will go out of business.

And now every single company is like,

we’re going fully electric by 2035.

And he kicked their asses so brutally

that they had no choice but then to step up their game.

And that’s what we want, right?

And this virus and this pandemic,

I think the great thing that will come out

of this horrible experience that we’ve all had

is psychologically death, learning,

just so many bad things occurred,

the economy, people losing their jobs.

But we also got to see the human spirit

with these mRNA vaccines and just how,

if we took out some of the regulation

and people were super motivated,

we might actually be able to eliminate

all pandemics from ever happening again.

And before that, Bill Gates was banging his fist

and Jeff Skoll was doing the movie Contagion.

I mean, for two decades, people have been banging their fist.

We have to be prepared for this.

And everybody’s like, yeah, whatever, YOLO.

It’s not gonna happen.

And now it’s happened and people are like,

we need to be able to destroy every pandemic and virus

before it happens.

And listen, you know a lot more about science than I do,

but these mRNA has been around for a while.

We’ve just never gotten aggressive about doing it.

And then you think about challenge trials.

I don’t know if you’ve been following this,

but they’re doing challenge trials now in the UK this month

where they’re introducing COVID into healthy young patients

and then giving them the vaccine or, you know.

And that is against all rules and regulations

about do no harm.

But then you think about it.

We kind of celebrate people jumping out of planes

and we got that one guy, Alex Honnold,

who’s climbing up mountains without a rope

and they give him a North Star, you know,

back page ad and an endorsement deal.

And we celebrate that.

We celebrate people surfing with sharks.

We celebrate people doing deep welding.

We pay them extra to go 200 feet underground

and weld stuff.

And people do dangerous stuff all day long, astronauts.

But we won’t, soldiers, firefighters,

but we won’t let people get paid to do a challenge trial.

Yeah, we’re weirdly risk averse in certain areas

that completely don’t make any sense.

And this is where the world needs it.

We could have said these thousand people, young people,

who we know are in all likelihood

not going to have a bad outcome,

but there’s a possibility.

There’s a possibility.

But it’s very low.

It’s certainly lower than riding a motorcycle.

It’s lower than riding a motorcycle.

People ride motorcycles everywhere.

We have ads for motorcycles.

We could have just said to those thousand people,

we’ll give you a million dollars each to do this.

Okay, there’s your billion dollars.

We’re printing trillions of dollars of money

to deal with this.

If we had just done a thousand people

for a million dollars each to do a challenge trial

in March, April, May, when they had the mRNA vaccines ready,

we could have deployed the vaccines in the summer.

We would have been done with this.

We would have been over by now.

So we get to challenge all of that thinking.

I think that’s what the great pause did.

It’s letting everybody challenge that thinking is,

why do we have that rule?

Okay, yeah, we don’t want to have people,

you know, like give up their organs for money.

Like we obviously understand,

but there’s a reasonable discussion about,

well, maybe there’s a level of risk in a global pandemic.

I mean, we fought the Nazis, right?

We defeated the Nazis.

That took a lot of deaths to do that,

but we had to kill that evil.

This is another evil, which we must fight.

And it’s going to result in,

it’s already resulting in thousands of people dying a day,

but we could have actually stopped it earlier

if we just had a reasonable discussion.

This is why podcasting is our respect what you do.

This is why intelligent people are so drawn to podcasts

because you and I can expand on this

and not cancel each other over this very suggestion.

When I make this suggestion,

are challenge trials reasonable or not?

If I were to do that on Twitter, they’d be like,

oh, Calacanis wants to give poor people coronavirus

in order to save rich people.

It’s like, no, I didn’t say that.

But you and I could have a reasonable discussion

about a challenge trial is something we should consider

in a acute situation

where millions of people are going to lose their lives.

Right, so that’s an example

of capitalism competition working really well.

There’s one of the, to me, sad thing to see

about coronavirus is that, for example,

testing at scale should have, it seems obvious.

I was a little clueless about it,

but because I thought there’s no way you can have

like antigen tests at hundreds of millions,

like order hundreds of millions of them and make them cheap.

But actually I realized recently

that there have been available since about like May.

Yeah. You were able to.

In Korea, in Finland, all over the place.

You could have done mass manufacture.

So there, there’s a little bit of a failure

of capitalism to step up.

And I don’t know if you agree with this,

but it seems that the blame is to be placed

at the regulators and the various institutions.

Chrony capitalism in all likelihood

is what stopped it here in America.

I mean, I had friends who had imported them

from other countries, the testing kits.

And you’ve probably been to parties

where people had these kinds of testing kits

from other countries and we’re sitting here

and they’re just approving them now.

Really, in February, month 11 of the pandemic in America,

we’re gonna have testing online, really.

I mean, even if these tests were 80% effective

and they’re 95% effective, mass producing them,

we should have sent them in every postal,

anybody with a post office box with a mailing address

should have had 10 of them put in their mailing address

just for free from the government.

And then everybody would be testing

and we would have contained it.

We don’t have test and trace here in the United States.

Well, all the countries that are on the other side of COVID

did it by having testing, tracing

and closing their borders and masks.

That’s the combination that works.

The problem with the coronavirus

is while there’s a lot of institutions

did not behave their best,

it’s also the case that there’s a lot of uncertainty.

So I tend to give a little bit of a pass

to everybody involved for the uncertainty.

We were all.

I give them that until June.

I wonder how history will remember this whole period.

I’d love to ask you,

because you were an early investor in Robinhoods

and you’re in a very nice place

of being a huge supporter of the sort of Wall Street bets

kind of distributed power of the people.

And at the same time, because of you being an investor,

like intellectually giving a chance to Robinhood

in this kind of chaotic time of conversations

to think about like, well, what did they do right?

What did they do wrong?

So you have a kind of a balance view on the whole thing,

which is really nice.

We’ve talked about what Robinhood did right, I think.

Can you sort of steel man at your mouth’s argument

of what Robinhood did wrong in the last few days?

Yeah, I mean, communication is always

the number one issue with these startups, right?

And if you, you have to get ahead of any problem

and you have to put all the bad news out immediately.

And in the case of Robinhood, it seems based on

what has been in the papers and what Robinhood said publicly

is that they had this kind of liquidity crisis, right?

Where they were being, because of these exchanges telling

them you have to put up this amount of money in collateral

and them being pinned at number one in the app store.

There were so many people trying to buy five shares

of this stock, five shares of this meme stock

that it kind of broke their system.

And then the people who clear the trades for them,

they said, you gotta put up a billion dollars,

two billion dollars, three billion dollars.

We can’t do that overnight.

And I think that they were in an uncomfortable situation

of like going on TV and saying, we have a liquidity crisis.

Like that could be like a run on the bag.

Everybody then logs in at the same time to Robinhood

and tries to sell every share they own

because they’re afraid that the whole thing’s

gonna collapse, right?

So I think there was this kind of like black swan event

and they probably didn’t communicate it all that well.

At the center of that, this is really interesting.

Maybe you can comment on the nature of communication.

Vlad, the CEO, the guy you met at the bar,

was I think at the center of the communication, right?

So Elon is an example of a guy who also is

at the center of the communication

for his particular set of companies.

And that on Twitter seems to be a really powerful way

to communicate.

And there was something, this is me saying it,

there was something about Vlad that sounded

like he’s hiding stuff.

As opposed to Elon, it doesn’t sound

like he’s hiding stuff.

It could be the nature, the beat,

the timing of the conversation.

Same thing with Mark Zuckerberg.

Mark Zuckerberg for some reason often sounds

like he’s hiding something.

And then there’s like Jack Dorsey is much less so.

And I don’t know what that is about the CEOs

that makes you trust them and not.

Might be the point in time, like in terms of escape velocity.

There might be nondisclosures in place

that we’re not aware of where they’re not allowed

to talk about certain relationships.

I see.

And that results like in Vlad’s case,

and that results in you being like acting weird and nervous.

Or nervous.

Yeah, it could just be the person is nervous.

So it’s really hard to be building one of these companies

and you’re at scale and oh my Lord,

the entire thing’s coming apart

and you’re the most hated person for that day.

You know how the rage cycle works

and the media is just so crazy

when they get their hooks into something.

I saw it happen with Uber.

We saw it happen with Facebook and even Tesla.

There were times when people did stupid things

with autopilot and it’s like, okay,

somebody is watching a movie and sleeping in their car

or leaving the driver’s seat

against all the rules of autopilot

and somehow Tesla’s responsible for that.

It’s like we have people who stand on top

of their motorcycles and drive down the road

on a motorcycle.

And we don’t blame Yamaha or Harley Davidson

for some idiot standing on the seat of their motorcycle

on a highway going 60 miles an hour.

We just say, that person’s an idiot.

But when new technology comes out,

we blame the technology, not the person operating it.

And if you are going to operate,

we basically vilify it and demonize it.

I think that is part of it.

Like when the person at, I remember Airbnb,

we always thought, what if somebody trashes your apartment?

And then sure enough, a bunch of meth heads

rented this poor woman’s apartment.

She left all of her stuff in it.

And then a bunch of meth heads had a drug party,

destroyed her apartment, ripped up all her photos

and went crazy.

And we knew that day would happen,

but nobody remembers it now.

But it was the number one story on every news channel

because wow, that’s an exciting story.

And I just thought to myself,

I wonder if there are any parties in hotel rooms

where the hotel room is being trashed

and people are doing drugs and crazy things.

It’s like, yes, that’s basically every hotel

in Los Angeles right now is being destroyed

by some rock band that’s throwing a TV out the window.

Like we expected in a hotel,

we just didn’t expect it in somebody’s house with Airbnb.

And then Airbnb created rules around,

you can’t rent an Airbnb for a party and they learn.

So I think there’s a learning curve with these companies

and they do get to scale at a level

that is unprecedented.

It used to take decades for a company

to become an international phenomenon.

Now it happens in two, three, four years.

I mean, look at Clubhouse.

This thing went from being a private beta six months ago

to being the number one app in Germany

and in Japan and here.

Like just like that, boom.

And it’s because there’s an ecosystem

that has never existed, the app store.

Then there’s payments online.

And then everybody has a supercomputer in their pocket.

The thing people got wrong

about entrepreneurship technology and business

over the last couple of decades

was just how big the market was

and then how quickly you could achieve relevancy

in these markets.

We thought the market was like the 60 million homes

were broadband.

And originally it was like maybe 10 or 20.

Then it became 60 million.

Then it was like, okay,

well, how many hours are you at your desktop computer?

Well, like probably at our computers for five hours a day,

10 hours a day at work, three hours a day on our own.

And then it was like,

yeah, nobody’s on their desktop computer.

Everybody’s on their mobile phone.

Oh, and by the way, they have it with them.

So the people with mobile phones

are now using this high speed device with an app store

with their credit card in it.

In the early days of the internet,

people were scared to put their credit card on the internet.

That was considered a really dumb thing to do.

If you put your credit card on the internet,

you’re gonna lose all your money.

They’re gonna hack you or whatever.

And now it’s just amazing to me

how quickly when a company hits,

how quickly it can get to a million subscribers

or 10 million or a billion users, right?

And there’s all these networks, like social networks

that allow the spread of the viral spread

of like a new startup, a new company, a new app

to be announced.


An idea, a podcast, right?

A single thing, a single meme could change the world.

Speaking of Clubhouse, I just wanna,

we’re saying so many interesting things,

but there was a magical moment with Vlad and Elon

on Clubhouse.

I don’t know if you got that.

That was wild.

Yes, is there, do you have thoughts about that interaction

which felt like so many aspects of this whole situation

feels like totally novel, surreal,

like it’s defining a new era.

It is, yes.

Like a billionaire, the richest human on earth

is interviewing the person at the center

of one of the most interesting mass scale

like power battles in finance ever, perhaps.

And by the way, seven movies have been sold two weeks.

Just think about how fast things are moving, Lex.

This thing happens.

Like people had the idea to short the stock six months ago.

They start doing their research.

They build an army.

They execute the trade.

The system goes down.

Robinhood raises $3.5 billion in four days.

Elon is interviewing them on Clubhouse on Sunday

after the Wednesday it happened.

And now here we are, it’s 10 days later.

Doesn’t it feel like it’s been 10 months?

It’s been 10 days, Lex.

It’s been 10 days.

10 days.

Plus, there’s like a new president,

all these things, and everyone forgot.

Oh, and there was an insurrection.

By the way, we also almost had a revolution at the Capitol

where a bunch of crazy people who have guns

and body armor, and then a bunch of them

who are just yoloing in cosplay, took over the Capitol.

Well, so, and the other more dramatic thing to me is.

That was one month ago.

That was one month.

And the president of the United States got banned

from every major social network,

and which I think I’m still deeply troubled by

is Parler being removed from AWS.

That changed the way, that changed a lot of things.

As somebody who’s an aspiring entrepreneur,

that changed the way I see the world.

That little, maybe I’m being over dramatic, but.

No, you’re not.

I think you’re paranoid for a reason.

You’re paranoid for a very good reason,

which is as big as these companies can become,

they are beholden to the mob.

And if the mob says, hey, this person needs to be canceled,

they’re going to get canceled

because you can’t lose your entire audience.

You could lose your whole customer base,

and you could lose all your employees.

I think what’s interesting about your fear

about Parler and AWS taking off

is we went from being like a social network,

which is the software layer.

And then we went to like the infrastructure layer,

and they’ll even go after like Cloudflare,

which is a CDN provider, right?

They’re just like a plumbing,

it’s like sort of like the telephone.

So we’re basically holding everybody responsible

on the whole chain of events here.

And what that’s going to do is,

I’m not a huge believer in crypto,

but distributed computing,

where nobody in decentralized

and distributed computing platforms and open standards,

podcasting is an open standard,

the web is an open standard, FTP was an open standard,

but Twitter and Facebook are closed.

And what’s going to happen is we will see

a group of individuals create peer to peer networks

for social media, where nobody can control it.

And the same for cloud computing,

where there’s a crypto project where everybody will,

and I invested in a company that tried to do this

and got sold and it didn’t work out,

but take your hard drive on your computer at home,

you give a terabyte of your 10 terabyte drive

over to the cloud,

and then everybody else does their terabyte.

And then all of a sudden you’ve got this virtual cloud

and anybody can store stuff on it and it’s all encrypted,

and then nobody can stop it.

And that could be tweets, it could be videos.

And so this idea that YouTube will be able to tell people,

to kick people off because they’re skeptics of,

I don’t know, the pandemic or the vaccine,

or they’ve, they’ll make things

that are more censorship resistant.

I think that’ll be the reaction to all of this.

This is my question for you,

going back to that crappy bar and people pitching you,

is there, like with Clubhouse, do you see competitors,

do you think it’s possible that another,

perhaps more decentralized or another kind

of social media will emerge

that will take on Twitter and Facebook

and might be able to replace them?

If you look at the whole landscape with Clubhouse

and everything else,

do you think some other company might emerge?

There’ll be 10 versions of Clubhouse.

We looked at social networking.

We thought Friendster was it.

Like Friendster was so good,

nobody would be able to compete with that.

It was growing so quickly.

And then MySpace was a juggernaut

and they hit a hundred million in revenue

and a hundred million users.

And it was like, well, that’s game over.

And then Facebook and LinkedIn and Snapchat

and FriendFeed and countless others.

So there’s usually 20 people who will win in a category

and 80% of the category will be owned

by the top two or three players.

But will those players change, do you think?

What’s your sense of that?

Oh yeah, for sure.

I mean, if Facebook hadn’t bought Instagram,

it would be a company in decline right now.

People would be shorting the stock, right?

Facebook peaked and then was sort of heading down

and Instagram saved them and WhatsApp saved them.

So, you know, that’s another kind of weird moment

in history that they were able to accumulate

that much power and consolidate that much power.

Instagram should have never sold to them.

That should have gone public.

They had just raised money from Sequoia

and they had raised $50 million at a $500 million valuation

and they didn’t need to sell.

And that was a big mistake to sell.

They should have kept going

and they should have took on Facebook.

And if Instagram was a standalone company right now,

it’d be worth 500 million, 500 billion, yeah.

Do you think Facebook might buy Clubhouse has been?

Oh, they’ll probably copy it.

I mean, Zuckerberg has no moral compass

or ethics or anything.

I mean, he’s a marauder.

I mean, he basically copied Snapchat seven times.

Like he did poke and he just kept trying

and trying and trying.

Part of the reason why the WhatsApp founders

and the Instagram founders left

is they found Zuckerberg so distasteful

in terms of his ability to copy.

What do you think makes a great leader in that sense?

Because, okay, so when I look at Zuckerberg.

He’s a great executor.

Is he a great executor?

I don’t think he’s a great leader.

I was bullish on,

I was excited by Facebook in the very early days.

I thought it was an exciting opportunity to connect people

and stuff started going wrong in certain kinds of ways.

And again, maybe it’s our human nature,

but I attribute a lot of that to the leadership.


I mean, the guy started it because he was unable

to ask girls if they were single and on a date.

I mean, that was his explicit.

That could be a good motivator.

Well, I mean, it does.

I mean, listen, the motivation of 18, 19 year old men

or his, yeah, pretty clear.

He was just trying to, he had no game.

He had no game and he needed to know who was single

so he could at least have a shot at getting a date.

It’s a little creepy.

A little creepy, yeah.

He, I think, was so obsessed with engagement and winning.

And he’s kind of like one of those friends you have

who’s just really good at playing a video game,

but maybe doesn’t see the bigger picture in life.

And I mean, there’s a reason why everybody who worked

for him hates him and doesn’t talk to him anymore

and then actively derides him.

Like so many, the people who sold WhatsApp to him

then backed other projects like Telegram

and said horrible things about him on the way out.

These are the people he made billionaires.

And they really don’t like him.

So I think there is something that he does

that does not breed loyalty,

but he’s very successful in his focus,

which is growth is all that matters.

He’s a marauder and taking friction out of products

and processes is the playbook of Silicon Valley

for the last decade or two.

So whatever the friction is.

It’s like poetry what you’re saying right now.

It’s like you’re speaking so fast

that I almost forget that you’re dropping bombs.

But so removing the, removing friction.

And you’re saying Facebook is exceptionally good

at removing friction. He was the best at it.

I mean, at Uber, they were like,

we’re gonna take out tipping.

We’re gonna take out the need for you

to take out your credit card and do payment.

It’s just gonna be in your wallet.

You got picked up, you leave, that’s it.

And I was like, we should have tipping.

And they’re like, it adds a step.

And we’re trying to have no steps.

You put your address in, you click the button

and you do nothing else.

And so we’ve been obsessed here in Silicon Valley

is how many clicks can we take out of the process?

I guess Amazon is incredible at that as well.

Absolutely, one click was the start of it.

And then you look at Clubhouse as an example,

you open Clubhouse and you see rooms,

you click on it, you’re listening.

So in one click, you’re listening.

And then in one click, if you raise your hand

or you get invited and you say, yes, you’re speaking.

So it’s two clicks to speak, one click to listen.

I mean, the only way they could make that app work

even faster is if you opened it up

and your microphone was turned on,

which is kind of scary, but that is the next evolution.

And what happens when you go that fast

is you get unintended consequences.

And so this is why Facebook has had more fines

than any company in the history of Silicon Valley,

just giant fines for doing stuff like this.

And one of them was, I don’t know if you remember

when they created groups

or if you have a group for your podcast,

but you can just add people to a group

without their permission.

And there was this famous case

when they first came out with it.

Somebody created a Nambla fake group,

National Man Love Boy Association or whatever,

like pedophilia association.

And they added Zuckerberg, Mike Arrington, myself,

and like 20 other famous people in Silicon Valley.

And I was like, and then somebody takes a screenshot of it

and they’re like, you’re in Nambla?

And I’m like, no.

Facebook, and then Zuckerberg’s response was,

well, if your friends put you in that Nambla group,

you should get new friends.

And it was like, you got put in there too.

And then the sad part about it was

there were a group of young men who were gay

and who were in college

and there was a gay choir in their college

and the person who was coordinating their Facebook group

added them.

So Zuckerberg, it wasn’t enough for Zuckerberg

to make it so anybody could add anybody to any group

because it will grow faster,

let alone you have to confirm

you wanna be added to the group.

What it also did was posted it on their walls

to increase engagement.

And what they inadvertently did was

they outed a bunch of 18, 19 year olds in college

to their families

because they joined the gay men’s choir at some college.

And this is the kind of way,

this is where Silicon Valley needs to check itself

and to do better is you have to really think,

well, there is my incentive to grow faster

and then there’s what’s right for society

and for the individual.

You gotta think it through, think it through.

It’s sometimes very difficult.

This is where vision is required

to anticipate the unintended consequences.

And it seems like Mark Zuckerberg is not very good at that.

You’ve talked to so many great leaders in this world,

privately and publicly.

What do you think makes a great leader

of these tech companies?

Do you have an example?

Is Elon to you a great leader?

He’s also a controversial one, right?

There’s a love and hate, a controversial sense

that there is, and I know a lot of people work with him,

for him, that there’s also a love, hate relationship.

The hate comes from the fact

that they get pushed extremely hard.

It’s a very competitive environment,

but it’s a positive one

because there’s a vision that’s underlying.

It’s similar to the Steve Jobs thing.

And it has to do with the,

back to our Michael Jordan discussion as well,

that there seems to be the demons involved in tension

and just anxiety, all those kinds of things.

If you wanna do great things,

there will be some suffering

and there’ll be some pain,

and it’s not easy if you wanna change the world.

And then some people have this expectation

that it’s going to be easy.

And what you’ll typically find for any great leader

who’s trying to do something super ambitious,

like if you wanna be like,

if you’re a rich guy and you start a restaurant

and you don’t care about making money

and people have made restaurants before,

you could be high fives

and everybody could love you or whatever.

But if you wanna change the world,

you wanna do something hard driving,

there’s gonna be sacrifice involved.

And so the problem is people are looking at something

that is an Olympic caliber sport

or a Navy SEALs like effort.

In other words, an effort that requires massive sacrifice.

We would not look at somebody who wins a gold medal,

like Michael Phelps and say,

oh my God, he had to get up at 4 a.m. every day

and he had to swim and he had to do an ice bath.

Oh my God, that poor guy, he suffered, he was tortured.

People were super mean to him,

they put him in an ice bath.

It was like, no, he wanted to be

the greatest swimmer of all time

and he knew what the sacrifice entailed.

And that what happens in work, in business,

is that people conflate like,

oh, well, I went to work to make a living to pay my bills

versus Michael Phelps approach to getting gold medals

or Michael Jordan or pick the person,

Elon or Jeff Bezos.

And when you look at the reviews of like a place like Amazon,

there was this incredible story in the New York Times

where people were, I don’t know if you remember it,

this is the worst place you could ever work, Amazon.

And we talked to 200 people and they all told us,

they all described for us in the New York Times,

a culture of cutthroatness and brutality

that has never before been seen.

And then you see all these people who work for Bezos

for 24 years from when they graduated

with their MBAs until today.

And they’ve never left the company

and they are ride or die forever.

And what you’re seeing there is,

there’s a mismatch of people going to work

in an extreme sport or an extreme endeavor

who should not do that.

There are people who should go out into the rice fields

and pick rice.

And then there’s another group of people who are samurai

and who wield a sword and who take on missions

that are dangerous.

But if you’re a rice picker and that’s what you do

and you feel safe, just getting a couple grains of rice,

put them in a basket, cleaning it and then whatever,

that’s valid work, no big deal.

I’m not deriding it, I’m sort of,

but that is one group.

And then there’s people who are samurai

and you cannot conflate the two,

you cannot compare the two.

And that’s what is happening right now in business.

Whenever you see these stories about,

this person at this company is like a tyrant

and they’re so horrible and they yelled at somebody.

Like if you’re in the field

and you’re taking the beach at Normandy and it’s D day

or you gotta take the hill

or you gotta whack Osama bin Laden

and you’re the Navy SEALs and like a rudder,

a rotor gets knocked off the back of the Black Hawk,

like this is serious shit.

Like don’t do it if you’re not serious.

And if you’re not serious about changing the world,

why would you go work for Bezos?

Why would you go work for Elon Musk?

Don’t do it, don’t go work there.

This is, let me just sit back

and enjoy the beauty of all of that.

That’s music to my ears,

but I’m not sure what to do with it

because it’s conflicting to a lot of the things I hear

from the way you’re supposed to kind of act.

And I think in order to do great things,

you have to, I always admired people

that lose their shit a little bit

because they’re so passionate.

And I apologize and all those kinds of things,

but like there’s a tension,

there’s a drama to the creative process

when especially in the early startup,

this is not like the work life balance idea

doesn’t even apply.

Work life balance, it’s ridiculous.

It’s a ridiculous concept.

Like the idea that there’s like work life balance

in a startup is ridiculous.

If you’re looking for work life balance,

do not go to a startup or any kind of ambitious company.

There is a series of places you can work in the world

where you do not need to do anything more

than what’s put in front of you.

And you just put the round peg in the round hole

and the square peg in the square hole and you go home.

And you get your little bits and grains of rice

and you go heat them up and eat them, that’s it.

And then there’s this other thing,

which is the extreme pursuit of changing the world

and sacrificing.

And we have a generation of people,

multi generations of people who are soft.

They’re just soft.

I mean, what is the big struggle we’ve had to deal with

in America in our lifetimes?

Like 9 11 and we didn’t have the Vietnam War

and then we had this like weird Iraq Wars

and Middle East Wars that were kind of like a small number

of people went and we sent drones.

Like we have not had to sacrifice.

Gen Xers, maybe the tail end of boomers

experienced the Vietnam War regrettably.

But we’ve had a couple of generations now, three I guess,

that just haven’t had to suffer.

And so we’re soft as Americans, we’re soft.

And then you look at people in China and we’re like,

oh my God, these poor Chinese people are living

in these tiny cramped apartments.

Like they were living in like essentially lean twos

in Northern China with no running water

or like one spigot of ice cold water for the entire village.

Like they’re thrilled to be joining the middle class.

Even if it’s the bottom of the middle class, right?

They’ve taken hundreds of millions of people in China

and moved them into the middle class.

And we’re like, oh my God, these people are suffering.

It’s like, they’re up to $4 an hour,

three or $4 an hour in the factories there.

And they were just two decades ago at,

I don’t know, it was probably 50 cents an hour,

something crazy like that.

And now they’ve improved the quality of life there so much,

just like America did 200 years ago or 100 years ago.

They’ve improved it so much in China

that now they’re getting outpriced for factories

from Vietnam, Sri Lanka, Pakistan, India,

and people are moving and people in China

are moving the factories out of China into other countries.

Because the Chinese are now outsourcing to Vietnam

and other countries.

So this is the way of the world.

People move up and they get a better lot in life

for their families.

And just in America, we’ve gotten soft.

And there’s a generation.

How do people die in America now?

Suicide, obesity, heart attacks, anxiety.

I mean, we’re suffering from things

that if you told people 100 years ago

that the number, the top ways Americans would die

would be overeating and suicide,

they’d be like, what?

You’re literally killing yourself

or eating yourself to death?

That’s what’s happening in America?

And when everybody, not everybody en masse,

there’s a large number of people

who have become softer and softer.

Capitalism creates an environment

where there is people that still step up amidst that

with a big dream and challenge the conventions.

And that human spirit just arise above that.

Elon’s example of that, Jeff Bezos’s example of that.

Countless, countless examples.

And they push the limits of those,

of human beings that are willing to step up.

And I think about sort of how to create a company

that amidst all of this softness

still creates a revolution.

It’s not, it doesn’t seem trivial.

It seems like how do you build a culture

that’s once healthy, but also unhealthy

in the way that an Olympic pursuit is.

It’s all top down.

Everybody just, you asked earlier what leadership was

and I never answered the question.

I think what leaders do is they set the example,

they set the bar.

And if you look at someone like Elon,

we’re personal friends for 20 years

and he is indefatigable.

Like, I mean, the guy has a stamina that is just phenomenal.

Like he does not get tired.

He works relentlessly

and he sets that standard for the rest of the team.

And I think Bezos is very sharp

and likes to debate stuff and is very,

and Jobs was just incredible at design

and figuring out how to bridge that gap.

So they just, leaders set the standard.

They set the standard.

And you know that your time is over as a leader

when you can’t set the standard.

And that’s when you have to pass the baton, right?

And Bezos did that.

And Bezos now is saying, you know what?

I’m 57, I’m the richest guy on the planet,

depending on the week.

And I would like to do some other challenges,

but I don’t wanna grind it out at Amazon

for another 25 years.

I wanna do other things.

And so he passed the baton.

And that’s the healthy thing to do in that regard.

I do think there is a time period

in which you can run that hot.

And then at a certain point you have to then change.

Just like an athlete might go to be a coach, right?

Or a commentator.

And so being an entrepreneur is brutal.

It’s seven days a week, 12 hours a day.

Anybody who says anything differently

is kidding themselves.

You’re gonna have to sacrifice.

And this competition, and America has to fight.

If America does not win capitalism, and China does,

it is literally the end of the human species.

It’s over for humanity.

Right now, everything has been going really well

in terms of the number of people living in poverty

is plummeting.

Lifespans have been rising.

Science is booming.

The economy is booming.

All these things are incredible.

The one thing that’s kind of stagnant right now

is the number of people living in democracy

versus under authoritarian rule.

It’s flat.

So when you look at all Steve Pinker’s charts,

and he’s really excited,

there’s one you’re gonna see that’s flat.

And I think we peaked with 53 or 54% of people

on the planet Earth being in a democracy,

and now it’s going below 50.

And it’s because some of the democratic Western countries

don’t have the population growth

of some of the communist and socialist countries

and authoritarian countries.

And we have to make sure that we win capitalism.

We must win economically.

That is the battlefield.

The battlefield is science, technology, and money,

and economy, finance.

That’s the battlefield.

China wins, authoritarians win.

And at any time, Xi Jinping can pull Jack Ma into a room

and say, it’s time for you to be reeducated.

Or they can put three or four million people,

Uighurs, into prison camps and say, you know what?

This religious thing,

that’s counter to what is productive for us.

Therefore, we’re gonna shave your heads

and we’re going to have you

literally pick cotton in the fields.

They have Uighurs with no sense of any kind of

arc of history in the fields picking cottons

as slaves in what can only be described

by every humanitarian organization as a concentration camp.

And every Jewish person I know takes great offense

when somebody uses the Holocaust as a metaphor,

except in the case of the Uighurs right now.

And every Jewish person I’ve talked to has said to me,

that is a Holocaust.

That is millions of people going to genocide

because of their religious beliefs.

And I’m an atheist,

but if people wanna believe a certain religion, fine.

But China’s approach is we need to win capitalism so bad,

we need to win on the global stage so bad,

we can’t have any of this religious stuff going on here.

That is a distraction from winning and beating America.

And then in America,

the people who are gonna make us win are the entrepreneurs

and the scientists and the technology

and our education system and finance.

And we’re vilifying those things.

It’s pretty dark.

It’s dark, but I still believe that the vilification

is just in the space of Twitter and the space of ideas.

I think that’s probably a good.

And entrepreneurs win out in the end.

They don’t listen to that.

I believe we’ll win.

And they’ll build, we’ll get the rocks up.

Some of them do actually in their darkest moments,

I can tell you that they turn off their Twitter accounts

and they, I’ve had to sit down

with a number of entrepreneurs and say, turn off Twitter.

This is not healthy for you.

This is not a healthy pursuit because,

don’t read the comments.

If you do, it’s like a full contact sport.

You should just take it as like professional wrestling

or something, but stay focused on building companies

and advancing the human species

through science and technology.

I mean.

As you’re describing, you’ve hosted this week in startups

for how many episodes?

11 years, almost 1200 now.



So you’ve talked to some of the great leaders

in business in general.

Is there a common thing that you see or?

Really, I’m in a relationship with their parents.

Like just find me a great entrepreneur.

I will, show me the trauma.

Their dad was like, you’re not good enough.

In the teenage years, is that truly, is there something?

There is definitely something.

Hardship at some point in their life kind of thing?

Yeah, I think so.

I mean, and there’s definitely something

with immigrant parents that is a bit of a stereotype

out here, but I’ve heard from many investors,

like that’s like their, oh, were your parents immigrants?

And did they beat into you that you have to succeed

and you feel the need to succeed

because they suffered to get you to this country?

Like there is an archetype there that I hear.

When I started investing, I heard from a lot of people.

It’s like, yeah, you wanna find those immigrant founders

who are coming out of Stanford

because they had to fight to get there

and their parents had to fight, right?

So it was like two huge fights and there’s so much at stake

as opposed to somebody who’s fifth generation

and like had everything handed to them

and they were legacy and got into schools for free.

But I think in general, the ability to get people

to join you on that journey is so critical.

So you have to be charismatic

and it doesn’t mean like you’re an extrovert.

There are introverts who are super charismatic

and there are soft spoken people.

They don’t have to be like super vivacious

or rambunctious people.

They could be just quiet assassins,

but you need to be able to get people

to come on the journey with you.

You have to be that storyteller

and you have to have that passion

and then you have to transfer that enthusiasm to investors,

the press, to customers, to all the stakeholders.

And if you’re enthusiastic about it and you’re engaged,

then it’s easier for people to come on that journey.

And that’s why people really start to think about,

well, what is the purpose of what I’m doing?

And it sounds corny and when I first heard that,

I was like, it’s kind of corny.

But then I read this book by,

I’ve got his name, Rick something.

He wrote the purpose driven church

and he had spoken at a TED or something

and everybody went crazy about it.

And he’s like, a church should have one purpose,

one single thing they do.

And like his church,

which was like one of these mega churches in San Diego,

just wanted to do education for this specific country.

And that’s all they did.

And they just, they benchmarked.

I think it’s very important to have a purpose and a mission,

not everything, but a specific purpose of some kind of joy

that you wanna put into the world.

You wanna solve some kind of big, hard problem.

And then everybody knows

why you’re coming to work every day.

And then for the founder,

when you dread going to work that day

and you don’t feel like solving that problem anymore,

that’s the tell.

And a lot of times I meet young founders,

I’m like, why are you doing this?

And they’re like, well, I was looking for an idea

and this is the one I came up with

because I think I’ll make a lot of money.

And it’s like, you’re gonna quit.

You’re gonna get to month nine or 10 of this

and you’re gonna run out of money

or like your CTO is gonna quit,

then your CFO is gonna quit

and you’re gonna lose your biggest customer

and you’re just gonna say, this is not worth it.

And if using Bezos or Elon as examples,

they just needed to see the world change

in very specific ways.

And Steve Jobs, they needed to see a change

and it doesn’t matter if they made money

or they were losing or winning,

they just went to work every day and they had to change it.

It’s almost like they didn’t have a choice.

No choice.

Elon makes it sound like his torture, his whole journey,

but he can’t help it.

Having been a witness to it, just as friends for that long,

I have never seen an entrepreneur suffer more than him.

And he’s been public about that, like you do not wanna be me.

He has suffered for those companies.

He has suffered to get them where they are.

It has not been easy.

Can you second analyze Elon in that aspect?

Like, is it just he can’t help it?

He must see the change that he hopes for in the world.

He’s just incredibly hardworking

and he’s very talented as well.

I don’t think people understand that.

He actually is a really brilliant man.

He actually is a really brilliant engineer.

At the end of the day, he actually knows what he’s doing

and he asked the right questions.

I mean, people were kind of aghast

that he was asking Vlad such good questions.

And they’re like, oh my God,

Elon’s the best journalist on the planet.

And it was like, anybody who knows Elon knows

he has great questions.

I mean, I used to have dinner in LA

and my book agent also was Sam Harris’s agent.

And Sam and I met through John Brockman

and we became friends because we lived near each other

and I was friends with Elon.

And then I used to invite them to both dinner in Brentwood

because one lived in Bel Air,

one lived in Santa Monica and I lived in Brentwood.

And we would go to this place,

Popone, this Italian restaurant.

And every Tuesday for years, we would just,

the three of us, every other Tuesday or so,

we’d have dinner and I’d sit there

and Sam wanted to know about AI

and Elon’s talking about artificial intelligence

because he’s on the board of DeepMind.

Elon wanted to know about atheism and meditation

and all this other stuff that Sam was an expert on.

I got to sit there and just listen to these two guys talk.

And they have both piercing intelligences,

but Elon, he goes straight to the gut,

like the questions that no engineer wants to hear

is just the basic stuff that,

it’s like, why the hell are you doing it this way

when the obvious solution is much easier or this or that?

Why haven’t you tried this?

He can figure things out.

I mean, he’s a problem solver.

I mean, and that’s another thing,

like I think the great entrepreneurs

can look at a problem with very fresh eyes,

like almost consistently.

And Bezos described that as day one thinking, right?

Like just pretend this is day one every day.

And then other people use the term first principles,

but it basically means like when you see a problem,

pause for a second and really think through

what is the best possible solution here?

What are some alternative solutions and get from everybody,

like how do we solve this problem?

What people do sometimes they get in a rut.

They just come to work and they just go through their email.

They do whatever they did the day before.

They don’t think, why are we doing this?

And is there a better way to do it?

Now you can get so obsessive about that

that you can over engineer stuff

and you can never actually ship a product.

So there have to be some pragmatism and some goals

and some dates associated with that.

But it is a very cool thing to really think like,

I wonder if we actually made the batteries ourselves,

what that would look like.

Or I wonder if we could get to two day shipping,

or what if we do same day shipping?

Like you need to have somebody who’s willing to say,

you know what, fuck it.

Let’s set a crazy audacious goal.

Two day shipping of any product

anywhere in the United States.

And once you throw the gauntlet down like that,

now everybody knows they’re rolling in the right direction.

Two day shipping, Amazon Prime.

And that’s what people didn’t realize about Amazon.

The business wasn’t shipping all those products.

It was getting you to sign up for Amazon Prime.

They have hundreds of millions of people doing Amazon Prime

for 10 bucks a month.

I think globally it’s probably cheaper.

But that was the driver of that business

was all of those people.

Cause they would, you’re an Amazon Prime subscriber?

Do you know how much you pay?



It started at $50.

And I think they even had like 40, 50, $60

was like the testing in the early days.

And now it’s, I think $149, 12, $13 a month.

If you pay for the year,

I think it goes down to 10 bucks a month, 120.

And you’re like, wow.

And it’s like, yeah, you’re paying $13 a month

for the privilege of shopping at Amazon.

But you say it’s the greatest thing in the world

because anything I need,

if you forgot a microphone or a cable goes bad

or a camera goes bad, you get it here within a day or less.

It’s pretty amazing.

You’ve already been dropping bombs,

incredible advice on startups in general.

But let me maybe go straight in and ask,

is there advice for somebody that wants to go big

to build the big startup to help them succeed?

Yeah, it’s very similar to the advice I give to investors

because now I teach angel investing

because there’s so many people who want to invest.

And so I wrote a book on that angel

and then I do a course called Angel University

that I teach six times a year.

And then I have a syndicate called thesyndicate.com

where I invest in companies.

There’s 6,500 people who are members of that.

It’s the largest syndicate in the world.

In fact, the first deal we ever did was calm.com,

the meditation app.

We put $378,000 into it

when it was a $5 million product.

A $5 million company.

So we bought six or 7% of the company.

It’s now worth 2 billion.

So you can do the math on that.

We still own 5%.

What year was that?

Six years ago.

So probably seven, yeah, maybe 2015, 2014.

And nobody else would invest in calm.

But Sam Harris was the reason I did because I asked Sam,

tell me about meditation.

And he’s explaining it to me.

And I said, what about this?

You have to have like a mantra.

How does it work exactly?

I know positive.

He was like, well, you know, you should just go to UCLA

and talk to Diana Winston.

And like, there’s this whole project there.

And I’m like, UCLA does meditation?

He’s like, yeah, there’s a mindful institute.

They’re like teaching people to be Tahitian meditation.

And they’re doing PTSD and I’m doing brain scans.

And I was like, oh.

And then I talked to the UCLA people and they’re like,

it’s real, yeah, like we taught Phil Jackson

and Kobe Bryant and Shaquille O Neal did,

you know, that’s how they won their championships.

They meditated.

And I was like, hmm, if UCLA is doing it,

Sam says it’s cool.

Well, fuck it, I’ll put money into that.

And that’s the second biggest investment

in my career after Uber.

And it will in all likelihood become the biggest.

I mean, it’s between Uber, Robinhood and Calm.

And long story short,

when I’m teaching people to angel invest,

there’s really two things that you cannot fake.

One is a product that is built really well.

So if you look at Calm, Robinhood, Uber, Tesla, Amazon,

these products are transcendent.

They’re well constructed.

There’s craftsmanship to them.

They’re great products.

So you’re saying not fundamentally like the idea,

but the execution of the actual craftsmanship

of the construction.

The actual product is amazing.

Then there’s customers.

And that every business has ultimately a customer.

And that customer, if they are in fact delighted

by that product, that’s the magic.

Because you need a team to build the product.

And then you need customers to use the product.

And really those three vectors are undeniable.

Now, you can have great teams that build a bad product,

doesn’t happen too often.

Or you can have customers who don’t like the product,

but generally speaking,

a great team will build a great product

or a good product that iterate,

and then eventually delight customers.

And so most people say the team is the most important,

but there’s a lot of smart people out there.

And let’s assume that you can raise money for your idea,

or you have money,

or you can just convince people to do it for free.

If you make a great product and it connects with users,

that’s the magic.

You look at Clubhouse,

it’s actually a really well designed product.

And that product is connecting with customers.

And if you were to talk to the customers

or look at the product,

you would see a well constructed product

and a delighted customer.

And you can tell the delighted customer

by just the amount of time they use it.

That’s called engagement.

It’s the fancy word for how much they use it.

And Snapchat, when that was going around

and they were trying to raise money,

they had a fraction of the number of users,

but the top maybe third were opening the app every hour.

And nobody had ever seen that before.

People were using Facebook a couple of times a day,

the top users,

but nobody had ever seen people using it every day

for a hundred days in a row, every hour.

And I was like, what’s going on here?

It’s like, oh, the ephemeral messaging,

and then the streaks.

They had created these streaks between people

where every day and then people would be like on vacation,

like, I just have to open my streak

and keep my streak with Lex

that we chatted every day going.

And so they had this like addictive nature to it.

And that’s why Clubhouse was able

to garner so much investment

is the number of hours people were using it every month

was just unbelievably off the charts.

Some of that is execution,

but some of it is the weird magic of the…

Product market fit.

Yeah, so there’s something, I mean, Clubhouse,

there’s a, it’s still a mystery to me

because I also use Discord voice.

There’s an intimacy to voice.

Oh, for sure.

Well, you have people’s, yeah, tent.

It’s, well, but like the video gets in the way actually,

in a weird way.

There’s a privacy when you just use voice.

People are not taking showers now, Lex.

I mean, we’re in a pandemic and people just roll out of bed.

And the hair thing, nobody’s getting haircuts.

Nobody’s hair is good, nobody’s getting haircuts.

People are wearing gym clothes.

I mean, Zoom is just horrific to be on Zoom

for five hours a day.

It is exhausting.

Well, it does make me wonder what,

once we emerge from the pandemic,

whether a product market fit,

how that evolves with Clubhouse

and all those kinds of things.

Yeah, I know Clubhouse is a beneficiary

of the pandemic for sure.

When do you think the pandemic,

when do you think deaths will be under,

let’s say 200 a day and we’ll have 200 million people

on the other side of this?

Because that’s kind of what it takes, right?

You gotta get to 150, 200 million people

on the other side in America?

I haven’t, you know,

I personally stopped deeply thinking about this

because I’ve been frustrated for so long that.

You checked out.

I almost checked out

because it psychologically allows me to carry on

because I thought for many months now

that testing needs to be done at scale.

And it still hasn’t gotten done.

It hasn’t been.

It’s so ridiculous.

We gave up basically on testing.

We gave up.

Because we’re, and we’re all sitting there

waiting for vaccine to come along.

And the distribution of the vaccine is not, you know,

it’s struggling from the same kind of things

as the testing.

It’s gonna take quite a bit of time.

So it does, if everything goes great,

meaning there’s not a second strand of the virus

that’s going to create a second major wave

that I am cynical enough to think

that it won’t be until mid summer

that we start opening back up.

Yeah, I think it’s gonna be May, June.

I’m a little bit earlier than you.

I’ve been tracking it.

There are 1.5 million shots in arms a day.

I think this vaccine’s been undersold.

I mean, it’s a miracle.

Not one person who was in the trials died, who took it,

and only one went to the hospital

and they weren’t even put on a ventilator.

So, and the hospitalizations are plummeting

and we’re at 10% now in the United States.

At the pace, we’re going at 1.5 a day.

I think when the Johnson & Johnson one comes out next month,

it’ll be 3 million a day maybe, two and a half.

And we already have 100 million people

who’ve likely had it.

So I’ve been doing the math.

I think we’re like 60 days away, February, March.

Yeah, sometime in April, I think.

Anybody’s gonna be able to get a shot

and the number of deaths is gonna go below 200 a day.

And once that happens,

I think people have had enough of this.

They’re just gonna go YOLO.

But see, the crucial piece for me

that I’ve been focusing on is the social media aspect

of how the, it’s not just about the reality of deaths.

It’s about the state of the collective intelligence

of the human species,

which is determined by our communication on social media.

So yeah, we can be collectively afraid,

the fear can spread, or it could be YOLO can spread,

or it could be like all different kinds of misinformation.

And of course, during the election year,

the politics influences our perception of what is true

and not, but having real rigorous nuanced conversation

about this kind of stuff is the way out of this.

And that’s where social media really comes in

because social media drives division,

where people form tribes and so on.

And it feels like it’s honestly a technology problem.

People say it’s a human problem,

but it just feels like, I believe humans are good.

Technology can enable them to be thoughtful.

We talked earlier about the magic of Silicon Valley

and then maybe going too far

with the Facebook groups example,

where you take out all that friction.

What happened was we used to have something called Rchron,

reverse chronological order.

That’s how you consume to feed.

So any kind of social feed,

like Twitter was in reverse chronological order.

The newest thing was up top

and you would just work your way backwards.

And so it gave this like really fresh feeling.

And then a guy named Dave Moran

and the team over at Facebook realized,

you know, there are some things

that got a lot of attention two hours ago.

And the stuff since then has not been as important.

But if you miss that, there was a really good tweet

where there was a really good update.

Like somebody had a baby.

Can we get the baby one at the top?

And it was like, well, how would we do that?

How would we know that that’s the important one?

It’s like, well, let’s put a like button on it

and let’s see how many comments there are.

So if it gets a lot of likes or comments or retweets,

let’s show those first

and then we’ll kind of mix in the most recent stuff.

And so when you’re on Twitter,

and then when Facebook did that,

Facebook became so addicting

because Facebook was on,

what has got the most engagement?

Put that first.

So every time you opened up Facebook,

you get the dopamine hit.

And then what happens when you see the Bar Mitzvah photo

or, you know, the enraging story

about some injustice in the world?

You retweet it, you write a comment,

you share it on your wall.

And thus this addiction to the outrageous,

the outlandish, the inspiring occurred.

And it used to be like inspiring stuff,

puppies or some heartwarming story.

And then it got dark.

And then people started to realize,

if I wanna show up on the top of my friend’s feeds,

if I say something controversial or I’m outraged,

I get to the top.

And then that’s when outrage culture came in.

And then that’s when cancel culture came in.

Everybody started to realize,

if I try to cancel that person for being a racist

or a sexist or a horrible human being

or whatever they did that’s wrong,

I get to the top of the feed.

And we all collectively started playing

a very weird video game,

which is how outraged can we all be?

And to get to the top of the list.

And then of course, with Trump, he realized it.

And he’s like, okay, yeah,

I’m just gonna make fun of a celebrity

and I get more retweets.

Okay, I’m gonna make fun of Rosie O’Donnell

for being overweight or something.

And he just starts attacking people.

And people are like, oh my God, what did he say?

And he copied that from Howard Stern.

Cause he was in New York and he used to be on Howard Stern.

Howard Stern took over all the dialogue

in the eighties and nineties because he was outrageous.

And then Trump did that.

And then social media incorporated that

into the operating system.

It became the actual device of social media

was the ding, ding, ding, ding, ding.

We’ve got something incredible for you.

Everybody salivates like Pavlov’s dog.

Oh my God, I can be outraged.

That’s what’s gotta be undone.

And the only way for that to be undone

is these things can’t be billions of people

where the most outrageous thing

that happened in the world today

in the last five minutes is now in front of you.

And that’s why people have anxiety.

They don’t sleep and they doom scroll all night.

It’s because the human mind was not meant to process

this much suffering, pain, anger.

And that’s why we have all this mental health issues.

Also, young girls or even adults watching other people

post their private jets and their vacations

and YOLO adventures on their Instagram

to the point at which young people are now faking

being on private jets to put on their Instagram

and creating this crazy FOMO around their Instagrams.

We wonder why people are unhappy.

If you think everybody’s on a private jet

going to some Michelin star restaurant

or whatever the coolest thing in the world is today,

going to the Grammys, going to whatever,

Coachella, Burning Man.

You’re like, ah, but I’m home.

I’m in my house and I’m not at Burning Man.

Getting inadequate.


So this whole system is creating

the wrong set of incentives.

I tend to believe it’s possible

to still have extremely high engagement

and create a successful profitable business

while encouraging personal growth,

like encouraging people to be the best version of themselves.

I just think we haven’t,

we got the first generation of social networks.

I think a new generation needs to be built.


Is that your plan for a business?

Well, I have a longer term plan in terms of ambition,

which is I believe in being able to have deep connection

between human and AI systems, like partners, friends.

There is a connection to there with social media.

I do think AI has a strong role to play in representing us,

in guiding us in how we consume social media.

So this algorithm that controls the feed for Facebook

is a somewhat centralized algorithm,

but instead to give more power to the people,

individuals to where each one of us have our own algorithm.

Bring your own algorithm.


BYOA, I like it.

Instead of bringing your own alcohol,

bring your own algorithm.

Well, I mean, if you thought about it,

if we came and said, when I look at my Twitter feed,

I would like to see the people with,

who are the most helpful in the world,

generous, kind, intelligent, considered,

commenting on things that I don’t already know about

because I want to open my worldview.

That could be a beautiful thing for society.

And actually Jack was talking about potentially on Twitter,

letting people bring their own algorithms

and sort their feeds themselves.

This would be a wonderful thing.

I think it’s one of the reasons Clubhouse has resonated

is it’s such a diverse group of people

that I’ve been able to drop in on conversations

with people who are nothing like me

and listen in and hear conversations

that I wouldn’t normally be privy to.

And everybody’s like, oh, come join as a speaker.

I want to do a room with you.

I get asked every day, can we do a room?

Can we do a room?

Ask an angel investor, talk about startups.

And I’m like, my usage of Clubhouse

is going on my Peloton treadmill,

putting Clubhouse on, picking a room and just listening.

It’s so delightful for me as a podcaster

where my job is to talk, to sit back

and just put in a couple of miles and play chess

and listen to a Clubhouse discussion

that is about relationships or some fashion or hip hop

or whatever it is that I’m not part of.

I just sit there and I listen and you learn.

It’s like such a delightful thing.

I always think about these kids who go to college

and I’ve always been so jealous of these Ivy League kids.

They go and they’re like, oh, I got to go to class.

And I’m like, I would just love to sit there

and listen to Professor Lex talk.

What a privilege to sit there

and let somebody else drive and talk and listen and learn.

Yeah, that’s the beauty of podcasting.

But of course, Clubhouse creates a whole nother experience

where it’s conversations, it’s different.

I think it’s going to be the in between.

I like it as a, you release your podcast.

Like you and I are going to release this podcast, right?

And then at some point I’ll have you on my pod

when you want your startup.

And then at some point somebody is going to be like,

you and I will run into, and I ran into you.

I saw you were on Clubhouse the other night

and I was busy, but I was almost going to click on you

and say, let’s start a room together.

But you and I will start a room together

with Eric Weinstein or somebody

or Sam Harris will jump in or Elon

and we’ll have a different experience,

which would just shoot the shit.

And it’ll act as like a fabric

and a little filler between the tent pole podcasts, right?

Like you and Eric, you’ve done three, I think, with Eric.

Yeah, it was your four, I haven’t released the fourth yet.

Oh, okay, so I watched all three

because I really thought your you way

and him like giving you advice

is very interesting dynamic.

I thought it was very interesting dynamic.

And I find him like a fascinating cat.

We know everybody in common, except we’ve never met.

It’s very weird because you think about the social graph

in the real world.

This is why I think augmented reality

is going to be such an amazing product.

I just have one killer feature I want

for augmented reality, we wear our glasses.

And when I look at you above your head,

I see the relationships we have

and the things we’ve done together, right?

So I see, oh, you both know Sam Harris

or you had Elon on the podcast on this date

or you and I were both at Burning Man in 2016.

So it’s the most meaningful element

of our connection in the network, yeah.

And then, cause we would discover that through small talk,

but imagine you’re like at a party and you look

and it just, people glow and you just see a glow

around a person and like green means

you have some financial relationship.

Blue means you have some friendship one

or yellow means you have friendship one.

Blue means you know nothing about each other.

You have no connections.

You’re like, wow, these blue people have no connection to.

These people, that one’s glowing red.

We know seven or more people in common.

And those are the seven people.

Oh, we should go talk about how we know each other.

That could, and that sort of happened with Facebook member

or MySpace where you were like, oh, you know that person,

friend of a friend.

But that’s what is going to be AR is like,

this is why I think if Apple figures out AR or Snapchat

and they just have those glasses, you know,

forget about VR, it’s just nauseating and whatever,

but AR where you put the glasses on,

you see the real world, but you augment it.

You make a, just like you were saying,

you make a frictionless, a very low friction

to make a deep human connection

because you have all the basic elements there already.

Now think about the unintended consequences

of what I just described.

It could get creepy and weird.

The privacy thing.

I mean, people will, here’s the thing,

people, your privacy is an illusion.

Like all this information is there.

And then people are more than willing to give up privacy

in exchange for some value, you know, it’s a value trade.

And giving, if my Tesla,

when I’m driving in the direction of my house,

just starts the navigation and saves me three clicks

and that friction’s gone,

I’m willing to give Tesla my location

and my home address, right?

I’m not willing to give Zuckerberg anything

because I don’t trust him, but you get the idea.

I mean, it will be that way with like DNA and other things

at some point we’ll just be like, yeah, just take my DNA.

Like I don’t, yeah, sure.

People can look and see that I’m a mental midget

and my IQ is like lower than,

I don’t want to bring the bell curve up or whatever,

but you could figure out,

like if we all put our DNA in a sequence online

and be like, oh yeah, you know, Lex has got 10 more IQ points

than Jcal and, you know, Sam’s got 10 more than Lex.

And all of a sudden people are like all bed out of shape

about it, but what if they, we did that?

And they were like, and by the way, you also,

all three of you are going to get Parkinson’s

unless you do X, Y, and Z,

unless you eat more blueberries or whatever we figure out.

They’re going to accept it pretty quickly.

Yeah, that’s brave new world.

Brave new world.

I have to ask you, you’re, just like you were saying,

you’re one of the world experts in investing

and in startups, yeah, VC and so on.

From the perspective of the startup,

I was always kind of skeptical of raising money.

It feels like people do it too quickly, too easily,

but I don’t know what the hell I’m talking about.

When is the, when should a startup raise money?

And from the perspective of the investor,

when should the investor invest in a startup?

Like, is there a timing thing here?

Is there a, what, yeah, what?

It’s a very important question

because the venture capital community

is only going to fund, you know, sub 1% of enterprises

started in the United States every year,

like maybe 10 basis points of them, like one in a thousand.

And the reason is it’s jet fuel.

You only want to take that money

if you really want to build something big

and you want to build it fast.

And when you put jet fuel behind a startup,

as we’ve seen with other rockets,

things can blow up and people can die.

You know, it’s not people literally dying,

but the business can go up in smoke, right?

Like rockets get blown up all the time at SpaceX

as part of their ambitious plans.

And startups, seven out of 10 startups we invest in,

go to zero.

Now, if you were to start the business

and only build it off customer revenue

and use your own money and go nice and slow

and grow 10% a year,

the chances of you blowing up the rocket are very low

because you’re riding a bicycle.

You can go a little faster,

but the bicycle can only go so fast.

And once you start taking that money,

the way venture capital is constructed

as in the mix of like MIT or Harvard’s endowments is,

you know, we’re going to put some money into safe things

and then we’re going to have

these really binary things over here.

And they probably put 5% in venture capital traditionally.

It’s grown to 20% just as a function

of how successful it’s been.

So, you know, the Harvards of the world and MIT

is probably want five or 10% in venture,

but it’s grown to 25% because, you know,

companies like Airbnb and Uber have grown so big and Tesla.

But the goal is in these venture funds,

we’re going to invest in 30 names

and one or two of them are going to return three times

the capital we’ve deployed.

So it’s a $300 million fund and there’s 30 names

and they each got 10 million.

That means one of the 10 million

is going to return the fund plus.

So that means it has to grow 30X and then 60X

to double the fund.

And you’re really supposed to be doing

three times cash on cash.

So that $300 million funds,

the expectation is in 10 years to return 900 million,

triple the person’s money as opposed to the stock market,

which doubles your money in the same period.

So you’re supposed to do 25% annualized returns

in order to triple the money.

And maybe I have an outlying chance

of four or five times the money,

which does happen sometimes when you have an outlier

in your portfolio like Uber or Facebook was.

And what that means is the venture capitalist behavior

in the game they’re playing is different

than you as the founder.

You as the founder, you may really care about this

and it dying really matters to you.

And then you got a venture capitalist who’s like,

we’re betting on 30 names,

we need two of them to hit it out of the park, maybe three,

and nothing else is meaningful.

So now you start thinking about the game theory there.

You’re dealing with money that is coming in

that only cares about you going 100X.

It’s a whole different ball game.

Whereas if you build off revenue, you don’t have to do that.

And if you look at a company like com.com,

we invested at 5 million, the next round they did was 250.

They were so capital efficient

that they grew from $10,000 a month in revenue

to millions of dollars a month in revenue

over those four years since we invested

and they didn’t raise money in between.

It was unbelievable.

And I’ve only seen this happen three or four times.

So it doesn’t happen all this capital efficient meaning

based on customer revenue alone

plus some small amount of fundraising, you’re able to go.

Like how hard is it to do that?

It takes extreme product market fit.

You have to have a great price for your product

that has a great margin.

Yeah, and if you’re doing something in hardware,

it’s probably impossible

because it’s super capital intensive.

So it’s probably gotta be a software business.

Hardware businesses take a lot more.

Do venture capitals get in the way at all of the business

or is it possible to get out of the way?

Yeah, if you get young venture capitalists

who are starting their career,

they’re very nervous and scared

because they’re putting all these bets.

And then there’s a very weird thing that happens.

The bad news comes first.

So companies that don’t work out

go out of business immediately.

So if it’s not gonna be Com or Robinhood or Uber,

you know you have one of those great successes

somewhere in your five, six, seven, eight as an investor.

What is the first five years like?

First five years, you feel like an idiot.

Let’s say you make these 10 bets.

In year two, two or three of them come back

and they don’t have product market fit

and they’re out of money.

And they say, can we have more money?

You say, no, we have to go get it from somebody else

because you have to prove

that there’s still a market for it.

We may keep our pro rata.

We may put a little bit in

to maintain our percentage ownership,

but we’re not going to give you another big chunk of money.

And that company dies.

So now you’ve got 10 million, poof, up in smoke.

Boom, 10 million up in smoke.

So this is called the J curve

where your performance goes down.

And then it’s only in years four or five and six

it starts going up.

And what you’re seeing right now is the people

who started like I did in 2000,

you know, just 11, 12 years ago.

In 2009, I started investing.

We all look like geniuses.


We’re at the end of the cycle.

We invested after when the stock market was on the floor

after the financial crisis.

And it’s gone straight up since.

So everybody looked,

there’s a couple of little blips in there,

but generally speaking,

there hasn’t been like a major crash

with the exception of the pandemic crash,

but that bounced right back.

And so, you know, it takes a decade to figure out

if you’re good at it.

And then if the market crashes again,

everybody feels like an idiot again,

the cycle starts again.

So you are now as a founder,

you are now inserting yourself into that casino.

And now you’ve got all these other forces

pushing and pulling.

And you’re growing,

let’s say your company was growing 50%.

You feel like, wow, I’m successful.

I made a million dollars last year.

Now I’m doing a million and a half.

And the first thing a VC is gonna say to you is,

how do we triple?

We’re growing too slow.

See, but that’s, like you said,

that beautifully is a rocket fuel.

It’s, in a sense, it’s a kind of motivation.

It’s a drive.

I mean, it’s a positive.

So if you want that.

Yes, if you want that.

If you want that,

if you want to go to Navy SEAL school,

you’re gonna be in pain

and they’re gonna put that hose in your face

while you’re underwater

with your hands tied behind your back in the pool

and you’re gonna be choking.

And they may have to do CPR on you.

And like every couple of years, tragically,

somebody dies in Navy SEAL school.

Yeah, well.

Does it mean we’re getting rid of the Navy SEALs?

Brock, if he dies, he dies.

I don’t know if you know David Goggins

as by any chance.

I do.

I mean, I don’t know him personally,

but oh my Lord.

So I’m running 48 miles together with him in person

in a month.

What, you’re doing an ultra marathon?

With him and probably other stuff

because he enjoys just breaking people,

making them cry.

Oh my God, I’m so jelly.

So no, well, I offered,

we agreed a while ago to do a podcast

and he’s like, oh yeah, come, we’ll do it this day.

Is he in the Bay Area?

I don’t know where the hell he is,

but we’re doing it.

And I don’t think I’m supposed to say where it is,

but it’s not anywhere close to anywhere of this.

It’s in the middle of nowhere.

But he seems to be in a bunch of different locations.

Like he’s in Oregon or something like that.

What does he do for outside of writing books

and being inspirational?

Does he actually train people or like?

No, he’s just, he’s a full time insane.

Like he fights forest fires like for a few months a year

as a farmer, like unpaid labor.

Like he, you know, there’s a bunch of people

who are like him, like Navy Seals and so on

that kind of make a career,

automotivational speak and all that kind of stuff.

He’s not interested in any of that.

He’s literally interested in just doing hard shit

all the time.

Breaking himself.

Breaking himself personally.

He seems like he wants to break himself.

And that book is amazing.

And the audio book’s amazing

when he’s talking about how fat he was

and how he just had to go and keep running

and his like legs are broken and he’s just super pain

and he just goes through it.

It’s really inspiring.

Inspiring thing also.

You could have videotaped yourself doing this.

I can’t wait to see you get destroyed.

This is gonna be so entertaining for the lax audience.

The pain.

But the other inspiring thing is he’s happily married

and there’s a partnership there that’s, you know,

everybody finds this attention as a push and pull

that’s beautiful, I think.

But in speaking of a beautiful push and pull,

how about that transition?

Yeah, here we go.

You and Chamath on, he’s a friend of yours.

Besties. Besties, yeah.

Yeah, good friend.

I mean, there’s very few people in my life,

him, Elon, David Sachs, John Brockmans.

Very few people have supported me as much as those folks.

I mean, I’m a huge debt.

So he’s also cohost on the All In podcast.

We taped episode 21 today.

Oh, today?

Yeah, every Friday now.

They wanna do every Friday.

They’re addicted like me and you are to podcasts.

So you’re going to release it when?

It’s probably released as we’re sitting here.

Okay, beautiful.

Special guest on it.

We had Draymond Green from the Warriors phone in.

So we had our first guest.


Yeah, so it’s really funny

because he plays poker with us and we’re all besties, so.


So you guys went pretty heated against each other

versus on Robin Hood.

There’s just two things I wanna ask.

First, on the actual Robin Hood discussion

and the Wall Street Best discussion,

can you steel man his argument?

What was the nature of the disagreement?

Where, yeah, what is the little,

because I don’t think it’s as big as spaces

it came off as sounding.

What is the nature of the disagreement?

He felt that Robin Hood turned off trading

because the hedge funds told them to

and that they were bowing down

to the pressure of the hedge funds.

That’s not true, but in a vacuum of information,

you know what happens to people’s minds,

conspiracy theories abound.

And sometimes there is a conspiracy theory

and sometimes there’s just the appearance of impropriety

or a bunch of related things.

Like when you look at the Trump situation with Russia,

like was Trump trying to coordinate with Russia

or the Russians just screwing with a bunch of like neophyte

idiotic dipshits like Donald Trump Jr.

who don’t know any better.

And they don’t know that you shouldn’t meet with the Russians

and if you do meet with the Russians,

you are probably a useful idiot.

You probably should tell the FBI.

Like they’re just a bunch of idiots in all likelihood,

who knows?

And there’s a vacuum of information.

And there’s a vacuum of information, we don’t know.

And the Russians are trying to compromise everybody.

So would you call it a conspiracy

or would you call it an attempted conspiracy?

There was no conspiracy here.

What it was was Robin Hood needed to raise billions

of dollars to say solvent in all likelihood.

And they weren’t allowed to talk about it.

So they were forced into not talking about it

in all likelihood and had to come up with that money

or shut down.

And then what got me upset with Chamath

and we had a talk afterwards that people don’t know about,

I’ll talk about it here for the first time.

On Sunday, we had to have a little, we had to air it out.

Yeah, in the episode after you guys sound like

you’ve had a private, you’ve made up.

We had a private discussion, just one on one.

And we said, listen, we love each other, we’re besties.

We’ve always been there for each other.

What happened here?

And what happened there is I’m fiercely loyal to my folks,

whether it’s Chamath or Travis from Uber or Saks or whoever.

I’m just a loyal guy.

And I’m always ride or die with my founders.

If I invest in them, even if they make a mistake

and Uber made plenty of mistakes,

I always went on CNBC, on my podcast and said,

hey, we’re gonna fix these things.

I’m in touch with the team.

Mistakes were made, we’re gonna solve them.

This is a group of people with great intent

who want to make the world a better place.

And you know what?

I was hated for a period of time with Uber.

I was hated for it last week with Robinhood.

I got a lot of blowback.

But I think in both of those cases, eventually I was right.

Uber is doing great stuff in the world.

Robinhood is doing great stuff in the world.

And I like to be loyal to my investments

and my partners to just,

I feel like if you invest and you’re on the team,

you have really three choices.

You either fight for your team, you can go silent,

or you can throw your team under the bus.

And I’ve watched investors throw the team

that they invested in that made them a bunch of money

under the bus, not acceptable to me.

And being quiet’s not acceptable to me.

So I always ask the founder, do you want me to,

is it okay if I go out and defend you publicly?

If they say yes, I do it.

And then.

That’s beautiful, by the way,

because what else do we have in this world

if not friendship?

Loyalty means everything to me.

I grew up in Brooklyn where if you were not loyal

and you were not loyal to your crew,

then you were a Ronin.

You were out there on your own flailing in the,

trust me, you do not want to be on your own

in 1970s, 80s, Brooklyn, Manhattan.

You need to have a crew with you.

I’ve gotten into, you don’t want to get into a fight

with 10 guys and be alone or just be with,

you need a crew to survive.

So I just learned early on, my dad owned a bar,

just drilled into me being loyal.

And so for whatever reason,

I’m a bulldog when it comes to loyalty.

And Shemov came out and said,

these guys need to go to jail and they’re scumbags.

And I’m trying to defend them.

And I’m in a position where I can’t defend them

because I don’t have complete information.

There is no complete information.

It’s in the heat of the moment.

And then it becomes the number one story.

And it’s my number three investment.

And Shemov has a competing company, SoFi.

And he’s killing my guys.

And then I started killing his guys.

And then all of a sudden we’re like,

wait a second, we’re best friends.

And we’re swinging our swords at each other.

And we’re a group of the seven samurai who fight together.

When did we turn on each other?

And then everybody else who’s on the pod,

the two Davids, you know, both on the spectrum a bit,

they got a little Asperger’s or whatever.

No offense, Les.

None taken.

I’m not saying, you know,

but there is, you’re into AI and you might be somewhere.

It’s not a coincidence, yeah.

Might not be a coincidence.

Anyway, we upgraded the two Davids firmware.

We’re gonna upgrade your firmware after this.

I’ll give you, yeah, you’re on the 1.5.

You have the three emotions now.

Or should we add a fourth?

Do you wanna go with joy?

I’m on the 2.0 already.

You’re on the 2.0, you got the joy.

How’s it working out for you, the joy chip?

It’s difficult.

It’s painful. It’s difficult.

You’ll get there.

Just let it happen, Lex.

Just let the joy happen.

So anyway, we just talked about it offline

and we decided like, listen,

we didn’t pregame that episode.

And I happened to be skiing with my family.

I had taken the first like vacation

since this goddamn pandemic started.

And I was having a wonderful time.

And then this whole thing blows up.

I’m coming off the mountain,

just having a great time with my daughter skiing.

And you know, and then I’m mixing it up with him.

And you know, he had a short fuse about it

because he was triggered, he told me,

because he really feels like he’s fighting

to defend, you know, the every man.

And I was like, that’s what my team’s doing.

That’s why they named the company Robinhood.

We’re on the same side here.

And then over time,

we’ve started to see the explanation come out.

And you know, people who are friends

are gonna have disagreements.

In the podcast, it happened to happen very publicly.

And we didn’t know it was gonna become

the number one story in the world.

If Trump still had his Twitter handle,

this would not have been a story.

Trump would have said something about GameStop

and he would have coopted the entire conversation.

So in a way, going back to our censorship discussion,

I might actually be in favor of Trump being censored

only because how delightful has it been since January 20th

that we can all focus on something other than him.

He was exhausting.

I mean, the amount of cycles he took on our processors.

He monetized the conversation.

And now this is a little bit more of a distributed,

like this bunch of.

Yeah, everybody gets a chance

to be the number one news story.

Everybody gets a chance to discuss it.

So on a scale of one to 10, how much do you love Chamath?

Oh, it’s 11.

I mean, I love Chamath.

I mean, we played cards last night.

We’re besties.

And you know, I would literally jump

in front of a bullet for him.

I mean, what’s the lesson in that discussion?

Because it was super, I wouldn’t.

I think the love was felt and the respect was felt

throughout even when you guys

are going pretty vicious on each other.

Is there a lesson to be learned?

Do you regret any of that conversation?

No, I mean, I think he told me

that he regretted some of the things he said.

He said publicly on the podcast,

like, listen, I was a little hot.

I may have said things in the heat of the moment.

But I don’t live with too much regret

because I always think about intent.

As one of the nuance and intent have been totally lost.

The idea that we could have any kind of a nuanced discussion

about things seems to have been forgotten.

And the fact that people don’t look at people’s intent.

If you hurt somebody’s feelings or you disrespect somebody

or you do something mean or whatever,

I always look at the intent, you know?

And I’ve had people attack me and I look at the intent

and I’m like, that person feels bad about themselves.

Or maybe I said something and I insulted them

and that’s why their blowback’s there.

So I always try to think what’s the intent of the person.

And then almost universally,

you talk to somebody and you find out,

you ascribe some crazy intent that’s not there.

And they’re like, oh yeah, you know what happened?

I got in a fight with my spouse

and I didn’t sleep last night

and I’ve had a lot of anxiety about my business.

And I just snapped and said something about you.

And it’s like, oh, okay.

Like I literally had somebody on Twitter this past summer.

I had said something.

I was complaining about a New York Times journalist

and something I thought was wrong.

And this person was a fan of that journalist.

And they went, I kid you not, onto my social media account,

found a picture I’d taken about how blue the sky was one day.

They reverse image search the tree line,

found the tree line on Google image search somehow

with a reverse image search,

found an old listing that some broker had listed

on their website of my house,

and then posted my home address, the value of my home,

and doxxed me on Twitter.

And I’m like, what is going on here?

So I call the person and I look them up

and they work in private equity in Boston.

And I look and I’m like, this person works in Boston.

This is July 4th week.

So, and when I look at the person’s LinkedIn,

we have seven people in common.

So going back to the AR conversation real quick,

I’m like, okay, this person literally just doxxed me.

I asked them to take it down.

They told me they won’t take it down.

And then I look at it.

So then I DM him back on Instagram, on Twitter.

And I said, by the way, your boss, Susan,

and I know seven people in common.

And these are the seven people.

Here’s a screenshot.

What is she going to think when I call her on Monday

and you’ve doxxed me?

Here’s my phone number if you’d like to talk.

He calls me.

I said, what’s going on?

Why would you do this?

He’s like, well, I really pissed off

about what you said about this person.

I was like, you understand I’ve had like two

or three stalkers and anybody who’s a high profile

like I am or medium profile,

you’re going to have weird things happen.

You literally put my home address.

You put my family at risk.

What if I put your home address on my,

I have 400,000 followers or 300,000 followers.

You have like 300.

What if I post your address?

He said, well, I wish you wouldn’t do that.

I was like, well, I asked you kindly

to take my address down.

And I said, are you married?

I said, how old are you?

Are you like 25 or something?

He’s like, no, I’m 42.

I was like, you’re 42 years old.

I was like, are you married?

Do you have kids?

He’s like, yeah, I just had a baby like six months ago.

I’m like, you’re home with your wife.

It’s July 4th weekend.

You’re doxxing Jason Calagans because you’re upset at me

because I said something about a New York Times writer.

He’s like, yeah, this is the biggest mistake of my life.

I said, I tell you what, let’s forget it ever happened.

And he wrote me back and he said,

I just wanted to thank you for how you handled it.

My wife said I’m a complete fucking moron.

And he literally sent me an email.

My wife says I’m a complete fucking moron.

And I’m really sorry, blah, blah, blah, blah, blah.

And I wrote her back.

I said, I wrote her back and I said,

my wife says the same thing to me all the time.

I said, welcome to the club.

It’s totally fine.

But intent, nuance, it matters, right?

And the person could be having a bad day

and they do something stupid they regret.

And what am I gonna do, cancel the guy?

Or if I had called his boss,

he would have been fired immediately.

And then I got to live with this guy got fired

and he’s got a kid.

And what is this personal destruction?

Why are we doing this to each other?

Life’s hard enough.

Life’s hard, right?

Like just getting through the day is hard.

Yeah, and that little bit of empathy,

thinking about the intent of the person

allows you to then sort of deescalate

this kind of conversation

that social media wants to escalate.

Yes, back to what we were saying.

If this, in my younger years,

I would have retweeted the guy’s home address

and my address and would have called his boss

and tried to get him fired or whatever.

And it’s like, now I’m just like,

why are we attacking each other?

Life is so hard.

I mean, this is what the pandemic,

I think we should make everybody realize is like,

look at how hard it is.

Life is hard.

And then just think about all the people suffering right now

who are at home, the single mom or dad

with two or three kids at home in public school.

Maybe they’ve been laid off

and their kids aren’t learning

and they’re in a tiny apartment.

I mean, this has been brutal for a lot of people.

Not to mention people losing loved ones

or maybe some people got Corona

and now their lungs are still not right.

Can I ask you about love?

Oh, sure.

I’m feeling it, you know,

like we’re an hour or two here, Lex.

Yeah, you’re feeling it.

Feeling like we could become besties.

We’re getting it.

I feel like we got a bromance going here, Lex.

I feel it too.

I don’t know if it’s Eric Weinstein level,

but I feel like it’s close.

Yeah, I’m feeling the love.

But we talked about those music to my ears,

your whole rant on the Olympic nature of a startup.

Is there a role,

like what role does love, family, friendship

play in that brutal pursuit of excellence

that is building a startup, building a company

or creating anything new in this world?

Such a great question and totally unprepared for it.

Because nobody would ever ask me about that.

So I think it’s why you’ve got quite a following

on your podcast is that you’re able to ask these questions.

And I can tell one story because, you know,

I don’t talk about,

I try not to talk about relationship with Elon that often

because, you know, he’s so famous now.

I mean, when we met, I used to go out to parties with him

and people were like, oh my God, you’re Jason Calacas.

I was like, yeah.

And like, who’s your friend?

I’m like, that’s my friend, Elon.

And they’d be like, what, he’s doing rocket ships?

But he’s told this story publicly.

So I can tell it,

and I would never talk about anything

that he hasn’t already talked about publicly,

especially since he’s so high profile,

but it was pretty funny moment.

There was a moment in time

when Tesla almost went out of business

and you’ve probably heard the story many times,

but it was during the financial crisis

and they were running out of money.

And they said, you know, let’s go get a steak.

And we’re in LA and we drove to BOA

and I had my orange Tesla Roadster

and he had his P1 or P2, like the red one

that I think is in space now.

And we drove to the valet and we had a steak together

and we’re sitting there.

And I said, you know, I read the story

and Gawker or whatever, you know,

and New York Times here,

you only got like five weeks of money left in Tesla.

He goes, it’s not true.

I was like, oh, thank God.

He goes, we have two weeks.

I was like, oh God.

I was like, well, what’s going on

with the rocket ship company?

You know, like, you know, I know you did the one last month

and don’t you have one coming up?

He’s like, yeah, we’ve got the third one coming up.

I was like, well, how’s that going?

I said, well, we blow that one up.

There’s no more SpaceX.

I was like, so two weeks of money left in Tesla

and SpaceX, you blew up the first two rockets,

you blow up the third SpaceX, it’s over.

He’s like, yeah.

I was like, I can loan you a couple million dollars.

I don’t have like a ton.

He’s like, it’s okay.

Our friend, beep, has loaned me some money.

And Elon’s been super public about this.

I would never tell the story unless he hadn’t been,

but he was talking, he never said who it was,

but somebody had loaned him money to keep him afloat.

He was functionally bankrupt.

I mean, he had the equity in the companies,

but the equity was quickly becoming worth zero

and the financial crisis.

And he’s figuring out if he’s going to go on vacation

for Christmas or not.

And he’s on the phone trying to, you know,

save both companies.

And I said, certainly there must be some good news.

And he takes out his Blackberry to date this conversation.

I don’t know iPhones.

Takes out his Blackberry and he starts swiping.

And he says, don’t tell anybody.

This is what I’m building.

And he shows me the Model S.

And nobody knew that he was working on the Model S.

We knew he was doing the roadster

and he was trying to save the company.

And I looked at it and I was like, that’s gorgeous.

It was the clay models.

So it was a full size clay model.

So there’s human beings standing around a clay version

of this tiny little Blackberry picture.

I’m scrolling through on the,

remember that little pad or the ball on the Blackberry.

I’m scrolling through it.

I’m like, this is fucking great.

And I just said to him, it’s like,

what’s the range going to be?

He says, well, I think we get 250 miles.

I was like, 250 miles?

He’s like, yeah, I think it’d be the safest car ever.

I said, what is it going to cost?

He says, I think this could cost eventually 50, $60,000.

I said, Elon, if you make that car,

you’ll change the goddamn world.

You have to, this company must survive

because the roadsters for like 2000 people in United States,

this car is for every person in the United States.

Every single person in the United States

will want this car if it’s $50,000.

And maybe some of the people who have 20 or 30,000 dollars

won’t be able to afford it, but they’ll all want it.

It’s gorgeous.

And he said, you really think so?

I said, yeah.

So I got home and I talked to my wife, Jade,

and I said, do you have the checkbook?

She does all the finances and stuff like that,

pays the bills and whatever.

And I said, don’t tell anybody,

Elon’s making this great car.

And I wrote two checks for $50,000.

And I just took out this paper and I wrote,

E, comma, love the new car, I’ll take two.

And I signed it.

I kissed the two $50,000 checks, put them in the envelope,

and I FedExed it to him for Monday delivery.

And I said to Jade, that $100,000 is going to be gone

in 48 hours because it will pay for one or two days

of payroll on Tesla.

So we just added like, instead of two weeks of runway,

he’s got 12 days.

And the checks don’t cash, but then I read a story

that he’s closed the money, saved the company

in like the next week or two.

And a couple of months later, the checks get cashed.

And I’m like, okay.

Three years later, I get an email,

your reservation number, it’s from Tesla,

your reservation number is 0000001.

And then five seconds later,

your reservation number is 000073.

And I forwarded the number one to Elon,

I said, you know, I can’t take number one,

a signature number one, I can’t take that, that’s yours.

And he’s like, oh, I got five of them.

And besides, you’re the first person who ordered it.

And I was the first person who had seen it.

You’re gonna get me to be teary eyed.

I mean, that’s beautiful.

No, it was a very…

That’s a beautiful moment.

It was an incredible moment for both of us.

And we talk about it sometimes, you know,

those moments in time.

And to your point about love, Elon…

That’s like the darkest moment,

one of the darkest moments in his life probably.

I think it was, I can tell you,

it was the darkest period of his life for sure.

And he’s been very public about how dark that was.

And I think, you know, this is why I have great sympathy

for the entrepreneurs of the world,

like the suffering and the pain.

And when he talks about the suffering and the pain

that all of these founders have felt,

and then we were throwing rocks at them

or criticizing them as they try to change the world

and save humanity, and in Tesla’s case,

I mean, they weren’t, you know,

they weren’t like delivering pizza.

I mean, they were trying to get us off of fossil fuels.

Like this was a big, heady mission

to literally save the environment, the planet, humanity.

And the way they shorted that stock and they attacked him,

it was always perplexing to me why any human being

who is standing on God’s green earth

would want to throw rocks at the guy

who is trying to stem the dam of global warming

that is about to engulf all of us.

How dare they throw rocks at that guy?

There’s so many people you could throw rocks at.

There’s somebody who’s making the Juul vaporizer,

throw rocks at that scumbag, no offense.

But like whoever’s making the Juul things

and is, you know, selling pina colada flavor

to 12 year olds, like throw rocks at them.

Somebody is doing something, you know, abhorrent,

but not E, I mean, and yeah.

Anyway, that car is, you know, up the road here,

sitting under a cover with 20,000 miles on it in my garage.

And then the Roadster number 16 is in the garage next to it.

And every day I walk by the two of them

and I get a warm feeling in my heart

because I know he did it.

Against all odds, against all odds, he pulled it off.

And it was that moment, that month in that 2000,

I think it was probably December, January,

December of 2008, I think.

You know, it’s just 12 years ago

when you think about 13 years ago, it was dark.

I mean, it was dark.

And they almost had the same thing happen,

you know, in the Model 3 production

in June of two years, three years ago.

And I remember him just trying to get the Model 3

out the door and the company almost crashed then.

Most of these companies have, you know,

these kinds of moments.

And I think friendship is you get what you give,

you get what you give.

And if you are there for people,

you’re gonna feel so good about having done that.

And then the reciprocation effect,

which you’d probably know very well,

is so great in the world that anytime you’re kind to people,

you build this incredible bond.

And then what are we at the end of the day, Lex,

besides a series of memories with the people we love?

That’s all it is.

It’s just a series of memories and moments.

It’s just moments.

You ever see Blade Runner?

Yes, of course.

Do you remember what Rucker Harris says at the end,

all of these memories gone, like tears in the rain?

I mean, that’s our existence.

It just all goes away at some point.

It’s just these drops of rain.

Each of those memories,

just like one snowflake or one drop of rain,

and they’re all lost at some point, but they’re here now.

And that’s why we have to be there for each other.

That’s why I feel like what I do

is so important in this world.

And I get such great meaning out of it.

Just being a friend, just having these conversations.

What you’re doing on your podcast,

just talking to intelligent people

and spreading the word and the gospel

of what they’re saying and amplifying it,

you’re inspiring so many people.

Every podcast, you get 500,000 people,

a million people watch these videos.

And there’s some kid in Sri Lanka

or some little girl in Afghanistan

who’s gonna stumble upon this on YouTube,

and they’re gonna change the world in the next century.

Because it’s not just about America.

Our story’s almost over, right?

We were the story of the last two or 300 years.

I hope it keeps going.

But there’s all these other places in the world,

Sao Paulo and Africa,

where people now have access to these videos.

And somebody will hear this video and go,

Elon did it.

Oh, and that guy Jason was his friend.

And, oh, and Lex does those interviews with him.

Oh yeah, I could do it too.

Your little magical moment of love

amidst the suffering with Elon

because you’ve talked about it,

it’ll have these ripple effects.

It’s fascinating to think about in decades to come.

And new entrepreneurs being born,

new, more love being put out there,

and more support through these rough times

when people are trying to create new things.

I mean, that’s a beautiful thing, that’s a beautiful,

I’m glad you think of friendship in this way.

I’m deeply grateful that you’re loyal.

Every time you invest.

In the way you are.

Here’s the thing,

it costs you nothing to make this investment either.

The amount of time it takes to be bitter or angry,

sitting at home, to be disappointed,

you could just channel that same amount of energy

into being loyal, loving, kind, and there for people.

It just only takes the intention, right?

The water is gonna, those emotions are gonna flow, right?

Like Sam would always tell me

when I was struggling in my life and I talked to him,

he’d say, you know, Jason,

your brain is spewing all these ideas.

Imagine you’re standing, sitting by a river,

and the river is all your ideas.

You are not a slave to any one of these ideas.

They’re just whipping by

like each of those little waves in the river.

You can pick one of those ideas out

and look at it and examine it,

and either keep it,

or throw it back in the river and let it go.

And I was like, wow, Sam, that was like,

of my entire friendship with Sam Harris,

that was like the one moment where I was just like,

oh my God, all my life,

I’ve wondered about all these thoughts in my head,

insecurities, you know, imposter syndrome.

Like I didn’t go to MIT, you know,

I’m not the smartest guy,

but somehow I made a career writing little 50K checks

and now, you know, $3 million checks,

but whatever, you know, little checks

and being a journalist and doing this little podcast,

and it’s ended up to something.

And I kind of, I’m proud of it.

I’m 50 and I’m kind of proud of what I did.

And I wake up every morning after I retired,

I say, I kind of like what I do.

I kind of like having the conversation

and writing the check and then being on somebody’s team.

And I got offered to be in these giant mega funds

and they said, Jason, you’re in it,

you invest in 60 companies a year,

you know, 500K at a time,

you put $30 million a year to work, come work with us,

write one $50 million check

and then you can go to Aspen and Cabo and Coachella

and not work.

But why are you doing all this work?

It’s like, well, the $50 million check

is like, it’s like a formality.

It’s just like being an ATM,

like the companies are already huge by that time.

I really want to meet the two people with the idea.

I want to meet them in year one.

I want to meet them on day zero.

I want to be the guy who wrote the first,

second or third check.

I want a guy who wrote the 3000th check, the last check.

It’s fucking boring.

And make that basic human connection

and also be with them through the rough times,

be with them with that first,

I mean, the first early successes,

I mean, that’s a beautiful.

So great.

When a founder and that team get product market fit

and you just know it’s going to work,

oh man, Lex, it’s,

when Comm would email me and they’d say,

we added, you know, the company’s been growing

and we’re not going to go out of business,

but we added some sleep stuff

and then we added this other function

and we have a streak now and we grew 10X

in the last, you know, three months.

And we’re good.

You know, I was like, ah, that’s nice.

It’s real nice.

It’s like, it’s a nice feeling when you,

well, because so many of them die.

We talked about that J curve early.

Imagine it’s like,

it’s like all these baby turtles going out to the ocean

and the seagulls are ripping them to shreds

and then the sharks are eating them.

But then like a couple of the turtles make it

and they become wise old 100 year old turtles, you know?

And you’re like, yep, I remember when you catched

and like all of your brothers and sisters

were ripped to shreds by the seagulls

and you made it into the water.

And then you made it out to the deep water.

Pretty great feeling.

I think there’s no better way to end it.

There it is.

The talk of the cruelty of life,

that suffering that is life

and the love amidst the suffering.

Jason, I’ve been a fan of yours for a long time.

You’re one of the most special people in Silicon Valley.

Thanks, Lex.

And maybe you’ll also call me in one of the rough times.

I’m sure there’ll be many.

There will be, yeah.

There’s one expression, nobody gets there alone.

Nobody gets there alone.

And anybody who thinks that they got there alone

is delusional and kidding themselves.

And they will at some point wake up and realize,

oh shit, there were a lot of people helped me get here.

I need to write a couple of gratitude letters.

I got a gratitude letter the other day

from a friend of mine who I helped.

And I was one of the,

you know about these gratitude letters people are writing?

It turns out Martin Seligman in, was it Authentic Happiness?

Anyway, the guy who really studied happiness and joy,

turns out one of the greatest amplifiers of joy in your life

is to thank somebody for doing something for you.

And somebody who I had helped just wrote me a letter

and I got in Christmas

and I had the stack of Christmas cards

and I hadn’t opened them.

And it’s the second week of January

and I was just getting to like the last stack

and I open it up and I almost missed it.

It’s incredibly heartwarming letter

about how meaningful like certain things I had done

to help along the way

and how he’d always appreciated my counsel.

And I was just like, well, this happened 25 years ago

and you wrote this letter now.

And it just hit me like a ton of bricks.

I was just like, wow, you know, if you’re hearing this,

there’s probably 10 people

who are really instrumental in your lives, in your lives.

Go ahead and call them on the phone,

write them an email or even better,

just write a letter and send it to them

and just tell them you’re thankful.

And let me tell you something,

the amplification of joy in your life will go a hundred X,

a hundred X when you tell somebody you love them

and that you really appreciate them

and that what they did for you was magical.

So just, and you can look it up, gratitude.

Gratitude is like one of these incredible forces.


I’m grateful for being on the pod.

I’m grateful you wasted all this time with me.

I love it.

Thank you for listening and hope to see you next time.

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