My First Million: Shaan's Story: How I Made My First $1,000,000 By Age 31

All right.

Quick break to tell you about another podcast that we're interested in right now.

HubSpot just launched a Shark Tank rewatch podcast called Another Bite.

Every week, the hosts relive the latest and greatest pitches from Shark Tank, from Squatty

Potty to the Mench on a Bench to Ring Doorbell.

And they break down why these pitches were winners or losers.

And each company's go-to-market strategy, branding, pricing, valuation, everything.

Basically all the things you want to know about how to survive the tank and scale your

company on your own.

If you want to give it a listen, you can find another bite on whatever podcast app you listen

to, like Apple or Spotify or whatever you're using right now.

All right.

Back to the show.

And so the thing I've learned.

So why do I say I would go back and do it differently is because I now realize something

I already knew, but I didn't have the guts to act on, which was that at any given time,

you're really only going to get to throw your all into one thing.

And so if you're going to do that, like choose really wisely.

We're in San Francisco.

We're outside of San Francisco.

We're doing a live pod for the first time in a while.

We're in this studio.

What is it?

Is this a music studio?

Is that what this is normally?

Did the instruments give it away?

Are you a Jerry Seinfeld fan?

No, but I know what you're about to talk about.

I didn't read it.

I saw the headline.

I opened the tab to save it.

It says like, what's the headline?

It's great.

It's like the one question or the most important question.

What is it?

Well, this one is called Life's Work, an interview with Jerry Seinfeld.

So not that good of a headline.

Maybe you...

Oh, they got posted on Hacker News.

That's why I saw it.

And somebody wrote like something like the deepest interview with Seinfeld or something

like that.

It says, yeah, I don't see what you're talking about, but I did find it on Hacker News as

well.

But here's why it's cool.

So they just asked like really simple questions and they get really simple answers.

But he says, the question is, you and Larry David wrote Seinfeld together without a traditional

writer's room and burnout was one of the reasons why you stopped.

Was there a sustainable way to do it?

Could McKinsey or someone have helped you find a better model?

And he goes, who's McKinsey?

And they go, it's a consulting firm.

And he says, oh, are they funny?

And he goes, no.

And then he says, well, then I don't need them because if you're efficient, you're doing

it the wrong way.

The right way is the hard way.

The show was successful because I micromanaged it.

Every word, every line, every take, every edit, every casting, that's my way of life.

And it's actually a pretty cool interview.

And he goes on to say something about how the interviewer says, can you teach being funny?

And he goes, no, you can't.

It's genetic.

You kind of have it or you don't.

And he also says being funny is one of the ultimate weapons a person can have in human

society.

It even competes with being really good looking.

And anyway, this was a really good interview.

This dude is like the Elon Musk of comedy.

You know what I mean?

He's just like a micromanaging asshole, but it's hard to argue with the results.

And I also, even though he's one of the types of people where I could just read this and

be like, oh, you're a jerk who I don't want to be around, but you're just so good and

you're right.

Well, what makes him a jerk?

Just because he's saying I care about every detail.

Like my feeling, I would have more negative feelings being around him than positive feelings.

Like, you know, I wouldn't want to necessarily be around him unless I was trying to further

my career in that, you know, vertical.

Right.

Right.

Yeah.

It's like, I have a buddy who was trying to decide what to do.

He sold his company.

He's got a bunch of money in the bank and this venture firm was like recruiting him.

They really loved him.

They think he's super smart.

And I was like, he's like, you know, on paper, he was just like, yeah, this makes total sense.

Like these guys are great.

They're great at what they do.

They have like a billion dollars of assets under management.

It's like, you know, it's really smart people, blah, blah, blah.

They're the best.

And I was like, yeah, but do you want to go to the Olympics?

And he's like, what?

I was like, you're basically saying like, I want to wake up every day and train for

the Olympics, which is fine as long as you really know that you want to train for the

Olympics right now.

You don't have to go and be with these people who are going to be obsessed perfectionists

who are grinding, grinding, grinding, even though they've already made it.

They've all already made it, but they're still grinding, grinding, grinding.

And that's cool if that's what you want.

But also, didn't you just like get married and just finally like sell your company?

You just like, you know, you have this life changing thing.

Are you sure you want to sign up to go train like an Olympian because it's optional and

you could just like, you know, instead of training with Michael Phelps, you could just

go swim for fun and like, you'll be fine, like you'll be totally fine and you can like

find some in between.

So what did he end up doing?

So he kind of came to the same conclusion over time.

He's just like, yeah, like that door is there, but I don't think I need to go through that

door because lifestyle is not the best.

And also just like, I don't know, maybe there's like more creative upside or more benefits

to doing this like other path, some other path.

And so he also said kind of like no to the Olympic training, like the Olympics.

And so like what you just said, unless I know I want to be the top of the top, then I shouldn't

necessarily follow in the footsteps or try to go work with the people who are, who are

trying to do that.

Well, and that's what actually, so the interview said, was it hard to figure out what your

career should look like after Seinfeld?

And he says, I never thought I had to do anything.

I was a sole standup for years and I just thought I'd go back to doing that.

But then he talks about, I never saw myself doing anything other than being a standup

comedian.

It would have been a mistake to try and springboard Seinfeld into a huge media company making

movies and TV shows.

And I thought that was cool.

So I respect this guy.

Right.

I actually think he's different than Elon Musk because he's more self aware and he's

trying to like, it seems to me like, like Elon gives me this vibe where he's just trying

to like, it's just power play after power play.

It's like, all right.

You know, first power play is like early career PayPal, all that stuff.

Then it's like SpaceX.

Okay.

I'm going to do rockets.

All right.

That's cool.

And I think that scratch is a little bit of his nerd itch there.

It's same with Tesla.

And then as they got bigger and bigger, it's like, all right, I'm going to buy Twitter.

I'm going to like, you know, implant this chip into people's brains.

I'm going to dig tunnels.

It's like, a lot of these are cool from an engineering perspective, but also like the

way he does it where he is the star and like, like this Twitter thing where he was like,

the text messages got leaked and he's texting, or somebody's like, Hey, I got this person.

They'd be great for, for like, you know, a CEO and he's like, are they an engineer?

And he's like, no, he's like, I only want to hire great engineers.

He was talking to the CEO of Twitter, I think, and it might have been to Jack, like, I want

to hire this one person or something like that.

And Elon goes, are they an engineer and the guy goes, no, but they're good at this.

He's like, Oh, well, I only want to hire engineers who can get in the nitty gritty.

He's like, we need, well, there's two.

One was he was talking to the currency of Twitter.

He's like, yeah, yeah, yeah.

He's like, and this currency was like, Hey, next time you have like a question, just come

to me and I'll route you to, I can probably answer it.

Otherwise I'll write you the right person to basically say, don't distract my team like

you're doing with these random questions out of left field constantly, and then they all

think we need to do what Elon wants.

You don't even own the company yet.

And Elon was like, I prefer to talk to people who like are actually doing the work and out

of manager.

And then he was like, well, you know, I'm a pretty good engineer.

I've been an engineer at Twitter for like eight, 10 years.

I touched pretty much all the code base.

Like, if I can't answer it, I definitely know who can.

And he's like, okay, good.

So that was one.

And then he served him with the, he messaged Elon this long paragraph that was like, you

know, you're allowed to tweet whatever you want, but I just want you to know the effects

of your tweet.

When you say, should we fire everybody, then people inside the company, you know, start

to feel, it's a very big distraction and it's really slowing us down from like doing the

work we need to do.

Did he just say like K?

You know, he goes, he goes, what have you accomplished this week?

Yeah.

That was the background of my computer at home.

It's what have you accomplished this week?

Yeah.

Like my new project, I screenshotted it and I said to everyone, I'm going to make this

your background.

Dude, I mean, it's the biggest own since I moved straight to the end.

And then, and then he's talking to somebody else, somebody else was like, oh, you should

hire this guy.

Michael, he was the CEO of Uber.

He's like, you should hire him as the new CEO.

I think he'd be great or head of business or whatever.

And he's like, I just want to hire great engineers.

And then they're like, cool, but like, I'm sure you need the engineers are going to roll

up.

They're going to report to somebody.

Somebody's going to manage the engineers.

Yeah.

And he goes, I will oversee all of software development.

And then he also says, frankly, I don't think anyone should manage anybody.

While also saying I will oversee all software development while also being CEO of Tesla and

also being CEO of SpaceX and also, right, it's like, come on, like what you're going

to sit there in the product reviews and like, you know, talk about, you know, the colors

of buttons and stuff.

It's crazy.

He's nuts.

I want to get to you, but really quick, one, I forgot to tell you one reason why I like

San Francisco.

Yesterday I visited my friend and she lives in a commune and it's like this weird, like

they own like four buildings in Oakland and there's like a middle part for each building.

So it feels like a campus and there's like a hot tub and crap in the middle.

And I was like, this is crazy.

I always wanted to do that.

Really?

Yeah.

But this is, this is not what you would want to do.

Only with my best friends.

And you'd want to be king.

You wouldn't be.

No, no, no, no.

You wouldn't want to be a participant.

I just wanted to be my best friend.

They like vote on everything and stuff like that.

Like they have like house meetings.

It's like the real world.

Like I just can't handle that, but listen, I think here's why this, this one line is

why I love San Francisco or the Bay Area.

I said, wow, this is interesting.

What was in here before?

And she goes, oh, it was just another commune.

Like that's how often this stuff, and then I was, they told me a story about how one

person got voted off the island for, they wanted to do something and they just got voted

out because they said, we're not going to allow you to do this.

And she goes, okay, I'll leave.

I was like, well, where'd you go?

She's like, oh, there's another, there's another one in like a few months away.

And I just thought, I go, this is why I love this place.

Just all these freaks.

You know, I just, it's freak central.

I love this stuff.

I love these extreme weirdos.

It's the best.

Yeah.

That's also why you can get like a, you know, a Lyft or a Airbnb starting here.

Cause it's like, yeah, just getting that dude's car, but you don't like Honda Accords.

It's like, no, they're fine, but who is this guy and why am I not getting in a taxi?

It's like, okay.

He cleans out the back every once in a while.

Like it's good.

And so it's like these weird like sharing economy things.

Like it makes sense that they like got so much steam here because people here are just

down with this.

Like, you know, it's crazy.

And in, in 2013, my good friend, I was playing like Frisbee or something with them at like

nine a.m. the next morning and we were playing like 20 minutes in, I was like, Hey man, why

are you so tough?

20 minutes of Frisbee.

Well, listen, no.

So outrageous.

Or we played disc golf.

We were playing disc golf and 20 minutes into the thing, I go, Hey man, you're pretty

bummed today.

What's going on?

And he goes, Oh, I was at the Shaman's house last night in Oakland doing ayahuasca puking

all night.

I'm like, what's ayahuasca?

It's like this like powder thing that you like drink and then you stay up all night having

like visions and there's a shaman guiding you.

And I remember just being like, huh, pretty rad.

You're turd.

And like, I was like, this is why I love this place.

And this was in 2013 before, you know, it was even like now, even in Austin, everyone

frickin does ayahuasca.

Right.

But I just remember that conversation.

Like this is why I like this place.

All right.

People were asking online.

They said they want us to do a pod.

We already did my story.

It's a second episode.

Now we'll do one on you.

All right.

So how old are you now?

Good question.

34.

Um, and you're from everywhere, everywhere where I was born in Oklahoma, believe it or

not.

And then Tulsa, uh, Denver, Texas, China, Indonesia, Australia, San Francisco.

Yeah.

That's it.

And maybe a little bit of London too, two months and you're living in Australia in pre

college or right, right college.

I studied abroad there.

And then also after college, I started a company with a well-known entrepreneur in Australia.

And that was pre college?

That was after.

But, and then you went to college in Duke too.

So you went from Duke to Australia.

Yes.

And at Australia, you did the sushi thing.

No, I did that.

Just at Duke, like that's where it started.

I thought the sushi thing was in Australia.

No, no, no.

That was here.

And then we moved to Denver because you know, like people move to Silicon Valley because

like, that's the tech hub and like people move to LA when they want to be an actor.

If you want to start a restaurant, Denver is the place to go.

So Chipotle started there, the first Chipotle started there, noodles and companies started

there, Quizna started there, Smashburger started there.

There's like seven or eight amounts of like open-minded white people.

Yeah.

People love lunch.

Lunch is a really big deal there.

But they, uh, like, so all the talent, the people who know how to like pick locations

and like roll out restaurant operations, all this stuff, they're all still there.

So when, when it was like, where are we going to start?

It was like, uh, because Denver is kind of like a big suburb.

Like this is how dumb we were.

We were like, we want to be the next Chipotle.

How do you do that?

Well, we're Chipotle start.

And so literally we found the location across the street from the original Chipotle to open

our restaurant.

That's a great plan.

And so we were like, yeah.

And like, I guess we'll just do the exact, and then we were like, who rolled out the

real estate?

Are these two brokers?

Okay.

Well, we'll go talk to them.

And then who did this?

Okay.

We'll go talk to them.

And that's basically, that was our whole plan, um, of like figuring out how to start

this restaurant.

And so we just moved to Denver because, and it was, it was funny.

My two co-founder, my two, two best friends at the time, Trevor and Dan, you're not really

a co-founder of a, of a, of a restaurant.

Yeah.

Co-owner.

Yeah.

Yeah.

That's a good point.

That should have been the single one that this was not a great idea.

It was like founding what?

You know, like, like, like my, my father-in-law owns a moving company.

He doesn't call himself like the founder of the, yeah.

Yeah.

He's just the owner.

Yeah.

That's fair.

So we, my two friends were trying to eat sushi and we basically started this thing.

And they were like, we were at Duke, so they were just trying to find a location near us.

And I'd actually quit the startup.

I didn't really tell people this, but I basically, when I graduated, I got a really good job

offer and it was $120,000 in Indonesia.

And so, and my sister was working at the place and the guy wanted, my sister was doing good

job.

So he was like, okay, I'll hire, you know, we need more.

The guy who ended up going with the prison?

I went to prison.

So I take the job.

And I'm like, I tell my friends again, like, stupid, I was like, I'm going to go learn

a bunch here.

And then dude, when I come back, think about how smart I'll be.

And they were just like, okay, I guess we'll just keep working on it over here.

Like, total jerk move.

I was just like, moved and took this job in a month.

In Indonesia.

Yeah.

In a month or two.

And you were working for like a mafia guy who like, did like junk bonds or what did he

do?

No, he just, he basically, what he had done was he, he's like a drop out of second grade

or something like that.

And like, he basically didn't speak English.

So my boss never spoke English to me, um, only like broken words, crazy guy.

You walk into his office and there's four, uh, like executive assistants or EAs or secretaries

or whatever.

And each of them have a giant TV screen and it's just his email because he can't read

or type.

And so they would say out loud his email, this person emailed you saying this and he

would just dictate.

He was pacing around.

He'd just say, tell them we're not doing the deal unless blah, blah, blah.

And then one would be typing.

And then the next one would be like, Hey, you got a, another email from this person.

So there's just four screens like that.

They were just like the brain.

Yeah.

He's just talking out loud.

Yeah.

Literally can't read or write.

And then when, and so what he was doing was what his, his genius plan was, he was like,

he recognized this arbitrage opportunity that was illegal, which is why he went to jail,

which was that US companies wanted to do business in Indonesia, Indonesia's like, I don't know,

maybe the fifth largest population in the world.

It's got a ton of natural resources like coal.

So ExxonMobil, BP, all the conico Phillips, they all wanted this coal.

And if you go there and you try to get the rights, you go to the auction and they're

like, uh, actually that guy owns it.

My cousin owns it.

And they're like, what, where was the process?

They're like, yeah, the process was done in the middle of the night.

You don't need to know.

Yeah, deal with it.

Basically you got to bribe somebody to get something.

So what he was doing was he was like, Oh, they want this.

So I'll just go and bribe all the local officials, get the, I'll get the leases and then I'll

just sell it.

So he bought up for $2 million total, like this huge amount of coal.

And then he sold each piece for 20 million and he amassed $500 million over the course

of like three years, just doing that.

And so when, but it's like liquid, so he was liquid.

He was over liquid.

Like if you, if you did something, if you like did a good job with the negotiation or

meeting or contract, you'd come into work and he'd just hand you keys to like a BMW

or a Mercedes or Rolls-Royce and then you'd be like, that was your bonus.

Like there's no, like,

But did he have paper?

Who's, who's, who's name was on the title?

Of the car?

Yeah.

Like we lived in this like four seasons resort, but it's his apartment, but you get to live

there.

Everything he owned and then he owned it under 72 shell companies.

So you'd be like, Hey, what's this name?

And then there's like this one woman who owns the file cabinet and she's got all these companies

inside.

And so that's what this guy's gig was.

And so he was basically, he was like, I don't need to know how he's like, he would just

talk to engineers or technologists and be like, what would you do with this call?

He's like, great.

Then when, when he would get a like, he had like all these geologists on and he'd be

like, do a survey, do a report that says this is fit for that purpose.

And they're like, well, it's kind of fit.

He's like, make it very fit.

And he just like basically fudge the whole thing.

It's my impression.

What do you think made him special?

He was just born and willing to cheat and steal.

And he wasn't cheating.

Like he was just like playing a business is done in Indonesia.

You don't get like that's how the property process is done.

If you don't want to do that, you cannot play.

So you think that he was playing by the rules of the game or was he on the unspoken street

rules of the game on that part.

And then on top of that, he was like smart and ruthless.

So for example, I met him because he met my dad.

My dad worked at BP for like 30 years.

And my dad was known as an expert of this one technology to get value out of coal.

You do this process, you turn coal, that's not that valuable into something pretty valuable.

So he meets my dad and he's like, tell me about this.

And my dad's talking to him and my dad's like, do you understand like these things that I'm

saying?

He's like, I understand that BP will want my coal basically.

He's like, I understand that like companies will believe this thing you're saying there's

potential here.

That's all I need to know.

And my dad was like, but like, should we test it or like, he's like, no, no, no, why would

we test it?

Let them test it.

They're buying it.

They can test it.

And like they can see for themselves.

Like, you know, if it works or doesn't work out, why would I add risk into this by like

doing this?

And my dad was just talking to me and then my dad at one day goes, I think I've told

this before, but he goes, he's like, he's like, I probably am like a top five expert

of this one coal like technology in the world, you know, pretty much nothing about coal yet

I've worked my whole career and I've been making 100,000, 150,000, 200,000 a year and

you're going to make like 300, 400 million this year, you're going to make more money

than me and I know more about this than you and he goes, yeah, of course.

And he was just like, he's like, yes.

And you idiot.

Yeah.

Do you think that that's relevant?

Basically he was just like, so matter of fact about it.

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So my job when I worked there was company comes in, he doesn't speak English.

So he needed English speaker to do the meeting and then he would just do the pleasantries

and the food and the drinks and all that stuff and like, you know, just like with a translator

make that work.

But he'd rely on us to like go over the presentation.

What was his name?

Cocos.

You're like, all right, gentlemen, Mr. Cocos would like you to feel welcomed here and

let you know that he's not here to play any games.

Yeah, it will be like Mr. Cocos and these two young women will now go to dinner with you

guys.

And I hope you have a great night, you know, like, because again, that's how business is

done.

There's like you go to karaoke.

I don't know if you know about all that.

It's like Asian cultures.

Like you go to these karaoke rooms and there's like, why are all these cute girls here?

It's like bottle surface at a club.

Were they prostitutes or something?

Or just, I don't know.

I've never like gotten that far into the lion's den, but like, there's something going on.

Like, you know, there's some service or I don't know if it's just flirtation or there's

more.

I don't really know.

But like, all I know is this guy was getting mad deals done using this like workflow or

during the day.

Love singing.

Don't stop believing.

Yeah.

I'm presenting at night.

They're singing songs.

And so that was, but that was a wild experience for me.

So how long did this guy go to jail for?

Well, he died in jail.

He's dead.

So.

Wow.

I think I'm sharing all this cause I'm like less afraid now that I've never really talked

about this.

How much did he get sentenced for?

I think he got like 20 years or something and he died a few years ago.

Cancer died.

Oh my God.

He was a nice guy.

He was really good to us.

He was really nice to us.

So you think he was like a, again, I asked this before you, like.

He was not evil.

He wasn't evil.

He was just doing business by the way that that game was done.

Whoever was going to own that land was going to do that.

He just decided it'll be me and he got fabulously rich off of it.

And all the things that seemed really crazy to me was also like kind of standard practice

in India and in China about like how business deals are done.

Yeah, you drink a lot.

You go out to the bars with the clients and like you, you know, yeah, you, you have to

grease the guy who's doing the deal, not necessarily so that you can win, but you won't get it

if you don't tip everybody basically that's involved in the process.

That's actually the, that's the first time of two times that you've buddied up with a

billionaire who says like, here's my playground.

You can run it.

And you, the sushi thing like it was only mildly, it wasn't a success, but you moved

to San Francisco and you got a job with Michael Birch.

Yeah.

That's right.

And who, who, who was he at the time?

He, uh, by the way, I don't think the, uh, hot wings are here, would you mind getting

them?

Uh, so I told you this when I got here, I was asking people, it's like, yeah, me and

Sam are in person.

We're going to just hang out.

We're going to have a good conversation.

How do we take advantage of the fact they're in person and to the two first two people

I say, they go, get a bunch of hot wings.

It'll make it hilarious.

They're going to have the same conversation while you're not wings.

And I think there's milk.

Yeah.

There's not.

There's no sides.

Um, so I moved to San Francisco.

Basically the story is I do the sushi thing pretty quickly.

I'm like, God, this can't be it.

Like no dude, it sucks.

Every day I'm waking up at five in the morning.

I'm driving to like the fucking fish market, picking up the fresh tuna for the day of job.

And then like the business was actually working.

Like we, we did it as a cloud kitchen and it was basically making money.

I was like, this can't be it.

Really at that time, my dad had met a guy in Australia who had sold his company and

in passing.

Did your dad is like this, looking at a king, he met this guy and he was, he was like in

passing.

He's like, you know, what are your, what are your kids do?

And he's like, oh, my daughter does this and my son is doing this like, you know, sushi

startup thing.

You should, you should check it out there.

They write this blog.

That's really entertaining.

It was like we were creating a word, we had a word dress blog that was really just for

our own amusement.

Like we used to do a lot of stuff to make content that in our mind was like somehow

going to help the sushi thing.

It didn't help the sushi thing at all.

But what it did do was anybody who found that really got behind us.

They like kind of started rooting for us or they thought these guys are good hustlers.

They're entertaining, blah, blah, blah.

So this guy who had just sold his company for like 450 million and he was looking for

his next thing to do.

He had a non-compete with current, with the business he knew, so he knew he needed to

do something new.

But he didn't know what and he read our blog and he was like, oh yeah, I want to do business

with you guys.

So he flew us out to Australia and we interviewed for a job with him and he was like, this guy

Nathan Mitchell.

So he's based in Brisbane and his family had a drilling company, sells a drilling company.

And so he wanted to do business with my dad.

He wanted to do business with us and he was like, okay, let's put a team together and

let's do this.

Dude, that's such a cool way of saying that you just, I want to do business with you.

Yeah.

Well, that's what I told myself.

I don't know what he wanted.

I can't put words in his mouth.

But he, all right, here we go.

So there's three, there's three flavors.

There's like a sweet, spicy, a spicy, and then what they called very, very spicy.

Which one's the very, very spicy one?

I'm not touching that one.

All right.

I'll leave the buffalo in a minute.

So basically, if we ever answer a question poorly or something, we got to eat.

I don't know.

We'll make up a game.

I'm going to eat them because I'm hungry.

So basically he's like, all right.

I got a bunch of like smart engineers, but this will be so academic unless we get some

hustlers.

You guys are hustlers.

Join me and let's make this happen.

He gave us a job offer.

I was just happy to live in Australia.

So I was like, great, I'll do this.

And so we started that company together as a biotech company in Australia.

As that goes on, it gets to a point that I thought was, you know, like kind of the transition

point where it's like, oh, we signed this deal, it's like ready to like change hands

or whatever.

And I was like, all right, I'm going to move to Silicon Valley because I don't know

about sushi.

I don't know about biotech, but I know I like this early stage stuff.

So I applied to two jobs, Stripe.

And then this place nobody ever heard of called Monkey Inferno.

Stripe would have been pretty sick.

It was probably 30 employees at the time.

Oh my God.

So if I joined even as just like what I was joining as like a biz dev manager or something

like that, I probably would have made like 10 or $20 million if I just stayed there.

You think 20?

I think so.

Yeah.

Cause I kind of, I went back one day and I did the math and I was like, I don't know.

There's a bunch of assumptions like when you vest out, would you get a promotion?

Like, you know, some bunch of things like that.

But based on when it was like 20, 2012, early 2012 at the time, which like a lot of people,

I tell people the story about me and they're like, Oh, you would have gotten fired.

And I actually think they're probably true.

In your case, I think you wouldn't have.

I think I would have played that guy.

I like that.

I'm good at that.

You wouldn't see it because that, that show was exciting and you seem like you would have

gotten, I don't know those guys, but you seem like you would have gotten along great

with them.

Yeah.

Like you're more of a cowboy.

Yeah.

But I think you legitimately would have made tens of millions of dollars.

I think so too.

Yeah.

But it all worked out in the end.

Like I have less than that, but I was able to like, got myself into a position where

I was able to do more.

So basically it's like either like self-development or just like getting lucky with those shares.

And not entirely lucky.

Like I only applied to Stripe because I thought that was going to be a winner.

But like, it still would have been lucky that it got to be such a huge winner.

Could you tell early on it was going to be a huge winner?

Yeah.

I don't know why.

I think I was just like at the time I was reading a lot of Paul Graham essays and I was

looking at Y Combinator companies within Y Combinator.

Those founders, I watched some of their interviews.

I'm a big like you bet on the person type of guy, you know, the person is who builds

all the value.

Did you talk to them?

The founders.

I never talked to the founders.

I basically, I had one interview with this guy, Ben, and he, and I blew it.

Like I had the strongest warm introduction.

That guy's mentor was also my mentor.

And the mentor thought so highly of me.

He was like,

How did you blow it?

Were you just cocky?

He was like, I'm not going to sell me this pen type of question.

That's a bullshit.

But it wasn't a pen.

He was like, he told me, he's like, I'm not going to do a sell me this pen type of thing.

But I am.

But I'm going to do sell me this software.

And I was like, okay, what's the software?

And he's like, you pick, you pick it.

And so I'm like, it's my first job interview ever.

I've never interviewed for a job.

And I go and I'm like, basically dating Angelina Jolie, like Stripe is my first job interview.

And I'm like, not prepared at all.

And he's like, what's a piece of software you like?

I'm like, I don't know.

Like, so I'm trying to think of what software other people like rather than what I like.

So I was like, base camp by 37 singles.

I knew that was like a popular, those guys were popular.

So you didn't even use it though.

And I didn't use it though.

So I didn't know what to say.

But now I'm pot committed.

I didn't, and I didn't want to admit that, hey, I just picked a random company that

I don't actually use.

Like that didn't make any sense either.

And so I'm like fumbling and stumbling.

And the way I got messed up was I started to explain it like I would, I'd be like, you

know, so what I would say, if I was selling this business, he goes, no ring ring.

Hello.

Go.

You're selling this thing to me now.

And I was like, oh God.

And I just, I think that's a bullshit way to interview someone by the way.

I think that's, I think those games are stupid.

Yeah.

I don't know.

Like, I guess, yeah, I guess I would agree.

I don't want to say it's stupid just because I sucked at it.

Like, that's not a good reason.

I tried doing those when I've interviewed the best way to the best way I found interviewing

someone is I just want to know if I enjoy being around you.

And the only way I'm going to judge if like you're qualified is by just looking at your

history.

Yeah.

That's fair.

Like, I just want to see what you've done in the past.

And I'm going to talk to your old coworkers and then I'm just here to decide if like this

is a good culture fit.

I heard of somebody got this guy, Kyle Samini, he's like a VC, he's, he put out a, or put

out some interview or whatever where he said, he's like, yeah, there's only one way to apply

to my firm.

I don't look at any resumes or reference, nothing.

He goes, just take one of our existing blog posts and write it better, like write a, write

a better blog post than we have on our blog.

You could take the same topic or a different topic, just write an amazing blog post.

And I was actually like, that's kind of a good test as a good initial filter.

I would still want to talk to the person, but like, that's a really good initial because

when you see someone, right, you see how they think and how, how good they are at like,

how good they're writing a blog post is actually a pretty good test for a lot of things.

So I'm kind of into that as a test.

What was, oh my God, he's brought milk.

Is that milk or it's tinted glasses.

So it almost makes it look like eggnog.

Should we, should we start with a, with the medium or you want to start with the light?

I want Buffalo.

I don't want sweet.

Okay.

Here's the Buffalo one.

We'll do, we'll start with the Buffalo.

The sweet can be our like a palate cleanser.

Nothing like eating on microphone, by the way.

Yeah.

Hot wings are the worst thing.

Give me your favorite towels.

You're going to hear me gnawing.

All right.

This is the Hot Ones episode of my first million.

Shout out to our sponsor, Wingit, providing these wings today.

Dude, have you ever had like a lunch or dinner at like one of the Chinese restaurants on

the inner sunset?

Yes.

Like it's like their hot wings are like breaded, like fried chicken, but then dipped in like

sticky sauces.

Yeah.

That's what those are going to be.

I think that's a thing.

I hate that sticky shit.

All the Chinese restaurants I go to, I was like, I was like, I don't know what that sticky

crap is, but don't give me that please.

Like I want to know.

Also, I went wing in because I knew you would not want a boneless wing.

Yeah.

I'm not an idiot.

I would have done boneless because I'm such a domestic cat, you're like a feral cat.

You know the right way to eat these is just, well, it's easier with the other ones, but

you got to stick the whole thing in your mouth and just pull it out.

Yeah.

That's like, I've seen so many TikToks of that.

Everyone who shows that is fat.

100% of people who have a strong opinion about how to eat buffalo wings are fat.

It's the hot wings that you eat.

What, wings?

This is good.

This one's not too spicy at all.

What was Monkey Inferno when you applied?

So I, I apply and it's basically, it's a startup studio or an idea lab.

I forgot what they called themselves at the time.

Basically it was like 16 engineers, a designer, one designer, and then Michael and Zochi Birch,

who were the like the owners and the husband and wife couple that was married.

Because they basically sold a company for like $850 million.

They sold Bebo for $850 million.

Yeah.

So Monkey Inferno is basically like, this guy's done what I want to do.

So let me just go work with him.

Again, like, how did Chipotle start?

I don't know.

How should we be successful like the next Chipotle?

Let's just go where Chipotle started and follow their footsteps.

Same thing.

I was like, this guy has built several tech companies, like maybe three or four companies

that have gotten millions of users, millions of dollars and one huge one for $850 million.

And when he sold that company, that company is considered, I read this article where they

said, here's the top 10 worst acquisitions of all time.

Number one was Mark Cuban's thing where he sold to Yahoo for $2 or $3 billion.

Number two is Bebo, which sold to AOL for like $850 or whatever.

And when he was doing that deal, he must have seen the numbers and been like, oh, Facebook's

way better.

We have like three weeks to get rid of this thing.

Yeah.

He told me that story.

Basically, he was like, yeah, Facebook was just growing super fast and they were just

better.

Like they were just better at what they were doing.

And he's like, we were just getting swamped with like, we had all these like spam bot problems.

And then we had like, you know, this other problem and then like, VCs wanted us to make

money and this, this is our, you know, I heard this president, she wanted to expand

and make money doing these like deals with, oh, Eminem is doing a takeover of the homepage

and like, wow, we made like half a million dollars doing that.

He's like, but Facebook was...

The candy or the wrapper?

The candy.

But they actually did have other stuff.

Like they started a reality TV show called like, I forgot what it's called, like Joanna

or something like that.

Yeah, that ain't going to work.

But like at the time, MySpace was like, MySpace was one model.

They were like the media company.

They sold for $400 or $500 million.

Bebo was looking at that, was like, okay, we can do that like Hollywood, you know, big

advertising, big marketing thing.

And Facebook was like, blue website, no ads, just focused on photos, engagement, growth,

like all that stuff.

And they were just growing like crazy because that, and they had a more controlled growth

because they were doing college to college first.

So they were able to like, not have all this like spam and all this other problems because

they were gated by, you had to have a university email address for a while.

And he sells this company and he has all, how much do you think he was worth after he's

sold it?

Well, they owned like 70%.

So no public math, but you know, 70% of 850 and then half to taxes, so hundreds of millions

of dollars.

Hundreds of millions of dollars.

And he comes to America and he basically hires like, but he was already in America

the whole time.

He was here.

He was literally this part of the Bay Area.

Oh, I didn't know that.

So he was here.

He buys a place in San Francisco and he hires 10 engineers and then they're all just working

on crazy shit.

He buys seven condos, smashes down the walls to create one huge office and it was the same

office that the Beats by Dre headphones were designed in and stuff like that.

So that was one part of the office.

The rest were just condos and he builds, he leaves one as a condo that was there.

You saw that the bedroom that was there.

And then he puts a bar in there.

He puts like a whole ping pong kitchen, entertainment area, and then huge office space where we

all worked.

So day one, I get off a plane from Australia.

I come straight for the airport to the office to interview and I get there a little early

and right across the street was a Burlington co-factor.

I walked to the Burlington co-factory and I'm just standing there in the Burlington co-factory

with a suitcase.

Yeah.

They're like, what is this guy doing?

You had a suit on?

Suitcase.

Oh, a suitcase.

What were you wearing?

I was just wearing like, you know, tech casual hoodies in that trench coats and Burlington

co-factory.

And I'm just standing there for like half an hour and then I walk across the street and

I ring the doorbell, I go inside and I'm just like, wow.

And the walls were mirrors that were one way.

So you could, if you were inside the restroom, you were looking at a mirror.

If you were outside the restroom, you could see into the restroom or something like that.

No.

The other way, if you're looking at the restroom, you look like a mirror.

If you're inside, you can see out.

Yeah.

The non-weird way.

It looked like people could see you, but they couldn't.

So they're like, this guy had a good sense of humor and sense of style with different

things.

So I'm just like, I don't know.

I've never seen anything like this.

That place probably has like a few million dollars worth of furnishings.

Yeah.

It was crazy.

That was a crazy place.

And then I interviewed with him and it was the easiest interview I've ever had.

Most chilled interview.

It was just like, tell me your stories, kind of amused with my story.

And then he's like a cheeky guy and he's just, he had already decided.

That's what he told me later.

He's like, you had applied with this like website resume where I was like, oh, why I'm

the guy for the job?

I wrote this email and then I started sending them like ideas for their current products.

I was like, Hey, I checked out the flow for this.

I think it could be improved here and here.

So I was like trying to make an impression.

I didn't do a job search and I did a job hunt.

I was like, this is the job I want.

I'm going to zone in on it.

Search versus a hunt.

And I'm going to go like hunt for that.

And I'm going to try to capture that job.

That's exactly what I did too.

And so that had worked.

Basically, by the time I got there, he was already interested as long as it wasn't a

weirdo.

I think I wouldn't have blown it.

And so chill.

And I got the job working under him.

And then like six months later, he was like, Hey, you should run this thing basically.

When you guys started, uh, three or two or three products, um, more that we did like

maybe six or seven or three that were like, some would only last a month.

Some would last.

What was the two years?

What was the MO?

He said, just all right, here's $2 million a year.

How much budget did you have?

We had a business that was already making about $2 million a year, but it was declining.

Birthday alarm.com.

Right.

Birthday alarm.com.

And then we, it was like a business.

One project was just maintain it.

And then at one point as it was just declining because it was like, you're just fixing bugs.

Like let's turn this around.

So we did a turnaround, then that got back up.

And that was a website where like my aunt would pay you $10 a year and you would be

reminded when it was someone's birthday.

Yeah.

She'll never forget Sammy's birthday.

And then when it's Sammy's birthday, if she's paying the reminders free, if you want to

send a card, you pay the subscription like $14 a year or something like that.

And it made between $2 and $3 million all profit almost other than hosting.

Exactly.

Um, and so that was the cash guy that funded the whole lab.

And then on top of that, if we, you know, if we needed more expenses, they would just

invest money into it.

So I think it funded, I think I funded half and he put half, uh, just cash.

And his, his mandate was like, we don't do B2B and we don't do real world like t-shirts

or Uber or things like that.

They don't do like physical work stuff.

Because he'd learned that from Beepo probably.

He was just like, yeah, like whatever, you got to pick a lane and like, we're pretty

broad.

Like it could be any idea, but like of the lanes, let's not, let's do only consumer and

let's do only software.

How many engineers did you have there?

Like 16 ish 18.

When I went there, I was like, Oh, this is a tech billionaires country club.

That's what it felt like.

Not even a country close.

Nobody else was there.

Like his play is like his man cave.

Yeah.

Playground.

Yeah.

Man cave is a better word because you had like old Mac computers as like, uh, art and

he had like really nice actual real art and like, it was just like, Oh, if I'm a billionaire

nerd in San Francisco, this is exactly what I would do as well.

So instead of like owning like old Ferraris, he just hired 16 engineers to make dumb shit.

Yeah.

He had those two, he just didn't keep them in the office.

Oh, he had those two.

Yeah.

Uh, and so, all right.

So he had all the, he's got an island, he's got cars, he's got, you know, his own projects.

He owns his own hotel.

His own private.

Do you think he was happier than you?

Did you think he, do you think he was happier for back then when he was a, you know, billionaire,

he was probably in his late thirties at that point, maybe early forties.

Forties.

Yeah.

Do you think he was happier than you are now?

He's definitely more at peace.

So I think I'm pretty joyful.

Like on a day-to-day basis, I'm kind of bouncing around and he's more stoic than that.

Like he's, he definitely has a good sense of humor and laughs a bunch and that doesn't

take stuff too seriously.

I get, I'm more easily excitable.

So I'm excited about random stuff, anything, I can get excited about anything.

I probably still want to prove yourself.

But I have this inner not peace.

I'm not just at rest.

I'm like trying to do something, prove something, be something, make something, earn something,

earn something and like, I, he just didn't have that, that same.

Because of the acquisition?

Because of that.

And I think just wisdom.

Like I think he saw, okay, you know, his whole cohort of friends mostly became super

successful.

They were, they were the who's who of Silicon Valley.

And so he told me once, he was, cause I was like, I was like, how come you don't blog?

Like I feel like all the VCs are blogging at the time.

That was like the big thing.

And I was like, why don't you, he's like, well, I just don't feel like I have anything

like that interesting to say.

And I thought that was the funniest answer.

Cause I was like, I could have heard him say, I should, or I do event, or he could have

said, no, I don't want to do that because of this, like I play the game this way instead.

But it was so humble to just say, I just don't feel like I have the, like, if I don't have

something interesting to contribute, why would I just blog in your face?

Like that would be rude.

Darmash shot the founder of HubSpot.

He's, you know, this billionaire guy who's like Uber successful.

He told me, he goes, yeah, I'm speaking at masters of scale.

Read Hoffman's thing, his conference.

And he was like, yeah, it's like, you know, the founders of Stripe, Bill Gates, the CEO

of Uber, whatever, like kind of the who's who of all these big shots.

He's like, I'm so humbled and honored and I can't believe like they're having me.

And I was like, I said, I go, really?

Can you really not believe that?

Like it seems like, it seems like pretty believable.

Like you're like, like that seems like a very believable thing.

Evidence.

Yeah.

Like from an outside perspective, you're like a billionaire, you're HubSpot at some, I don't

know what the cutoff of a fortune 500 is, but like it's definitely there or right around

there.

You know, at times it's worth 20 to 30 billion dollars and you made it.

I mean, I can believe that you'd be there and he's like, well, you know, they're just,

I'm just honored.

And I just, and then like, I, you know, I cannot believe I'm actually going to be there.

And I was like, well, I don't, I don't even know what to say.

That's just so hard for me to grasp because from the outside, you guys all seem like the

same thing.

Yeah.

You know what I mean?

Totally.

But I thought that was weird.

So I'll give you, I'll give you an example of a way where I saw that he was more at

peace.

Like we had a product that was launching and the press was covering it, TechCrunch was

covering it.

And it was like, oh sweet, TechCrunch wants to do an article and they sent over the draft

or they sent over like some bullet points or whatever.

No, no, no, it was good, but it was like, they had said something that was like more than

it was like, they had said 200,000 and actually it was 20,000 users or whatever, like whatever.

Some number was inflated.

And I was like so happy.

I was like, yes, this is great.

Like they're just going to say a great thing about us even greater than reality.

Like, but I was the sort of like, I wasn't going to correct the record.

Like that's on them, right?

You know, like in my mind, I was like, this is a good thing.

They're over giving us credit.

They're giving us more credit than we deserve.

And he was like, he's like, well, we should just correct it.

So it's the real number.

And I was like, but then it's like worse for us, right?

He's like, yeah, but like, you know, we don't need to.

We don't need to do that.

And that was the first one.

Then the second one, he was, he was talking about, I think he had a bad experience with

his VCs at Bebo.

And when we had some VCs interested in funding us at Blab and he was just like, he was sharing

some stories and he had told me, he was like, I was like, do you think that they'll follow

through?

He's like, oh, they'll follow through like Silica Valley.

He's like, I would never not follow through.

He's like, if I commit and even there's not a contract and then I realized that, oh, it's

not going to work out for this, I committed, I'm in.

He's like, because this, this is a town where you play the game for like 30 years with the

same people.

And if you make a move that's like self advantageous now, like your reputation is worth more than

whatever that's, whatever that is.

That was his approach.

And like, actually I've, there's many examples of people who are like, sure, my reputation

is bad, but like I banked 40 million or 80 million or a hundred.

There's like all these examples of that in Silica Valley too.

And you, you know what?

They won in their way, but when he's like, he was just so high integrity and I was not

as high integrity.

And I realized the reason why I wasn't high integrity is not because I'm evil, not because

I'm a bad dude or because I've like, I just don't have moral short-term thinking.

I was just short-term oriented and I was, I was afraid of failing.

I was like, you know, so it was like, okay, what can I do to like increase my odds of

winning where he was just more confident.

He was just like, we're going to win and we don't need to, we don't need to play the

game in any way other than the straight way to win.

And like, I hadn't really internalized that, but once I saw that, that was really sick

to see because then I was able to like adjust my knob and be like, oh, yeah, I just never

going to lie.

Like I just don't want to lie, even though my instinct was to exaggerate or my instinct

was to not correct if somebody else believed something about me that wasn't true, like

whereas, you know, he would just, he was just totally comfortable in his own skin.

So is he happier than me?

I would say yes, because he's more comfortable in his own skin.

He's more comfortable with where he's at, he's more at peace with where he's at.

He's not like at this like inner fire or war to whatever, not at the same time.

I'm sure he misses like the adventure, the thrill of like building something and having

it succeed and having that mean something.

Because now, no matter what he does, like it's very hard to have it mean something unless

it's like intrinsic motivation.

Like I just love the product or it's helping impact people, but like the thrill of winning

is kind of gone because he's already won at like such a high, you know, if you go to the

arcade machine and you set the high score and it's so out of reach, you know, like you

can play and have a good game, but like you're still going to never touch that high score

again.

I think he knows that.

You guys like launched two or three things.

But the last thing was the last thing was blab, which I remember so that's when we became

friends when you were one or two years into being the CEO, I think, and I was like, what

do you do?

And you're like, well, we're launching this thing.

And then you kept jumping and I would criticize you.

I'm like, dude, you just got to stick to this one thing.

Right.

You're probably right.

Well, who knows?

I used to firmly believe that was the way then I've seen some of the things you've done.

I've seen some of the ways some of our other friends have done.

Like there's tons of ways to get things done.

What was the final thing that sold?

The final thing that sold was we, after pivot, after pivot, after pivot, we got to a thing

that was like a eSports app.

So basically eSports is like trend where people are playing and back then it was just starting.

It's like it's still just starting.

It's like it was around, but whatever.

But it was really just starting.

I mean, Twitch was like only six or seven years old at the time.

No, no, this, yeah, I guess, I don't know.

Twitch was around.

Twitch was big, but it wasn't, that wasn't really the thing.

It was basically the last idea we had, the one that we got acquired for.

We basically built an app that was like the way a high schooler could go and play.

You could sign up for basketball or soccer or whatever.

Like some game you could go play in a league for it and you would pay your league dues

and like there's literally baseball and then there's like, you know, AAU sports, there's

all these youth leagues, youth sports is a big deal.

There was no youth eSports.

That was the whole idea.

And so we had had a bunch of technology.

We'd already been doing stuff in streaming and gaming.

And so we took all that tech and we made an app that let any high schooler sign up and

play in a Fortnite league.

Fortnite was the big game at the time.

It was like Fortnite was ripping.

And there were more people that played Fortnite in the world than played basketball.

And so we were like, that's crazy.

This has more players, but there's no organized league.

There's only the pros.

There's no like amateurs.

And so we created the high school Fortnite league and we had an app that you would sign

up.

You'd make your team.

You could invite friends.

And then you would compete against other teams and you get like ranked.

You play in tournaments and all of it was streamed, which is cool because it turned into

like a spectator sport.

How big did that get?

It was the biggest eSports league, but it was small overall.

We were only maybe six or nine months into that version of it.

They maybe had 10 to 25,000 active players at the time, which was big because in theory,

those people would pay us, if I go take my daughters three and put her in a soccer league,

I'm going to pay 99 bucks or whatever for her to be in that league.

So same thing.

If we started charging for it, if we could have this like SaaS business that was going

to generate, I thought millions of dollars a year, but maybe tens, probably never hundreds.

So that was the problem.

I was like, oh, if we do this really well and we succeed at this, it'll get to maybe

like 10 million a year, maybe 20 million a year in revenue, but never really beyond that.

And it isn't that fucked up.

That's not what we signed up for.

It's not the way that the game is played.

It's not.

It doesn't suck because I agree that that, well, that's just the game that just sucks

at that.

That's not enough.

Yeah.

If you owned 100% of that, you could have made a, maybe a similar ish amount of wealth

as my perch.

Yeah, exactly.

But it wasn't structured that way.

I know.

It sucks.

And so once I kind of got that feeling, and I was six or seven years into the whole Monkey

Inferno experiment with creating products with that same team, same group, it was like,

let's sell this and let's shake things up.

I had a guy, I was lucky, a friend, Suley, like on the outside, everything was amazing.

Office was amazing.

Dude, when I met you.

Product was cool.

You were like, I'm making 150 grand a year and I'm like, oh my God, you're like the wealthiest

person I've ever met.

It's like you have $150,000 a year.

That's crazy.

If you're only in your 20s, I remember you told me that and I was like shocked.

I was like, Ann, you have this sick office.

Like you're set.

I felt that way at that time.

And then over time, your expectations change.

You meet other people who are doing better, better.

And you're like, oh man, I was like 160, 160, that's nothing.

Like I'm way underpaid.

And in general, I was just like, I just wanted to get a win.

I don't think you're underpaid.

Well for a startup founder, I wasn't underpaid.

But if I just worked at a job, I would install the equity.

The equity was what mattered.

And so I owned 20% of the business.

And so anyways, we decided to sell and then that was a crazy process.

Life changing?

Yeah, for sure.

Financially life changing?

Yeah.

Because go from no millions to millions, that's life changing.

And you actually stayed there, so Amazon bought the company and you stayed there for two years,

right?

Yeah.

You stayed?

Like I don't really think about the past, like, what's like, am I happy I stayed?

Yeah, sure.

Like, you know, fine.

In retrospect, if I could go advise myself now, I would have stayed only one year.

I stayed two.

But I also got a bunch of other benefits.

Like I popped out two kids and was able to like spend time with them and didn't have

to stress about my own business.

Yeah, you like collectively had like 10 months of paternity leave.

What's that?

I mean, you had like 10 months of paternity leave.

No, actually, stupidly, I only took two weeks with the first kid.

What were you thinking?

I fell into all the traps you could fall into.

Like at a big count, it's like, oh, they put me on this special project and the CEO really

loves it and cares.

Now's the critical time.

And also being at home, honestly, being at home is harder than being at work, so it was

like actually kind of easier to go back to work in a way.

But like, I should have taken more time and I just sort of like didn't.

And I think a lot of employees fall into this trap in companies.

They don't take, that's like, the company has unlimited time off.

You don't take it.

You could take this much for paternity maternity, it's like, oh, you feel pressured to cut

it short because you want to get back to your team or your whatever, stupid.

But the second year, I was way more chill and basically did very little work.

When did you start the Ecom thing?

Somewhere around that time.

We don't talk about it on purpose, so we won't talk about it much.

But what do you want to say?

Anything about it?

It's a big business.

I think we'll start talking about it soon.

Maybe that'll be a special episode.

Do you want to say how big it is?

Yeah, it does like 15 million a year, profitable.

Damn, dude.

I've been trapped in two years.

I remember you told me you were doing it and I was like, why would you ever do that?

And are you happy that you did that or not?

Same thing.

In retrospect, I would go advise myself, don't do this path.

Because you already had like clout a little bit.

And now, so during the sale of the first company, you started this podcast and that's

been the hustle and this podcast kind of collaborated.

But this podcast, people asked me how to grow a pod and I'm like, I don't know because

Sean like started doing it my way and it kind of worked the day one.

Like we got like, I think the first episode was 60,000 downloads.

The first one was just, hey, there's a new thing and people will go check it out.

Yeah, but it still was a good start.

But it got to a good start and then when we switched it to this format, it got even better.

It like took off in a better way and then just time.

Time like, time has been three years.

Yeah.

And so the thing I've learned, so why do I say I would go back and do it differently

is because I now realize something I already knew, but I didn't have the guts to act on,

which was that at any given time, you're really only going to get to throw your all into one

thing.

And so why not throw like, if you're going to do that, like choose really wisely.

So for example, when we got acquired by Twitch, I didn't want to throw my all into that.

That wasn't like going to be my, my, my baby, my future was to be an employee at Twitch.

I wanted to earn out the deal and I was feeling like I needed to get that check, right?

So there was like a desperation to secure the bag.

Which by the way is the right move, I think.

Maybe.

I think selling out is the way to go.

I had asked a buddy who was more successful at the time and I was like, what would you

do if you were me?

He's like, I would quit on day one.

He's like, I would sell so that your team and your investors are happy and then I would

quit on day one.

I go, why?

Like it's so much money.

If I just stay even one year, what do you get?

No big deal.

And he's like, he goes, the surface area of opportunity is too wide.

Who said that?

Suley.

He's so smart, man.

Cause I went, I remember we went for a walk and we walked for like an hour and a half

in the mission.

We just walked back and forth through the mission on the streets.

It was like, everything's closing, the missions get to his hell.

And we were just like, imagine like pacing furiously, we were doing that and we were

just talking through what's next.

And I said, I really want to do this podcast.

I want to create a podcast.

He's like podcast.

I was like, yeah.

I was like, I think if I could just be in a million people's ear balls every morning,

that's like, that would be the most fulfilling thing for me.

And it'd be awesome.

You're like 20% of the way there maybe.

Yeah.

I don't know.

A million is now I realize like very aggressive of like every morning, but like, you know,

if you just keep going for five years, it could happen.

Like that, that, that's realistic now.

But I remember thinking that's what I want to do.

And I couldn't explain why I was just sure I wanted to do it, which in retrospect is

a really good signal.

Like that's the type of stuff you should go do.

And I did that.

But then the other thing he was just like, yeah, we just quit from day one, the surface

area of opportunity is too wide.

And I looked at it and like, and I was like, well, what would I do if it wasn't this?

And he's like, again, the surface area is so wide and anything, and I was like, give

me an example.

He goes, all right, I got a company for you.

We could do right now.

I'll co-found this with you.

And he totally talked you into it because the, Sully was all, he had just sold an econ

business that he had just.

No, no.

This is a different idea.

Not even the econ business.

Oh.

This is a different thing.

He goes, he goes in e-commerce.

There's this company called Clavio.

They're an email sending company.

Yeah.

They're taking off.

He goes, Clavio for SMS.

And I go, doesn't Clavio do SMS?

He goes, no, I'll go one thing.

He goes, yeah, they're probably well.

Aren't there these other companies?

Yeah.

Sure.

But he's like, you're focusing on the wrong thing.

I'm telling you, I'm in e-com and SMS is like, it's like email, but better.

People open it.

And he's like, he's like, if we just build SMS for e-com, I think we can go get like a

hundred brands that matter and this would be a valuable company.

And I was like, okay, it kind of sounds like, I don't know, it was just like this idea.

Boring.

Boring.

Because it was like, here's a ready-made idea.

There was like nothing else to think.

It was like, anything I said was basically a distraction.

You think he was right?

He was absolutely right.

Because, so we talked about it.

We went kind of down that rabbit hole for like a little bit.

We tried to find maybe a different operator to come run it.

And then I see this company in YC called PostScript and I send it to him and I go, hey, they're

doing Clavio for SMS.

And he goes, all right, I'm going to invest.

So he goes and him and his brother invested in it.

And PostScript is now like a multi-hundred million dollar company in the same, there's

the same period of time, right?

And so like, that was a path.

Sure, maybe it wouldn't have worked out for us, but like, I don't know, I would guess

it probably would.

But like physics has allowed it to happen.

And like possible.

And it played out.

And so, whether it's that one or even just the Ecom thing, if I just started it at day

one, like the Ecom thing is more valuable than what I earned out at Twitch, like it

will be.

And so like, again, the surface of our opportunity was very wide and I was, one thing was a guarantee

and it was right in front of me.

Everything else was unknown.

And so I've learned now that like, you should just keep going until you like go, like, turn

down a thing that's known.

If it's not what you want, if it's not the real thing that you want.

Because only when you turn that down, then do you get the opportunity to go find the

thing you want.

It's like dating, right?

You're dating somebody who you don't want to marry.

But they're okay.

They're good.

It's just not, they're not the one.

And you might try to talk yourself into it.

But like, if you're talking yourself into it, you're already losing.

You got to break up in order to meet the next person.

In like six or 12, I forget when you started the milk road eight months ago.

We launched in January.

Yeah.

So, and that's actually going really nicely.

You have 150 to 250,000 subscribers.

Yeah.

Over 200.

Wow.

Okay.

And maybe you'll run that forever.

Maybe you'll sell it.

Who knows.

Have you ever thought about what you want to do for the rest of your life?

I think about that all the time.

I want to brainstorm that with you.

Okay.

What would you like to do?

Well, assuming that milk road is not a thing.

Yeah, assuming that milk road is not a thing and assuming that the e-commerce thing is

not a thing.

So let's assume two things right there.

Cause in the spirit of what I'm talking about, if it's not the one, then you got to find

a different way.

So let's just say that there's something else that's the one.

What would it look like?

What would it be like?

I think there's one version of it that's like this podcast, just more, like what if this

podcast, if this podcast was 10 times bigger, would I really care to do anything else financially

10 times bigger?

Either way, audience, I think, translates to money.

Is there an amount of money, like whether money is important or not, I think you should

work backwards from that.

Is there an amount of money that you'd want per year?

The target currently is 50.

In net worth.

Yeah.

Total net worth.

That's not like tied up in one company that's like can die next month, like in assets you

own, kind of like liquid, but it could be a little bit more.

Ownable against.

Yeah.

Like not concentrated into one paper valuation of one company.

But a podcast would more so be a, or a media company for you would be more so an annual

income thing, I would imagine.

Right.

So it could stack up to 50 or it could just wait and then sell for 50 or net 50 in the

end in some way.

Well, I think that you, so.

And by the way, 50 is just a random number.

You just made it up.

Yeah.

So maybe we should start there.

Maybe that's the wrong number.

No, I think that's a good number.

I know what you like.

You like nice shit.

You like spending a lot of stuff.

I think 50 is a good number for you.

Okay.

I think the difference between 30 and 50 for you or me is actually not a significant amount.

Right.

So shoot for 50 and then land where you land.

Shoot for 50.

I think that's a good number.

The difference between anything above a hundred is enough today that you would really, really

have to work hard.

Like you'd have to be, you'd purposely have to be a jackass to go through it.

That's mostly true for 50, 10 you can go through, you know, that's just like a big house and

like a medical emergency and like, you can like kind of blow through that.

A bad investment.

Yeah.

I mean, it is.

You know what I mean?

A lawsuit.

Yeah.

Give me back on a two or three like pretty quickly.

30 is in the range of where it's enough that like you can't screw it up a hundred for

sure.

Like you would have to have like some crooks around you or a stupid, like your dad's smart

enough to be like, Hey man, can we have a, can we talk about this?

I think you're going too hard.

You don't need a Lamborghini.

Yeah.

You know what I mean?

Buffalo time.

We'll do hot one.

Yeah.

We're talking money now.

50 is enough.

I think that's a good goal.

And I think that I've seen you grow to be this like tech person to a media person.

You are better at media than you are tech.

I believe that.

You are better at investing than you are at running things.

I believe that.

You are better at starting things than you are running things.

And you are horrible at managing like theoretically at managing 50 plus people.

Yeah.

I don't even know.

I think you'd be awesome at leading them, but horrible at managing them.

You just don't want to.

Yeah.

But you're really good at being like a leader.

I bet you'd actually be a really good CEO too.

I think you'd be a horrible.

Just like what?

Like inspirational speeches.

Yeah.

You're, you're naturally inspired.

Like Jerry, Jerry Seinfeld said comedy is like a secret weapon that most people understand.

Comedy is kind of in storytelling and just charisma, the ability to capture someone's

like imagination and make them believe something or capture emotion from them or make them

feel certain emotion.

You definitely have that.

You have that.

And everyone, a lot of people ask me, was Sean always good at this?

I'm like, yeah, he was actually always good at it.

And then he's gotten better.

So I think that you, you have that.

So I would say you could be a CEO, but you're, you actually got really lucky.

And Ben Levy doesn't publicly get enough credit, but that's like your partner and all

these things.

Yeah.

He 100% is your ying to the yang.

And if I was you, I would go way harder on that partnership with him and potentially

launch more things and let him operate.

Who's having the most fun?

Like who's got the, who's having the most fun with, with their life stuff?

You are doing pretty good.

Okay.

Besides me.

Who else?

Rob Deirdeck was pretty amazing.

I think they're like, like you're more of a Rob Deirdeck than you are Mark Zuckerberg.

That's for sure.

You know what I mean?

Like if it's like just like one guy, one company, hardcore tech versus like little here, little

there, little here, all based around like a personality.

What is like, okay.

You exited recently.

You had to think about what you're going to do next.

Yeah.

How did you think about it?

I actually gave this advice to someone.

So what I did, I sold.

So I sold for enough that you don't have to do anything.

I don't have to do anything.

Not enough that like I'm going to go and buy a crazy jet, enough that I still am ambitious,

but enough that like a fairly luxury level of needs are met forever.

And I did that and I realized, okay, for the next 12 months, but it could be longer.

All I'm going to do is research and think.

And I never give anyone that advice because I say, you just got to start and do stuff.

And by the end of this weekend, like have something live, but I'm like, no, I already,

I know I do that.

I have that ability.

So for the next 12 months, forever long, I'm going to feel, this sounds like I'm fucking

Oprah.

I'm going to be not guilty about like, yeah, this is so Oprah.

There's like some boo boo.

Is that actually from Oprah?

No, but I just like it sounds like you feel guilty.

Not doing shit.

You're like, oh, I'm missing out.

I'm missing out.

I'm like, no, this is like really Oprah.

I'm going to, I'm going to let, I'm going to forgive myself.

Yeah.

Because I sound like I need one of those Coachella hats.

Like I was like, I'm just not going to be guilty about doing stuff.

I'm just going to research.

I'm going to read.

And when the feeling feels right, it's going to feel right and I'm going to go all in.

But until then, I'm not going to, I'm not going to say maybe this stuff.

I'm not going to say yes to anything.

I'm going to say no to everything.

I'm just not going to, I'm just not going to worry about it.

And I just read and I researched and I think that I actually think you suck at sitting

still.

Yeah.

That's why I got to, I got to do it and forgive myself, give myself grace.

Yeah.

But you have to, you've got to chill because like someone like you, you can execute.

Like you, you already, you can do stuff, right?

But then, okay.

So you chill, you read, you do all the stuff, talk to people and you talk to people.

I mean, the business that I'm talking about, the business that I end up doing now, I interviewed

them on the pod.

Right.

Multiple.

I was like, I'm just going to talk to you.

Like I got that.

Go and interview people.

So you do that.

But how did you resist the temptation to, okay.

How many ideas did you have before this one?

None.

That you were, none.

You weren't tempted to do anything before that?

No, I, no, I was not.

This was the first idea that you were like, I got, I'm going to do it and then you just

did it.

It was the first one that I felt, okay, I did investing.

So I did angel investing.

I realized that's stupid and I hate it.

I hate angel investing.

You're good at it and you love it.

I think I'm only good at it because I'm popular, but I don't like, I don't like it.

And I hate it.

It's so boring.

Okay.

Dude, it's so stupid.

I invested $15 million in one year into 70 companies.

And so I kind of like went fast on that and then I realized, uh-uh, I'm out.

I hate this.

So I bailed.

And so I like tinkered with that, but that wasn't like a full-time thing.

We only worked on that 10 hours a week.

So anyway, I do, I just read like crazy and talked to people.

I think you should do that.

Why wouldn't you just take like 18 months and just like,

That is my plan.

Not 18, but like,

Just however long it takes.

12.

Basically I was like, let's take 12.

Listen, here, this is this analogy or this visualization will help.

Imagine your life is this line, all right?

You're about a third or the way through, maybe 25% of the way, maybe if we live a long time.

This amount of time, this like one inch on this 15 inch segment, this one inch of time

was going to impact the rest of the 10 inches.

Do you know what I'm saying?

It changes the color of the rest.

It changes the entire trajectory.

So why not spend like a ton of time early on, right?

Really focusing instead of, because there's a chance that had you done that previously,

which you didn't have the luxury to, but had you done that previously, or maybe you didn't

have the luxury to.

It would have made better decisions.

You would have made better decisions and you would have gone all in on one thing, which

would have cumulatively made more than all the other stuff combined.

Right.

And so the question then is, the fear I have is, how do I make sure that's not just a kind

of like, sort of like a, how will I know also, how do I do it in a way that's not just absolutely

meandering?

Or maybe that's all right.

Maybe it is.

I think that's all right.

I think that's all right because that's not your personality.

And so just by meandering, it's almost like, it's almost like most people, we have to tell

them that hit on the gas harder with you.

You're a car whose back wheels, we lift it up and you're already going all the way as

hard as you can.

And all we're going to be doing is just figuring out which direction we're going to place that

car.

And then when we're ready, we're just going to drop it.

That's a good analogy.

Do you know what I mean?

Yeah.

Most people, we got to feel cool too.

Because I'm like a really fast car or something.

Most people, we have to like fuel that car and like, no, go harder and you're good.

You're good.

You're good.

Like, all right, you're already moving a little bit.

I'll go leave it harder.

With you, it's like, dude, that gas is down already.

Right.

Like we might as well just find out the right place to put it.

Then when we put it, you're going all in.

Yeah.

That's exact.

So that's how I would look at it.

All right.

I like that.

Like people who are, who are, who's oven burn hot.

That's what I say.

Like they're going to be burning shit.

It's just like pick the right thing.

Yeah.

Like, you know what I'm saying?

That's kind of how I feel about like whatever our stupid industry is.

It's like, I don't know, man.

Just like give me a computer.

Get out of the way and I can figure out how to make something at least somewhat intriguing

because that's just what I love doing.

And I think the same 100% with you.

All right.

I like that.

That's good.

Right.

Yeah.

I like it.

Also, you last podcast, you have me 100% convinced that AI is the thing.

So I would go into AI.

Yeah.

That could be it.

I just think that that's like a huge pond and you just cast anywhere out in that pond

and you're going to have a winner.

Yeah.

That's fair.

You think so?

It seems that way at the moment, but I think it's more like, if it's like, if I was going

to meander or wander around, I'll definitely spend some time in that neighborhood to see

what's up.

I'm trying all the different bars.

It's still early.

I'm asking people where the best tacos are.

I'm talking to people and being like, what was here before this?

And that's, that's what I would do in that space before I just do something.

Dude, it's still early enough to it.

You could take time.

You could take six to 12 months off and just relax.

I talked to someone the other day who works at OpenAI and this guy is like a little bit

naturally of a pessimist.

He's like, no, he doesn't just believe in hype.

And I was like, hey, is this legit?

And he goes, yeah, it's legit.

I was like, do I have to be worried that it's going to take over the world?

He's like, no, I don't know when that will happen or even if it will happen because we

are a bit away, but in terms of just replacing developers' jobs or just making life easier

and like just like for art, making new types of art, it's 100% legit and it's almost here.

It's basically here.

Right.

And so I think that's like, that stuff's pretty amazing.

Should we do a hot one?

Yeah.

I guess.

All right.

Let's try it.

How hot is it?

I don't know.

I've never tried this before.

I don't want to get like a panic attack.

Is it hot?

No.

It's not hot?

Maybe this is not the hot one.

Let's see.

No.

I don't think so.

I think this is supposed to be the hot one, but not hot.

That's not hot, right?

No.

This one's hotter.

I don't want to eat like a ton of it and for it to like...

Kick in?

Yeah.

Yeah.

It's like it's not hot.

I don't think it's bad at all.

Yeah.

I think you got got.

Yeah.

It's all right.

Tastes good though.

Rick Ross probably owns this wing place.

Does he have a wing place?

Yeah.

He owns like 30 wing stops.

He's like the rap version of Shaq.

You know what I'm saying?

Like he owns like five guys and shit.

Should we just do that?

No, dude.

So I've been in the Airbnb and like real estate game.

That's whack too.

I thought that was dope.

It's whack.

It's just...

It takes too long.

It's just too slow.

Like I will come up with an idea and want to do something and like you don't get results

if you're building something for 18 months, 24 months or with like a rental like let's

do this, this, and this.

And like I don't know if it's any cool for three months or if it's like, you know, if

it's actually a good idea.

No, I think real estate is stupid.

I think it's really cool to invest in, but like as a creative person, it's whack.

Yeah.

It's like no dopamine rush either.

Yeah.

When people are like, oh, buy boring businesses and invest in boring businesses.

I'm like...

I don't want to live a boring life.

Yeah.

It's in the name.

Yeah.

It's also in the name guys.

Yeah.

Like where's the buy exciting businesses at?

Yeah.

They talk about boring businesses like bro, I don't...

What you want is something that's boring to other people, but not boring to you.

If it's also boring to you, like, come on, you wasted your talent.

I don't want boring life.

Yeah, exactly.

I see that stuff too.

I'm like, man, I don't want... and I don't want to work with a guy who runs a dry cleaning

company.

I just like...

You know, I'll be like sitting outside on the corner like King of the Hill, like, yep.

Like, I don't want to have that conversation.

You know what I mean?

I don't want to talk about it.

Yeah.

I want to like do stuff.

Yeah.

These are all right.

That's not hot though, is it?

Yeah.

You're looking spelt by the way.

Thank you.

You want to finish with like a rapid fire hot seat questions?

Yeah.

I think that's the hot one.

This one, right?

Yeah.

This one's hotter.

That one's hotter.

That one actually is hot for me.

There we go.

The milk is coming into play.

That one's hot.

All right.

Let me dip this one in.

Oh, this is almond milk, by the way.

All right.

What's the rapid fire?

All right.

Let me think of a couple of questions.

Oh, how's your portfolio doing?

You want to do an update on that?

Oh, dude.

End on a sad note.

All right.

Hot seat question, here's number one.

Would you rather be three times as famous and half as rich as you are today or stay

as you are?

Stay as I am.

Why?

I'm married.

Being famous isn't that cool.

I mean, what's the point?

It's for single people.

Yeah.

What advantage does fame have at this point?

Well, some people bet that.

I mean, they pulled my ego, but like I...

Some people just feels good.

And then also, you could argue that if you were three times more famous, you could actually

earn a bunch more too.

So, you know, it could make other things easier.

I'd rather be two times as rich.

Twice as funny and half as ripped or twice as ripped and half as funny.

Being funnier is better for like picking up girls and having guy friends, probably.

So, funny.

You said you're married.

Why are you trying to pick up girls?

I said, meet guys too.

Did I say that?

I know being ripped seems to do it too.

Dude, being funny is better.

Being funny is way better.

What would you rather be?

Funny.

I'm all in on funny.

What about the fame or wealth?

Being half as funny, that would be like, that would be really sad.

Like, you could be half as fit and you could kind of recover.

If you're half as funny, there's just no recovering from that.

That's like the end of the game for you.

And you were half as fit three years ago and you were doing fine.

Yeah, exactly.

I've been there before.

Hello, my old friend.

Nice to see you again.

What about the other one?

Tell me, what's the highest stakes negotiation you've ever been in?

Selling the company.

What about you?

Well, when did it feel high stakes for you?

Was there a moment?

Every single day.

I'm almost positive every single day there's a chance I can kill the deal.

The HubSpot CEO, did I tell you this?

No.

Oh, the car, the skiing accident, the day after, right?

His accident was even worse.

Brian was on the podge.

He told you about it.

Him and his son were snowmobiling in Vermont or wherever people snowmobile.

I don't fucking know.

And like his son hit the gas instead of the break and they ran into his dad, Brian.

And they fall over a cliff and it was either like 12 or 24 hours that he just sat there.

He's like, and he said goodbye to his son and he's like, you know, this is it.

And suddenly they get cell phone service and someone comes and finds them and then afterwards

he comes back and quits.

And close the deal.

Did you text Sam today?

One more thing.

So funny.

Well, dude, that happened two weeks after the deal closed.

And like, I think that company is big enough that him like frankly died.

Would have put a pause on it.

Yeah, I don't know if that would have, like, I don't know if that would have happened.

Hey guys, not to be insensitive.

Just wanted to check in if we're still on for the whole acquisition.

RIP, Brian, but so.

I'm sending out the docusign in case you guys are still ready.

So that I mean,

I totally understand if you need a day.

Yeah.

So anything could have killed it.

No pun intended.

Anything.

I'll do respect, Brian.

I love Brian.

So I'm only joking.

But any anything could have like destroyed that deal.

And I think that is stressful.

So that was the highest one.

What was yours?

Well, I have two.

One was, I think I've had to tell the auction story when we bought the Bebo brand back.

I've never heard before.

So Michael tells me at one point he goes, Hey, we have an opportunity to buy Bebo back.

Oh yeah.

And you had to go like looking like a schmuck so no one knew who you were.

I'm just how I look.

Thanks though.

But the, we go to a courthouse basically.

So, so he tells me we're going to buy it back.

And we, and my mind, I'm like, awesome.

What are we going to do with it?

And he's like, I don't know.

We got to figure something out.

He's like, but it's a good domain.

You get the email list.

You get the domain.

You get the hardware and you get like the legal ownership of that.

Hardware.

Like whatever servers or whatever they had.

So, and so we were like, okay, what is this worth?

And so we came up with was like, my, we sat in this room trying to speculate.

And then Michael was just like, put down the hammer at one point.

He's like, I don't think we're going to be able to buy it for less than a million.

And I don't think I really want to pay much more than a million.

So let's go with a million.

That's your bid.

So we fly to LA.

It's me, our lawyer and our COO.

And we get to a courthouse and I'm like, is that a courthouse?

What do we can do with staying in front of a judge?

And the judge goes, okay, are there multiple parties here to buy it out of bankruptcy?

Yeah.

And then we don't know who else is going to be there.

We don't know if anyone else is going to be there.

And there's two other groups that raised their hand.

And they say, she's like, all right, go to that room and you're going to auction

against each other to see who wins.

I was like, what?

So we go to this tiny room.

Just going to fight.

Yeah.

Basically.

And one person from each one person from each team got to sit at the table.

Everybody else was behind them like, oh, and so then it's us.

And then it's match.com.

And it's some other social.

Well, like IAC, they own a bunch of internet properties.

So they wanted to buy it.

It's kind of like volaturing.

Yeah.

They were like, we're going to harvest the profiles and use them for dating.

It's like, what?

Like the SEO.

We need that SEO juice.

It's like, damn, I hope you guys don't win.

That sounds awful.

Were the people kind of one another?

Or were they like pulling up?

You just sit down and it's like bid.

And we're like, oh, here I'm the representative from this, this and this.

All right.

So it starts and it's like, we'll start the bidding at 100,000.

And then it'll go up by 50,000 increments up to 500,000.

And then it'll just be free form after that.

We'll be here as long as it takes to finish the bid.

And you get like a minute between, a minute or two minutes or something like that in

between bids to decide if you're going to bid.

And so it goes 100, 150, 200, 250, so on and so forth.

It goes up to 700,000.

And then the guy, one guy drops out.

So then it's just us and match.

Time out.

He's like, we need to go make a phone call right before seven.

Dude, that's like getting in a fight with someone and being like, time out.

You can't do that.

It's exactly what happened.

He got punched in the nose and it was like, time out.

So we're at 750,000.

And they go outside.

They had to make a phone call to their boss.

And I was like, oh, what's up?

Having a boss.

Yeah.

If you like tattled on him, you're like, sir, is that.

So I try to go eavesdrop.

I walk outside.

They immediately stop talking.

I just go to the restroom twice just to see if I can pick up anything.

And then the, and I come back in.

I'm like, I talked to our lawyer.

I was like, okay, they're calling at 750,000.

They're probably getting authorization to go up.

That was probably their max.

They're probably getting authorization.

Probably the highest thing goes a million.

And I told the like auctioneer person, I was like, no more time outs.

Like that can't, we can't do that again.

And so they come back in and she's like, there's no more time outs.

I'm like, okay, cool.

Pressure is on them now.

And bidding goes 800, 850, 900, 950.

When you are going, when you make your bid for 900, do you just say like, ugh.

So we had been acting like that to be like, are you kidding me guys?

And then I, then I told the lawyer between like, I built this thing.

It was not worth that.

I go, I go, we got to just act like we have an infinite bank roll so that they

just feel like they can't win this auction.

And so I said, as soon as they say a number, just top it.

Immediately top it with no hesitation.

Just like, not like we're here all day.

I could say, I could go on and on and on.

And so that's what she did.

She changed up her demeanor, started doing that.

And basically we got to a million and at a million, she pulls a great move.

She doesn't say a million.

She goes, one million, 25,000 to just up it.

Because you know that they were all were stopped at a million.

We knew they had gotten authorization for a round number.

So I think it was actually one million and 10.

I think she did.

She had 10,000 above and they just go, you guys can have it.

You guys can take it.

And they were like, yo, our max was a million.

Just maximum.

I was like, yeah.

And so we got it.

And then we like came back.

That was like the most high stakes like hand of poker I've ever been involved in

basically.

All right, we'll do, we'll do one more.

So something that you thought you were on to something, but it turned out to

become totally wrong.

Yeah.

You thought you were on to something you turned out.

What's yours?

We had one when building blab basically, like when we built blab,

it looked like it was taking off.

And this is now like four years in.

And imagine you're four years in and you feel like you might have just like

made the next big, like basically what clubhouse ended became.

That's what blab was.

And we started seeing this like rapid growth and people loved it.

And everybody felt it was new and fresh.

Everything else we had made people like, oh, this is just like Snapchat.

No matter what we did, they're like, this is kind of like Snapchat.

And we're like, God damn it.

Like the next thing we built is not going to be like Snapchat, no matter what.

That was blab.

And it takes off to 200,000 users pretty quickly.

It gets to a million users and VC, you know, founders fund wants to invest and

all the stuff.

And it felt like we did it.

Like this is going to be the next social thing and we own it.

Like we are actually going to own one of those things.

And then it got to about four million.

And then it started to just, we started to realize, why isn't the number going up

as much as like, I don't know, signups are still up.

It's like, oh, it's super leaky.

The retention, like the retention has been getting worse and worse.

It started out okay.

And now it's just pretty bad.

And this was all in the span of like six months.

And it's like an impossible problem to solve too.

It's not like, even if you operate at a plus level, it's just like a, you just can't.

Retention is like the, retention is the thing that's worth anything in business.

And retention is the thing that's also the hardest to solve.

Because like, it's like dating.

Like you, if you wanted to pick up somebody, that's like just getting users.

Like you could change the way you look.

You could teach you to pick up lines and like, you know,

If I can get you some, you know, a shirt that fits you a little bit better and like,

you know, whatever, pick the booger out of your nose.

You can get the, you can go get their number.

But you can't make them date you.

You can't make them marry you.

And like, that's what retention is.

It's like, are they going to marry your product or not?

And so once I knew that was a problem, I was like, oh God,

we tried so many things to try to fix it.

It was just like, not move it.

Cause it's more fundamental.

It's like, is this a thing people want to do all the time or not?

It's very hard to like spam them with notifications to try to get that number up.

So the year we sold the hustle, you know, we sold it in February.

So we set a whole year ahead of us.

But I think we probably would have done around 20 million in sales.

And I started the company wanting to hit a hundred million in revenue before year 10.

And we sold it between four and five, I think year four and five.

So we were kind of on track.

We would have got there.

We could have maybe could have gotten there.

And I knew I could like, I started the company with just an email,

even though people said it's stupid because I was like,

I remember telling you it's stupid.

I was like, do video dude, do Facebook video, Snapchat, Instagram.

The math is such that like, I'm pretty sure that like, you know,

people are kind of dismissing this as like a hobby.

But look, if you like just change a 10,000 person email list to like five million,

like the numbers add up to a hundred million dollars.

I don't know anyone who's ever done that, but I'm pretty sure that could happen.

Like I understand the math and like each seller of advertising would sell

$1.5 million of ads and there are already people that do that.

So if I just hired like, you know, a hundred of them, like things add up.

Like this could all work out fine, actually.

But I didn't truly believe my own prediction, even though I knew like this list lines up.

Yeah, you could tell everybody else, but yeah,

telling yourself in your head is different.

I was like, this works actually, this works.

And I didn't entirely believe it.

And so I sold right when I got like a pretty decent offer

because I wanted to secure the bag.

But in reality, I made a mistake.

I didn't make a mistake because I actually would have done the same thing again.

But I could have achieved my goal.

Right.

Now looking back at it, I know.

Well, Morning Brew's kind of doing that, right?

They are doing it.

They're like 7500 million, something like that.

Well, they're at, they're probably 80 million in sales.

Yeah.

So they're close.

So they're like getting close.

And I knew, and him and I, Austin are good friends now.

And we both talk and I'm like, he's like, yeah,

you guys actually would have been there like,

they're a year older than us in terms of company.

They're like, you guys actually would have been there even better

because you had subscription revenue.

And he was like, you're, and he's, he was like,

I'm actually amazing at operating things,

but you guys are always way better at like inventing new shit.

And we would just copy you.

And, or, you know, he said something like that.

And he is really good at operating though.

And that was my biggest mistake.

Yeah.

We got to tell the story.

100 million plus.

Of Nikita's app, which is also kind of in this boat right now

of like almost on this.

This is going to be its own clip.

So tell the story.

All right.

So our friend Nikita, Nikita beer has this crazy story.

He built an app right now.

That's the number one app in the world or in the U.S.

Above Tik Tok.

Above Tik Tok.

Facebook.

Be real Facebook, Instagram, all that stuff.

So it's the number one ranked app in the store.

And he called it.

He called it.

So we bleeped out his name a while back,

but now I think it's fair game to say.

And he's been Instagram like sharing as he's been going.

So he's been showing that.

So a year ago, I was on a call with Nikita.

I don't know him super well.

Actually, like we're in this group chat together,

but I don't actually know the guy that well,

like in person or anything like that.

And we're on this call and he just goes,

he had his previous app was called TBH gets acquired by Facebook.

And he's been at Facebook for four years.

Some of that he's about ready to leave.

I'm like, all right, what are you thinking about?

What are you going to do next?

He goes, I want to come up with an app that's going to make

$10 million.

He goes, I want an app that's going to make $10 million.

$10 million in 90 days.

Yeah.

And I was like,

which is so ridiculous thing to say.

And I was like, what?

And he's like, yeah, that's my brainstorm.

It's just what app is going to make me $10 million in 90 days?

I was like, that's not a thing.

He's like, no, there's apps to do that.

Like he showed me four apps that were like,

here's this app.

I remember one was like a plant,

like a plant identification app.

He's like, yeah, this app that you like take picture of a plant,

tells you about the plant and how to water it and all this stuff.

This app does this much money and like there's,

there's a bunch.

And that's what he did in the past was he launched consumer apps

that grew quickly.

They grew, never made about a bunch of money, but he's like,

oh, TBH.

I learned from my mistakes.

Yeah, I learned from my mistakes.

TBH was, I figured out how to make an app go viral amongst high

schoolers.

But then it was like the same retention problem we were just talking

about.

It's hard to retain, but we were lucky that like Facebook swooped in

and bought it.

And then they shut it down.

And if I own the whole thing, I can just launch it,

cash out, throw down.

Basically.

Who's already throwing down before?

Cash in.

I don't know.

What is it?

Startup, cash out, throw down.

So he was like, so that was his mindset.

So he says that idea.

All right, fast forward.

All right.

You got some concepts.

He had different ideas and he's like, all right,

I know what I'm going to make.

It's an app that basically says who likes you for high schoolers.

So you get on, you take a quiz.

You're like, who's most likely to be famous?

I don't know.

I haven't downloaded that.

This is what I think it does.

It's like, who do you have a crush on?

Who do you like?

Who do you think is the hottest person?

Blah, blah, blah, stuff like that.

And then it invites you to like, it tells you to invite friends

so that they take the quiz.

You can see who thinks what about you.

You send it to them.

It sends them a text message that says, somebody said,

you're the cutest person in 11th grade.

Download this app to find out who.

So obviously you're going to download this app, right?

It's the same flow that a bunch of apps like down to lunch

and others had been using.

We did the same thing.

We did it.

It's pretty spammy, but it goes viral in high schools.

And so he had it now down to a science.

He's like, I know how to pick a high school,

deploy it into the high school, and it will go viral

by the next day.

Like, you know, within X number of hours,

it'll have like 40% of the population using it.

And his life was measured by hours.

He would say, he's like...

Yeah, you'd be like, how's it going?

Yeah.

And he would be like, this hour, this is what's happening.

So we're doing horrible.

We're adding X percent, we're growing X percent by hour.

Yeah.

It was by hour.

Well, I'd subscribe, right?

Last hour was this, but hopefully,

if it doesn't pick up by midnight tonight,

then I know it's horrible.

Yeah.

Like it was by hour.

It reminded me of...

Scientific.

Yeah.

I think I said, I was like, it reminds me of like someone

saying like, dude, I know just how,

I know exactly how you feel.

I used to feel just like you yesterday.

Like he was measuring like where days were years.

Like look, I've done that.

I was there this morning.

Done day, baby.

Yeah.

So anyway, so he does it.

So then he's like, all right, here's the app.

He sends us the like the clip of it.

He's like, it's going live.

And we're testing it just in Georgia.

Just six high schools in Georgia.

And then we're like, how's it going?

Not viral yet.

Next day.

Tweak the invite flow.

Virality is at this.

The K factor.

Next day.

Tweak it.

K factor 1.4.

Viral.

And then next day.

Graph.

Going up like this.

Oh yeah.

Monetization.

We're making $1,000 a day.

We're making $10,000 a day.

Right?

Like it's crazy.

It was like by the hours.

Like this is how...

Yeah.

Like this is all the hourly revenue.

Crazy numbers, right?

So we're like, wow, dude, you called your shop.

You're doing it.

Fantastic.

I think the worst thing and yet the best thing for the

sake of the story happens.

Worst thing for our friend and best thing for the show started

to happen.

That makes this very interesting.

So tell the story.

What happens?

So basically he's blaming it on Chinese.

So let's see what happens.

So it's like everything's going good.

This is going to crush.

People start accusing him of having a sex trafficking app.

Yeah.

They're like, oh, that app?

Like now it's called gas.

The first one was called simp.

So it was like, oh, the simp app.

You should delete that app off your phone.

It's got your location.

It's being used for sex trafficking.

And then the same thing happened with the next version.

There's a really funny in between.

I don't know if we're allowed to share this part, but he changed.

So it's simp.

Then he changes it to crush.

He's like, oh, we had to change the name.

Just like the soda.

The orange soda.

Yes.

So we see that logo.

We're like, oh, delicious logo, dude.

Love it.

He's like, dude, craziest AB test ever.

It's the same app.

We just changed the name and logo.

And it somehow switched from being like, you know.

And this whole thing we had spent eight months or six months working on it.

But then like it launched, went amazing.

Rumors start shaking up.

It goes viral.

It's taken down in the app store.

All in a matter of literally 15 days.

Like this is everything that we're talking about is in like two

week in increment.

So maybe a week increment.

So he goes to crush.

That's like week one.

Then he changes it to gas.

Gas is the one that's number one in the store right now.

It was on the cover of the Wall Street Journal this morning.

But what's happening is that same thing happens.

The rumors are coming out.

The reviews are getting hammered saying this app is evil.

This app is a hoax.

He's like, dude, we're just getting attacked by this hoax.

I would have.

And we know it's true.

We would have millions of users.

Yeah.

We're like, obviously he's not using it for that.

Like what are you talking about?

A competitor or somebody is like immediately soon as he launches,

they're just flooding social media with this rumor that, oh,

look at this, the permissions for location.

It's trying to track you.

I don't know.

I downloaded the app and a white van was behind me.

It's like, like the dumbest thing.

You downloaded an app and a white van showed up behind you.

Like, come on.

And last night he tweeted out blaming.

Did he say it was Chinese?

Yeah.

And he's like, because we were like, dude, who would,

who is trying to do this to you?

And like, and how are they paying so close to?

How are they so good at taking you down like this?

This is insane.

And he's like, dude, I don't know.

I don't know.

I don't know.

Maybe it's, and then last night he's like,

I think it's originating out of China because like,

we noticed that it started right when all these Chinese things

signed up for our app.

And so he's like, I don't know.

He's still in the middle of some firefight with this right now.

What's crazy is that we are so close to like such a,

so many ridiculous things happens.

One, he called his shot.

He said what was going to happen.

He called a ridiculous shot.

A ridiculous shot.

And he's done it now three times in a row.

Each time you relaunches this app, it works.

Well, it's the same app.

It's a different name, but like, yeah.

But like it's not, it's not a coincidence.

Yeah.

It wasn't a fluke that the app got viral once.

It's scientifically engineered to spread like, you know, COVID.

Number two, it's crazy that all these people are using it

and talking about it.

That's just wild.

It's crazy that somebody can hoax this thing like out.

Like basically like it's going to get taken down.

People are, he's like, we're getting, you know,

2% deletions of the user base by hour right now.

It's not worth, I guess it's going to die.

And it's also crazy that like, who knows if he's,

he says stuff that I roll my eyes to.

And then I saw that he was in the cover of the Wall Street Journal

and I'm like, oh, like all this nonsense that you say.

The only reason I think it's nonsense is because you're.

Of course nonsense.

What do you mean?

Like he's like, yeah, like we're going to go,

we're going to be number one and we're probably going to beat

wish and Facebook.

And then we just got to worry about like competitors.

I'm like, dude, no one cares about you.

There's no way that you're going to be better.

Like it's just you and three engineers and some stupid house

in LA.

Like you guys aren't going to beat those guys.

Like you're just saying the most ridiculous things ever.

But they're only ridiculous not because of him,

just because those are outlandish words to put in the same sentence.

Right.

You know, like me and my.

Even when he was telling us like months before this, he's like,

yeah, there's these seven engineers just cause he used to throw

parties all the time in his house.

I was bragging about it.

Yeah.

I used to call him the Jewish Mr. Mr. Gatsby or whatever.

Or the, you know, cause he was like, he would like,

he's like this young guy with all this money in LA.

Yeah.

Living single.

What did you do?

They're like, what do you do for living?

And so then he's like, no house parties are done.

There's like seven engineers sleeping in my living room.

We're just working around the clock on this app.

That's going to go viral.

Yeah.

Like just that sentence.

I'm like, okay, sure.

Yeah, exactly.

Like, and so, but he called a shot.

He did it.

It's gone crazy.

It's gone viral.

It's crazy that it's getting hoaxed out of existence.

And who knows?

Maybe he'll fight it off.

Maybe they'll, maybe the thing we get,

maybe all the fake reviews will get taken down or whatever.

I don't know.

But.

Wild.

Wild.

Wild.

And that's basically like a, I don't know,

some of like a 20 to 50 million dollar prize that's just getting

snatched by like the rumor mill.

What's even crazier.

We have to do a proper episode on this one day.

Is that group that we are in, this is like the third or fourth

or fifth thing that a group of six or seven of us have gone through

where it's been like a fairly epic on a grant,

a fairly grand scale thing that has happened,

that has been manipulated like it or not manipulated,

but like texted into reality.

Intentionally.

Yeah.

Yes.

It's just crazy that the stuff we have to do a whole,

like yeah, it's a crazy story.

Nikita is killing it.

I downloaded the app, but then.

You're not allowed to, you can't join unless you have like a high school.

Yeah.

This guy just kept following me around.

I don't know what.

Probably a coincidence.

And then he delivered us hot wings.

You just kept insisting that I drink this drink.

All right.

I think that's the episode, right?

Yeah.

I feel like I can rule the world.

I know I could be what I want to put my all in it like the days off on the road.

Let's travel never looking back.

Machine-generated transcript that may contain inaccuracies.