Shaan's Backstory (#377)

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.

We, uh, we're in San Francisco. We're outside of San Francisco. We're doing a doing a live pod the first time in a while.

We're in the studio. What is this, a music studio? Is that what this is normally, music studio?

Did the instruments give it away? Uh, all right, people were asking online, they said they want us to do a pod. We already did my story, it's the second episode. Uh, now we'll do one on you.

All right, let's do it.

So how old are you now?

Good question. Uh, 34.

Um, and you're from everywhere.

Everywhere.

Where?

I was born in Oklahoma, believe it or not.

What part?

Tulsa. Yeah. Denver, Texas, China, Indonesia, Australia, San Francisco. Yeah, that's it. And maybe a little bit of London too. 2 months.

And you're living in Australia in pre-college or right college age?

I studied abroad there. And then also after college, I started a company with a guy who, uh, like kind of a well-known entrepreneur in Australia.

And that was pre-college?

That was after.

But, and 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 at just at Duke. Like that's where I started.

I thought the sushi thing was in Australia.

No, no, no. That was here. And then we moved to Denver because, um, basically, you know, like people move to Silicon Valley because it's 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 Company started there. Quiznos started there. Smashburger started there. There's like 700—

amounts of like open-minded white people.

Yeah. 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 it was like, where are we going to start? It was like, uh, because Denver's 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, where Chipotle start? Look. 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? Oh, these two brokers. Okay, well, we'll go talk to them. And then who did their 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 funny, my two co-founders, my two best friends at the time, Trevor and Dan.

You're not really a co-founder of a sushi. Of a restaurant? Yeah. Co-owner, maybe.

Yeah. Yeah. That's, that's a good point. That should have been signal one that this was not a great idea. It was like founding what?

You know, like, like my, my father-in-law owns a moving company. He doesn't call himself like the founder of the moving company. Creator. Yeah.

Creator.

Yeah. He's just the owner.

Yeah, that's fair. So me and 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 had gone, I had actually quit the startup. I didn't really tell people this, but I basically, when we 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 a good job. So he's like, okay, I'll hire, you know, we need more.

The guy who ended up going to prison, 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 dudes, 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 just like moved and took this job in Indonesia.

Yeah. In a month you're 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's like a dropout of second grade or something like that. So he's like, he basically didn't speak English. So my boss never spoke English to me, um, only like broken words. Crazy guy. Like, um, 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, uh, 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 another email from this person. So there's just 4 screens like that and they were just—

he's just like the brain.

Yeah, he's just talking out loud. Yeah, he literally can't read or write, just like his hands. And then when— and so what he was doing was, well, 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 is like, I don't know, maybe the 5th largest population in the world. It's got a ton of natural resources like coal. And they— so ExxonMobil, BP, all the ConocoPhillips, they all wanted this coal. But if you go there and you try to get the rights, you go to the auction and they're like, actually, that guy owns it. My cousin owns it. And they're like, where was the process? Like, yeah, the process was done in the middle of the night. You don't need to know about it.

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 pro— 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 3 years just doing that. And so when—

but it's like liquid. So he was liquid.

He was uber 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— whose name was on the title of the car?

Yeah, everything's his. Like, we lived in this like 4-season 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 coal? He's like, great. Um, then when, when he would get a, like, he had like all these geologists on and he'd be like, do a survey or 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 they just like basically fudged the whole thing. That's my impression.

What do you think made him special? He was just bold and willing to cheat and lie and steal.

And he wasn't cheating. Like, he was just like playing. That's how 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 playing by the unspoken street rules of the game?

Um, 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 at 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 my, 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. So like, you know, if it works or doesn't work, why would I add risk into this by like doing this? And my dad was just talking to me and then my dad one day goes, I think I've told this story before, but he goes, he's like, he's like, I probably am like a top 5 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, um, you idiot. Yeah. Like, do you think that that's relevant? Basically he was just like so matter of fact about it. And so I was like, oh wow. So my job when, when I worked there was company comes in, he doesn't speak English. So he needed an 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?

Kokos.

You're like, all right, gentlemen, Mr. Kokos would like you to feel welcomed here and let you know that he's not here to play any games.

Yeah. It would be like, Mr. Kokos 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. It's like you go to karaoke. I don't know if you know about all this, like Asian cultures, like you go to these karaoke rooms. And there's like, why are there all these cute girls here? It's like bottle service at a club.

What are 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 during the day.

They just love singing Don't Stop Believin'.

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, uh, wow. Why do you think I'm sharing all this? Because 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. He got cancer, died.

Oh my God.

He was a nice guy. He was a nice— he was really good to us. He was really nice to us.

I mean, I think he was like a— again, I asked this before, like, he was not 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 seem 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, with the clients and like you, you, you know, yeah, you, you have to grease the, the, the, 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. So you, the sushi thing, like, was only mildly suc— it wasn't a success.

Was not a success though.

But you moved to San Francisco and you got a job with Michael Birch, right?

That's right.

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

He, uh, by the way, Jonathan, 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, I was 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 make— 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. Try to have the same conversation while eating hot wings.

And I think there's milk.

Yeah, there's not. There's no sides. Um, so I moved to San Francisco pretty quickly. I'm like, God, this can't be it.

Like, no dude, it sucks.

Every day I'm waking up at 5 in the morning, I'm driving to like the fucking fish market, picking up the fresh tuna for the day of chop. And like, the business was actually working. Like, we did it as a cloud kitchen and it was basically making money. I was like, this can't be it. Luckily at that time, my dad had met a guy in Australia who had sold his company and in passing, dude, your dad is like just hooking it up.

A king.

He met this guy and he was, he was like in passing, he's like, you know, what do your, what do 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, should check it out. They, they write this blog that's really entertaining. It was like, I was, we were creating a WordPress, we had a WordPress blog. That was really just for our own amusement, but 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 his 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. Like, 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, 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.

Like, 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— I don't know what he wanted. I can't put words in his mouth, but he, um, all right, here we go. So there's 3, there's 3 flavors. There's like a sweet and 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.

You think it's that one?

Yeah.

Yeah. The 6 and the buffalo.

All right.

I'll eat 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 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. Because 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, will 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 a 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. Yeah, I'm good at that.

You would have seen, because that shit was exciting and you seem like you would have gotten— I don't know those guys, but you seem like you would have got along great with them.

Yeah, like you're, you're more of a cowboy.

Yeah, like, but I think you legitimately would have made tens of millions of dollars.

I think so too. Uh, 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. Um, 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 that 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. 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. Like, you know, the person who builds all the value. I never talked to the founders. I basically, I had one interview with this guy, Ben, and, um, 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?

No, they did a sell me this pen type of question.

That's 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. 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, uh, Basecamp by 37signals. I, I knew that was like a popular, those guys were popular.

So I thought 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 wanna 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 I, no, the, the, 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, he goes, no, ring ring.

Hello.

Go. You're selling this thing to me now. And I was like, oh God. And I just did.

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, no, that's not a good reason. But the best way— so 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, 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, I heard of somebody got this guy Kyle Samini. He's like a VC. He's, he put out a post or he put out some interview or whatever where he said, he's like, yeah, there's only one way to apply to my firm. Uh, 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 filter because when you see someone write, you see how they think and how, 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, so I'm kind of into that as a test.

What was— oh my God, he's brought milk. Is that milk or is it tinted glasses? So it almost makes it look like eggnog.

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

Yeah. Do you want Buffalo or sweet?

Well, that's the— should we go?

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 palate cleanser. Ugh, nothing like eating on microphone, by the way.

Yeah, hot wings are the worst.

You have any paper towels?

You're gonna hear me gnawing.

All right, this is the Hot Ones episode of My First Million. Thank you, dude. I'm doing no milk.

What brand? I mean, what, what restaurant?

Shout out to our sponsor Wing It for providing these wings today.

Dude, I used to live in an Asian neighborhood here in San Francisco. And the Chinese and like Hong Kong restaurants would make hot wings. They are the worst at making those hot wings because they put like—

too crazy.

It's too breaded and they put like sticky shit on it. You know what I'm saying? You know, I don't know what that crap— you know, that sauce that like—

I don't know what you're talking about.

Dude, have you ever had like 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 gonna be. I think that's a thing.

I hate that sticky shit. All the Chinese restaurants I go to, 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.

Dude, that's such a weak take.

Because I'm such a domestic cat. No, this is— You're like a feral cat.

You know, the right way to eat these is you 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 a healthy thing to eat.

What, wings? This is good. This one's not too spicy at all.

What was Monkey Inferno when you applied?

So I, um, 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, uh, designer, one designer, and then Michael and Zocchi Birch, who were the like the owners and the, the husband and wife couple that was married. They were—

they sold their company for like $850 million.

They sold Bebo for $850 million.

This is how you do it.

Do it into the camera. Wow. Clean.

Clean.

Yeah, it looks like you're having fun over there. I'm gonna stick to just nibbling on the outside.

It's all good for me. I like my wing bones like I like my women. Clean.

I thought you were saying in your mouth. I was like, where is he going with this?

Oh, wow.

Uh, yeah, so Mugyafredo was 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. Or 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 3 or 4 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 1 was Mark Cuban's thing where he sold to Yahoo for $2 or $3 billion.

Right.

Number 2 is Bebo, which sold to AOL for like $850 million 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 3 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, you know, I hired 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 the candy or the rapper? The candy. But they actually did have other stuff. Like they started a reality TV show called like, I forget I was like Joanna or something.

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.

Yeah, yeah, yeah.

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— 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 sold?

Well, they owned like 70%.

So, you know, no public math, but, you know, 70% of $850 million 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 in 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 7 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 a like a whole ping pong kitchen entertainment area, and then huge office space, uh, where we all worked. So day one, I get off a plane from Australia. I come straight from the airport to the office to interview, and I get there a little early, and right across the street was a Burlington Coat Factory.

I remember that pretty good.

I walked to the Burlington Coat Factory, and I'm just standing there in the Burlington Coat Factory with a suitcase.

Yeah.

They're like, what is this guy doing?

You had a suit on?

Suitcase.

But what were you wearing? I was just wearing like, you know, tech casual, like trench coats and Burberry Dakota Factory, just walking around.

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— no, the other way. If you're looking at the person, it would look like a mirror. If you're inside, you could see out. Yeah, the non-weird way. Looked like people could see you, but they couldn't. So 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 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 ever had. Most chill interview. It was just like, tell me your story. He's 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, 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, um, 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 was, I didn't do a job search. I did a job hunt. I was like, this is the job I want. I'm going to zone in on it 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 into interested. As long as I wasn't a weirdo, I think I wouldn't have blown it. And, uh, so chill. And I got the job working under him. And then like 6 months later, he was like, hey, um, you should run this thing basically.

And you guys started, uh, 3 or 2 or 3 products.

Um, more than that. We did like maybe 6 or 7, 2 or 3 that were like, some would only last a month. Some would last, what was the 2 years.

What was the MO? He said just, all right, here's $2 million a year. Or how much budget did you have?

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

BirthdayAlarm.com, right?

BirthdayAlarm.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, it's 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 reminder is 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 cow 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 it funded half and he put half, uh, just cash. And his mandate was like, uh, we don't do B2B and we don't do real world, like t-shirts or Uber or things like that. We don't do like physical world stuff.

He learned that from Bebo 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?

It's like 16-ish, 18-ish.

When I went there, I was like, oh, this is a tech a billionaire's country club. That's what it felt like.

Not even a country club, nobody else was there. It was just like his play— it was like his man cave.

Yeah, playground. Just like, yeah, man cave is a better word because you had like old Mac computers as like art. Yeah. 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-inch nerds to make dumb shit.

Yeah. He had those too. He just didn't keep them in the office.

Oh, he had those too. 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 company.

Do you think he was happier than you? Did you think he— Back then? Do you think he was happier for back then when he was a billionaire? He was probably in his late 30s at that point, maybe early 40s.

40s, 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 definitely has a good sense of humor and laughs a bunch and doesn't take stuff too seriously. I'm more easily excitable, so I'm excited about random stuff. Anything. I can get excited about anything.

And 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, win 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, I, or I do. And then, or he could have said, no, I don't wanna 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, I have the, like, if I don't have something interesting to contribute, why would I just blog in your face?

Dude, today that would be rude. Dharmesh Shah, uh, the founder of HubSpot, he's, you know, this billionaire guy, he's like uber successful. He told me, he goes, yeah, I'm speaking at Masters of Scale, Reid 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.

There's evidence. Yeah.

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

Uh, but I thought that was weird. So you're this—

I'll give you, I'll give you an example of a way where I saw that he was more at peace. Like, uh, 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, they, they either sent over the draft or they sent over like some bullet points or whatever. No, no, no. It was good. But it was like, um, 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 just sort of like, I wasn't going to correct the record. Like that's on them. Right. You know, like I, 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 like, uh, he was talking about, um, I think he had a bad experience with his VCs at Bebo. And when, and 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, um, I was like, do you think that they'll follow through? He's like, oh, they'll follow through. Like Silicon Valley. He's like, he's like, I think 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, Um, like your reputation is worth more than whatever that's, whatever that is.

That was, that I did.

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 $100 million. There's like all these examples of that in Silicon Valley too. And you, you know what, like 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 cuz I'm evil, not cuz I'm a bad dude or because I have like, I just don't have morals.

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, uh, what can I do to like increase my odds of winning? Where he was just more confident. He was just like, we're gonna win and we don't need to, we don't need to play the game in any way other than the, 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'm 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, inner fire or war to whatever. At the same time, I'm sure he misses like the adventure and 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 just 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 it like such a high score. 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. And I think he knows that.

You guys like launched 2 or 3 things, but the last thing was Blab, which I remember. So that's where we became friends when you were 1 or 2 years into being the CEO, I think. Yeah. And I was like, what do you do? And you're like, well, we're launching this thing. And then you kept jumping from thing and I would criticize you. I'm like, dude, you just got to stick to this one thing.

Right. But 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. 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 an esports app. So basically esports is this trend where people are playing video games.

Back then it was just starting.

It's still just starting. It was around, but whatever.

But it was really just starting. I mean, Twitch was only 6 or 7 years old at the time.

No, no, this, yeah, I guess. I don't know. Twitch was, 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 Little League 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. Um, 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'd get like ranked, you'd play in tournaments and all of it was streamed, which was 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 6 or 9 months into that version of it. It maybe had 10,000 to 25,000 players, active players at the time, which was big 'cause it like in youth, like, you know, in theory those people would pay us, like if I go take my daughter's 3 and put her in a soccer league, I'm gonna pay $99 or whatever for her to be in that league. So same thing, if we started charging for it, it would have this like SaaS business that was gonna generate, I thought, millions of dollars a year, but maybe tens, probably never hundreds. And so that was the problem. I was like, oh, if we do this really well and we succeed at this, um, it'll get to maybe like $10 million a year, maybe $20 million a year in revenue, but never really beyond that.

And dude, isn't that fucked up?

That's not what we signed up for.

It's not the way that the game is played. It sucks. It's not, it doesn't suck because I agree that, that, well, that's just the game that just sucks at that. Because not enough. Yeah. If you owned 100% of that, you could have made a sim— maybe a similar-ish amount of wealth as Michael Birch.

Yeah, exactly. Uh, you know, but it wasn't structured that way.

I know, that sucks.

And so once, once I kind of got that feeling and I was 6 or 7 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. You know, I had a guy, I was lucky, a friend, Suli, like like on the outside, everything was amazing. Office was amazing.

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. And you're only in your 20s. I remember you told me that and I was like shocked. I was like, and you have this sick office. Like you're set.

It 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 making $160,000. $160,000, that's nothing. Like, I'm way underpaid. And, 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 have sold the equity. The equity was what mattered. And so, um, I owned 20% of that, of that, of the business. And so anyways, we decided to sell, and then that was, you know, crazy process and it's all life-changing. Yeah, for sure.

Financially life-changing.

Yeah. Because go from no millions to millions is, you know, that's life-changing.

And you actually stayed there. And so Amazon bought the company and you stayed there for 2 years, right? Yeah. And are you happy you stayed?

Um, like, I don't really think about the past. Like, what's like, am I happy I stayed? Yeah, sure. Like, you know, fine with it. In retrospect, if I could go advise myself now, I would have stayed only one year. I stayed two. Um, 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 did. I fell into all the traps you could fall into. Like at a big company, 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, as a, like, 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. Uh, you could take this much for paternity, maternity. It's like, oh, you feel pressure to cut it short because you want to get back to your team or your whatever stupid. Um, but the second year I was way more chill and basically did very little work.

When did you start the e-com thing?

Somewhere around that time.

And we don't talk about it on purpose.

Yeah.

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.

Bootstrapped in 2 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. So then that's when The Hustle and this podcast kind of collaborated. But this podcast, people ask me how to grow a pod and I'm like, I don't know, because Sean like started doing it right away and it kind of worked day one. Like we got, 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. Right. Yeah.

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 3 years. Yeah. And so the thing I've learned, so, 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, um, when we got acquired by Twitch, I didn't want to throw my all into that. Um, 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. I was like, I would sell so that your team is fine 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, one year, no big deal. And he's like, uh, he goes, the surface area of opportunity is too wide.

Who said that?

Suli.

And he's so smart, man.

Because 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. Mission's ghetto as 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 pod— 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 earballs every morning, that's like, that would be the most fulfilling thing for me. And it'd be awesome.

I was just 20% of the way there. Maybe. Yeah.

I don't know. Million is now I realize like very aggressive of like every morning, but like, you know, if you just keep going for 5 years, it could happen like 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. Um, but then the other thing, he was just like, yeah, I would just quit from day one. The surface area of opportunity is too wide. And I looked at it and like, uh, 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, 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 Suli was all, he had just sold an e-com business that he had just—

no, no, this is a different idea. Not even the e-com business. This is a different thing. He goes, He goes, in e-commerce there's this company called Klaviyo. They're, uh, email sending company.

Yeah. They were like really taking off.

He goes, Klaviyo for SMS. And I go, doesn't Klaviyo do SMS? He goes, no. I go, won't they? He goes, yeah, they probably will. Uh, 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, it's like a 90%. He's like, you just need a bit. Like if we just build SMS for e-com, I think we can go get like 100 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. It was almost 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, uh, 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, this is, they're doing Klaviyo for SMS. And he goes, all right, I'm going to invest. So he goes and him and his brother invest in it. And PostScript is now like a multi-hundred million dollar company in the same, this is the same period of time, right? 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, it, it played out. And so whether it's that one or even just the e-com thing, if I just started it at day one, like the e-com thing is more valuable than what I earned out at Twitch. Um, like it will be. And so like. Again, the surface of 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, don't 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. And then like, you gotta, you gotta break up in order to meet the next person.

And like 6 or 12, I forget when you started the Milk Road, 8 months ago?

We launched in January.

Yeah. So, so, and that's actually going really nicely. You have 150,000 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 wanna do for the rest of your life?

I think about that all the time. I wanna brainstorm that with you.

Okay. What, what, what would you like to do? Well, um, assuming that Milk Road's not a thing.

Yeah. Assuming that Milk Road's not a thing and assuming that, uh, 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, um, if it's not the one, then you gotta find a different way. So let's just say, let's say that there's something else that's the one. What would it look like? What would it be like? I, I think there's one version of it that's like this podcast, just more, right? Like, what if this podcast, if this podcast was 10 times bigger, would I really care to do anything else?

Financially, 10 times bigger?

Uh, either way, audience, I think, well, is there translates to money.

So is there a, is there an amount of money, like whether money is important or not, it is kind of, you have, I think you should work backwards from that.

Yeah.

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

The target currently is 50.

In net worth?

Yeah. Total net worth. Uh, that's not like in tied up in one company that's like, can, can die next month. Like in, uh, you know, assets you own kind of like liquid, you know, But it could be a little bit more like loanable 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.

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 it's a lot. 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, then buy where you land.

I think that's a good number. The difference between anything above 100 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, you know what I mean? And you can go and you can be back down to 2 or 3 like pretty quickly. 30 is in the range of where it's enough that like you can't screw it up. 100 for sure. Like you're, you're, you would have to have like some crooks around you or like 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 yacht. You know what I mean?

Buffalo, Buffalo time.

So anyway, hot one. We'll do a hot one.

Dude, we're talking money now.

50, 50 is enough. I think that's a good goal. But, 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 you are better at starting things than you are running things. And you are horrible at managing, like, I, I don't, theoretically at managing 50+ people.

Yeah. I don't even know.

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

Just don't want to.

Um, 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 naturally inspir— like what Jerry Seinfeld said, comedy is like a secret weapon that most people don't understand. Comedy is kind of in storytelling, 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. You— 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 actually got really lucky. And Ben Levy doesn't publicly get enough credit, but that's like your partner in all these things. Yeah, he 100% is your yin 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, uh, I mean, you with their life stuff, you are doing pretty good. Okay. Besides me, who else?

Um, Rob Dyrdek was pretty amazing. I think they're like, like you're more of a Rob Dyrdek 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, a little there, a little here, all based around like a personality.

Yeah. You know, um, 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?

What I actually gave this advice to someone. So what I did, I sold. So I sold for enough that I'm—

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 crazy enough that I still am ambitious, but enough that like a fairly luxury level of needs are met forever. And when I did, 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 or however 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 woo-woo stuff.

Is that actually from Oprah?

No, but I just like—

it sounds like—

because 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. Yeah. I sound like I need one of those Coachella hats that chicks wear. 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 to stuff. I'm not going to say yes to anything. I'm going to say no to everything. I'm just not gonna 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 gotta do it and forgive myself, give myself grace.

Yeah, yeah.

Have grace for myself.

Dude, but you have to. You gotta chill because someone like you, you can execute. You can do stuff, right?

But then, okay, so you chill, you read, you do other stuff.

Talk to people and you talk to people, you, you inter— I mean, dude, and then ideas come up or the business that I'm talking about, the business that I end up doing now, I interviewed them on the pod, like multiple. I was like, I'm just gonna talk to you. Like, I got that. Go and interview people.

So, 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, no, I, no, I was not.

This was the first idea that you were like, I, I'm gonna 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. So I did that and we 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 tinkered with that, but that wasn't a full-time thing. We only worked on that 10 hours a week.

Yeah.

So anyway, I just read like crazy and talked to people. I think you should do that. Why wouldn't you just take 18 months and just like—

That is my plan. Not 18, but like—

Just however long it takes. 12.

Basically, it's like, let's take 12 and let's—

Listen, this analogy or this visualization will help. Imagine your life is this line. All right. You're about a third of the way through, maybe 25% of the way. Maybe if we live a long time, this amount of time, this like 1 inch on this 15-inch segment, this 1 inch of time can— was going to impact the rest of the 10 inches. Do you know what I'm saying? It changes the color of it, changes the entire trajectory. So why not spend like a ton of time early on, 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 did have the luxury to—

You would've made better decisions.

You would've made better decisions and you would've gone all in on one thing, which would've 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 supposed to be meandering.

I think that's all right because that's not your personality. And so just by meandering, like, it, it's almost like, it's almost like most people, we have to tell them to hit on the gas harder. With you, you're a car whose back wheels we lifted 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 going to drop it.

That's a good analogy. Analogy.

Do you know what I mean?

Yeah.

Most people, we got to feel cool too.

Well, like a really fast car.

Well, like most people, we have to like fuel that car and like, no, go harder.

You're good.

You're good. You're good. Like, all right, you're already moving a little bit. Now go even harder. With you, it's like, no, that gas is down already, right? Like, we might as well just find out the right place to put it. And then we put it, you're going all in. Yeah, that's exact. So that's how I would look at it.

All right.

Like people who are, who are, whose oven burn hot, 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? Remember I made a joke that people made fun of me, but I actually stole it from The Departed. They're like, John Lennon, give him a fucking tuba and he's going to make art. That's what he does. You know what I mean? 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 like be cool. Not be cool, but like 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 also the 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 gonna have a winner.

Yeah, that's fair.

You think so?

Um, it seems that way at the moment, but I think it's more like if it's like if I was gonna 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 enough.

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, right? Just do something.

Dude, it's still early enough to, you could take time. Like you take your time. You could take 6 to 12 months off and just relax. I talked to someone the other day who works at OpenAI and I was like, you're, and this guy's like a little bit naturally of a pessimist. Like he's like not, he doesn't just believe in hype. Uh, and I was like, hey, is this legit? And he goes, yeah, it's legit. I was like, should I, do I have to be worried that it's going to like take over the world? He's like, no, like, I don't know when that will happen or even if it will happen because we are a bit away, but like in terms of just like replacing like developers' jobs or, um, just like 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 these before.

I don't want to get like a panic attack. Where's this place?

That'll make a good thumbnail though.

Where's this place from?

I DoorDashed it.

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 that 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, 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. You know, 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 on like 30 Wing Stops? No, dude.

So I've been in the Airbnb and like real estate game, it's— 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, right? Or with like a rental, I'm like, let's do this, this, and this. And like, I don't know if it's any cool for 3 months or if it's like, you know, if it's actually a good idea. No, I think real estate's 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, but people are like, oh, buy boring businesses, invest in boring businesses.

I'm like, I want to look boring.

It's in the name. Yeah, it's also in the name, guys.

Yeah, like, where's the buy exciting businesses at? Yeah, they're talking about boring businesses.

Like, bro, what you want is something that's boring to other people but not boring to you. If it's also boring to you, like, ah, 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. Our software is the worst. Have you heard of HubSpot?

See, most CRMs are a cobbled-together mess, but HubSpot is easy to adopt and actually looks gorgeous.

I think I love our new CRM.

Our software is the best.

HubSpot, grow better.

Um, where do we want to go with this episode?

Uh, I don't know, what would make it interesting?

You're looking svelte, by the way.

Oh, thank you. You want to finish with like a rapid-fire hot seat questions? Yeah, that—

I think that's a hot one.

This one, right? This one's hotter.

That one's hotter. Um, that one actually is hot for me. There we go.

The milk is coming into play. That was hot.

All right.

Let me dip this one in.

Oh, this is almond milk, by the way. All right. What's the rapid fire?

Um, all right. Let me think of a couple questions. All right. Hot seat question. Uh, here's number one. Would you rather be 3 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? I mean, it's cool for my ego, but like, I—

Some people just feels good. And then also, uh, you could argue that if you were 3 times more famous, you could actually earn a bunch more too. So, you know, it could make other things easier.

I'd rather be 2 times as rich.

Twice as funny and half as ripped, or twice as ripped and half as funny?

Being funnier is better for, 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.

Both of those. No, dude, there's— being funny is better. Being funny is way better. What would you rather be?

Funny. I'm all in on funny.

What about, uh, the fame or wealth?

Being half as funny, that would be like— that'd 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 3 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 a story. 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 a deal. Uh, the HubSpot CEO, did I tell you this?

No.

You know, he got into a—

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

It was even worse. Brian was on the pod. He told you about it. Uh, he, 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 brake 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, might be it. Yeah, 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 closed the deal. Did you text Sam today? One more thing.

That's so funny.

Well, dude, that happened 2 weeks after the deal closed. And like, I think that company is big enough that him, like, frankly, dying—

would have put a pause on it.

Yeah. Like, I don't know if that would have— like, I don't know if that would happen.

Hey guys, not to be insensitive, just wanted to check in if we're still on for the whole acquisition. RIP Brian, but, uh, so, uh, sending out the DocuSign in case you guys are still ready.

So that—

I mean, totally understand if you need a day.

Yeah. So. Anything could have killed it. No pun intended. Anything. All due respect, Brian. I love Brian, so I'm only joking. But, uh, 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 tell the story 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.

This is 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, uh, and in 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, 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. What hardware? Like whatever, servers or whatever they had. So, um, and so we were like, okay, what is this worth? And so we came up with— it was like, my— we sat in this room trying to speculate, and then Michael just like put down the hammer at one point. He's like, I don't think we're gonna 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 are we gonna do, stand in front of a judge? Like And the judge goes, okay, are there multiple, multiple parties here to buy it out of bankruptcy? Um, 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 raise 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? We go to this tiny room, just get a fight. And yeah, basically. And one person from each, it's like a wrap. One out, 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, uh, some other social network. Well, like IAC, they own a bunch of internet properties, so they wanted to buy—

it's kind of like vulturing.

Yeah, they were like, we're gonna 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.

Um, were the people kind to one another or were they like pulling off—

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, um, up to $500,000 and then it'll just be freeform after that. We'll be here as long as it takes to finish the bid. And you get like a minute in between, or you get like a minute between, minute or 2 minutes or something like that in between bids to decide if you're gonna bid. And so it goes $100,000, $150,000, $200,000, $250,000, so on and so forth. $700,000 and then the guy, One guy drops out, so then it's just us and Match. He calls timeout. He's like, we need to go make a phone call right before 7.

Dude, that's like getting in a fight with someone and being like, timeout. You can't do that.

It's exactly what happened. He got punched in the nose and he's like, timeout. 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, must suck having a boss.

Yeah. And you like tattled on him. You're like, uh, 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 could 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 they can go is a million. Um, and I told the like auctioneer person, I was like, no more timeouts. Like that can't, we can't do that again. And so she, they come back in and she's like, there's no more timeouts. I'm like, okay, cool. The pressure's on them now. And bidding goes $800,000, $850,000, $900,000. $950.

When you were going— when you make your bid for $900, you say like, oh, well, that's the thing. So we had been acting like that to be like, are you kidding me, guys? And then, then I told the lawyer, but you're like, I built this thing, I know it's not worth that.

I go, I go, we gotta just act like we have an infinite bankroll 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'm, I could sit, I could go, 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 1,025,000 to just up it.

And then 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 1,010,000. I think she did. She did 10,000 above and they just go, you guys can have it. You guys can take it. And they were like, yeah, our max was a million.

Just smacked them in the face.

I was like, yeah. And so we got it and then we like came back. But that was like the most high stakes, like, hand of poker I've ever been involved in, basically.

Um, all right, we'll do, we'll do one more. Um, I can't read it from back here. What were the questions that you told me?

Uh, another one was like, what is the, um, I don't know, like, what's the—

oh, so something that you thought you were onto something, but it turned out to be totally wrong. Yeah.

You thought you were onto something. You turned out—

what's yours?

We had one when, uh, building Blab, basically, like when we built Blab, it looked like it was taking off. And this is now like 4 years in. And imagine you're 4 years in and you feel like you might've just like made the next big, like basically what Clubhouse ended up becoming. 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 were like, oh, this is just like Snapchat. Like no matter what we did, they're like, ah, this is kind of like Snapchat. And we were like, goddammit. Like the next thing we build is not gonna 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 this stuff. And it felt like we did it. Like this is gonna be the next social thing and we own it. Like we are actually gonna own one of those things. And then it got to about 4 million and then it started to just, we started to realize why isn't the number going up as much? It's 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 6 months.

And it's like an impossible problem to solve too. It's not like, like even if you operate at an A+ level, it's just like a, you just can't.

Retention is like the pro, 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 2 pickup lines and like, you know, finding a keeper that no one wants to use. Yeah. 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 'em date you. You can't make 'em marry you. And like, that's what retention is. It's like, are they gonna 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. And it was just like, not, not moving because it's more fundamental. It's like, is this a thing people want to do all the time or not? And 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 in February. So we said 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 $100 million in revenue. Before year 10. And we sold it between 4 and 5, I think. Year 4 and 5. So we were kind of on track.

We would've got there, yeah, probably.

We could've, maybe could've 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 5 million. Like the numbers add up to $100 million. No one's real. 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 hire like, you know, 100 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, this 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 Morning Brew is kind of doing that, right?

They're like $7,500 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, and I knew him and I, Austin, are good friends now. And we both talk. 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 I— that was my biggest mistake.