How fortnite made me a millionaire

Summary

Podcast Summary: My First Million

Episode: How Fortnite Made Me a Millionaire
Date: November 19, 2025
Hosts: Sam Parr and Shaan Puri

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Overview

In this open and insightful episode, Shaan Puri walks listeners through every business attempt he made before finally hitting it big with an e-sports startup centered around Fortnite. Alongside Sam Parr, he shares candid stories of failure, learning, accidental breakthroughs, and the mindset shifts that eventually made him a millionaire (and more). The conversation evolves into deeper questions of happiness, enoughness, and the urge to climb a “Second Mountain,” making this episode as much about entrepreneurial philosophy as practical business lessons.

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Key Discussion Points & Insights

1. Chronicle of Failed (and Eventually Successful) Businesses

• Chipotle of Sushi (Sabi Sushi)

  • [00:39–04:49] Shaan describes his first major entrepreneurial attempt: a fast-casual sushi concept.
  • Key lessons about brutal operating reality, high startup costs, and low margins in restaurants.
  • “My hand smelled like tuna all the time. It was just a brutal business.” — Shaan [01:09]
  • Lesson: Your first business is your worst business—and that’s okay.

• Wristband Dropshipping (thefatban.com)

  • [04:51–08:43] Jumping on the Livestrong bracelet trend, Shaan and his friend build a wristband store in 48 hours, learning the power of constraints and action.
  • “Creativity loves constraints. The power of setting a time box constraint…” — Shaan [07:32]
  • Lesson: Tight constraints spur creativity and action.

• Australian Biotech Adventure

  • [09:36–12:56] Shaan partners with an ex-billionaire’s son on a coal-to-gas biotech project.
  • Insight: The power of being the best at something no one else in the room can do (e.g., video/animation).
  • “Rather than focusing on our disadvantage, we tried to figure out what's our advantage.” — Shaan [11:39]

• App-Focused Startup Studio (Monkey Inferno)

  • [12:59–17:33] Creation of numerous apps, some with millions of users but little retention or profit.
  • Burned millions in VC money, made critical connections in Silicon Valley.
  • “I felt like I was running around with a bottle trying to catch lightning.” — Shaan [15:07]
  • Lesson: Use your 20s for adventure and learning, not just earning; value the experiences and people met along the way.

• Big Break: Youth Fortnite E-Sports League

  • [17:34–18:31] Shaan finally rides the trend with a high school Fortnite league, eventually getting acquired by Twitch.
  • “That was the big win…turned 30, crossed the million-dollar mark, made a few million dollars…that 10 years of sucking was worth it.” — Shaan [18:12]

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2. Reflections on Near-Misses and Alternative Paths

• Applying unsuccessfully for early roles at Uber, Facebook, and Stripe (which would’ve been worth $20M+).
• Recognizing—sometimes with pain—how fortune and timing play big roles, but so does persistent effort.

3. Mindset Shifts after Success

• From “Moonshots” to Predictable Wins:

  • [26:38–29:12] Shaan attributes his later consistent success (5 for 5 post age 30) to better project selection and focusing on execution over wild ideas.

• Three Pillars of His Improved Hit Rate:

  • Project Selection: Picking straightforward, non-moonshot businesses with clear needs (“Stop chasing these like moonshots…” [26:43]).
  • More Action, Less Planning: “Action produces information.” Directly seeking feedback before building at scale.
  • Surround Yourself With Smart People: “Pay attention to what works. Success leaves clues.”

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4. Second Mountain: Redefining Success

• [31:54–34:06] After financial freedom, Shaan feels drawn toward creative projects (writing, making content) rather than starting more businesses.

• “I think I’m a B entrepreneur, but I think I’m A+ at content. So, like, why not do your A+ thing?” — Shaan [32:53]

• The transition from “proving oneself” to embracing creative fulfillment.

• Sam’s Reflection:

  • “You sound A, more confident and B, more happy than you have in the past. Does that sound right?” — Sam [41:23]

5. Enoughness, Wealth, and the ‘Last Dollar’ Concept

• [41:36–45:38] Powerful discussion on defining “enough,” both financially and emotionally.

• “You’ve already earned the last dollar you’re ever going to spend. So you’re now throwing good hours after bad dollars.” — Shaan [44:39]

• The importance of proactively considering what you actually want, and not falling into the ‘more for more’s sake’ trap.

• Universal Advice from Shaan:

  • In your 20s: Optimize to learn from smart, ambitious people (even if it means earning less for a while).
  • It’s okay if it takes 10 years. “You only have to get rich once.” [49:15]
  • Be more honest with yourself about what you prioritize.

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6. On First Mountain vs. Second Mountain

• [51:38–52:51] The “Second Mountain” metaphor (from David Brooks’ book) is used to explain how goals and satisfactions shift after early success.
  • “This wouldn't have been the right message for us when we were on our first mountain… The mindset is so different.” — Shaan [52:51]

7. Memorable Quotes & Humorous Moments

• On first business blunders: “My hand smelled like tuna all the time. It was just a brutal business.” — Shaan [01:09]
• On “selling the pen” at Stripe:
  • "He gave me the sort of ‘sell me this pen’ exercise. And, brother, I did not sell that pen." — Shaan [24:03]
• On fast lessons: “He who studies success learns little. He who studies failure learns truth.” — Shaan [07:27]
• On Halloween Dad Fails: “If I had dressed up as a little goofy fireman and I met this real fireman who's a friend, that's like the biggest L I could have took. Man to man, that's the biggest L you could take.” — Shaan [57:08]
• On post-success pursuits: “I started going and trying to make dope stuff…that to me seems more of an interesting life, and so I’m just more attracted to it.” — Shaan [33:29]

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8. Lighthearted Closing: Life Outside of Work

• [53:57–59:03] Fun exchange about Halloween traditions with young kids, including creative costumes and the freshly appreciated New York “apartment trick-or-treating.”
• Playful banter about the dangers of “Elf on the Shelf” and the hazards of outdressing real firefighters.

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Key Timestamps for Reference

• [00:39–04:49] Sabi Sushi: The brutal realities of a first business
• [04:51–08:43] Dropshipping wristbands and lessons in constraints
• [09:36–12:56] Australian biotech: finding your unique advantage
• [12:59–17:33] The Monkey Inferno app lab, the “lightning in a bottle” problem
• [17:34–18:31] Success with the Fortnite youth e-sports league
• [26:38–29:12] What changed? From repeated failures to consistent wins
• [31:54–34:06] Transitioning from “business for success” to “work for fulfillment”
• [41:36–45:38] Defining “enough” and the “Last Dollar” concept
• [49:15–51:50] Shaan’s universal advice for entrepreneurs
• [53:57–59:03] Halloween dad stories and life ethos outside of business

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Notable Quotes (with Timestamps)

• “My hand smelled like tuna all the time. It was just a brutal business.” — Shaan [01:09]
• “Creativity loves constraints. The power of setting a time box constraint…” — Shaan [07:32]
• “He who studies success learns little. He who studies failure learns truth.” — Shaan [07:27]
• “Rather than focusing on our disadvantage, we tried to figure out what's our advantage.” — Shaan [11:39]
• “You only have to get rich once.” — Shaan [49:15]
• “You’ve already earned the last dollar you’re ever going to spend.” — Shaan [44:39]
• “I'm a B entrepreneur, but I think I'm A+ at content. So why not do your A+ thing?” — Shaan [32:53]
• “If you have more than $500,000 and you want to be happy…the second half of this episode is the number one thing you have to listen to.” — Sam [51:18]
• “You can't be smart before you're stupid. You gotta be stupid before you're smart. Like, there's an order of the universe here.” — Shaan [53:27]

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Tone and Style Notes

• Lively, honest, cheerful, and self-deprecating.
• Shaan and Sam joke with each other but often push through to hard-won wisdom.
• Language is clear, direct, occasionally irreverent, and always candid about both failures and successes.

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Conclusion

This episode is an inspirational, step-by-step look not just at the mechanics of entrepreneurial trial and error, but at the deeper, more human questions of purpose, fulfillment, and enoughness. It’s a masterclass in long-term persistence, learning from failures, and—ultimately—redefining success as your priorities and age change. The personal stories, failures, and “next mountain” reflections make this a valuable listen for anyone at any stage of the entrepreneurial journey.

Transcript

[A]

I made my first million when I turned 30 years old. But I'm going to walk you through every single business I tried before I made something that worked. And Sam, you can roast me for how bad my ideas were. I feel like I can rule the world. I know I could be what I want to put my all in it. Like no days off on a road.

[B]

Let's travel.

[A]

All right, you.

[B]

So I did this previously. You totally went up to me by having a presentation. So that's a little unfair.

[A]

But.

[B]

But it's like in Mean Girls where she shows up to the Halloween party and she doesn't know that she supposed to dress slutty and she dresses scary. That's kind of how I feel right now. But that's okay. I'm incredibly excited to see what. What you have to do.

[A]

Business number one, I tried to create the Chipotle of sushi. So this was my first big harebrained idea. It was called Sabi Sushi. And we, even though I didn't know anything about sushi, I had just tried sushi for the first time a month prior to. I just thought, this is it. This is the big idea. I can create the Chipotle of sushi. We partnered with a Food Network chef. We launched the thing. I learned how to make, you know, spicy tuna and like, all kinds of stuff.

[B]

And that was the guy who. What was your buddy's name? Who bought the bag company?

[A]

Dan. Yeah. So if you've seen the episode with Dan who? Dan the bag man, where he bought a. A paper bag company now and is thriving. He was right next to me in the sushi trenches. Okay. So, you know, just kind of the summary of that whole venture. Restaurants suck as a business. You know, 10% operating margins. You're working morning, afternoon and night. You're open on weekends. There's no let up. My hand smelled like tuna all the time. It was just a brutal business to be in. And we literally did every dumb thing you could possibly think of. I sort of took a buffet tour of all the possible mistakes you could make in doing a business. And then, oh, my grade for this, by the way. A for effort. But this business was an F. And I think in the end, we made something like $20,000 of profit before we voluntarily shut down the business because it was so brutal. But if you to look at that in terms of the one year of full time effort that it took us, I was making $1.82 an hour. So that was my big, big profit out of that business.

[B]

How much did it cost to start.

[A]

We got lucky. It was gonna cost half a million dollars to build out the restaurant. That was a combination of signing the lease with a personal guarantee, by the way, which is bad because restaurants fail.

[B]

And you had nothing to guarantee and.

[A]

I had nothing to back it up. So it was like, you'll be on the hook for this for 10 years unless you declare personal bankruptcy. And then you have to buy all the equipment you got to do the build out, all this shit. We hired the fancy. We hired this architect who built the Vidara. He was the architect of the Vidara in Vegas. And we again, every dumb mistake you could, but we thought, oh wow, he's the best, so he should design our restaurant. And he came up with this plan that was going to cost us half a million dollars to build out.

[B]

I mean, that's pretty ridiculous. That's like having like the guy who like developed the World Trade center to like make your kids background playset.

[A]

My play structure. Exactly. But we were like, yo, this is so sick. We're really, we're really just chang the game out here. Did you tell them that?

[B]

Was that your.

[A]

We were crossing our eyes and dotting our TE's. But that's not what you're supposed to do. That's not how those letters look. So yeah, we were doing everything wrong in. In with maximal effort. So how much did it cost? We ended up, luckily this beautiful, beautiful man with a beautiful set of hair named John Prendergast met us and was like, hey guys, maybe test your concept before you commit 10 years and a personal guarantee to this thing. And we were like, how do you test a restaurant? And so he convinced us to basically do a delivery only restaurant out of a commissary kitchen. What today is called a cloud kitchen. Yeah, it's very fancy today. Back then there was no Uber Eats, no doordash, and we just looked like bums who couldn't afford a restaurant. And so we tested it that way. That's why it actually cost us almost nothing to start. And we made $20,000 of profit in like, I don't know, one or two months. But we also were like, this is a trap. Every day that this succeeds is another day we're going to be in this business and I just want out. I'm only 21 years old. It's not too late. I'm still a minor and I don't need to have a life sentence in this business. Get me out of here.

[B]

All right. Which we, we have to say this really quick every so you gave yourself an F and you said it was horrible and you want to escape. We can give examples of every, for every type of business and probably everything you're going to mention of someone who actually did it. So, for example, the chicken tenders guy, Todd Graves, who's now like, you know, the 30th richest fan in America. And it sounds awesome. Obviously it sounds awesome because it's successful.

[A]

But yeah, I'm sure Jimmy John's is not like regretting it. You know what I mean? He's cool, he's got, he likes it.

[B]

Yeah.

[A]

But for us, it was not the right business to be in. So, you know, I'm giving you a little bit of wisdom. So here we go. Sean the Elder. Now, that went with my elder wisdom. Sean the Elder says, lesson number one. Your first business is your worst business. And that's okay. The most important thing of this entire business was just that I started and I kind of got the itch and I kind of got some momentum and I saw, man, if I can make that much progress with something I knew nothing about, then, you know, the next thing didn't scare me. So I think that was the only good thing out of this business, which is that, you know, all success requires a start. And it was a start.

[B]

All right, number two, number two, I.

[A]

Tried selling wristbands online.

[B]

Then they're done. That man Livestrong.

[A]

I saw the Livestrong band trend, which, for those who don't know, Lance Armstrong had these yellow wristbands that were like all the rage. So what happened? Everything I did wrong in the first business. I was like, jerry, I'm doing the opposite now. And I basically, well, here's what we did. We set a 48 hour time constraint. So we said, last time we spent nine months planning and researching and planning and researching and no action. This time it's all action. And so we gave ourselves 48 hours. And I said, look, I feel like we've been playing dress up as entrepreneurs, we're just playing house like my daughter does. And instead what we need to do is like, do the real thing. So I said, the rule is I, I don't care what business we do, we gotta launch it and we gotta make a dollar of revenue from a real customer in 48 hours. And that constraint was actually pretty amazing. So what did we do? We were too dumb to really like do anything fancy online, but we're like, make something online, no physical location. And I had just discovered Alibaba. This was now in back in like 2011, I was like, wow, it's amazing. You know, all the shit we buy comes from China. There's a website where the factory is just like online. You just go talk to the factory and they will, they'll just ship it straight to the customer. You don't even need to buy the inventory. And basically I stumbled into what is now obviously drop shipping. So we did this drop shipping business and in 48 hours, this one is actually a pretty cool idea. As you can see my website here, it says thefatban.com that was our website. And then it says 1 inch silicone wristbands, free shipping as seen on TV. So I was just lying. This is a huge liar already. I don't even know what TV this would have been on at that time. But we went with as seen on TV and, and then we had. This is what was hot at the time. You can see what was hot by the. The three examples. The London 2012 Olympics were coming up. So we thought maybe, maybe people want to wear that and we don't have the license. But let's just. Again, if we're already lying, why not also steal. The next thing was gtl. Do you even know what that is?

[B]

Gtl? No. Is it like, good get to it or I don't know. Good luck.

[A]

I'll give you a guess. Go ahead, go ahead. Just make something up.

[B]

Gtl. I got to love. I. I don't know, like this.

[A]

Gtl. If you remember, the hottest show in the world back in 2011 was the jersey Shore. And they used to say.

[B]

We were.

[A]

Like, oh, yeah, dude, gym, tan, laundry. That's the thing. There's another one on here that says Bieber fever.

[B]

Back then you didn't gym, you were tan. You definitely probably weren't doing laundry over three.

[A]

But here's the good news. I give this business an A because in the 48 hours, we actually got two orders. We made $750. I learned how to make a website. I learned how to take payments online. I learned how to use Alibaba. And we did it like way faster than everything we had done before. So it was like actually way better of a business in two days than the previous year had been for me. So I give it an A. Although I'm pretty sure one of the orders, like, I did this with my buddy Trevor. I think he was just like hooking up with one of the girls who ordered and she wanted to get back together with him or something. But hey, a dub's a dub. We take what we can get. Beggars can't be choosers. So Sean the elder says, he who studies success learns little. He who studies failure learns truth. I think the real lesson out of this one was basically creativity loves constraints. The power of setting a time box constraint. If we had said this will be our next big business, we would have again spent six months planning. It was when we said, come hell or high water, we're doing it for real. We're going to get revenue in 48 hours. All our ideas then had to like fit in that box. And so there's this lie in creativity which is you're going to think outside the box. No, no, no. What the pros do is you put yourself in a tight box and then watch how you MacGyver your way out. And so that's really what this business was.

[B]

All right, so a lot of people watch it, listen to the show because they want to hear us just tell them and exactly what to do when it comes to starting or growing a business. And really a lot of people who are listening, they have a full time job and they want to start something on the side. A side hustle. Now a lot of people message Sean and I and they say, all right, I want to start something on the side. Is this a good idea? Is that a good idea? And again, what they're really just saying is just give me the ideas. Well, my friends, you're in luck. So my old company, the Hustle, they put together a hundred different side Hustle ideas and they have appropriately called it the side Hustle Idea Database. It's a list of a hundred pretty good ideas. Frankly. I went through them, they're awesome. And it gives you how to start them, how to grow them. Things like that gives you a little bit of inspiration. So check it out. It's called the side Hustle Idea Database. It's in the description below. You'll see the link, click it, check it out, let me know in the comments what you think. All right, next.

[A]

All right. I tried to start a biotech company with this billionaire in Australia.

[B]

Wait, how old were you?

[A]

I was 22. 21 years old. 22 years old at the time.

[B]

Was he like a criminal?

[A]

No, he was not a criminal. Stand up guy.

[B]

Not a Elizabeth Holmes type of person.

[A]

No, no, he was super legit. He had just sold. He wasn't a billionaire actually. He had just sold his company for $450 million and he had a non compete. So he had a lot of money. It was his parents company originally. So he had a chip on his shoulder. He wanted to Prove that he could do it. So guy had four cash, a chip on his shoulder, and he was non competed out of the business he knew, so he had to do something new. And biotech sounded really interesting.

[B]

And you were. And I was. I'm making it sound like you're a dummy, but you actually graduated from Duke and you were. Yeah, you're okay. Okay. So it's not like you're just like a dumb E Commerce bro. You.

[A]

Well, I think there was some stupidity in this, so I thought, I'm a bio major, I should do something in bio. Honestly, what you studied in college means very little here. It's not like I truly had a passion.

[B]

Yeah, but you like took a class at least.

[A]

Yeah, I used the wrong heuristic. What I really should have done, which was smart, was I got around smart people. So this guy was a really smart guy and working with him was actually really cool. So like that was actually much more important than the biotech link. Now what did we try to do? We tried to create a biotech company where you could take coal that was too deep to mine. Unminable coal. I don't know if you know, like 90% of the world's coal is unminable. It's too deep, too uneconomic to mine. So the idea was there was little microbes that would go down and eat the coal down there and they would like basically fart out natural gas. You could just collect the gas without mining the coal. Kind of a cool idea. Unproven if it could actually work. I got this opportunity because he was reading our blog. He. He read our. He met my dad and my, he asked my dad, what do, what do your kids do? And he went and checked out our blog and thought it was cool. He thought it, our hustle was cool. And it was kind of the first time that content or building in public, like doing a portfolio mattered more than a resume. And that has now become like very true in 2025. Back then, like I didn't intentionally do that, but it really worked. I failed forward in that way and I used content to kind of create opportunities. The second thing that happened was when I got there, I realized, oh, wow, I don't know anything about oil and gas industry. I don't have no experience. And at first I tried to like catch up. But how are you going to catch up to like 20 years of this guy's experience? Very hard to do. And so I had a different idea, which was instead of being the worst in the room at the thing, they're all good at. How do I become the best in the room at something they don't know how to do? And so we started, me and my buddy Trevor, we started learning to animate videos to take their ideas and turn it into like a one minute video that they could show their investors or their prospects or whatever. And they loved it. The owner was like, oh, my video guys. Yes, because you're making me look cool. You have a new power. You're. You guys are good with computers and shit. So, like, we found a way to like bring something to the table. So rather than like focusing on our disadvantage, we tried to figure out what's our advantage. So that was like a lesson that I, you know, took forward from that. But overall, I give this business a C because it didn't really work. The business didn't really work. And, you know, I made like 120 grand a year as like a job essentially doing this.

[B]

Where's he?

[A]

He's still in Australia, still doing his thing. I haven't talked to him in a long time, but I hope he's. Hope he's doing well. Lesson earn your spot at the table is kind of the thing I just.

[B]

Said, all right, making the next billion dollar app.

[A]

So I tried to. Basically, this was a period of life where I tried to make the next billion dollar app. And so it was like 12 different apps. I tried, I tried. We made this like clubhouse style app where people would get on and hang out in these rooms and talk all night. And it got to 4 million users and we thought we were doing it. This is the next big thing. But we couldn't grow from there. It just kept. It just stayed at 4 million. 4 million is a big number, but a social app needs like 100 million. So we were playing this like very difficult game and it wasn't really working.

[B]

So. So I used to use blab. And for those listening, this was back when Martin Shkreli was like in his first upand cominging scandal.

[A]

No, no, he had just gotten out of jail.

[B]

Had he?

[A]

I thought, oh, no, no, he was on trial because I remember he did a blab from the courthouse back home. And like in the courthouse he had pled the fifth. But then he got on blab and just started talking shit. And we were like, this is incredible.

[B]

This was like, yeah, this was pre prison and he was basically on the uprise in terms of notoriety. Speak as farmer bro. That was when the photo of him like sitting back, like smoking a cigar and you could just hop on and talk to him. And it was kind of funny. It was kind of like the beginning of incel culture a little bit.

[A]

My legacy, I mean, wasn't.

[B]

Was.

[A]

You're right. I also tried to build a beer app where you would check in new beers. This is a giant mistake because I didn't even care about craft beer. So why am I trying to build something for other people who I don't even really. It's not like scratching my own itch. We built a messaging app that got to number three in the worldwide charts. I remember above Facebook, which was kind of incredible, but had no retention. Incredibly viral, but no retention. I think we got a million users in the first week or something like that. And then a month later we had like, I don't know, 10,000 users. Like, they were all gone, basically.

[B]

Huh. What was that one called?

[A]

That was called Bebo Messenger. So this business, I would give a B. And our profit was minus $8 billion of investor capital. So we basically were burning something like a million and a half dollars, maybe $2 million for four or five years.

[B]

And that was called. Was this all under the umbrella of Monkey Inferno?

[A]

Yes. So this was, you know, playing the wrong. Playing a very hard game. I felt like I was running around with a bottle trying to catch lightning. Since then, I have done the exact opposite. I now look for the most straightforward businesses that are, you know, still fun to do, but I think have a high, high shot of success because I was so scarred from this.

[B]

It was pretty magical experience, though. You met. We met so many. I mean, I met them via you, but you met so many amazing people in Silicon Valley. Like, you know, we told the story 10,000 times. The calm app founders were at your office all the time. Yeah, Moyes and, And. And Ryan Hoover and C. Like, it.

[A]

Was amazing people, met amazing people and learned a lot. So my lesson here from Sean the Elder is I asked the right question. I said, where can I go that will give me 20 years of experience in the next four? I basically took my 20s as a period for adventure and learning and not earning money. I remember when I got this job, they told me how many shares I had. They're like, oh, yeah, you got. I think I was making 120k a year when I joined. And then they said, and it was something like 40,000 a year of stock in the Monkey Inferno, like, portfolio. And he was about to tell. He's like, that represents. He was about to tell me what percent that was. And I had already seen, like, kind of like I'd seen in the tech industry. If you join a startup, you might earn like 1% or less of the. You don't. You don't get more than 1%. You get like 0.4%,.5%,.6%,.2% of the company. And that just sounds like a minuscule number. But I wanted to go there and treat this like it was my own startup. So I remember telling him on the phone, I did the, like, finger to the lips and I was like, don't tell me out of how many shares, I'd rather not know. I want to work like, this is my company. I own 100% of this. That's how much I'm going to care. And he was like, good answer. The benefit that came out of the kind of takeaway was, I never went and asked for. Actually, that's a lie. I asked one time, but I didn't really go back and ask for more for a while. And if you pick the right people to work with, they will reward you based on what value you're actually creating without you needing to ask. And so I went from. It turns out I had 0.4% at the time. Then he bumped me to 10% and then over time, I got to 20%. I owned 20% of the company by the end of the deal, or, sorry, of that, of that thing. It didn't end up mattering in because of the way the structure of how we sold the company. But I did take away that of like, you know what, just go there, try to learn, do as best work as you can, and, like, let the chips fall where they may. And I think that was the right approach.

[B]

All right, what do you got? Now?

[A]

The last business before this is the one where I ended up, you know, actually making money, which was that at some point we were like, Fortnite had just come out and we were like, we should ride a wave of something that's popular. So we took Fortnite, which was popular, and we had this idea which was, hey, you know how there's youth sports, you know, little league baseball, youth soccer, stuff like that? Like, you know, more people play Fortnite than play basketball, right? I was like, wow, that's kind of crazy. It's like, so why isn't there like a league you can join as a teenager to play this with other people and have it live streamed and all that stuff? Like, it should be just like youth sports. And so we created like our version of youth esports, basically, and it was an app. And then that was. And we built the largest high school Fortnite League in the country and then we got acquired by Twitch and then that was the kind of the big win. The I turned 30 made, you know, crossed the million dollar mark, made a few million dollars and was like, yay, this is amazing. That 10 years of sucking was, was worth it. And so that's my, that's my story there.

[B]

You had so many more interesting like near near misses or near hits. So the stripe one was crazy when I was running. So I had a, I had a thing, a startup that wasn't working and then we ended up getting like Aqua hired. And when it wasn't working, I went into, I went and applied at jobs. I applied at Uber, I applied at Google and shockingly got like an interview. I got one interview. I applied at Facebook. Obviously they didn't call me back. I applied at a Zero Cater at Easy Cater. Do you remember those companies?

[A]

Yeah, they were hot. Those were really hot at the time.

[B]

These were all the hot companies. I wanted to be an Uber launcher. It was called like you go to city to city.

[A]

Dude, you would have been so good at that. That was a miss on their part.

[B]

Yeah, screw you guys.

[A]

The Google Facebook one, I'm like, I think maybe the, the, the recruiter did well to like kind of like, I don't think you were the fit for that. But dude, if you worked at Uber and you were like a city launcher, you would have crushed.

[B]

I think so. And so it was, it's fun to look back at like all the I, I actually the way Jack Smith, one of my best friends, I applied at Vungle. That's how I met Jack. I applied at his company and they didn't, he didn't hire me.

[A]

Uh, the consolation was he's like, I'll be your friend.

[B]

Yeah, we became friends. But you did hire me.

[A]

You're an idiot. But you're a good hang. Wait, did Jack say why he didn't hire you, by the way?

[B]

Dude, his co founder was in charge. His co founder was like, was like this all knowing, kind of smug guy who's now my friend too, Zane. But he was like, so you think you're good at sales? Go around the office right now. Leave our little room right now. And I want you to go and talk to every single person in that room right now and convince them why we should hire you. And it was so demeaning. And I did it and I did not get it. I did not, I guess I did not convince them.

[A]

Dude, I had to do the same thing at Monkey Inferno to Get the job. Did I ever tell you this?

[B]

No.

[A]

So they were like, okay, you clearly don't know anything about technology. You're not an engineer. You're not a designer. You've never worked in tech. So, like, we really like you, but we don't really know what the hell you'll do. And we all just keep saying, like, yeah, he's a real hustler. And so can you do some hustle? Like, how would you hustle today to add value to what we're doing?

[B]

Hustle now.

[A]

They're like, can you show me that hustle thing? And I was like, we're just sitting in a conference room. And so I was like, yeah, I got you. So I was like, hey, you have this app that you're working on. I'm gonna go get you customer feedback, like, now. And they're like, okay, how are you gonna do that? I was like. And on my way in, I had flown into San Francisco for this, but I. I was killing time before the interview. And there was a Burlington Co. Factory, if you remember, right next to our office. And next to it, next to that was the Westfield Mall. So I was like, there's a mall, right? They're like, yeah. I was like, I'm gonna go to the mall. So I go to the mall, and the guy comes with me, and he's like, I'm going to observe. And I was like, oh, my God.

[B]

Was this Michael?

[A]

This is Paul Whitten. No, the CTO came with me. So, like, the most introverted engineer was like, let's see what this guy can do. And so I go. And I've never done this. I'm like, I don't even have a product to sell. I was like, I'm going to get, like, feedback, I guess. And so I was like, I'm going to cold approach, like a pickup artist at the mall, random people, and try to get them to come over to this table and give feedback on our app. I was like, how the hell am I going to do this? And then I realized the easiest hack. I just went to them, and I go, hey, I'm on a job interview right now, and I get the job if I can get people to come over this desk and just give five minutes of feedback. Would you do that just so I can get this job? And they're like, yeah, no problem. And I was like, that was so. I was like, this is so much better. Because the first three people I approached, I was like, hey, have you ever been. Have you ever had to plan a party and needed to use an online evite planner. Like, I have a new one coming out in six months and I would love your feedback. And they were like, you literally get away from me.

[B]

They like give you their like Annie's like rappers, can you throw this away, please?

[A]

Exactly. I should have been like the guy in the bathroom who like pulls the paper towel out and hands it to people. That would have got me more success than what I was trying. So just switching to like, dude, there's like a camera following me right now and I'm screwed if I don't do this. Whenever I see reality tv, I'm like, why don't they just say that that works way better anyway.

[B]

But my point being, my point being is for a lot of people in these situations where the things that's not working, going to ask for a job. A, it's normal. B, it's incredibly mortifying because you're like, shit, I'm supposed to be this guy who has this business. I put all my identity into it. Now I'm applying. It feels weird, it feels uncomfortable. But we've all done it. And you did it in one company that, well, it just adds to the list of screw ups.

[A]

So in 2011 or 12, before the monkey fire thing, I only applied to one other job and it was this company called Stripe that I thought was going to be maybe a good company, maybe a good startup. And I think it was maybe valued 100 million or less at the time.

[B]

Oh my God.

[A]

It's now almost, I don't know what it is now. It's 100 billion, 100 billion, so. So, you know, I did the math a few years ago and I was like, wow, my entry level sales type of job would have made me like $20 million if I held. And that was then. It's probably doubled since then. So I did what you did. I applied to the job. I didn't know how to do it. It was my first job interview ever, didn't know how to do it. And I, I had a layup, dude, because my mentor, that guy John Pendergrass, I mentioned from the sushi thing, he was the mentor of the guy hiring me. So I asked him, I was like, yo, can you put in a word? He put in the strongest word. He was like, yo, this guy's, this kid's amazing. Yeah, hire this kid. He's an entrepreneur. You're lucky he's even applying for a job. He gave me like such a strong interest. I don't remember what it was, but it was I remember thinking, like. Like, lay up. Like, this is, like, so easy. Oh, my God. And that bit me in the ass, that attitude. Because I got on the call and the guy was like, hey, you know, he says great things, but I just want to, you know, ask you a few questions. And I just started bombing the interview and to the point where he gave me the. The sort of, sell me this pen exercise. And, brother, I did not sell that pen. You didn't buy that penny? That pen stayed in my pocket. It did not fly off the shelf.

[B]

What would your answer have if you. Look, I'm sure you, like, replayed it in your head at 10,000 times. How would you have.

[A]

No. I was so traumatized. You know, I'm like, I'm a student of the game of life. I love to learn. Not this one, dude. I just buried that deep down and moved on with life. Sometimes you just take the L on your soul and you just move on.

[B]

Do you. So I was thinking about this the other day. Do. Do you agree with this? Where, you know, we. We just summarized 10 years of your life in 38 minutes, and we laughed about it. But a. It's not funny when you're going through it.

[A]

Incredibly unfunny.

[B]

It feels like the worst part is you're comparing yourself to your friends, right? And you're like, why is this so much easier for them? Why are they getting this and that and that, like, eats you. That, like, you turn green with envy. But the second thing is, like, you do it for 10 years, and then all of a sudden, in, like, the 10th, 11th, to 12th year, you look back and you're like, oh, it's kind of working. And then it feels like slow progress, slow progress, a little bit better progress. And all of a sudden, you snap your fingers, and it's like, holy moly. Like, I've just grown so much. It's like. I don't know if you ever. Like, when you. When you've been getting fit, where it's like, I feel nothing. I feel. I feel nothing. I feel nothing. And then eight weeks pass, and finally you're like, oh, man. I think I. I feel my stomach. It definitely feels different today. And that's the new baseline. And so. And so it's. I guess what I'm getting at is it's months or years of hard work, and then overnight you feel progress.

[A]

Yeah, slowly. And then. And then all at once. So I just gave you. I just gave you 10 years. And I think, in truth, because I. I fast forwarded through some of the apps we tried, we tried many apps in that like app phase. So I, I think I did 12 different failed companies in the 10 years. So over 12, 10 years, brutal. In the, I'm 37 now. In the seven years since, I think I've gone like five for five. Everything has worked right away. And I don't know, the portfolio of the companies where I own either majority or just a huge chunk is probably close to 100 million in revenue now. And I think it's 75 million in revenue. And the feeling is so different. Not just because it's successful, but because you just, it's like a route you know how to drive. You just know what potholes to avoid. Much better. Still hit some, right? Like it's not like you're, you're foolproof but like man, the hit rate going from 0 for 12 to 5 for 5 in the last few years is so different. It's unbelievable.

[B]

What allowed you to go from 5 to 5 and 75 million in revenue.

[A]

So project selection is the first one, right? Because I try, think about what I tried. A restaurant, this like innovative biotechnology that's like a science project. I tried creating the next hit app, the next billion dollar app, the next Twitter, the next YouTube, the next Facebook. Like we launched a messenger, we launched like a social network. We like those are just one in a million type of success ideas. So the odds were against me even if I was good at executing and I wasn't. So I was like bad at executing and then trying these like moonshot things that I really didn't understand what the hell I was getting myself into. Whereas since then I chose projects that were like way less risky, you know, like I kind of understood how to do them. High hit rate, I just need to execute, you know, so I did an E commerce company. I did, you know, a services business. I did, you know, we have somewhere.com, it's like a overseas staffing business. Like every company needs to hire people. And I in my own businesses was hiring a ton of people overseas. It was like a no brainer. It was or it was a business I was already working. I bought into it and helped grow it, right? Like that's just like a much more foolproof way to do things. So I, so project selection was number one. Stop chasing these like moonshots that if they work you make a trillion dollars and you get to have a movie about you but most likely are not going to work. So I stopped doing that. I stopped playing the like Silicon Valley dream. The second thing was More action, less planning. So understanding, like what amount of research and planning is helpful and at what point you need action because action produces information. And I told you kind of in the first start, we spent nine months basically in the planning phase. And that was a huge mistake. We didn't confront reality of the business. I remember when you started Hampton, before you ever announced it, you showed me your calendar and we called it the zebra calendar because it was just 20 minute stripes on the, on your calendar, on your day. And it was just calls with founders and you were like personally selling. You could have offloaded that. You could have launched the business. You could have done any number of things. But you were like hand to hand combat selling to try to figure out like, yo, does this, Is this something people want? And what message, what version of this, what message of this actually like gets me that kind of like real quick. Yes. Reaction versus like people just being polite to me. So going for action rather than planning and knowing, knowing when to use which gear was that second thing, and third was just like, pay attention to what works. Get around really smart people and pay attention to what works. Because success leaves clues.

[B]

Do you think, okay, so you're 37 now. First of all, would you have predicted, when did you sell blab bebo?

[A]

20, 19, something like that.

[B]

So that was six years, 20, maybe six years ago. So 31ish. So let's just say that was six years ago. Let's round up to 47. Well, first of all, at 30 or 31, did you think you're going to be here where you are at 37?

[A]

No way.

[B]

Where did you think you were going to be?

[A]

I thought, all right, I'm going to earn out this deal every year we vest. I was like, I'm going to do two years of that deal, which is what I did. I did two years of the deal and then I'm going to go start another company. And this time I'm going to start like a, you know, if this one sold for tens of millions, the next one I'm going to do is going to be hundreds of millions or a billion dollar company. I still didn't really understand what to do. But the beauty of the situation was because I was earning out my deal, I couldn't go start another tech company. It would be like they'd look at me and be like, what the hell are you doing? So I was forced to do things that didn't look competitive, that didn't. I was forced out of my comfort zone. So, like, all I knew was start A tech company, raise venture capital type of deal and go for the big shot. When I was earning out the deal at Twitch, I couldn't do that. So I started this podcast. I was like, I'll do this for fun. And this podcast has turned into a phenomenal business and opened up all these doors. Then doing the podcast taught me about all these other types of businesses that I then went and was able to be like, oh, that's a great indi. That's a great way to do a business that doesn't require, like, getting super fucking lucky. That doesn't require, like, being the most competitive, you know, like most hardcore person. Like, you just do the obvious and it works. So, like, that was one. I did the e commerce business because I knew that that would not be seen as competitive, you know, by people at Twitch. I was like, oh, here's a business. Like, you know, it's kind of this, like, cute little, like, physical products selling, you know, it's like I created a brand, right? And I don't talk too much about what that brand is on here yet. I think I'll buy probably. By the way, I think I'll do the reveal of that maybe this year.

[B]

You sell prosthetic legs. Is that what it is?

[A]

Yes, something like that. So, yeah, so basically I started doing other types of businesses not by choice, but out of force because I was earning out the deal and I couldn't do another tech startup at the time. Today's episode is brought to you by HubSpot because using only 20% of your business data is like dating somebody who only texts you in emojis. First of all, that's annoying. And second, you're missing a lot of the content. But that's how most businesses are operating today. They're only using 20% of their data. Unless you use HubSpot. That's when all your emails, your call logs, your chat messages, they turn into insights to help you grow your business because all that data makes all the difference.

[B]

Learn [e-mail] okay, next question. At 47, what do you think? What do you think? Have you made predictions on where you'll be?

[A]

I think I'm just going to be doing creative projects. I think I'm going to be writing books and making movies and doing this, doing content. And I'm going to just be all in as a creative person. And, like, business will be secondary to me.

[B]

When will that shift happen now?

[A]

It's already happening. It's already happened.

[B]

Yeah.

[A]

That's what I've been doing. The last year. And so like that happened now. I would say there's still like some vestiges of it because I still invest in businesses but I don't run them. I don't start them and run them myself. So that shift has already happened.

[B]

So you think you're done starting businesses?

[A]

I think so. I mean, so I've, I basically only said like, only if something like really just slaps me in the face. Something that like I can't like, I'm not looking for a business to start, which has been the mode I was in for 15 years.

[B]

And is that because you feel financially secure or because you feel emotionally secure?

[A]

I don't know.

[B]

Like, is it because I lay down.

[A]

On the couch for this part? I don't know.

[B]

What I mean is like, what I mean is like, did you like discover this makes me happy? This doesn't make me happy.

[A]

Yeah, yeah, it's that this makes me happy. I think I'm better at this. I think I'm a B entrepreneur but I think I'm A plus at content. So like, why not do your A plus thing? I think doing content is now like an incredible way to make money. So like, you know, like we make great money here. Like you look at other content creators, they make a ton of money. So it's like you don't have to do a company and then do content on the side. Like you could just do content as your main thing and make, you'll make all the money you want, don't worry. And the last thing is it's kind of like the test of what would 20 year old me think is dope. And I remember thinking this at the time was like, I think a cool version of a career is like these 5, 5 year arc, 7 year arc type type of chapters where you just go do like really creative endeavors. You're like, oh, I'm going to like, I'm going to go and try to like do stand up for a few years. I'm going to do, I'm going to go try to make a TV show that I think is cool. That version of life. If I look back at my resume, I'm like, either I just kept starting businesses, like tech companies and our businesses and I already had more money than I need. I made even more money that I didn't need versus like no, I started going and trying to make dope stuff. Like I had the creative challenge of that and yeah, I actually made that show and I made this musical and I made this book and I that to Me seems more of an interesting life, and so I'm just more attracted to it.

[B]

I think every. Not every. I think many entrepreneurs go through this period. I mean, I'm in the thick of it, too, where you try to get paid, you try to feel secure, you try to feel accepted. You get a little bit of that, or maybe you get a lot of that. And then you go through the phase of what I call the second mountain, which is like, what else is there? And that's when you see a lot of people get obsessed with beautiful things or art, in your case, content, which is basically art or just interesting ideas. Where before you're like, ideas, ideas are worthless. And then you're like, I don't know, man. Just talk about ideas that is actually exciting or being around, like, pretty things. That's exciting.

[A]

Can I give you an example of someone who I think is. Is a. Has. Did both. So Joe Gabbia, friend of the pod, one of our. One of our guys that we were a big fan of. So he started Airbnb, obviously. Colossal success, you know, like grand slam type of success.

[B]

Like, he's the 96th richest man in America.

[A]

Yeah. And household name, blah, blah, blah. Great. Did that. Still pretty young, right? So he's like, all right, I'm not like, dead. What am I going to do? What am I going to do now? And so he was like, what's the second mountain? So I remember going out to dinner with him once and he was telling me about what he was doing next. Do you even know what he did next after Airbnb, do you know the next thing he did was that.

[B]

The museum, the architecture thing?

[A]

No, no, no, no. He has a company. He has another startup.

[B]

Do you know what the. The ADU thing.

[A]

Exactly. So he created this company. I don't know how you pronounce it. Samara or Samsara.

[B]

I think it's Samara. Yeah. It's Basically, they raised $40 million. And I believe what it is, is you can spend fifty to a hundred thousand dollars and they will give you an adu, meaning a guest house, basically, in the. In your backyard.

[A]

Backyard guest house in law unit, adu, whatever you call it. And beautifully designed because he's a designer. So, like, you know, a lot of times these ADUs looked very cookie cutter, cheap materials, like, poorly made. He made like a really nice one, like one you would. That, like, adds value to your house, aside from whatever rental income you might be able to get out of it. So he creates this company and he's doing it and when we went to dinner, I was like, dude, the product looks awesome. I want one of these in my backyard. But at the same time, like, dude, why are you doing this? You have all the money. Like, you have all the money you'll ever need. You made it. Like, why do the grind again? Because he was like, you know, having to think about SEO again and how do we. How do I. How are we going to grow this thing? And I was like, oh, dude, all the pain of doing a company. Why are you doing that? And, you know, he said something at the time. He said, you know, he said. He said a good answer. But one of the things he said was like, you know, I want to prove that it wasn't luck. I want to prove that I could do it. And I remember in my head, I didn't have the guts to say it, but I was like, man, what a dumb answer. Like, there's nobody out there who's like, you know what, Joe? You just got lucky, you know? Like, and even if there were people who said that, who cares? But, dude, nobody thinks that. Everybody only thinks Airbnb is incredible. What you guys did is absolutely incredible. But he had this kind of like, maybe I need to prove it again, because what else do I do? Where else do I get motivation? Right?

[B]

I've totally. I think most people have that feeling. I had that feeling.

[A]

So I remember hearing that being like, oh, man. Like, I wish I could, like, go into his brain and find that line of code and be like, oh, you have a bug here, let me just pick. Bug, fix, patch, boom, you're better now. But I did. Yeah, whatever. So he. But now what is he doing? So he basically is. So he did that and somewhere in the middle, he got pretty inspired by Doge. He's friends with Elon, like, all that stuff. He goes and he joins the administration and he's. He starts with a very simple project which was like the retirement process for government workers was like a six, six month to one 18 month process. Like, you could just. You couldn't just retire, get your papers and move on with life. It was like, hold on, a guy needs to go into this cave and find your paperwork and, like, it'll be a year and we'll get back to you. And so he was like, I'm going to just solve this problem and I'm going to solve it well. I'm going to design a product. I'm going to make the government product stuff work well. And somehow that's turned into. He's now the chief design Officer of the United States of America. And I'm like, wow, what an inspired second mountain. Like, creative endeavor has an impact, grand scale. So cool. Like, you created a role that didn't even exist, but it's so perfect for you, you know, like, he's proud and he wants to serve. He's proud, and he's extremely talented. Design. I'm like, that's the type of second Mountain. That's awesome. I think his ADU company is cool, will be successful. I want one of them in my backyard. But I just felt like more inspired personally by the kind of the new thing that he's doing. More so than when I first heard, oh, I'm just going to do another business and try to create another billion dollar company, you know?

[B]

Well, the other thing that he did was there's these famous designers, Charles and Ray Ames, or Eames. Is it Eames? You know, they make the famous chair. The Eames chair.

[A]

Yeah, yeah.

[B]

It was a husband and wife couple, and they were prolific designers, and I think they lived in Arizona, and they had, like, their home, which was famous, and it was full of, like, their prototyped furniture and things like that. And I think he also bought all of it and restored it just as a preservation thing. And so he's done. He's done a bunch of stuff. Don't call me. You guys will have to Google this to get everything right. But something like that, where he's, like, preserving history of these two designers. And so he's done a bunch of this, like, second mountain stuff that I think, really, I admire.

[A]

I'm. I'm a very thoughtful guy. I really admire, like, a lot of the way he approaches work and life. He's a very kind of, like, principled and thoughtful person. And I think I like that because I find I'm less principled and thoughtful than I wish I was. And so when you see somebody who's like, very on that end of the spectrum, it stands out.

[B]

This is for the folks out there who have a business that does at least $3 million a year in revenue. Because around this point, that's when you're able to look up after being heads down for years building your company, and you realize two things. One, you've done something great, but you're still a long way from your final destination. And two, you look around and you realize, I am all alone. I've outrun my peers, which means you're now making $10 million decisions alone, by yourself. And that is when mediocrity can creep in. My company, Hampton we solved this problem by giving a room of vetted peers of other entrepreneurs who are going to hold you accountable, call you out on your nonsense and help show you the way. Because the fact is, is that there's only a tiny number of people in your town who know what you're going through and who have been there and they're hard to find. The biggest risk is not failing. You have a company and it's working. You're going to be fine. But the biggest risk is waking up 10 years from now and saying, shit, I barely grew in business and in life. And for people like you who are ambitious, wasted potential and regret is what we want to help you to avoid. We have made so many of these groups and we have a thousand plus members. And I know this stuff actually works. It can change your life. It changed Min, and I know it will change yours. So check it out. Joinhampton.com I think that this is. I personally am quite inspired by this thing that you're saying. Now. I will be extra inspired if you actually follow through on this for a couple of years because. Because it sounds like, amazing now. And if you follow through on this, you will be my hero. And the idea being you're kind of, in other words, saying you're retiring a little bit from business and focused on purely on creative, which that's not entirely true because the creative things you do will make money, but you're not like, seeking money for money, money's sake, which is what most people do when they go into business. And I think that that's really, really cool. I think it's inspiring. And when you say these things, you sound A, more confident and B, more happy than you have in the past. Does that sound right?

[A]

100%. I. I have this framework called your last dollar. Have I told you this?

[B]

Is that the one where you have that really cool line of you've already earned the last dollar that you're going to spend?

[A]

Yeah. You've already earned the last dollar you're ever going to spend. So there comes a point because people think about these ideas like, I want to be rich. How rich? What's rich? What's rich to you? I want to be wealthy. What's wealthy? I want to be. I want to be financially free for you to do what? What are you not free to do today? Maybe you could actually do a lot of those things today. So I think people are. Money's this like, very big motivator. You're ashamed to talk about it and then you actually don't put A lot of thought into it and man, that's what a shame because it's driving a lot of your decisions.

[B]

I'm going to ask you a question and you don't have. Don't say a number, only say what you're comfortable with. But like, for example, for me, rich is. I define it as two ways. One, your, your ability to spend 3% of your liquid net worth. So if you have $10 million, you could spend $300,000 a year. Another way I define rich is your passive income. So just from your investments pays for your life. So do you have a definition for yourself on what rich is?

[A]

Yeah, similar. So basically I said if I want to spend half a million dollars a year of burn rate, which I wasn't, when I came up with this number, I was spending maybe five times less than that. But I was just like, I talked, talked to him all the time. What do you spend? What do you spend? What's kind of like if I went crazy? Okay, no, I don't care about boats and planes, so don't worry about that side of things, you know, but just like, give me a sense, like I do care about this type of shit and I don't want to have to worry about this. And like, if we go to Disneyland, I want to do. What's that thing you do where you don't have to wait in line? I like that. I want to go to the, you know, like, I just don't want to be able to do all that. And I don't care about some of these other things. For now, let's just assume that to be true. And I wanted to live in California. So I rounded all the way up and I said, if I'm spending half a million dollars a year as my like personal life burn rate, what do I need to be making in passive income or the passive gains of my investments to where that's like not an issue at all. Like, as long as my passive earnings are higher than my active burn, I'm free. Yeah, I don't have to, I don't have to prioritize money. And then you apply even some factor on top of that of like safety net cushion, big swings, whatever. And I came up with a number that was like, cool, that's the last dollar I ever need to make. And actually this came because I met, you know, other people. I did an episode of this podcast with my brother in law. You can go see it. Sanjeev Chopra, he's a real estate guy and he's done incredibly well. I'M sit. I was sitting in his, like, Vegas, like, mega mansion type of thing. And, you know, he had just come home from driving to go see a property he owns in, like, Idaho or something. And he drove back, and he got back at 11, and then he was, like, up at 6am the next day to, like, take his kids to school. And I was like, dude, you're really, like, grinding. And he had this goal of, like, I want to, you know, make all this money, and I want to be able to buy the Raiders. I want to do all this. He had these cool dreams, right? But I was like, the truth is. And at one point he was talking about, like, I want to leave. You know, my. My dad didn't kind of leave me. He didn't support me when I wanted to go do business. I want to leave each of my kids. Like, I think he said some crazy number, like, $20 million. And I was like, dude, your kids don't need $20 million when they're 21 years old to go start a business. You'll actually, like, poison their entrepreneurial career if you do that. But, like, I get the ethos you want to support your kids. I like that. Okay. I totally get what you're saying. And he wasn't like. It's not like he was fixed on those. These are things that were bubbling up in his thoughts. And I just remember telling him, dude, you've already earned the last dollar you're ever going to spend, and your kids are ever going to spend, so you're now throwing good hours after bad dollars. And that stuck with me. I was like, because I'm trading good hours. I'm trading good energy right now.

[B]

I just said, fire.

[A]

Yeah, life energy, right? I'm trading good hours for bad dollars because I don't need that dollar. It has zero utility in my life at this point. And so that thought's there. Now, am I perfect? Am I a monk? Have I, like, do I just not invest in things? Do I not have the itch sometimes, like, oh, we could make this. No, I have that itch. I have that thought. I do make investments, but so far, so good as far as, like, I'm going to do projects now where the main criteria cannot be because I think it will be successful or it'll make money. It's like, I'm only going to do it because I think it's fun and interesting and a challenge to do if I'm actively the one building it, working on it.

[B]

That I think that's a massive turn that you've made. Because I think that, like, I've known you for this whole time, and there was this period of, like, you wanting to be the man, which we all wanted to be the man, you know, in Silicon Valley. That was, like, the point of us being there. It was like going to Hollywood and seeing, like, who's gonna get a role.

[A]

Right, right.

[B]

And then there was the period of, like, okay, I, like, have a hit, but, like, I still don't necessarily feel, why am I not prominent? Like, you know, like, why, like, I. I've gotten some wealth, but why am I not king, you know? Or you also see that there's so many more levels, and you get on this treadmill, which I think I compare myself to others way more than you. And so I'm far more guilty of this. Of, like, more, more, more. You know, someone says, I think it was in the movie Wall street where they're like, how much is enough? And the guy's like, oh, I know. How much is enough? It's more. That's how much. That's how much. It's enough. But then you come with this other side of it where you're like, nope, it is. I know what it is. Enough. And I have enough. And now I need to pursue, like, truth and happiness and all this wonderful stuff. And I think that's, like, a beautiful message. I think that's an amazing message. And I think, frankly, I think I need to hear it. And I think if I need to hear it, I think so many other people do need to hear it, because I think I'm far more a normie in terms of self comparison or comparison to others and jealousy and all that stuff. And so it's very refreshing to hear you say that. And you sort of. I think your Uncle Sean shtick is kind of lame, but in this case, you are my Uncle Sean. Like, this is the. This is straight to the heart. You're 36. You're 37 years old, but you gotta be at least 45 to be an uncle, okay?

[A]

Like, dude, I'm trying to grow this gray beard.

[B]

No, you're 37. You're still, like. You're still like a child.

[A]

I'm too old to be a hot guy. I'm too young to be a cool old uncle. You're not an uncle. What am I supposed to be doing right now?

[B]

Yeah, you're in the awkward middle. But in this case, I do feel like you are, like, frankly teaching me. I feel. I feel like this is a bit of a mentor, mentee situation. And for that I'm very thankful because I do think this is quite magical. And I think if you're listening to this and I think if you're 24 years old, you think, Sean, you're an idiot. What do you know? I need to get rich. I need to do this. You're so fortunate that you get to this. Like, what the hell? And to that I say, go and find it out for yourself. But I do think that I have seen, you know, both of us have seen a lot of wealthy people, a lot of successful people. What you are saying is 100 the best path of like, get what you can and then reflect on, do you actually need more and pursue what truly makes you happy versus more, more, more, more, more. Because I'm telling you for a fact that virtually 100 of the people that go down that, that route are unhappy.

[A]

Things that I'm sure of and things that I'm not sure of. Here's my list. Things I'm sure of. In your 20s, if you're smart and ambitious, just prioritize getting around the smartest and most ambitious people you can that you like to hang out with. Right. You gotta like them too. Prioritize things that sound more interesting rather than things that sound more likely to succeed. And be cool if something gives you a lot of learning and not a lot of earning because don't worry, you got time. That's one thing I know about my 20s. I think it's pretty universal advice. It wasn't just for me. Another piece of universal advice I think that's in the, you know, the early entrepreneur phases is like, dude, if it, it's okay if it takes 10 years because you only got to get rich once and at the time, sure, I, dude, I wish it happened earlier. And I did not enjoy going over 12 and I did not enjoy that it took 10 years. But like, that's fine to get rich at 30. It's actually like no problem. I actually, that, that works really well. And it's. You're very, it's very hard to predict if you're gonna get your first business idea to work or get rich when you're 24 years old. But if you commit and you're going to iterate and you're going to be good at learning, you will probably get there. You flip your odds from like 10% chance of success to 80, 90% chance of success, which is as good as you're going to get.

[B]

Yeah, as long as the timeline is long enough, at least 10 years, it will work.

[A]

Exactly. So I'm pretty sure of those two things. I'm also pretty sure that you should be more thoughtful and more honest with yourself about money and what you're actually going to prioritize and where, if there is ever a stopping point or not a stopping point where you just stop trying, stop making money, but you stop prioritizing that as like the decision making thing of what, what. What you're going to do next with your time and energy. So I think people should definitely think more about it. I find very few people that are actually thoughtful about this and have done the kind of like the asking themselves enough questions to be clear. Now will everybody land at the same answer as me? No. I think there's tons of people who actually want more. They're going to affect change. They do want to own the Raiders. They do want to, like, be a Titan. And that is the thing that's going to make them happiest. It's just not what it was going to make me the happiest. I had to ask myself, like, it's like I'd been ordering this burger and it was like, yo, like, do I even like pickles? Like, why do I keep ordering this burger with pickles? Like, I actually don't like pickles. Get this stuff off. And so I had kind of, like, kind of just borrowed off the shelf goals and getting more clear about like, what actually would be a dope life to me. And for me, it's this, like every five, seven years, I do a bunch of creative endeavors. I make shit. I'm gonna go try to, like, succeed in these different areas. The variety is the spice of life type of. That's me. But, like, that wouldn't be it for someone else. So that part is not universal. And like, making art is not universal. So, like, you know, that part I wouldn't really put on anybody else.

[B]

I kind of feel bad that I gave you a hard time with Uncle Sean thing. I didn't mean it that way. I was only teasing, but I thought I want to because. Because.

[A]

Don't worry, no offense.

[B]

The reason I want to take that.

[A]

I'm wearing a Mickey Mouse shirt, bro.

[B]

No, the.

[A]

Let me.

[B]

Let me say I want to be serious. The reason I want to take that back is basically, if you want to get rich, go listen to Sean's previous episode that was titled how to Get Rich without Getting Lucky. That's virtually perfect for everyone who has less than a million dollars. But if you have more than, let's say, $500,000, if you make more than $250,000 a year. And you want to be happy. The last. The second half of this episode is the number one thing you have to listen to because I am going through exactly what you were discussing now. And this made me feel better, and this has inspired me. And so the second half of this episode is probably one of the best things that I think you've said all. All year.

[A]

And I don't know if you made up this Second Mountain thing or that's a book or something like that.

[B]

I think I've been feeling that way. And I heard it via. I heard that phrase, I think via a book. I think there's a book called Second Mountain, which everyone has said is great.

[A]

Yeah. So I think what. What me and you are talking about is like, Second Mountain stuff. This wouldn't have been the right message for us when we were on our first mountain. Like you're saying, so, you know, when.

[B]

I was 23, it was, how do I make $2,000 per month? That's all I need. Just tell me what to do.

[A]

You know, I saw you come to my office and you did a copywriting one day workshop with Neville and you guys made $10,000. And I thought, I just watched Ocean's Thirteen. I thought I saw a man rob the bank. And I could not believe what just happened in front of me. And I felt like such a loser that Sunday that I was like, dude, that guy just came in here and just talked to like 30 people about copywriting. It was cool. They were happy. And he made 10 grand for that this Saturday. And I just looked at myself like, you're a little piece of shit if you. What are you doing? You don't even have any idea of how to do that.

[B]

You went and taught a copywriting course and made a decade later, you know.

[A]

Took me 10 years, but later I was like, oh, yeah, that's good.

[B]

A substantial amount more in a weekend. So it kind of like became full circle.

[A]

But like, you're right. The First Mountain mindset is so different. Right. And it should be. It's supposed to be, I think. Can I ask you one thing? Have you ever met a young person that tries to do all the wise, like Yoda? The. Like, I'm already past success and money and status, and I'm like, on this. And I. It honestly kind of disgusts me.

[B]

I'm like, so I'm like, can you go get drunk and try to pick up a girl?

[A]

Exactly, like, pay your dues. You don't just get to. You don't Just get to skip all that stuff and be enlightened. Like I, you know, that comes later. I have this. There's a kid who I know that like, I like the kid, he's awesome. And it's. I don't know why. It's probably a good thing that he's already like wisened up, but there's something about it that like pisses me off inside and I can't, I'm just like, dude, you can't skip that. Go be stupid. You can't be smart before you're stupid. You got to be stupid before you're smart. Like there's an order of the universe here. And I feel like he's like kind of spitting on that order, that way of doing things.

[B]

Yeah, man, I do meet people like that.

[A]

Can we, before we leave, can I create a new segment real quick called Life Happens?

[B]

Yeah, what is it?

[A]

So I wanted to know what you did for Halloween. Did you. It was a quick life corner. I was just thinking, did you do Halloween and did you dress up this year? And then I also wanted to know, I just have this hunch that you are great at Halloween and that you've had some epic Halloween, either traditions or costumes in the past. And I just needed to answer that question. So what did you do for this Halloween?

[B]

This Halloween, I have a two year old, a two year old and a three week old kid. And we went to my mother in law's apartment building in New York City. They probably have 400 units in the apartment building. I wore suspenders. Indoor trick or treating, dude, it was the best. You go from floor to floor. Literally. We hit, you could hit 400 houses, you know what I mean?

[A]

Just like Halloween is meant to be.

[B]

And it's a very fancy, it's a very fancy building. And, and I didn't even have bars. Well, yeah, it was, it was lovely. And I didn't have to buy a costume. I just wore my overalls but no shirt and one of, one of my cowboy hats.

[A]

You bought that for Halloween? I already owned it.

[B]

I already owned it. I wore my overalls but no shirt with cowboy boots.

[A]

How'd you get it to look so used, so pre worn?

[B]

And my little girl was a mermaid and we went from door to door and it just looked fantastic.

[A]

Do you have a philosophy, a framework of Halloween? Like for example, I have one which is like Halloween is about looking cute, not looking realistic. So you know, I remember one time somebody dressed up when we were 21, like we went on a booze cruise for Halloween and they dressed up as a bushel of grapes. And they were. It was a great costume. Looked super realistic. They had balloons all over their body. But it was. They had such a bad time. And I remember just learning that lesson, like, never, ever try to be realistic.

[B]

We're gonna be our future. It was hard this year because my wife had just given birth, and so she wasn't like, we're not gonna, like, do a bunch of crazy stuff, but our future costumes are gonna be group costumes. And so my wife has big hair, and so next year she's going to be Slash and I'll be Axl Rose. And, like, my kids will look like little rock stars. But no, we're going to do. We do. We're going to do themes, because I think they're just darling. And we trick or treated in New York City. That's how New York kids do it. Building the building, which is absolutely insane. Do you remember growing up as a kid watching movies of, like, 12 year olds, like, Richie Rich or whatever, like, in the inner city and, like, thinking like, oh, my God, that's crazy. I was around those kids. It was awesome. And my kid is going to be one of those kids, which is crazy. What did you do?

[A]

We dressed up. We were astronauts, which was the first good year in a while because my wife does the matching thing, and she always stiffs me with like, my daughter wants to be Elsa. So you're like, Kristoff. I'm like, who the hell is Kristoff? Or like, you know, you're like, you're Olaf and I'm just a giant, like, snowman. It's like, I don't want to do all this. So I've been getting screwed lately. This year was better. But I dodged a bullet. I gotta. I'm not gonna lie. I dodged a bullet. So I was gonna come up with a costume, and I was like, you know what? Maybe I'll do fireman this year. My kid loves fire trucks. He wanted to be a truck. So I was like, oh, you could be the truck, and I'll be the, you know, semi sexy fireman. And I was like, I'm gonna do that. And I'm so glad I didn't do it, because you know why? When we were out, we bumped into my kids friends from soccer, and their dads are. One dad is a fireman, and then the other kid's dad is a police officer, actually.

[B]

And they wore their suits.

[A]

No, but. But, like, he was. He wasn't even dressed up because he's like, I'm a man. I don't do this. And I was like, if I had dressed up as a little goofy fireman and I met this real fireman who's a friend, I was like, that's like the biggest L I could have took. Just man to man. That's the biggest L you could take. I'm gonna dress up as, like, the loser version of you. The wacky version of you.

[B]

I saw.

[A]

It's like, if he dressed up as a podcaster and jumped and bumped into me, I'd be like, oh, that's cool.

[B]

It's. I saw this is the pod, by the way.

[A]

I hope he hears this dude.

[B]

Also that guy. You may be a cop, and thank you for your service. You may be a fireman, thank you for your service, but if you don't dress up. Come on, bruh. Like, that's lame. I saw the video or I saw a photo of what your wife gave to your children. Like a gift basketball. Like a, like, they woke up one morning and they had, like, a presence.

[A]

She's a good mom. Great.

[B]

She goes over the top, man. She's on top of it. That was wild.

[A]

Yeah.

[B]

Does she, she does that for every holiday, doesn't she?

[A]

Yeah, she does.

[B]

Which that looked like it took, like, eight hours.

[A]

Yeah, she, like, just sacrifices, like, full nights of sleep. Like, pulls an all nighter and gives them something. Her, you know, she loves arts and crafts. Anyways, it's like, you know, it's not like it's terrible for her, but she just wants them to have these, like, kind of like, magical moments and like, like the spirit of holidays, which growing up, I didn't have, which kind of explains why I also don' feel the same way she does about holidays, so.

[B]

And your eldest is just now old enough where she's probably. Or no, your, your boy, your middle is old enough now. He's probably, like, understanding traditions.

[A]

Oh, yeah, yeah. They, they, they, they get it. They like it, they anticipate it, they're excited for it, so it works.

[B]

Dude, that's awesome. All right, well, great wholesome episode.

[A]

Oh, by the way, we're about to enter Elf in the Shelf season, so, like, which is, it's like, what's the thing called for Navy Seals Buds. This is like my wife's version of Bud's training or whatever. Buds Hell Week, dude. Hell month for her.

[B]

I will never do Elf on the Shelf. I, I, it's so weird.

[A]

You are a wise and smart individual.

[B]

You're telling me. And of course it's easy for me. To say. Now, let's see if I actually stick with it. But you're telling me that this elf is supposed to be watching the children at all times. Big brother. You know, let's just call it Palantir. That's what it's going to be. It's. I'm just gonna carp on the shelf. Yeah, Carp on the shelf. Peter Thiel's in the house. He knows exactly what you did.

[A]

Better be contrarian this year. Yeah, fuck off.

[B]

The elf on the shelf.

[A]

Have you been contra or consensus is the new naughty or nice?

[B]

I just want a little, like a little doll of Peter Teal and it just. You click a button and it, like, says, well, well.

[A]

Oh, it comes with the authentic stutter. That's incredible.

[B]

Well, well, you. Yeah. All right. That's it. That's the pod.

[A]

I feel like I can rule the.

[B]

World I know I could be what.

[A]

I want to I put my all.

[B]

In it like no days off on a road let's travel Never looking back.

[A]

Hey, let's take a quick break. I want to tell you about a podcast that you could check out. It is called the Science of Scaling by Mark Roberge. He was the founding CRO of HubSpot, and he's a guest lecturer at Harvard Business School. The guy's smart and he sits down every week with different sales leaders from cool companies like Klaviyo and Vanta and OpenAI. And he's asked, asking about their strategies, their tactics, and how they're growing their companies. As head of sales or chief revenue officer, if you're looking to scale a company up, if you're a CRO or a head of sales that's looking to level up in your career, I think a podcast like this could be great for you. Listen to the Science of Scaling. Wherever you get your podcasts.