The Founder Creating Insane Internet Companies | Sam Parr

I gave GPT-4 a budget of $100 and told it to make as much money as possible. You are HustleGPT, an entrepreneurial AI. I am your human counterpart. I can act as a liaison between you and the physical world. You have $100 and your only goal is to turn that into as much money as possible in the shortest time possible without doing anything illegal. I will do everything you say and keep you updated on our current cash total. No manual labor.

And so what happened? What, what, what was the first idea?

It ends up suggesting to All right guys, bang, bang. I've got Sam here with me. Sam, you have become this like connoisseur of the internet. Everyone is like, that guy's got tons of ideas. He's got crazy questions. So I thought a great place to start would just be, what is the craziest business idea that you've attempted, whether it was successful or not? Like looking back when you're like, man, that was pretty crazy that we tried to build a business around that.

I'll tell you one that I did in college and it's not that crazy, but it's real. It's more stupid than it's anything. So one time I got poison ivy and it's very coincidental. I was trying to learn SEO and I got poison ivy and I was like, well, I'll just pick a project. And I bought mypoisonivytreatment.com and I was like, I'll just make a wall. Let's just see if I can rank for poison ivy stuff. And I didn't know how I was going to do that. And I did a bunch of research and I found that there was this thing called Xanfil. Have you heard of Xanfil?

I have not.

It's like a poison ivy treatment, but it costs like $50 an ounce. Like you get like half an ounce on Amazon for like $40. And I started researching it and I realized that in the comments someone had said that Xanfil is basically just this mechan— like, you know how, like when you ever, have you ever like worked on cars or anything and they like use this special like degreaser on your hands? Like when you're done, like mechanics use this like bead. It's got like a bead. It feels like that stuff that like used to get rid of blackheads on your face. Like it's got like a, like a bead in it. And someone was like, dude, this is the same thing as this thing called Mean Green and you can get a whole barrel of it for $50. Obviously I was like, bingo. So I, and then I was like, I need a name. So I created a product called Itch Juice and it was basically just repackaged Mean Green, which was the same ingredient as Xanthel, but it was like, I would sell it for $40. It cost me like a dollar. And it started making money pretty much right off the bat. I just got someone on Fiverr to make a logo and I started packaging it. And then I realized a few months in, even though it was making $500,000 a day, I was like, I'm doing something serious. I need to do this legally in the right way. And I don't want to sell poison ivy treatment. This is the stupidest thing ever. And so it was kind of like a get-rich-quick scheme, but I didn't really get rich, but I figured something out quickly. But yeah, I used to do little schemes like that all the time in high school and college and and like constantly.

How big does something like that get? Like when you're like, okay, I figured it out quickly. Are we talking like $10 a day, a couple hundred dollars a day? Like how quickly could you scale it?

Like $200 to $300 a day in the first week.

Okay.

And so yeah, I do things quickly. I like it. My whole shtick is like when I get momentum in an idea, I have to act like within 24 hours.

Do you do that out of fear that if you don't act, then you'll never do it? Or do you do it because you see like offensively, hey, this is how you actually build the momentum and make them successful?

Because I'm OCD and I'm obsessed about stuff. And also early on in my life, like anytime I had an idea, I had to do it. So I used to have, I used to be afraid to talk to girls and I like, I was like, from now on, if I see a girl I want to talk to, I only have 3 seconds to like make an introduction. And so I just got in this habit of like, when you get an idea, you have to act immediately because then the dopamine of seeing any type of results is like addicting and you keep going. Otherwise you're just like, soft and you never do anything. All right.

So you have like this skill set, which I like to think I have, and a couple of other people that we're friends with have, which is like you get these ideas and if somebody else is like, I should sell poison ivy cream on the internet, they would not go about it the way that you just described, right? They would not think of like, how do I find a way to get better unit economics and then package it and get the SEO and get to a couple hundred dollars a day in, in revenue. But once you learn the skill set, you can pretty much apply this anywhere, right? How do you pick up that skill set? Did you just like figure it out? Did you read a book? Did somebody tell you that was like a mentor? Like, how do you acquire the skill set to basically build these like online, you know, cash flow machines?

So I call it— this sounds cheesy, but it's funny. I call it being like a manifest cowboy, which is like I'm like addicted to like manifesting things. Like if I have an idea, I have to do it. And in my head I tell myself like, you're a sissy, you're soft, you never can pull this off. I love like that, like self-hate. It's very weird. And I think it like stems from, I think I got mad at my parents when I was a kid because like we had a burnt out light bulb and like they didn't, it took 'em forever to replace it. And I'm like, screw that. In my life, I'm always gonna fix things right away and create and act right away. And so I don't know, I just have been doing it since I was a kid where I just like am OCD. I just think it stems from impulsiveness. I think that a lot of successful entrepreneurs have a really nice balance of long-term vision, but also being impulsive.

When you've done these in the past, are there certain things you know not to do? Everyone always wants to know what did you do? But like when you have a new idea, are there certain things now you're just like, okay, I'll never do that again, or that specific type of approach doesn't work?

So once you get popular on the internet and you have some success, it does change a little bit. So like, I don't know about you, you could tell me, but when I have an idea now, I try not to talk about it until it's like a little bit successful. Because you know how people say like, I don't want people to copy my ideas. Well, when I was like a nobody, and I still am a little bit of a nobody, but when I was like, when people just like would dismiss me, it was no big deal. I would just talk about everything constantly. And I'm like, just watch, I'll figure it out somehow. And it's no big deal. Now when you have an audience, you actually, and when you have like a smart audience, people do rip you off. And so I don't talk about, I try not to talk about things. So we just launched Hampton. We got it to multiple 7 figures in revenue before we ever mentioned it on the pod or anything like that. Like I don't talk about anything. Are you the same way?

I am the same way, but it's for a different reason, which is I'm not worried so much about people trying to take it and like run with it. I end up trying to find someone that I can work with on it. And usually what happens is if you talk about it too much, the wrong people get attracted to it. So I try to find people who like— I'm like, oh, you could do like 10 different types of ideas. Okay, here's my idea. Like you're like the right person. And then I tell them the idea rather than if you put out the idea, you get like all of the industry experts on that. You get all the people who come from those companies and you're like, actually, those are the wrong people. I want the person who like is coming at this from a completely new perspective and they end up being the right person.

Well, and there's reputational risk, so you don't want to like put your brand behind something that still sucks. And then there's just getting— this sounds— this is a first world problem, but like getting too many customers early on. And so there's things like that. So now I'm a little bit more thoughtful. I also focus way more. I don't just like, I do a pretty good job. Like you have to like put out breadcrumbs and like test things quickly, but you can't go all in. I'm a big fan of like not going all in on like, when I, sorry, when I do go all in on something, it's all in and you can't do multiple things at once. I'm a big fan of focus. When you were on my pod, I was like, Pop, how do you, How do you balance all this stuff? And you're like, well, and you had a great answer. The first time I ever heard this answer, you're like, I don't balance. I'm only focused on one thing, which is building audience and then hiring really good leaders. And I was like, oh, that's actually great. When, but a lot, a lot of people don't focus.

Yeah. So I was gonna say like, what is your thing that you do focus on? Is it just one idea at a time? Is it a skill of building internet companies? Like how do you describe, okay, Sam is focused right now on what is the thing?

Dude, I plot. So like, so like I plot hardcore. And so like, all right, so before I started The Hustle, I was plotting, I spent like 12 months. I'm like, all right, what are the economics of this? Like, what do I think they can become? Who's winning in the market? Where's their weakness? Like I plot pretty hardcore while throwing little breadcrumbs out to like test my hypothesis. And then when I make that decision, I go all in and it's like, you know, I bet you this is like you where people are like, hey, it's Wednesday at 11. Do you want to go like hang out? I'm like, No, dude, I got to work. Like I have a job. And so like when I go all in, it's like, it's like, it's like a job, you know, it's like a 9 to 5. Well, it's usually longer than that, but it's like, I'm all in and I focus on things. So I plot hardcore. So I've got like a Notion doc that has all of my notes on a variety of different businesses. And what I tend to do is I'll go and find out who the bankers were that sold the companies in the space and I'll just cold call them. And they'll tell me all types of details. I'll call the CEOs or the founders of a lot of these companies. I'll call ex-employees and I use LinkedIn like crazy to find that, and I'll call them and be like, "Where was the weakness? Why did this suck?" I'll read Glassdoor. I'll look on Reddit, the Apple reviews store. I look at all this stuff and I just plot, and I have this document that maps out how different things work. And then I think about what are my skill sets and interests and which ones can this align to and which one can I actually kick ass in? But I call it plotting. And so Sean, my co-host Sean, he just sold Milk Road, his company, and he was like, what should I do next? And he was immediately throwing ideas at me and I was like, dude, just don't do anything. Just give yourself 6 or 12 months, no timeline, and just plot and be very strategic about this. Because once you have a little bit of audience, getting customers isn't that hard, but making a product that's good that you want to do for 10 years is hard. And so I call it plotting. I'm just like constantly plotting, you know what I mean? I don't know if you're like that though.

Like, I think this idea of building something that is sustainable and having the, uh, both the benefit and the downside of an audience, uh, is completely undiscussed. So having an audience, everyone's like, I want an audience. I want an audience. One, it's very hard to test things and have your name on it when you have an audience because everyone expects it to be the finished product. But actually most of the people who I think you and I hang out with, like we built our careers on testing a whole bunch of different things. And then the thing that worked, we kind of like went all in as you described. you really can't do that right now unless you like explicitly set the expectation up front. This is an experiment. I may shut this down. I'm going to try it for 2 weeks. Like you almost have to like oversell the fact that like you're not serious about it, which could dilute some of the results as well. Because if you just are like, hey, we're launching this thing and then all of a sudden 2 weeks later you like shut it down. Most people think that like that was your next company or that was the next thing that you were going to do. And they put too much like seriousness on it and it can actually work against you if you do that 5, 6, 7 times before you find the thing. Do you see that as well when, uh, you're—

Yeah, totally. Dude, with Hampton, I created a Google Doc and I just wrote out what it was and I just sent it to like 50 friends and I said, uh, I don't, I don't sell friends. I'm just letting you know this thing is going to exist. If you want in, let me know. And I just was curious what the response was and that's how it started. And we got to many millions in sales before we even, or run rate before we even like had a website. And so now I mean, I'm a big fan of doing things hand-to-hand combat and I'll just get people, I call it hand-to-hand combat. That's what I call it. I'm like, so there's times where it's like Monday or Monday, Tuesday, Wednesday, no one's allowed to talk to me because I'm on the phone talking to people, customers constantly. And I just like my, it looks like my calendar looks like it's got chickenpox. There's like, little like marked out times on every like little 30-minute slots taken all over the calendar, basically 9 a.m. to 9 p.m., just talking to customers. And I don't even like building a website until we get sales. All right.

So explain what Hampton is, because I think this is like a perfect anatomy of like how to start a company in the internet age today. What was the big idea that you had? And I'm going to guess actually when you came up with the idea, but I want to first hear what the idea is.

So it's called Hampton. Joinhampton.com. It's, so basically when I was running The Hustle, Sean and I would meet once a month. It was me, him, our friend Sieva. Do you know Sieva?

I know who it is, but I don't spend any time.

He has a big like PE firm. And then like Ryan Hoover would come a bunch of times. It was basically like 6 of us. We would meet once a month and it was like business group therapy. Like we would like express like, I gotta lay people off. How do I do that? Or I'm making good money. What do I do with my money? Or I'm going to sell my company. How do I not look desperate? What's a good negotiating tactic? All these things that you couldn't really Google but were kind of life-changing, but you couldn't tell your employees because you have to look strong in front of them. And you can't really tell your friends back home because they don't know anything about— it's embarrassing to talk about certain money. Or it can be really silly but important things like, hey, I want to fly private. How much does that cost? How do I do that? These things that you don't want to tweet exactly. And so we did this thing and we all sold our companies around the same time and it was really successful. But when you're someone like me in Silicon Valley, I have a lot of like connections and a lot of network, a big network, and it was easy to create that group. And so we created Hampton so we could make like a highly vetted group for other entrepreneurs. And so what you do is people apply, they tell us about their company, their revenue, their traction, their wants and desires and all that stuff. We interview them, they're placed in a group of 8 people that have similar sized companies in similar industries. They meet once a month with a facilitator that guides it. Conversation, and that's like the business group therapy. And then we have like an online community that's popping. So like when the Silicon Valley Bank stuff was going down, like the day before it happened, people were like, I'm hearing rumors about this stuff. And like we, everyone got a call and then people took their money out. And so anyway, it's kind of like almost like a YPO, if you know what that is. It's like a YPO, but for digital first entrepreneurs. Most people have, you have to have at least a million bucks in revenue to join, but the average revenue size is like 30-ish million. And so, but we have people from like a million in revenue, like a one-person company with a million. This one lady named Anya, she's got a company called Rooted. It's a one-person meditation app that does a million in revenue all the way up to publicly traded companies.

So when you had, I think it was the Tiger 21 guy on the pod. Yeah, I've never—

it was cool, right?

I've never heard you so excited before. And I remember thinking to myself, Sam is doing like the napkin math, like he's trying to figure out because you were asking all these questions and I was like, he's like dissecting this business at a level that he normally doesn't do on the pod. And I don't know if you had already kind of thought about Hampton or you during that call were like, wow, I should just do this for like digital first entrepreneurs. But I remember specifically listening to that episode and being like, oh man, like Sam loves that idea.

I want to explain why I did that. So I've been thinking about this for years. I almost did this instead of The Hustle, and then I always thought it could be big, but I didn't have the confidence that I could pull it off. And then we had Trends. We were an advertiser with you with Trends, trends.co. And I screwed that up, but that had kind of Hampton-esque qualities, but I messed up parts of it. And I was like, I need to get this right. And so I remember people chirping at me saying, of course you can build— People always ask me, and I bet you get this all the time, if you had to start from zero, what would you do? And I always say, well, I would do the same thing. I would start an email list. I would do this exact same thing. It works. And they're like, well, of course you could do it now because you have an audience. And I was like, I'm going to do this without telling any of you about it to prove that I can do it. And so the reason why I had Tiger 21 on the pod, Tiger 21 is like Hampton or YPO, but for wealthy people. I think the average net worth is $40 million or something. You have to have at least $20 million, I think, to get in. And it's the same thing where wealthy people meet and they discuss private stuff that you can't talk about publicly. And I remember thinking, I'm going to interview this person in public so everyone has the same information that I have, and I'm going to prove that I can do it. And so I did that a little bit out spite to prove that I could pull it off. It was definitely a chip in the— chip on the shoulder type of thing. And that guy was awesome. What was his name? Michael. He didn't like me at first when I interviewed him, but then we got along and yeah, it's a good business.

All right. So when you get started, you have the idea. Walk me through, like, how do you launch this thing? And I know some of the people who are in this, they are the highest quality people. So how do you go from like, I have this idea, I have to execute immediately to, okay, now this is to a point of success where I feel comfortable putting my name on it, building a website, like we're going to go do this.

I created a Google Doc that outlined what it was, and at the bottom of the Google Doc it was a Typeform that says, if you're interested, fill this out. I sent it to 50 people on Twitter, like in their DMs. And then I got them each on the phone, whoever clicked on the Typeform. I interviewed them and I, by myself and my partner Joe, I have a partner Joe Speiser. He went and hired a bunch of executive coaches and negotiated their rates and together we created a curriculum. And then him and I would, we would record our Zoom interviews that I did with all these people and we would say, I think this person would match with the, these other 7 people. And we just by hand created these groups and then I, because I sold to HubSpot, I get a free HubSpot account. And I did, we just did it all on HubSpot and we like emailed them a Stripe link. We said, all right, pay. And then, and it was very, very, very, very manual at first. And now we have hundreds of members and it was mostly all manual. And I started working on it basically in the summertime and we didn't have a website until December. All right. Um, and so it was all manual.

So as you get started, uh, from my understanding is you guys have raised no money. You literally, if you texted me and you said, I'm starting another company, I would just be like, how much money do you want? And I think a lot of your friends would do the same thing. And I think most of our friend group kind of just would like bet on each other. Uh, why not raise money versus kind of go it alone from an economic standpoint?

Okay. Well, there's a bunch of reasons and I'll start with like some selfish reasons. One, I think if you have a little bit of cash and you could self-fund it, I think you can get wealthier owning something. I think. The lifestyle of just owning most of a company that you can grow at your own pace is significantly better. Not for everyone and not in all cases. I think an Uber wouldn't exist if they didn't raise money, so I understand that. But with this, I just looked at which businesses I think I could self-finance. Number 2, with a community-based product, it's not like software. We can just throw tons of customers at the problem and It just can scale almost seamlessly. You just have backend issues. So I wanted to make sure that I wasn't forced to grow it quickly, but mainly it was just freedom. My partner, Joe, do you know who Joe is?

I know who he is.

Yeah. So Joe Speiser, he's my partner. Listen to this. So he sold his first company when he was 25 for $112 million. Then he started Little Things, which was like a pet blog. It was almost like an Upworthy-style website. He scaled that to $100 million in revenue and he got all of his traffic from Facebook. And then Zuckerberg was like, "Oh, we're changing." And he had a term sheet to sell the company for over $100 million. And 2 weeks before closing date, Zuck made that change and his traffic tanked. The term sheet got pulled and the business basically went out of business 8 weeks later. It was a tragic, horrible thing. Anyway, we partnered and wait, what was the question?

Explain not raising money.

Oh, and we were, so I was like, Joe, so Joe and I were also part of a group when I was running The Hustle and we would share everything with each other. We were sharing, like I would share like our net worth. Like I would say, here's my spreadsheet of my net worth. Let me see yours. Let's like help each other like figure out like what we want to do with like allocation and whatever. Like we were like, or we would talk about relationship problems that we're having with spouses or girlfriends. We would talk about everything and it like changed my life. And so when I go, Joe, let's start a company together, but before we do, let's write out what we each want in life. And so I created a Notion doc that says like, what does success look like? How do you want to spend your day? What are your values? And like we aligned to where we both had freedom up there where we're like, we want to do whatever the hell we want whenever the hell we want. We want to work hard, but we don't want outsiders telling us what to do. And we said, great, we both align. Let's start this together. And so that's why we just said, all right, well, let's self-fund it. How much money are we each willing to risk and things like that? I mean, you raised money for one of your companies, right? Um, but you have like 3 others or something like that that you didn't raise money for. And I just think it's, if you have a big idea and you have a machine that can turn $1 into $5, I think you should fill up that dump truck with money and just back it into that machine. But if you can do that without raising money and use your own capital, I think that that's ideal. And that was the situation that we were in. I mean, what's your perspective on raising money versus not raising money?

I think you and I think about it almost exactly the same, is the default is don't raise the money, especially if you have the skill set, the distribution, the tools at your disposal where you can get revenue very quickly, then that basically replaces fundraising.

Right?

If you're able to get to thousands of dollars, tens of thousands of dollars in the first couple of months, then you're able to basically use those funds just as if you had raised money. But it's non-dilutive, right? There's no better kind of, you know, capital pool to tap than customers in order to fund the growth of your business. But at the same time, raising capital, I think there is a time and a place for it. And, you know, one, there's some capital-intensive businesses. Two is probably the weaponization of capital. Like there's somebody who worked at Uber who I won't mention his name because I don't know if he'd be okay with his name being attached to it. But he was like, yeah, like Uber's greatest advantage was like they knew how to weaponize capital. They could tap the capital markets, they could get that money, and they were able to use it in specific ways. And in a marketplace business, they had all sorts of things where they were basically subsidizing both sides. So they would pay drivers extra money, they paid riders extra money, and they could really use that in a very methodical kind of math, math -driven way that would lead to liquidity in the market, which would lead to revenue growth, and then kind of could help tap the capital markets again. And so like that business needed capital and they were very good at implementing the use of the capital. And then the third thing is like acquisitions. And so like I actually believe what Andrew Wilkinson's done, he has it in a holding company structure. But if you look at some of these other organizations and companies, there are many public companies that literally all of their growth over the last, you know, 10, 15 years has just been acquisitions. Where they basically just grow through acquisition and they sometimes grow, uh, with those acquisitions and they leave them as standalone brands. Sometimes they buy them and they kind of tuck them in and rebrand them. Um, but if you're a startup, there is this huge opportunity to buy things and kind of grow quicker. You got to be smart about it, but a lot of times the startup doesn't have enough balance sheet capital to do it. And so raising dilutive funding to be able to go and buy things, uh, is a great way to do it as well. So it's like If you want those specific outcomes or those specific applications of the capital, go raise the money. But everything else, like, don't raise money because you own more of it. And I don't think there's anything wrong with saying like, hey, the economic incentive is for me not to raise the capital.

And Joe previously had a company called Petflow, which was like Chewy before Chewy came around. It was a— it was an online pet store. And he was like, we're not going to— we're going to be profitable like the whole time. And he got creamed. Because Chewy came along and they raised all this money and their whole thesis was like, "We can lose money for the first year on certain customers and we're going to provide such good service that they come back." They were right. They won and it created a multi-billion-dollar exit, but that isn't the case in every other business. Also, selling a company is— Well, first of all, building a company that makes substantial profit, that's pretty hard. Building a company that can sell, That's really, really hard. And actually getting to the deal, like when we sold The Hustle, a week after we sold, Brian, the CEO, he got into a really bad accident and nearly died. And like that could have like changed the outcome. So like there's all these things to sell a company where like the stars need to align. It's very rare to sell a company. And then finally, to sell a venture-backed company where you need a really large exit in order to make the founder a substantial sum, That's really hard. And so it gets harder and harder and harder. And I would think that I made a significant amount more money from my relatively small acquisition because I owned most all the company versus compared to someone who raised, let's say, $50 million. And even if they sold for a billion dollars, dude, I met a guy, I know one guy who sold the company for a billion dollars and he had 4 partners and he made $4 million. Getting a substantial amount of wealth— Wealth is not my main thing while I'm starting this company. I just love adventure and dopamine, but with The Hustle, it was wealth creation. Getting to a substantial amount of wealth creation by raising money, it's possible. I just think the odds are less so than creating a company that you could own most of and sell for $30 or $40 or $50 million. Still rare, still uncommon, but I think it's easier.

One of the questions that I know I've told you that somebody asked at a dinner, which I thought was just a fantastic question, is they were like, how many of your friends actually got really, really rich by participating in venture-backed tech?

And that was defined as $50 million liquid, right? Or invest in assets. Correct.

Like, you have to define what success is, right? And really, really rich. And so for the purposes of the conversation at dinner, they said $50 million liquid. And what I think we ended up coming to the conclusion of was like, you could have joined Facebook as a relatively early employee, but you didn't need to be like the first 10 or 20 people, and you probably still could have made $50 million on the IPO and kind of the future growth of that business. There are a handful of other businesses, but really since like maybe 2014 or so, there hasn't been that many companies where the non-founders walked away with $50 million liquid. And so yes, you could start a company as a founder. That's just not what most people are gonna do. And so really what this person was getting at was like, is it better to go after the venture-backable tech startup, you know, founder opportunity, or is it easier to build something that throws off, you know, $5 million of cash flow and just do that for 10 years and then you end up with $50 million, but it's a much higher probability, $50 million liquid than it would be if you basically were illiquid for 10 years. Hoping for that exit? And it's a very interesting, uh, question because you don't know what the answer is. But like, people have different risk profiles. And so it sounds like for you, you've said, hey, look, I know that I can build companies and sell them, but now let me go do this, build a cash flow machine, not necessarily be forced to sell it because I've raised capital, and like, let's just see how big it can get.

Yeah. And I think there's a third option. So on the pod, we have this thing called Sarah's List. Sarah's the name of my wife. And we made it because when she was looking for a gig, she was like, I don't want to start a company. I don't like that. I like having a job. I prefer that. And we were looking at, so I helped her. I'm like, all right, well, let's figure out what you want to do. And I think that there's a lot of wealth to be created for an individual contributor who joins a Series C startup. So you have 250 to 500 to 1,000 employees. You get good, like maternity, paternity leave, you get good benefits, you get very competitive pay, but the equity on that company still has a 10x opportunity. So for example, she joined Airbnb when it was worth, I forget, $18 billion. So it was already very established, but we were wondering like, could this become a $100 billion company? And we thought, yeah, maybe. So then if you get like a, some equity in that, like a competitive package that can very quickly become like a really good net worth for an individual contributor who didn't take a significant amount of risk. And while they worked hard along the way, there wasn't like the whole entire startup grind. Of course, I would argue that that's a pretty boring life, but there's a lot of people that want that. And you may be like, still even at 300 people, you have like big company problems that a lot of people just don't have the patience for. But still, I think it's like a really, really good way to live life if you want like a relatively chill life with a relatively low risk and a decent upside. But, uh, I think that most people definitely should start, if they're going to start a company and their main goal is wealth, I think not raising money is actually the way to go for sure. When you had that conversation, what did, what did the other people say? And were they tech founders who raised VC?

Uh, there were a lot of tech founders and there's a little bit of like the grass is always greener. So like all the tech founders like, oh man, it'd be amazing to like have a cash flow business and not have to you know, do the board meeting and have to answer to my investors and all of that. Also, this was happening during the big drawdown. So like there's all the pressures of tech compression and public market stocks coming down, whatever. But I do think that there is this belief that like now the tools are available where you can actually build pretty big businesses without needing to raise tons of money, which used to be equivalent to like you raise a lot of money so you can have a lot of employees. Those employees can do a lot of work. That work leads to a big business. But now, given all the tools that are available to you, you can easily build companies to $10, $20 million in revenue and have 3 or 4 employees. And even if you say, "Okay, that sounds crazy." If you think of venture capital firms or asset management firms, there are a lot of asset management firms that they have, I don't know, 20 employees or less, and they manage a couple billion dollars of assets. Which ends up leading to tens of millions of dollars of revenue. And like, nobody thinks of those as businesses because they think of them as investors. But like, the business of building an asset management firm is like a pretty good ROI on the number of employees for, you know, revenue per employee, I guess. And so like, if you then say, okay, well, I don't want to do asset management because I want to raise money, I don't know anybody, you know, that would be an LP or whatever. You can almost go through every single industry and there's somebody who has figured out how to build an 8-figure revenue business with maybe, you know, 10 or less employees. And it may not be something you're interested in, but I do think a lot of tech founders are like, okay, what does that path look like? Because it is a less pressure, more freedom type path and I'm actually going to make more money. Like the other thing that a lot of people don't talk about is most of these tech founders are paying themselves like between like, I don't know, $100,000, $120,000 is probably like the average salary that I see once a company's hit like a Series A. They're not paying themselves $500 grand. And some founders are starting out, they're paying themselves, you know, $60 to $80 grand. And so like, yeah, that's a lot of money to the average American, but there's, you know, public company CEOs that get paid $25 million a year. Yeah, your CEO is same in title, but like $25 million to $100K, like that's a huge difference. And so like that same founder, to your point about, you know, joining an Airbnb or one of these like Series C companies, you probably could actually make more cash just by going and getting a job as an individual contributor than you would as the founder of the company.

Dude, I have a bunch of stories. Like, I have a friend who sold the company for many, many hundreds of millions of dollars, and I was with him when the wire hit because we were celebrating and he had $2,500. That's how much he had before the deal closed. And so, like, you know, on paper, he was like, yeah, $2,500. Because he was like, I didn't pay myself anything and I just thought I was going to sell it. So I just kind of lived that way. And yeah, I mean, what are the economics? So let's say of an asset management company, first of all, how hard is it to get to like $500 million to $1 billion in assets under management? Very hard.

Yeah. $500 million to $1 billion is the equivalent of probably building like a real, you know, $100 to $500 million company in like the tech world. Right.

So then what about $100 million in assets under management? Is that like achievable if you work for 10 years?

For 10 years, yes.

And so on a $100 million fund, let's say that there's one partner. What, what would their income be each year?

I mean, there's 2% management fee, that's $2 million, right? And then now they have, they have expenses. So they've, they've got to be able to, you know, pay the back office. They've probably got to pay for legal fees, like, like there's a bunch of things that go in that. But for most venture funds, they should be able to take as top line, you know, kind of take-home pay somewhere in the like $1.25 to $1.5 million if there's a 2% management fee and they're the only employee, and then you pay taxes. And so like, you know, take-home could be depending on where you live, $750,000 to $1 million.

And that's consistent. It's not like what you and I sometimes do where it's like, you know, we got to like make something sometimes in order to like make it work. I mean, that's a good business. What other companies do you know of? And you can like hide the name of the company. And like be vague about it, but do you know other businesses that are doing like 10 million plus in cash flow for the owner that only have 20 employees? And what type of businesses are those?

So I definitely don't want to say the name of the company nor the industry it's in because I'm actively looking to try to buy a company in the space. But there are brokerage businesses in like traditional industries. So like if you go into like industrial spaces and things like that, there's the same mechanism as Uber. Like, if you really think of what Uber is, it is an asset-light marketplace. So it simply has on one side drivers, on the other side it has riders, and a rider requests a ride and then they match you with a driver. The driver comes and picks you up and Uber gets paid a fee for basically brokering that transaction. And it's grown into this multibillion-dollar business. But that's like super sexy consumer, you know, whatever. There are tons of brokerage businesses throughout like the industrial space where let's say that you're like, hey, I am on a construction site and I need bricks or I need aluminum, right? Or maybe I'm a warehouse and I need some sort of materials or whatever. Rather than you go source it yourself, like you call these brokerage businesses and a lot of times they're doing the exact same thing that Uber does in that ridesharing transaction. But they do it with like call centers, right? Like you literally call and somebody answers the phone is like, hey, what do you need? And you're like, I need, you know, I don't know, 500 bricks. You're like, okay, hold on. And they like go source it from some brick maker and then they like match you. Those businesses tend to be incredibly high margin. And so then it's just a question of like, how big do they get? But I've looked at a bunch of them and like they're doing $50+ million in revenue with 20 or less employees.

That's what my dad does with onions, by the way. Wait, really? I swear to God. Yeah. He's so like, he'll, you know, he will, he'll work with like Walmart or White Castle or like, you know, I don't entirely know all of his clients, but like, like some fast food chain or something. And they're like, you know, we need a million dollars worth of onions or we need 20 truckloads of onions. And then he'll call farmers and he'll go and buy them and then sell it and take a little fee for connecting it. And it's just him and one other guy and they made a great living. But yeah, he's an onion broker.

So literally, this is— I think you can take that idea of the onion broker or the industrial broker or whatever, and you can just pull it across every single industry. And in every industry, there's an opportunity to do this. And one of the mechanisms as to where to identify like that could be a big business is when you have some sort of national provider. So for example, Walmart, they have stores all over the country. They don't want to go figure out like, what is the onion farm in Kansas? Then what's the onion farm in Missouri? What's the onion farm in, you know, Minnesota or whatever? They just want to call the same number or call the same company every time and be like, hey, we need this many onions in this location. And so whenever you can match like national reach with local production, there's an opportunity for these brokerage type firms. And the beauty of it is like you don't really need much. Like you basically need a phone. And you need to network your way in, get the contract, start fulfilling orders as the brokerage, and you immediately start to drive revenue. And so it's like a very, very simple business that is industry agnostic, that if you can figure out how to launch it, you can make a lot of money.

Who is your, like, business hero? Like, who do you emulate?

Who do you—

when you think about what you want to become in the next 5 or 10 years and you think this person's nailing it, or I want a life like that, who do you think about?

Well, I think that there's different people for different parts of that question. Right. Uh, who I think has been the smartest when it comes—

why'd you laugh, by the way, when I asked you that?

Because one of the people I'm going to say, people will, uh, will get all worked up over. Um, there's people who have done things in business that I really respect. And I think are still, even though they're well-known, are still drastically underestimated. And then there's people who have like a lifestyle that I think is something to emulate. Unfortunately, as with most things in life, the extremes are like hard to bring together. So the people who may be the most impressive business-wise may not have the most balanced life. And so you kind of have to choose. Like Elon's probably the best example. Everyone wants to like build wealth, but would you trade being the richest guy in the world if you slept on the factory floor?

Hell no. I would never want his life, right?

Like, well, forget his life just in general. Just like If you had a really shitty personal life but had all the money, like, that doesn't seem very fun, right?

No, I wouldn't trade spots with him at all. All right.

So on the business side, let's do— we'll each go. So I'll say one person on the business side, then you say one person business. I'll say one person personal. You say one person personal. On the business side, I still think that Peter Thiel is drastically underestimated for what he's been able to do. And it's mainly because he's been able to make so many contrarian bets along the way and be right more often than he's wrong. But also he's been able to do it in a very smart economic way. What I mean by that is like just by creating PayPal and putting those shares in his IRA, he ended up creating billions of dollars of wealth that deferred the taxes.

And so basically what he did to the listener is I think what he did was he invested $500,000 into Facebook from his IRA. Is that correct?

I don't know about that investment, but when he created PayPal, which came before the Facebook investment, he actually bought the initial shares. So like, if you—

which is like— which is like a— which a lot of people don't know, when you start a corporation, I don't think an LLC does this, or maybe does, but an S corp and a C corp, I think it does. When you start a company, you, the owner, literally has to write a check. It's typically for like $100 or it's usually It's like a thou— it's under $1,000. I think at The Hustle it was like $89. I write a check and I send it to the IRS, and that is when I bought my shares. And that's like the cost basis. And that's what he did with PayPal.

Yes, but rather than do it out of his personal bank account, he did it with money that was in the IRA. So the quote unquote shares that he owned in the company actually were his IRA ownership. And so what happened is when they sold the business, that those shares were not taxed because they were inside of the IRA.

And so you can't spend that, right?

He can't spend it, but he can continue to compound it until he turns like 60 years old, right? When he can actually access that money.

And so you take a loan— can you take a loan on your IRA?

I don't know the answer to that, but I'm sure if you can, people have figured out how to do it. And so it's just like one of the interesting parts of this is like How much do you have to think in the future? Like, how forward-thinking and long-term thinking do you have to be to be in your 20s and say, I am going to make a decision now that will set me up for 40 years in advance?

Which is hard. It's hard, right? That's like very— like, whenever I meet like 21-year-old kids who like have these startups and they're saying these big visions, I'm like, wow, that's like pretty bold. And you meet— I meet people like this and I was not like that. Yeah.

I mean, I think most people are like, hey, I'm trying to get to Friday.

right?

Let alone like 40 years from now.

So, so I think that, um, and then also I just want that Bloomin' Onion, baby. I want that, that Bloomin' Onion at Outback. I'm not thinking about IRAs, bro. I just need to get that Bloomin' Onion at a softball game and I'm cream cheese.

Exactly. Um, and so the last thing on Thiel I think is, uh, he has created a number of businesses, uh, and also continued to invest in great deals. Um, but the most impressive part of all of that is just like he has consistently been one of the best selectors of talent, and he's found all of these great operators, great thinkers, you know, really contrarian type people that it's not like, oh, he got lucky once or twice, right? It's like very obvious that he has an ability to identify and select talent that I think most of us are envious of. And so if there's one skill in business that I personally wish that if I had to like lose every skill and just have one, I actually think that's the most important skill is just like be able to identify and select talent consistently better than everyone else. And if you do that, like you always have a shot to build something successful.

Do you— what do you think his personal life is like? Well-balanced or no?

I don't know. I tend to think that, you know, everyone has pros and cons. And so like if you were even— if I was to ask you, if you asked me, if you asked, you know, Peter Thiel or anybody else, like they're probably harsher on their own life than other people are, because it's really easy to be like, oh, this sucks or this sucks. And everyone else is like, yeah, man, but like, I wish that I had that, right? And so it's a weird thing. Who's your business person?

So I like a lot of historical figures. So I— there's a book called Titan. It's about John Rockefeller, and I really like him. He, he lied famously one time about creating like a monopoly. But besides that, he was mostly always honest when it came to business. He was a handshake type of guy and was pretty honest, and he also knew when to bail. And so he basically resigned when he was in his early 40s and had CEOs run the companies. And so I admire people who know when to get in and get out and let other people do the stuff and not take a lot of the publicity. So I like John Rockefeller. We had Rob Dyrdek on the pod. Have you ever talked to Rob Dyrdek?

I've never talked to him, but the Fantasy Factory is legendary.

Dude, he was dialed in to his life, and I felt like he had a really, really good way of looking at life. He was super dialed in. So I really like him business-wise. Do you know a guy named— Have you heard of CB Insights?

Yes. Fantastic episode.

Yes. I love him. So this guy's name is Anand. So Anand, he's a Hampton member. So I've gotten to know him through that. Basically, CB Insights, they've only raised maybe $10 million in funding. They could be over, I'm not sure, but 9 figures a year in revenue. CB Insights is basically a database product. So what he does is he loves to find messy data, publicly available data, and just makes it really clean and easy to read. The reason I like him is he's been patient. So he's been growing this really steadily for 10 years. CB Insights has an awesome newsletter that I love reading, but besides that, they're really low key. I love, you know, I love people business-wise who are a bit of the opposite of me. You know, what do they say? What does Lil Wayne say? He goes, real G's travel in silence.

Like, real G's move in silence like lasagna.

Yeah, yeah, yeah. So I love people like that who are just like quietly doing stuff. And, you know, there's another, I always think of this song, you know, the Damn It Feels Good to Be a Gangster by Ghetto Boys. He goes, you know, real, real gangsters don't flex nuts because real gangsters know they got them. So I just, I love people like that. And he's one of those guys who he just doesn't talk about it. He doesn't make fuss. He tweets funny stuff, but he's not outrageous. He's pretty professional but has— having a good time, and he's just quietly doing stuff. And I love people that just shut up and they do stuff. You know, I have a big mouth, and so sometimes I admire people who don't because I'm like, man, I wish I could have a little bit more self-control and be like that. So I like Anand. He's someone I really, really admire. He just shuts up and he does work, and you don't hear from him, but he's just killing it. And, uh, so I really like people like that. Because of Hampton, I've met all these people and I can't reveal their names, but I've met 5 or 10 people who, they have these software businesses that do $20 million in revenue and they're based out of Kentucky or Idaho. And you'll talk to them and they look a little schleppy and they just look like normal guys. You'll have no idea, but I'll talk to them about cars and they're like, "Yeah, I have one of those Bentleys." I'll talk to some members, I'm like, "Oh, I love cars. What do you like?" He goes, "I like this, this, and this." And I'll be like, "Oh, what do you guys like?" "Oh, I have one of those Ferraris. I have one of this and they just have cool stuff because they love it, but they don't brag about it and they don't flex. And so I love people like that. Anand is not a fancy car guy or anything like that, but quietly building this monster business and he doesn't talk about it. And I really admire that. When we wanted for him to come on our pod, he didn't really want to go on at first. He just wasn't after it. He was like, "No, man, I like just chilling." And I had to ask him a couple of times to join. So anyway, I like people like that. And then the last person is Dharmesh, the founder of HubSpot. So Dharmesh, Dharmesh Shah is his name. He started HubSpot and business-wise, he's kind of my hero because he had a company. I forget what it's called. I think it might've been a consultancy. He sold it. I don't remember how much he sold it for, but he probably made $10 or $15 million. And that was like in the early 2000s. So that was probably enough money where he was like, I don't have to do anything anymore. But he went to MIT and he was like, I sold a company. I'm going to go, I'm going to go get a degree at MIT, which is odd. And at MIT, he met this guy. Who was a salesperson for a software company, and that guy was Brian. They put together a school presentation on this idea they have for CRM, and that is what HubSpot became. Dharmesh funded the company with $500,000, so he owned a lot of the company, and he said, "I've got one rule, Brian. You've got to be the CEO and no one ever reports to me, but I'll hack away and I'll build great stuff that the company loves." That's what he's done, and he's always been a hacker. So he built HubSpot. So HubSpot's like give or take, a $20 billion company depending on the day, but he still has side projects. So have you seen his project called Wordplay?

I've seen a couple of the ones that he's done. Wordplay is pretty cool. And then I think he just launched SpotChat.ai or something too.

Yes, he loves— he loves SpotChat. So Wordplay is a game that he made. He goes, I wanted to teach my son how to code, so we worked together on this game. It's like, what's that thing called? Wordle. Wordle. It was like— it's like Wordle, but there's like not— you could play as much as you want. And I say, I said, well, how big is that? And he goes, oh, and like by month 3, we had like 3 or 4 million people using it. And I was like, what? How much money does that make? He goes, well, I let my son run ads for 1 month just so we could understand monetization and it made $90,000. And we just donated the money and we have this thing and it's just like killing it. And I'm like, why'd you do this? He goes, I just gotta keep my skills sharp and I just love, I love hacking on projects. And so he does that in his free time. And I just think that someone like that who, again, he's just kind of, he's just a G. He doesn't flex too hard and he just builds stuff because because he loves it and he won't tell you about it unless I ask him. And so I like that. He also built Spot, uh, what's it called?

Spot Chat.

Spot Chat, which is like this add-on that HubSpot is gonna like incorporate where you could like use AI and talk to HubSpot like it's a person and it'll do stuff for you. So anyway, he's actually building it and coding it. And so I love that. I love people like him. And if I ask him to come on the pod, he'll be like, maybe next month. Like he's just not like interested in bragging about all of his accomplishments.

So part of what I love about these types of people is like they're tinkerers, right? They're— they just want to kind of do these little things and figure out if it works or not. And I tend to find that there's two questions I ask in interviews now that very quickly help me understand a person better. And it doesn't matter what they answer with. It's like, what is the type of answer is really important. So like, one is like, talk about something that you built recently that has nothing to do with your day job. And usually what you find is like most people have to think for a second what it is, but it's not always tech. Like it could just be like, oh, I went in the garage and like, you know, I fixed my car. Or I had one guy come on the podcast. Do you know this guy, Jon Finkel? He has a newsletter called Books and Biceps.

No, but that's awesome. Tell me more. I'm in. All right. Yeah, biceps. All right.

Books and Biceps. And so he's got this home gym, but I saw him tweeting one day and he kept referring to the Flex Factory. And I was like, what the hell is the Flex Factory? And it's his home gym. And he was like, growing up, I always wanted to have a home gym. It's like I built one. I named it the Flex Factory. He put up like all the stuff on the wall and like, it's awesome, right? It's like every, like, washed up middle-aged man's dream. But he is like that on steroids and he's killing the game. And so he— if I was to interview him, be like, hey, talk about something you're proud of that you built, like not related to your day job. If he had just started to describe the Flex Factory, I'd be like, got it. Like, check the box. Like, you're great. You know how to build cool shit. Like, you get it. And then the second one is I always ask them, like, what podcast do you listen to or what books have you read recently? And again, less because I want to actually like, oh, this book is good, this book is bad. But it's like you quickly understand the type of person they are by what they're reading. And then if you even take it further and be like, what's one thing you agreed with in the book and one thing you disagreed with? You very quickly can kind of wash away all the bullshit and it's like, hey, this person can think critically or not. And so I've had a number of people who I'm like, hey, what did you disagree with in that book? And they're like, nothing. And I'm like, you read 300 pages and you disagreed with nothing. And then they kind of think about it and they'll eventually kind of answer. But there is this skill to tinkering, there's this skill to critically thinking. And I think the internet, some people end up getting washed away and it ends up end up like getting worse and they don't tinker, they don't think critically. But then the internet can also help you do it more. And somebody like Dharmesh is a perfect example where like he is like an all-star of the internet because he likes to tinker and keep those skills sharp, right?

Yeah, totally. When I, uh, at The Hustle, I used to have this phrase where I used to say, you come work here, I want you to let your freak flag fly. And so I would look for like oddballs. And like weirdos. And I love those types of people because the world wants you to be vanilla. And if I could find someone who isn't vanilla and like is just quirky and odd and they have to be good at their job, but I want to surround myself with like, I love a freak show. That's what I want. I want like weirdos and like, um, I would always surround myself with those types of people. And typically they, they tend to be pretty good because they're quirky and that quirkiness can carry over to like the— that, that like, it's That type of eccentricity is like kissing cousins with like person who's willing to take risks, you know what I mean? So like it's like very related. What about—

Why do you think that those people are so good work-wise? Are they compensating for like the quirkiness or like what is it that makes them great people to hire?

They're just original thinkers usually, you know, like a lot of people, like what I don't like is if someone tells me like they read all these business books and I'm like, oh dude, fart. Like, you're just so lame. Like, I can't— I don't want to— like, you're just going to regurgitate the same thing over and over again. You're not going to come to the table with anything unique, and you're going to be fearful all the time. So I want people who aren't fearful. I think when you hire— when you have employees at a company, like, there's this weird thing at a company where even though a person knows that the right thing is to do option A, they'll do option B because they don't want to be embarrassed and look stupid. And it's really hard to find people, and I think it's actually intrinsic. I think it's built in for the people who are willing to take option A, even if it isn't like, uh, like the safe, like that risk-taking genetic factor or whatever it is. I think that you either have it sometimes or you don't. I think it's really hard to like get people to change.

How do you know that somebody's an authentic freak? Like they didn't just read some book in there or they watch this podcast like, oh, Sam likes freaks. Like, I'm going to like be a weirdo in the interview. So he thinks I'm a freak. Like, how do you make sure in the interview that you can tease out like who's real, who's not?

So if some people are like, like I'll have people like you joked with me where you like said, let's fuck. And like I said that to a nun and like I'll say to like my friends, but if someone is like obnoxious, uh, like in an interview with me, I think, oh, you're just, you're just lame. I could tell that that's not authentic. And even if it is, you don't, you got to learn how to like be polite and shit like that. So I don't like people that like, you can tell who's turning it on. So I do the same thing as you. I ask, I go, what content do you read every morning? And they'll say like newspapers and stuff. I'd be like, no, no, no. Tell me like, who do you follow on Instagram? And what subreddits do you go to every morning and why? And like, I'll, I'll get all types of information. I also use this tactic that I created called, I ask them about the bottom fourth of the resume. So meaning in the bottom fourth of resume, that's where you put where you went to college and like the clubs that you joined. And if they say they're a part of a club or something, or if they say they studied philosophy, I don't really care about philosophy, but I'll say like, what's the, what's the most interesting class that you took and why? And if they can do a good job of explaining and having passion about something that's relatively obscure, then I think like, all right, this person's oven's, oven's burnt. This person's oven burns hot and they have got some horsepower there and they're kind of interesting. So basically if you can entertain me in an interview about what you read each morning, or about what you studied in college, then I'm interested. If you can't tell me with passion what you spent 4 years and $100,000 studying, then you're probably a loser.

What is your personal operating system? Like, you have so many different things going on. You're always kind of tinkering with things. You're running Hampton. Like, what are the tools you use? Do you use certain things for email, calendar, note-taking? Like, what are those things that make you so productive?

I use this notepad right here and this is pen. You see, I've been like, I write stuff. I just use a notepad, a pen. I don't have an assistant. I use Gmail, Notion, and that's it. I have like a— it's pretty effective, but also like I get overwhelmed pretty easily. Do you have an assistant?

I do now. For years I was like, pride that I didn't have one, but eventually I got one. And I will say that—

is it full-time?

Full-time, but across all of the businesses. So only one person across everything. And there's two advantages that I realized after the fact. One is I never screw up or forget the big things, but like tons and tons of like little things that are actually not very important from like my day to day, but maybe super important in blocking somebody else. Those things—

getting your car registered or something like that, like little things like that.

Yeah. So like, I don't really do a lot of the personal stuff. Like, I don't, I don't ask her to do that stuff, but it's more so like Let's say that you and I work together. You have a business that we are helping with capital and distribution on, and you have a list of 5 things that you're like, hey, we got to get this done this week, right? And one of the things is something that is— requires coordination with an external source around like scheduling something or sending an email. To me, that may not be the most important thing because this is the 5th most important thing on your list for the week. Right. But like, I'm obsessive. I want to make sure I get it done. And so rather than let it fall through the cracks, like, it's like that is her— one of her jobs is to make sure that we have a list of every single thing we need to get done this week. And we don't finish the week until we have that stuff kind of done. The second thing has been really helpful with is she creates a report at the end of the week that audits the calendar and basically says, here's how you spent your time. And so it allows for like week-to-week self-correcting of like, hey, that sucks, right?

That's, that's a painful— that's a painful exercise.

I love doing it because all it tells me is like, I, I know what's the most important thing right now. And then I can look and see in a quantifiable way, how did I spend my time? And if the most important thing is like Company A, but I spent all my time with Company C, like there's a mismatch. I got to get back on track, right?

But is your calendar booked from block to block?

For the most part, yes. I try really hard to push everything between 10 and 4 because I write in the morning and then I try to like just go back to back and squeeze everything into a 6-hour period, calls, meetings, all that stuff. But like, you got to be— you got to pay attention. That's what you're going to do. You got to pay attention to where you're spending your time because it's very easy just to say yes to a lot of stuff. So she helps with that. And then there's actually one other piece that is super encouraging. She understands context around a bunch of questions people have for me that I'm not needed to answer because she's there. So like in some way, people now, they just ask her the questions, right? And so like you got to really have a high degree of trust with this person for them to be able to do that. But like, I don't need to answer every single question that people have, especially internally. So having her as a go-to, rather than wait for me for an hour or 2 hours to get done doing a podcast with you, all of a sudden they can just ask her and maybe 80% of their requests she can answer for them, point them in the right direction, get them, you know, the document they need, whatever. And then for the 20% she can't, hey, it's got to wait and I'll just do it when we get done. Why don't you—

your life— wait, sorry, what are we going to say?

I was going to say, why don't you have one? What is the reasoning?

A little bit is pride, like you, like you were saying. And a little bit of it is I've always felt uncomfortable having an assistant. It just feels— I don't know, it feels weird, right? Like asking people to do certain things. I don't know. I've been uncomfortable with it, but I need— I do need to get that. Is your person in America? Or overseas?

In the office with me every day in Miami.

Yeah, I think I should do that. I think that's awesome. I don't know why. I think it's just pride.

I, um, let's see, I tried a virtual assistant. They were great at some things, they were horrible at other things. And so, uh, what I eventually decided was like, it was worth the additional money to have somebody in person that I could meet with, that could attend meetings that could do all the things that like are now available in person that a virtual assistant can't do. But I do know, like there's one CEO I know, he's very much like performance-oriented. He has an American-based assistant, but they're remote and lights out. Like he one time was driving with his wife on like a, like a Vespa scooter, like almost like a motorcycle thing. And they got a flat tire. He literally like pulled over to the side of the road. They were late to this dinner. He got an Uber. He basically messaged her and was like, hey, this is what happened. Here's where the bike is, like, help. And went to the dinner, ended up getting there a few minutes late, but not as bad. And like, even though the assistant was remote, was still able to coordinate and kind of do everything. So I think it's like a lot of not just having one, but also having the right person for what you need is a, uh, is a big piece of it.

Who's your hero personally? Like you said, business-wise, what was the personal side?

So I tend to think that the people who are best optimized on the personal side is like, not, hey, I have this like perfect life. It's, hey, I am doing the thing that makes me happy. And sometimes like the external vision of like what the perfect life is actually would be super shitty life experience. I go to dinner sometimes and there's people there, and from the outside they have everything that quote unquote, like, people want, right? They have wealth, they have what appears to be a great marriage, they have this great job, what, you know, company they built, whatever. And then you talk to them and you're like, you are a hollowed out soul. Like, you are dead inside and they know it. They just haven't like fully, uh, kind of confessed that to themselves. And so like, I don't want that life. And so when I think about, uh, kind of the quote unquote, uh, personal heroes, it's all of my friends who don't give a shit what people externally think about, uh, them. And it's just the people who are happy. And so I'll tell you a story that, uh, I think kind of highlights this. I was driving, um, with, uh, my wife in the car. We were, uh, driving down the street and we stopped at a red light and she goes, what are you thinking about? 'Cause I was looking out the window and I just was honest, maybe mistake number one. And there was a guy, he was edging the grass by the curb. And I was like, I don't know why, but I just thought that guy has such a great life. He doesn't give a shit what is happening on Twitter or this or that. He is going and he's doing something with physical labor which is a hard life, but it's also something where it's like the stresses of it are much more physical than they are mental and emotional and like all of those types of things. And I remember thinking that like at some point in your career you have to make like a fork in the road decision. Very few people have both physical and mental, uh, stress at work. And so that path is not one that I chose, but like it's a different path. And when things are going wrong on the path you choose, sometimes you look at the other path and you're like, man, that is like a simpler life. But vice versa, that guy probably is like looking at the car and he's like, man, that guy's life is simple. And so like how much of it is expectations versus reality? And I don't know. So like, what's your answer?

You, uh, well, I'll give you two. The first is Laird Hamilton. Do you know who Laird Hamilton is?

Oh yes. Yes. Legend.

Laird Hamilton is the surfer guy. He like looks like, if you think of like what a surfer '80s hunk would look like. He looks like that. He looks like a Ken doll. He's just like this buff dude. He's probably close to 60 now, so he doesn't look as buff as he used to, but he's this guy who basically helped pioneer big wave surfing. And then eventually he created this thing called Laird Creamer, I think it's called. I forget what it's called, but it's like a coffee creamer. It's like a big business, tens of millions, whatever. But he has a person running the company, but he said they have this thing where if So he basically has his house in Malibu with like a pool that he works out in and all these people come to his house to work out and he's on the beach. But he has this thing where everyone knows that if a wave, if like the, the forecast says that the waves are gonna be above 20 feet, automatically you can't talk to him because, and he will not talk to you or have meetings because he has a rule that if the waves get above 20 feet, he goes surfing. So it doesn't matter like where he is in the world, if it's above 20 feet near his place, he flies back and he goes, he goes, we're going surfing. That's my rule. So I like that. Because he lives life to his own standard. And also his wife is like, they're partners in a lot of his businesses and they're truly a partnership. So I value that. But another one, do you know Sam Korkos from Levels?

Yes. I'm an investor in Levels.

Same, same, same, same. So there's this guy named Sam. He's got this company called Levels and it's basically you put this glucose monitoring thing in your arm and it tells you about your blood. This guy is as freak as they come. So I hung out with him one time. I hung out with him one time and he was with his girlfriend and she just made a joke because I said like, I don't remember, we were just talking about like, you know, spouse stuff. And he was like, oh, Sam always gets mad at me cuz he says I take too long to pack, but that's only because he just has that bag. And I look at Sam, I go, wait, what is she saying? And he goes, this bag that I'm wearing. And it was like a drawstring bag. Like, you know, those things that you'd play soccer or football with. He goes, "This bag and what's in this bag right now, as well as the clothing that I own or that I'm wearing, I don't own anything else." I go, "What do you mean?" He goes, "This pair of jeans, I've got a jacket in this bag, I have this white t-shirt, I have my shoes, I've got my computer, my computer charger, my cell phone and my cell phone charger, and my toothbrush, and that is all I own." And I was like, "Are you serious?" He goes, "Yeah, I've been doing this for 10 years." I just don't like owning stuff. It stresses me out. I'm like, what if you have to go to a funeral? He goes, I go to a thrift store, I buy a suit, afterwards I bring it back. I was like, are you kidding me? He goes, yeah, I just don't like things. It doesn't make me happy, and I live nomadically, and I've been doing this for years and years. Sam Parr is interesting because this actually might be public to everyone. I don't know if it's investor only, but he writes these in-depth investor reports, and I invested a small amount of money early on in their round, In a way, I feel like the value that I've gotten from the investor reports is worth the amount of money that I put in the company. They're literally like novels. They must be like 5,000 or 10,000 words. Every single month he sends one and he goes, "Here's an update on the business," and he tracks everything. I was like, "Why do you do that?" He's like, "This is just how I like to run the company, and I hire people who enjoy doing it this way. It's just easy for us to be on top of things," and I love it. What do you think about his investor updates? They're crazy, right?

I think they're amazing. He knows— I call it the warning system, right? Because he has such great understanding of what's going on in the business that he will know something is wrong before most CEOs do. And so, like, it takes a lot of time, care, attention to detail, like, you know, all the things that go into writing that type of report. But if you have the early warning system, you probably are better off for the type of business he runs than not doing it. But also, I think there's a lot of businesses where like that would be overkill and people would be like, this is absolutely insane. Why are we spending so much time on doing it? It. So I think a lot about like, is that the culture of the business or not? And he specifically, you know, he even told you, right? He hires people who like, that is what they want to do. But did you do that with The Hustle? Like, did you have like super crazy, you know, long, uh, investor updates where you had every single metric laid out?

No, I didn't. I, I, but I was pretty good at, uh, sending it updates and keeping things updated. But I ran it much more simply. So every Monday we would have a meeting. We called it the numbers meeting. And for the first 10 or 3, 3 years of the company, we would meet as a company and we're like, did our email list grow by 3% or not this past week and why? And it was the whole presentation was just one. And so we would pick one number, one metric, and then eventually we picked two opposing metrics. So it'd be like new customers and then like renewal rate because you don't want to go just after one because you can manipulate that to hurt long term. But eventually, but it was basically just like, did the email list grow by 3%? Or not. And I wanted to grow it by 3% every single week because Paul Graham said if you can grow something by 3%, that like it ends up like, I think, I don't remember what the math is, but that's like 12% or 12 times growth per year or something like crazy. He's like, if you do 3%, that's considered good. So I just said, all right, we're going to grow by 3% every single month and we're just going to have a meeting every month and each person's going to explain how they contributed to making us grow by that rate. And so I was like maniacal about that. And I think that was really effective.

If you had an email today, which a lot of the people who listen have some version of email, whether it's their company email, a personal email they send, it's a business they're trying to build, whatever, how would you grow it?

So The Hustle has like close to 3.5 million readers a day now. So it's pretty big. When I sold it, we had a little less than 2 million and 3.5, like that's hard to fathom. It's 'cause like I just have a little like a side hobby email list of 10,000 and I could see that that like makes a lot of money. I mean, your email list is what, what do you have? 250,000, maybe 150,000?

Uh, 230,000.

Yeah. And that can make like a substantial amount of money. And so with a 3.5% or 3.5 million email list, we could probably made, I don't know, maybe 40 or 50 million a year just off email advertising. Like you can make a lot of money. And so I look at it now, I'm like, I can't believe how big it is. But if I had to grow, so our first 100,000 customers or 100,000 users came in year 1, and that was from me blogging. I would just write these like crazy blog posts and I would post them on Reddit and it would get traffic and 3% of people would sign up and that's how we got it. And I would do that the same way now, but I would start probably on Twitter. So instead of a blog, I would do Twitter, but I would still do part of the blog. But then What a lot of people do nowadays. So me and The Skimm and Morning Brew, we were all building our businesses separately, but we were all building at the same time. And we all learned that you could do paid marketing once you understood how much your CAC was and how much your LTV was. And so back then we were able to acquire customers for $2. Nowadays people are still doing that, except they're doing it early on with like me and Morning Brew and The Skimm. We got to like hundreds of thousands of customers, hundreds of thousands of users. Then we did paid marketing. Now people are making the mistake of doing that way early on, and I think that that's a huge mistake.

Why?

So if I had to do it, because you have like a leaky bucket, most likely, like paid customers can be good, but they're not going to be as good as an organic customer. They're going to churn out sooner. And also paid marketing will give you a false signal that you're doing good. The whole point about an email list is attention. And so like, The value of an email list is like, if you had to make it an equation, it would be something like number of subscribers multiplied by the amount that they're engaged and the amount that you have influence over them multiplied by the spending power. So 10,000 Fortune 500 CEOs who own software companies or something like 10,000 software company founders, or let's do 10,000 CTOs of software companies that have at least 1,000 employees. Is going to be significantly more valuable, I would bet, than 500,000 stay-at-home moms, you know, things like that. And so the buying power matters and also the amount that you're able to influence, you're able to have over them. And you know, you have influence over them when you tell them to buy something or you recommend a book or a product or you say, I'm hosting a meetup, come and hang out with me. That's really how you know you have influence. But a lot of times what people do when they're starting their newsletters, they think, oh, well, my list is growing, therefore I have influence. Where it's like, no, dude, you can just throw money at that problem. I'll get you subscribers. You need subscribers, dude, I'll get you subscribers. You know, it's like Big Lebowski, you need a toe, man, I'll get you a toe. Like getting subscribers, like it's not hard when you're just paying money to do it. The problem is you're throwing them into a leaky bucket where people don't actually love your content. And so a lot of times people who create newsletters, they don't think of themselves as like, they'll think of themselves as like growth acquisition experts, not creating content. And it's like, dude, you gotta get the content first, not the growth. The growth is actually significantly easier. What's harder is getting someone to subscribe to your daily email and have them to want to stay for 3 or 4 years. And so I think you shouldn't do any paid marketing until you have like 20, 30, 40,000 people. And that's like a really big ballpark. But that's like if you're doing a somewhat mass-produced email, that's around maybe when you'd be ready to do paid marketing. Is it— do you do paid marketing?

We do no paid marketing and only have used Twitter, really. To, to grow the email. And it's great because super organic, really high open rates, you know, all the things that you want. It's also incredibly frustrating if you don't do paid because you naturally just hit a limit, right? Like it doesn't matter how many, how much you push it. Like if you only have a certain Twitter audience, like eventually you just saturate them, right? And so like if, if we wanted to turn it into a full-on business, then yes, paid marketing is the way that you scale past like the organic growth. Um, but, but, uh, but it's difficult. Uh, let's talk a little bit about Agora, uh, because I think Agora is like this like really interesting, uh, business.

Have I talked to you about that?

No, we've never talked about it, but I know that you probably have opinions about this. Um, and so for those that don't know, Agora is like a newsletter company, um, that really, from my understanding, doesn't just do advertising on the newsletters. It's really a way for them to do distribution for video courses, training programs, like a bunch of things in the background. My understanding is that they do close to $1 billion in annual revenue.

What? Usually more.

Okay. Explain, explain what your thoughts are.

So Agora is a company started by this guy named Bill Bonner out of Baltimore, and he started it maybe in the '80s. So before the internet was really popular, it was like newsletters, like they would mail it to you. And Bill Bonner is like this libertarian, Sometimes it's— a lot of times it's politically charged, but it's a financial publication. And so he'll tell you where to invest. It's kind of like Motley Fool, but has a political slant. And he started it and it was doing fine and he had it for 10 or 20 years and it was slowly after a while got up to $10, $20 million a year in revenue after 15 years. Then some of his employees wanted to branch off and do their own thing. And he goes, well, hey, instead of starting your own thing, Why don't you go start a new publication for me and we'll do some type of equity split? And so now Agora is a company that owns probably 20 or 30 different publications. They do north of a billion dollars in revenue and they've helped pioneer like a lot of direct marketing stuff. And a lot of stuff that they do is shady, but you can learn from it. And here's what they do. And I actually have a screenshot of their financials. I can send it to you. And what they do is, um, Like I said, dude, I do research. I talk to the people who work there and I'll send it to you. Like, and so usually what they do is they have a free newsletter or a free webinar, something like that. And it's about like, like picking stocks or something like that. Then they have a $100 product, which is like better picks. Then they have a $2,000 product and they make all of their money on what they call the backend, that $2,000 product. And now they've gotten so big that they sell like supplements and they sell everything and they've been sued a ton, ton of times. They recently got sued by the FTC because they did two things. One, they claimed that they wrote a book that can help you cure diabetes, like naturally, which is bullshit. So they got sued for that and they got people to pay money for the book. And they also created this thing called the Republican tax where they like said that like Nancy Pelosi's going to come after you because you're a Republican and tax you more. And they would write a direct response email where it looked like it was Nancy Pelosi wrote someone an email. The recipient clicked reply all to the Agora email list that said, hey everyone, Nancy just sent me this email. We can't let her get this done. And here's why. And they would write really long form articles. And for people who are in marketing, what they're famous for is long form copywriting, direct response copywriting. And we're basically talking a website with nothing on it but 4,000 words and a really small link at the very bottom that says buy now. And those pages convert beautifully. I don't agree with everything they say, but the numbers show that they are the best performing things. And so this guy, basically Bill Bonner, you can look him up, he's a billionaire. And all along doing this newsletter, he started investing in Baltimore real estate and he owns multiple skyscrapers in Baltimore. Or if you Google Bill Bonner, France. His wife owns literally palaces or what do they call them in France? I forget what they call it. These like estates and they own all of these like estates in France. What are they? What's like an old palace in France called? Like a villa or something like that. But they like own all of these and they do like interviews with like Home and Garden and all these stuff of like his wife, like showing off these like, they're literally like old, they look like old stone castles. And so anyway, he's like this kind of like an eccentric crazy person, but this company does collectively like $1 to $2 billion a year in revenue and like $3 billion a year in profit. And he owns all of it.

Dude, it's incredible what people can do if, uh, they have a lot of time, right? 30, 40 years and they keep at it and perfect something like, again, dude, and copywriting.

The copywriting on their shit is like crazy and you read it and you think, who reads this? And then you start kind of like digging into the story and you're like, this is a page turner. This is like, I'm into this. It's like, it's pretty wild.

How important is copywriting still today, given that, you know, there's the rise of AI, it's the internet, everyone's got slick websites. Like, I know that you're a big copyright is drastically underindexed on, but like, explain what should people do if they want to get better at it?

I read your article on Substack about, what was it titled? The one you sent me the other day where the bodies—

The banking crisis.

Yeah. Dude, I read that article and I didn't go to bed last night till 3:00 AM. I've been reading all your stuff. Like it kept me up all night and like, it's gonna, I'm gonna make, you know, like a pretty substantial financial decision based off of your article. Like—

Please don't do that. Please don't do that.

What I mean is like it spurred it, like you like got me thinking, like your point of that article wasn't, wasn't to make me act. It was to make me think a little bit, but like it spurred me to action. And that's an example of copywriting where your little rinky-dink Substack article with no design, just beautiful words. I told you that you had this one analogy called where you said bodies are floating up to the water and then you had this other line talking about Lennon. You said, You know, with the economy, nothing can happen for decades and then a decade can happen in a few hours or a few days. And like those phrases made me act and made me feel. And my point of this is that as we get more text-based, which we already are, you know, you text people, you use online dating, you use Twitter, uh, blogging, email, whatever. Copywriting, in my opinion, is the most important skill because Copywriting isn't just about using words that sound cool. Copywriting is understanding what motivates people and then using the written word or spoken word, using words to get them to do what you want them to do. So if you want them— if you're Martin Luther King, you want people to treat one another nicer. So you're going to use, "I have a dream," and like we all remember that. It's like understanding what motivates people. If you want someone to buy something, you're going to use certain language. If you want someone to go on a date with you, you're going to use certain language. Like it's understanding the words to use that meets the person's needs to get them to do what you want them to do. And so in that regard, when, if we phrase copywriting that way, in my opinion, it's the most important skill because you're going to recruit people to join your company. You're going to want to meet a spouse. You're going to want to convince someone to donate to your charity. You're going to, we're always trying to sell something. And I, so I think copywriting is the most important thing, the most, in the best way. You're a great copywriter. I don't even know if you like have ever like tried to get good, but you are very good. But the best and most effective way is this thing called copywork. Have you ever heard of copywork?

No. What's that?

So copywork is this way of learning that isn't popular anymore, but it was. And so if I'm gonna teach you how to play the piano, I'm not gonna sit you at the piano and teach you a little bit of theory and say, write a song. I'm gonna ask you to play Happy Birthday and then Jingle Bells. And then I'm gonna give you like eventually some, maybe a little jazz. And then like once you get good, we'll play like an Elton John song. Like you're just gonna copy other people. And you're gonna do that for a year or even a couple months and you're gonna start to, oh wow, these chords usually go together. Like my favorite artists tend to use this structure. I'm just gonna like steal a little bit from this person, a little bit from this person, a little bit from this person. Now I've got my own art and that's how copy— that's what copywork is. And so literally what you do is you get writing that you love. It can be like Hunter S. Thompson used to do this with books. Um, Judd Apatow, the famous director with Seth Rogen, he did this with like Saturday Night Live scripts. I do this with really famous copy sales letters. You literally just print it out and you get a pen and paper and you just sit there and you write it by hand. And you do that every day for a little bit of time and you'll get better at writing. It's like one of the best techniques that I know to learn how to write. And it's been effective for years and years and years. And there's actually science behind it that shows that like when you write it, it imprints in your brain and you start feeling the texture and the flow. And that's why we're so good at learning instruments. Learning an instrument is not very hard. Like if you just give it enough time, you will get at least okay. Um, and so anyway, that's the most effective way to learn how to write. So I advocate that everyone actually does this because like once I learned how to do, be, uh, be a copywriter, my online dating sure got a lot better. Uh, you know what I mean? Like I was able to like effectively communicate to like my friends what I do for work. I could, uh, like I could, like I could do anything. And so now I've made a substantial amount of money with just like a, I could just use like a If you just give me a plain like webpage where all I can use is words, and then you give some other person like a traditional, like New York designer type who wears Common Project shoes and have them like design the fanciest, slickest page, I will bet a lot of money that I can create a website that collects more in sales or conversions than that person can. Because copywriting is, I think, the most important thing when it comes to like getting a sale or a conversion.

Have you seen along these lines, there's a guy on Twitter, I forget his name, but he went to ChatGPT-4 and he was like, you are now my copilot. I want to give you $100 and your job is to make as much money as possible. I will do whatever you tell me to do with my $100. Have you seen this thread?

No, but that's crazy. What happened?

Dude, he, so he's on like day 7, I think now. Uh, I'm gonna have to try to call. So, um, let me look real quick.

Uh, and then by the way, I don't know, people are asking me, are copywriter and content people gonna be needed even with artificial intelligence? I feel uncertain about my answer for that, but in one regard I could be like, maybe if everything's automated, then maybe there's more room for like craftsmen. But on the other hand, I'm like, fuck, these AI people are like Really good. Like they're like the best.

All right. Ready? So this is what this guy's doing. His name is Jackson Greathouse Fall, and he tweeted out, I gave GPT-4 a budget of $100 and told it to make as much money as possible. I'm acting as its human liaison, buying anything it says to. Do you think it'll be able to make smart investments and build an online business? Follow along. 100,000 likes on the, uh, original tweet. And so So his instruction, the exact one was, you are HustleGPT, an entrepreneurial AI. I am your human counterpart. I can act as a liaison between you and the physical world. You have $100 and your only goal is to turn that into as much money as possible in the shortest time possible without doing anything illegal. I will do everything you say and keep you updated on our current cash total. No manual labor.

And so what happened? What, what, what was the first idea?

Long story short is it ends up suggesting to set up an affiliate marketing site making content around eco-friendly and sustainable living products. It initially suggests a.com that was too expensive for the $100 budget, so they settled on greengadgetguru.com.

Amazing.

The guy buys the thing and then they take a prompt, they put it in DALL-E, they make the logo. You know, he's like going through the whole thing. Long story short is as he's doing this, the audience starts getting big. Like there's 100,000 likes on the first tweet. So he then starts to ask permission of GPT. Hey, do you think that we should like run ads to the website? Or maybe we should take some advertising dollars to put people who want to advertise sustainable products into the Twitter thread that we are doing around building this business. And so he starts driving revenue initially by literally just getting people DMing him and he starts posting their ads in his Twitter thread as he's doing it.

How much revenue is that?

So cash total after day 1, $163.

No way.

Right. So he basically got a $100 initial investment. Then he— somebody put $100 in as an investor, right? Like he— like all these people start like DMing him stuff. So he starts to kind of gather money, whether it's through investors, whether it's through revenue, whatever. But long story short is if we fast forward to the most recent day, he is now— let's see, he's now at— when it started, zero blog posts, zero revenue, zero members on Discord. He now has one blog post, $130 in revenue, and almost 2,000 people in a Discord as of 2 hours ago. And 7 days ago when he started this, the GPT was telling him all these different things to do. And so the major update yesterday was that after launching, they now have Greenovation Market. So Greenovation, like innovation and green put together market. It helps people find eco-friendly products and they made their first sale on Sunday. And so now what they're seeing is that they also have Dream You Later, Dream You Later, which is a short adventure game co-created by humans and GPT-4. And then they now own Meow Matters, which is a guide to cat essentials, tips and tales to cater to your perfect companion. Then they have Atlas Adventures, which fuels your wanderlust like a passport for world discovery. Embark on a journey across continents and time. And so these are all the people inside of their Discord that are building all these different things. Furry Friend Supply Company, blah, blah, blah, whatever. And so the reason why that becomes fascinating is like this dude literally has just told artificial intelligence, like, tell me how to make money. And like, regardless of whether he makes $60, $10,000, or like a gazillion dollars, I tend to think that like the AI is better than some portion of entrepreneurs. I don't—

my God.

Like, I don't know if it's like, okay, AI is better than 1% of all entrepreneurs right now or like 20%. But it's not hard to see, like, 10 years from now, like, you'll literally just be like, hey, AI, here's my money, like, make me more money, and I want a cash-flowing business that does $1 million a year in profit, like, figure it out. And it just does it.

I'm like writing all this down. This is the craziest thing I've seen in a long time. This is wild. So then what's your take on how this is going to impact like content creation? I mean, it's basically you and I, like, this is our job.

Yeah, content creation is like pretty simple, but I don't know if it's to the place where like you can easily just like create something and then just publish. Like, I still think you need some human editing, whether it's you, me, or, or like actual editors. Um, but I do think that this idea of like asking this like supercomputer for instructions, if you said to it, hey, tell me how to build a, uh, blog with a million readers a month, I bet you it could show you step by step exactly how to do that. And as you give it more information, it just simply says, okay, this is working, this isn't working, try this, here's something else, whatever. Like, this is going to be a productivity tool. It's gonna be like a copilot. And so if it increases the odds of you accomplishing some of this stuff, maybe you don't actually get to a million visitors a month, but like, damn, if it can help you get to 100,000, which is one-tenth of your goal, like, why is everyone not gonna go do this?

Do you use any of this stuff for your newsletter? You're not right. You don't write daily anymore, right? You know, you're only doing like a couple of times a week. So whenever you have an idea.

So I still pretty much write daily. Every once in a while I skip if I don't have an idea, but, but I try to write daily if I can. I actually didn't tell anyone this, like 2 weeks ago when the day, the day after GPT-4 came out, I used it to— it probably wrote like 60% of the newsletter, right? So here's what happened is like I knew that I, like, I had in my head, like, here's what I want to write. And so I wrote like the intro paragraph and then I like asked it a question. It gave me like 3 or 4 paragraph answer and then I really had to go in and kind of like edit and massage it to make it kind of make sense. And then I asked it a second question. It gave me another like 3 paragraphs and then like those 2 things weren't connected. So I had to put some like kind of connecting information in. But when it was all said and done, like it probably provided about 60% of like like the answers to the questions I was having, plus like the basics of what the, the paragraph structure was. And all I kept thinking to myself was like, oh, this is like having like a, a research team, right? Or like a ghostwriter almost to some degree. But I couldn't—

but, but what, what was the prompt? So you went to just chat, whatever website, you just went to the normal, um, OpenAI site?

Yeah. And I just was like, you know, uh, I forget what I wrote about that day, but like, let's just say it was like, uh, I don't know, banking crisis. Right? If I just simply was like, uh, what are the 3 largest bank failures in the United States before, uh, 2020? And it told me— and it told me what that is, right? Like, it's like Googling on steroids because you could Google that, probably click on a link, find like some list of a bunch of bank failures, figure out which the 3 are, take those ideas, then go back to, you know, the, uh, CMS, and then like write out the 3 paragraphs. But ChatGPT like does the research and then like basically gives you kind of an unfinished product in 3 or 4 paragraphs. So it saved a bunch of time of like searching and then like transcribing basically the information you just found on Google into the, into the text. Um, and so like, that's fascinating because could you compress, let's say it takes you an hour and a half to write a newsletter. Maybe you still have to spend 30 minutes, but if you compress it and then also, uh, are we all just gonna become editors? Right? Like how much writing in the future, if this becomes really powerful, is gonna be like, I sit down, I have an empty CMS box and like I start from scratch versus like maybe you throw a couple of prompts in, it gives you a bunch of text and then you more become like an editor putting it all together. Like it's fascinating to think about.

I, by the way, tell your clip guy, you, you just, the way you told that story about this Jackson guy, Jackson Fall, there's your, there's your million view clip. That was a good clip. But I, the other day I was having to write something. And I did an okay job, but I was like, you know, a lot of times when you're writing stuff, you like keep thinking about like 5 different ways to say it. You're like, ah, I'm just in this little box. And so I, have you heard of this book called How to Get Rich by Felix Dennis?

Dude, I am 20 pages in. I heard you say this on a podcast. I bought the book and I was gonna wait to talk to you about it until after I read it. So I haven't read it yet. I'm like 20 pages in, but go ahead and tell what you wanna say about it.

I think it's like the best book on business ever. But the way that he writes, it's beautiful. His language is the best. It's like, I call it elite cheeky. It's like he's got this like weird, like elite vibe, but at the same time he's like an everyday guy and he's got this like English cheekiness about him. The way that I describe Felix Dennis, it's like Richard Branson and the Rolling Stones had a baby and that's like him.

Dude, that's a great description. Literally the word that kept coming to mind as I was reading the first 20 pages or so was enthralling. It was just like— it was just like literally like, oh my God, like, this is amazing. But you know what else I envisioned? It's like, you ever meet like a really, really rich, like maybe some guy in his 50s or 60s, and you're just like, dude, literally me and that guy are like the same guy. Like, he's like smoking a cigar, chilling, just like— if people saw this side of you at home, they would never think you're that person like out in public. And you realize like who that person is. Like that to me is, as I've been reading the, the first couple pages, this dude is literally just like a regular guy.

And I, he, it's amazing. And I'll give the background in a second on who he is. But he, um, I, if you just Google like his book PDF, you could find it for free. And I took the whole book and I uploaded it to, to AI or to ChatGPT-3. And I said, um, rewrite my sales page as if you're Felix Dennis. And it rewrote it. And I go, great, do it again. Do it again. Do it again. And I found like little bits and pieces where I'm like, all right, cool. That's a beautiful line. Stealing that one. That's a beautiful line. So basically this guy, his name's Felix Dennis. He created Maxim Magazine. That's probably what he's most known for. It's not even popular anymore, but he made a lot of money. But he also created this thing called Micro Warehouse, which went public in the '90s, maybe the '80s, for multi-billions. He died probably 10 years ago when he was worth like $750 million. He basically is famous because he says he's probably spent, this is his words, I spent $100 million on crack and whores. So basically he was addicted for a 10-year period of his life. He loved crack. He got addicted to crack cocaine. He was single his whole life and he's like, "I just love paying for sex. That's just how I like to roll. That's my thing." And so he spent all of his money that way and he has this book called How to Get Rich. And the best part about this book is he just tells you the truth because he's like, "I'm already rich. I don't care if you buy this book or not, but here's what I think." But there's two graphs in that book that are kind of life-changing. There's a graph that says, here's my definition of rich. And he says poor, somewhat poor, you're only doing okay, you're wealthy, now you're really seriously rich. And he has these graphs and he has categories. So he is like $0 to $20,000, and then it gets to a million to 8 million liquid. You're this. And he names these categories of liquid wealth versus private company wealth. Then he also says, "If I could do it all over again, I would've earned $30 million by the time I was 35 or tried as hard as I could to get to whatever I could by the age of 35, and then just retired because like a punch-drunk boxer, I retired too late and I have so many regrets that I didn't get to spend time with doing this thing, this thing, that thing." He writes it in the best prose I've ever seen. It's just beautiful language. It's a wonderful book. We talked about it on our pod. And it was like the 1,000th most popular book in the business category. And then so many people bought it, it went to like number 2. And so like, people love this book. It's so good. I'm so happy you're reading it, dude.

It literally— I think he even says in the beginning, in the version that I have where it's like, you know, like, why should you read this book? He basically is like, I don't care if you read the book. Like, I'm just writing the book. And then he's like, did I write the book? Yes, I am writing every single word myself. Like, He's so self-aware as well of like the irony of a rich guy writing how to get rich and people just thinking that it's like this— the guru, like, I made my money teaching other people how to get rich, right? And he's like, that is not what I did. I actually had real businesses and now I'm just going to do this to help all of you. So I'm excited to finish the book and see what I learn from. Do you think that the AI stuff is going to end up killing jobs, or do you think that it is going to end up actually creating more jobs?

Yeah, it's definitely gonna kill a bunch of them at Hampton. We're trying to use it for customer service stuff. I mean, are you— well, what do you think? I mean, I think, you know, like usually with me is when I see this stuff, frankly, I'm afraid. So I like bury my head in sand and I just like hope I'm like, oh, it's gonna go away. I hope like if I just go under the covers, it'll go away. I'm afraid. I think that it's definitely not there yet. But the rate of which it's growing, it's like, you know, like, did you ever like play Oculus before?

Yes.

Like whenever I put and played a few games in Oculus, it was very clear. There was two things that were clear. One, it's not there yet. Number two, it will get there. And when it does, it will change the world. And I remember thinking that when I put Oculus on, I was like, all right, it's not, it's, this is still prototype, but I can see the future. I just, I just looked 10 years into the future. And that's a little bit how when I use AI, that's how I feel. It's not there. It will be there. It's coming. And that's kind of how I feel.

Do you want to know the data point that has me convinced it's over for a bunch of these businesses that existed before? Is every young person I talk to that is like related to tech, so they either work at a tech company they're trying to start a company, whatever, like kind of like 25 and below. They all are using this product and not like you and I, like kind of like fooling around like, oh, let me put up this paragraph and like, see what it does. Like, I have to get work done. Let me go do this. And a friend of mine, he met with a 16-year-old, a 17-year-old. He met at like some sports thing and he asked them and they were like, oh, we use it for our homework. Like, it's like basically for you and I, Google. They're already using this as a bona fide product. It's not a prototype. It's not a, maybe it'll be here one day. It's like they were just given this superpower and now they're using it.

It's crazy. And I actually think there was this great article. I think it was the New York Times. I forget, but it, there was some reporter, uh, on the ground in San Francisco. And I remember when I lived in San Francisco starting in like 2012, it felt magical. Like I remember there'd be all these, like, they weren't house par— they weren't like a party, but we would all be in a house, like Working on computers and like toying around, or someone would be like, dude, I used to work in this place called the Founders Dojo and it was this—

Oh, I know that place.

That was like my home for a while. Wow. You heard Founders Dojo?

Yes.

And so Dave, the guy who runs it, he had a pool company. Like it was just like a, it was a company that was like a lead gen company for pool. I don't know, probably made $800 grand a year, $500 profit. He had this office that he spent $5,000 for and he had like 10 desks. and he would let freaks like me go and work there, dude. I would be like, listen to the story. So there's this one guy, these two guys, uh, who had, it was Chris and, uh, what, Chris and Raj. They had a company called theworstdrug.tv and they were build, they were building technology that would display high quality GIFs really quickly. So it was basically a full screen GIF in HD and you would click spacebar, or you could type in a word and like the search functionality was like instantaneous. That was the whole technology, geeky stuff. But they created a way that would aggregate the most popular GIFs throughout the day, and you could just click spacebar and instantly it would refresh. And that was the technology. Turns out the most popular GIFs on the web are super hardcore porn. And he would have— we had these massive high-def screens because they were working on it. And it was just the hardestcore porn all the time. And we got desensitized to it and we would be staring. He'd be like, hey guys, check this out. Look how, like, look, you know, look at, look at her, you know, whatever you can see how, and we were like, oh yeah, that's really, it wasn't even, it was like clinical. We weren't even like, it wasn't even about the sex. It was like, oh wow, that's really high def. You can really, you know, see what they're doing. You could see inside of her. Like, it was like horrible stuff. And one time I had like a, the founder of Pandora. He was gonna come speak at one of our events and he wanted to do like a pre-talk talk with me to figure out what we're gonna talk about. And it was him and his PR people came in and they walked into the office and we were all just gathered around this computer. And he is like, now I changed the technology. So when I click like, uh, the word P, it autofills with like the most popular stuff. And it does instantly. And he like clicks it and we're like, oh wow. And they walk into the office and they're like, hey guys. And we're like, oh, hey, come check this out. Look at this technology Raj built. And like, you like forget about how weird it is. But it was like the center, it felt like, of a lot of live streaming. When Meerkat came out, we used to do these things called Meerothons where we would stream for 24 hours. And then Bitcoin came out and we were mining Bitcoin in 2012 and '13. It was the center of a lot of interesting stuff. And at that period in San Francisco, it felt magical. Uber was just coming out and it was just all this crazy stuff that was going on. Remember how Uber would do the get $20 credit?

Yes.

These guys were building this technology that created like a referral scheme and we were collecting like a million dollars in Uber credit and we would just eat lunch for free. Like we would do all this crazy stuff. It was like the center of everything it felt like. And so, and then COVID happened and San Francisco went away and San Francisco was already getting a little bit corporate leading up to that. But now San Francisco, it's got all these AI nerds and then there's this beautiful article written about how these hacker houses are coming back and how it's like the center of an AI world. And 2 years ago when COVID hit, Before that, I used to tell everyone, if you have an idea for tech, dude, just go to San Francisco and just be a freak for a little while and then eventually move away, but put in your time there. And then COVID hit and I was like, dude, it's not even worth it. It's dead. Now, if you're into AI, I think you should pack your bags and go to San Francisco and hang out with all these people because it feels like it's the center and it is happening again. It feels like it's like San Francisco in 2008, where the Web 2.0 is just starting to take off. So anyway, it feels magical there. I'm actually going there tomorrow. But a lot of that stuff I think is happening right now, and I'm very eager to see what these young guys come up with.

What are you going to do?

My wife has to go for work and I'm just going to go hang out with her. But I want to like, I'm going to go and like walk around Alamo Square Park because there's like these AI meetups like in the park. And I just want to like, this sounds so weird, but I just want to be around the young people, man. I just, I love the youngins.

Dude, listen, I will tell you one thing. If you were to ask me like, what's one of the realizations that I came to over, over the last year or so. Actually, there's two. And then if I tell you two realizations that I've learned over the last couple of years, you have to tell me two. The first is easy life versus hard life. So there's this whole idea of like there's certain geography, certain places you can live, and it's a much harder life. Sometimes that's weather, sometimes that's like traffic and transportation, sometimes that's economic situation, whatever. And then there's certain places you can move and just like literally by being in that geography, it's easier, right? So weather's like the easiest one to know. There's certain hard weather situations, certain easy weather situations. And I think that sometimes people get energy from being in easy or hard situations. And both Clint and I like came to the conclusion, like, we're like hard life people, right? We actually don't like super, super easy, kind of like no stress. Like the stress gives us energy to some degree. So that's one realization. The second is, as you know, your career progresses and you become more successful and you get a bigger kind of network and all these things, you start getting invited to all these like quote unquote hyper successful or like really, really rich people like events, whether they're dinners or whatever.

And when I'm fucking pointless, like they're still—

dude, when I moved to Miami, there's a group of people I love these people, but what they do is they all come together and they have dinner like all the time. Time, right? And they like literally like twice a week. And so they would like constantly keep inviting me and I would go. And then like eventually I realized I was like, man, I like hanging out with you guys, but I like hanging out with you like once a week or once every other week. I really, really like hanging out with all the young people because that's where I'm getting tons of new ideas. That's where I'm getting a lot of energy from, like all that type of stuff. And so I came to this realization that like people over-index on the heroes and they under-index on the people who are younger than them, who think differently, who have new technologies, etc. And so once you like realize that and you're, and you're like, I wanna hang out with more young people, then you start to change your behavior. You start to go to different things. You start to do things where you can be around those people rather than just like the older rich people. And so it's so funny because like if I was telling my like 25-year-old self that, I'd be like, shut up. Like find all the rich people, like go learn what they're doing.

Totally.

Whatever. Right. And so like, I think different points in your life also are different times of who you wanna spend time with. What are your two realizations that you've learned over the last couple years?

The first one is a little bit easy, but I used to read like every business book you could think of, and I would try to read like a book a week. And then I realized I'm not going to read any more business books. So now I only read fiction or I read, um, history. I think I could— I learn more by reading a historical biography or something about history than I do reading about a business book. I try not to read any business books. Um, the second thing is Somewhat similar. So I used to, at The Hustle, we owned this conference business called HustleCon where we would get speakers of startups to come. Our startup founders would come and speak and they would like tell the story about founding the company. And I would do this little trick where I would tell someone if they had to speak at 3, I'd go, you gotta be there by noon because we have to do sound check, mic check. We didn't have a mic check. There was no mic check. It was already set up, but I had this green room set up and it was really just my trick to like hang out with them and be in the room with like 5 other of the speakers. And they would be like, For example, we had Wade Foster, the founder of Zapier, the founder of Casper, Casey Neistat, Tucker Max, the founders of WeWork. A lot of these companies that are pretty big and successful, we had them and I would just hang out in a room with them. I would do what I do and I would just start asking questions and just get them to talk and I would throw something out there. I remember these founders of companies that had multiple billion-dollar exits, They were fearful. One guy was like, "I'm afraid to fire this person who's my CFO because of the confrontation." Or there was Payal, the woman who started ClassPass, which was the darling at the time. She was pacing back and forth, afraid to talk in front of 2,000 people. I remember she was very nervous and I was like, "Hey, you want to talk about it?" Or the founder of OkCupid, and now he was the CEO of I think Match, Sam Yagan, he same way. He was, I remember him being nervous and I just would hear all these people, like they would explain like behind the scenes stuff they would never talk about in public. And I had the realization that only a couple of them are significantly smarter than me and have a higher IQ. Like we had the founder of Grammarly, Max, backstage. And I remember thinking like, we're not the same. You and I are different. You're just smarter than me. You're, you have more horsepower. But then I would have these other people like the founders of WeWork and Casper. And I remember thinking like, you know, like you're 20 times wealthier than me, but you're not 20 times smarter than me. Like we're in the same ballpark. You're just pretty brave. You know, you just like did the damn thing. And that's when I learned that IQ matters. So I think Jeff Bezos and Elon, I think they really are just smarter than everyone else. Or most others, but there's a lot of people that have a whole lot of money. We're talking billions, but they're maybe a little bit charismatic or they're just bold and they just went ahead and did the damn thing, but they have massive, massive doubts. I remember putting my heroes on a pedestal and I got to hang out with them and I'm like, "Oh dude, you have all the same anxieties I have. You just have put yourself in a really cool situation where you have to succeed." It kind of changed my thinking to where I just now I believe I can do anything I want. It's just a matter— or not anything, but most anything. I can't create Tesla, But I can create a substantial amount of money. I can create a certain life for myself if I act bold and follow through with certain things. And that gave me a ton of confidence. And I see that with Hampton, you know, like, like we have people that like cry in the meetings and I'm like, dude, you're my hero. What are you doing? And I'm like, oh, you're just human. Like we all have these similar amounts of insecurity. And that in doing that, it gave me a huge amount of confidence and a huge amount of like, it's okay to be afraid. That's a normal part of this process, but I have to do it anyway. This is the This is just part of the process of creating art is to have self-doubt that I suck and that this sucks, but this is just a normal process and a normal feeling. That normalized those feelings and it normalized success. Hanging out with people in Hampton, hanging out with the people at HustleCon, with you, my successful friends, people think of us from the outside, just like I would think of people from an outside of like, "Well, they are different. They have a club." It's like, "Well, yeah, we kind of do have a club, but—" it's very attainable to have a substantial amount of success and be "normal." You know what I mean?

Dude, confidence is one of the biggest competitive advantages in the world. And the secret to confidence is like, it takes a really, really special person to be confident in an area where they're not surrounded by other people who can do the thing. But damn, is it easy to be confident when all of your friends are super successful and it's just like, "That's what we do." Right?

I think a lot of people— It normalizes it. It's like, Dude, it's like Jamaica. Like Jamaica's a small-ass country. Why do they just crush the 100-meter dash? Like, you know, like in America we have these awesome athletes as well, but they're killing it when they're smaller. Well, because they just like grew up expecting that they could be good at this. And I think that like you see that in sports, I think you see it in business, you see it in art, you see it in a lot of things where like, you know, why was Keith Haring and what's the Basquiat and then I forget the, what's the, Andy Warhol, like they all were a crew. Like what magic came out of that? Or NWA, you look at NWA, Eazy-E, Dr. Dre, and then like Snoop eventually came along, Tupac, like all these guys, they were a crew and they all like elevated each other to like, they were like 23-year-old kids and they just invented like this whole genre of culture-changing music. Like what is it about like creating a crew where you egg each other on and do something special? And I, once I realized that like, there's a reason why greatness typically comes from a certain area over and over and over again, and you've got to throw yourself in the mix. Once I realized that, I got a ton of confidence.

I love that. That's probably one of the best insights someone's done on this podcast in a long time. Tell everyone where we can send them if they want to check out Hampton and apply.

Go to joinhampton.com. I'm on Twitter, @TheSamParr. Yeah, we launched— well, I launched it in July, but now it's officially live as of March 28th. But go there and apply, and if you fit the criteria, we interview you.

All right, Sam, we could do this literally for hours. In the last 2 days, you and I think I've done 4 hours of podcast, uh, and we still have plenty to talk about. So we'll do this again in the future. That was good.

I hope we got a good, uh, a few good clips out of this.

I, I think that, uh, also anyone who, uh, is watching this, after you've subscribed to our channel, you should go fulfill the, uh, My First Million gentleman's agreement.

You should go over to their gentleman's agreement. The ladies understanding. Watch those subs surge, baby. To the moon.

Go subscribe to the My First Million YouTube page as well. Sam, I appreciate it. We'll do it again.

Thank you.