This $50M/Yr Side Hustle Is On Track To Make $1 Billion By 2030

Sam Parr

Yeah, actually, call him right now and put him on speakerphone.

Preston Holland

Yo.

Shaan Puri

Preston, you're live on the podcast right now.

Preston Holland

What's going on?

Sam Parr

Alright, we're live. Sean, I've got a weird thing for you. Do you remember, like, 12 months ago, I told you about Craig Fuller? You know who Craig Fuller is?

Shaan Puri

Yeah, he's at FreightWaves, right?

Sam Parr

Yeah, so FreightWaves is a data product for people, I guess, who are freight brokers or something like that. They're pretty big for some reason. If you Google them, they run their company like they're publicly traded in that you can see all their revenue and profit. I don't know the exact numbers, but you guys can just Google "FreightWaves revenue." They put out quarterly statements, which is interesting. It's like a large software business or subscription data business, making around $60 to $80 million a year. Anyway, Craig is an entrepreneur, and I told you about how he bought this thing called Flying Magazine. What he did was he was a big fan of flying, and he's wealthy on paper, but I don't know how wealthy he is in liquid assets. I think this was a big deal for him. He bought Flying Magazine, and then he also purchased a $7 million, 300-acre plot of land in Tennessee. He was turning that into basically a flying club. It's kind of like a country club where you can own a home on a golf course, except now you own it around an airplane strip and an airplane hangar. They use the magazine to sell plots of land.

Shaan Puri

It was like a neighborhood, and basically they were like, "You could buy a house. It's going to be... you know, the middle of this neighborhood is basically the airstrip. So we're going to be able to take off if you like, you know, either flying your own plane or private flights." And so they were like, "We're going to... that's the vision. That's the field of dreams. We're going to start doing this." And I think it was working extremely well.

Sam Parr

I have an update. I will tell you how it's going. So, Craig has now acquired 44 different magazines, and they are going to do roughly $50,000,000 this year with an 18% EBITDA. It's his prediction that by 2030, this side business that he started can reach $1,000,000,000 in revenue with 30% profit margins. That's an update on what he's doing. He tweeted out recently his quarterly revenue. I think last quarter, Q4 of 2024, was $15,000,000 in revenue, and he's doing it profitably. Here's what he does: he finds an old title, like an old magazine, that revolves around an expensive hobby. For example, I think he has a boating magazine, and he is even looking at RC planes and RC cars—things like that. He uses a strategy he calls "negative CAC," meaning people pay for the magazine. This is how he acquires a customer; they are paying for the magazine instead of him trying to advertise to get the user. Then he goes on to say, "I want to create commerce products to sell to the audience." The media businesses pay for the company, they pay for the audience creations, and then they help bootstrap other businesses that can sell to this audience.

Sam Parr

He's buying companies for 3 to 5 times EBITDA, which is... I think that's pretty cheap. But it's a dying medium, so maybe that's not that cheap. It does require some sophistication in order to turn them around, but it's really fascinating that he's pulling this off. And this is his side hustle, this is his side business. His main business is FreightWaves.

Shaan Puri

Well, a couple of questions. So, he bought this personally. It's not a part of FreightWaves.

Sam Parr

No, it's its own thing. So that's why I said it was kind of a big deal for him. I don't know Craig's personal situation, but I don't think he sold any of FreightWaves other than taking on venture capital to build the company.

Shaan Puri

This is wildly impressive! So, first of all, it's called **FireCrown**—you can find it at **firecrown.com**. If you go to their brand section, you can see all the things that they bought. **FireCrown** is a great name. They've got **44 brands**. You're right; basically, it's a bunch of things about private flight, boating, sailing, fishing, yachting, and wakeboarding. Then there are things like classic toy trains, garden railways, and trains.com. It looks like there's some astronomy stuff as well. This is a lot of things that he rolled up. He must have found a kind of repeatable, rinse-and-repeat model. It says here that he buys them for **3 to 5 times EBITDA** as his typical range. Was he using debt? Was he using revenue from the business? What was he using, or cash flows from the business? How was he buying these?

Sam Parr

I think he got a bunch of friends to invest, but I don't know exactly. He's gonna come on the pod; I asked him to come on to explain the strategy. But what he did was... there's a bunch of companies that own tons and tons of magazine titles. So Meredith Corporation owns, like, Martha Stewart Magazine, and then I think there's Rodale, and then there's Bonner. There's all these companies that are like old family companies that have been in business since the '30s or '40s, whatever. And they've got these publications that are just sitting there, and they're like, "Just take them."

Shaan Puri

and

Sam Parr

And so, he could buy them like 5 or 10 at a time. I think he's tweeted out that he bought like 13 the other day. He buys them in bulk a little bit.

Shaan Puri

I mean, this is super impressive. The side hustle that's now **$50,000,000** a year profitable—really, really specific, you know, expensive hobby magazines. Then, basically, it has a better business model, sounds like. Right? So it sounds like the old business model was, "It's a media business, so we make money on the media." He's like, "No, no, it's a media business, so we're gonna use media to acquire customers for a much more valuable business model." You know, for example, with the flying thing, they're selling these homes on this plot of land for like a couple **$1,000,000** each. So I think you said what? **$7,000,000** to buy that **300-acre** plot of land.

Sam Parr

Something like that.

Shaan Puri

Yeah, so roughly, you know, let's even round it up to **$10,000,000** to buy the thing. But then they're selling each home at **$2,000,000**. They sold **50** homes, right? So, you know, just rough numbers.

Sam Parr

I don't know how many they sold, but they sold enough that it's worthwhile. It's a beautiful piece of land. On Flying Magazine, if you follow Preston Holland, he's the CEO of Fly Magazine. Yeah, he's brokering jets; he's selling jets. He's like, "Alright, yeah," on Twitter he goes, "We've got this jet for sale. It's $7,000,000."

Shaan Puri

He's a good dude. We text all the time and I'm like, "He almost gets me to buy a plane!" I'm like, "Dude, stay away from me, man!" [laughs] I'm not gonna buy a plane just because you've made a funny joke this day.

Sam Parr

Dude, Nick Huber... I'm gonna do it. This is a Hampton plug. Nick Huber and Craig are in the same Hampton crew. They bought a plane together, and so now Nick owns a plane. I guess they... I don't know how you buy a plane together, if they did it. But Preston's selling these like $10,000,000 jets online. It's... or on Twitter. It's crazy.

Shaan Puri

Nick shared the economics of buying these small planes. By the way, we should ask him for permission to share the numbers. For example, we bought it for X. Here's how much it costs to do each flight and how the rules work. It's kind of a timeshare; it's like him and six other guys or whatever who bought the plane. You pay for the pilot and the fuel when you need it, but then you just pay on an ongoing basis. Additionally, you get this tax benefit from buying a plane. So, how does it all work out? What does the cost per flight ultimately come to? He's shared the numbers with me before, so we should do a segment on here talking about that.

Sam Parr

But isn't this crazy that this is this guy's side thing? And how amazing it is! It's pretty... it's...

Shaan Puri

Like, about to be his main thing is what I'm hearing.

Sam Parr

Well, what's crazy is here's kind of a takeaway. Most people couldn't imagine this being their main thing. When you get into business like him and you have some success with FreightWaves, you start seeing how things work. It's like you get these weird unlocking moments where you don't see certain things as risk. I've never bought a business before. I see buying a business and think, "That's really risky." But he's like, "No, I've done it enough times that I know how to unlock value. I don't think this is risky because we're going to do this, this, this, and this." It really is a confidence game as much as it is a knowledge game. It's pretty amazing how he's been able to pull this off.

Shaan Puri

I'm super impressed by this. This is one of my favorite kinds of businesses that you've brought to the pod, to the people's attention. Really, really impressive what he's done. So where do you think this goes? What do you think he's going to do? And what does he do for the boating ones? Like, is he doing the same thing? Is he selling boats? Or what is he doing to make the business work out of those?

Sam Parr

I don't know.

Shaan Puri

I mean, I don't know yet.

Sam Parr

I don't think he knows yet. I'm not sure; he hasn't shared it publicly. But I guess you could do similar things where you have a marina. I mean, have you ever... like, my parents used to have boats, and I know that they would spend like $500 to $1,000 a month on a boat slip rental. It became a community where we would hang out and stuff like that. Something like that... I'm not sure what he's going to do selling boats. I mean, I'm not sure how he's going to pull it off, but there are plenty of options. Alright everyone, really quick: if you've heard this podcast before, you know that Sean and I think that the most important skill set you need in business is **copywriting**. So what we did was we went through all of the podcasts that we've done—it's like 500 of them—and we found all the best copywriting tips, resources, frameworks, and templates. We aggregated all of them into one simple document. You can skim it all and get everything that we've ever talked about with copywriting. It's in the link below; it's awesome!

Shaan Puri

Check it out.

Sam Parr

Should we call this Preston guide right now and just get him on here?

Shaan Puri

To explain this, yeah, actually call him right now and put him on speakerphone. "Yo, Preston, you're live on the podcast right now! What's going on, dude? We are talking about flying and we're talking about Firecrown, and I'm blown away. I didn't know about Firecrown; I only knew about flying. Sam is telling me about the growth of this thing. I have two questions for you. Number one: when you guys started this, was this the plan, or did you sort of stumble into, 'Oh wow, this might be bigger and better than we thought?'"

Preston Holland

So, when Craig called me in 2021, it was about a lifestyle side hustle. Basically, he said, "Hey, you want to come help me run this?" I asked him, "Why are you buying a magazine? I can't tell you the last time I read a magazine." He replied, "Well, it's just going to be kind of like a side hobby. Freightways is really my business, but yeah, keep it small." But if you know anything about Craig as a person, that's not in his nature. All of a sudden, we started rolling things up as we saw opportunities. Now, it's ballooned up in Seattle. We're at 257 employees and there's...

Shaan Puri

The side hustle has 250 employees. Alright, amazing! Can you give a little bit of a peek of the... because Sam has a bunch of the numbers of Firecracker (I think Craig tweeted out), but can you talk about the thing you guys did where you basically bought the land and then you started building a neighborhood on top of it?

Preston Holland

So really, what we did was we let the content inform the commercial decisions that we made. We had an idea to kind of build an airport. We're like, "That'd be cool." You know, it's hard to find hangar space around Chattanooga, and so... as we're looking at it...

Shaan Puri

I always tell myself that too. Where's the hangar space in Chattanooga?

Preston Holland

Yeah, right, exactly. Well, we've got three airports, and each of them has a waitlist of like 7 to 10 years long. So we're like, "Well, I guess we're going to have to build an airport if we're going to be able to get hangar space for any airplanes we get on demo or whatever." We wanted to build a media center on a runway, and you know, every airport was like, "Yeah, good luck. It's going to take at least 10 years." So we said, "Hey, let's build our own runway." If we build a runway, we should do something unique. These fine communities are interesting, and we started writing about it. We realized that there was really high-performing content. From a Google Analytics standpoint, we could see the content being engaged with, and we're like, "Okay, people actually care about this. They care about air parks." So we said, "Okay, let's go ahead and build an air park." We announced it, bought the land—1,500 acres about 45 minutes outside of Chattanooga, Tennessee. Through advertising in our own magazine, we said, "Alright, this will probably be like a 5 to 7 year project before we get started, you know, kind of underwriting." We basically met our three-year pro forma in pre-reservations in like the first three months. So we're like, "Alright, there's definitely demand here." So, yeah, we're set to break ground. We just finished some regulatory stuff that the government loves to tell you about, like where water should go. We just finished that and are set to break ground probably here in the next 30 days.

Shaan Puri

Could you give us a sense of the numbers? What can you share?

Preston Holland

On the numbers, so like you...

Shaan Puri

How much did you guys buy the land for? How did you finance this whole big construction endeavor?

Preston Holland

Yeah, for sure. So, we bought the acreage around $1,500 to $1,515 an acre. It was really cheap land. It's also in an opportunity zone, so there are a lot of tax incentives for making investments in that area. Then, we have taken $25,000,000 of pre-deposits. That's people basically sending us a percentage of the deposit.

Shaan Puri

You basically funded it through the deposits, kind of like how Tesla does with their trucks. Before they build the trucks, they take the deposits and use that to basically finance the manufacturing.

Preston Holland

If you've got those deposits, it proves to the banks that you can go to the bank and basically say, "Okay, look, we've got $25,000,000 of these lots presold." That represents future cash flows of $25,000,000. They say, "Oh, okay." So, let's say, using round numbers, round one of infrastructure costs, I don't know, $10,000,000 or $15,000,000. The bank's going to go, "Oh, okay. Well, you've got $25,000,000 representative of future sales, so that $10,000,000 to $15,000,000 of phase one infrastructure is a super low-risk bet for them."

Shaan Puri

Nice! And then, are you guys bootstrapped, or did you raise money to buy all these magazines? How did you do it?

Preston Holland

Yeah, so we have been really fortunate. You know, since we've got some private capital behind us that is patient, which is really key, right? It's not venture; it's more patient capital that says, "Okay, we're going to take a 15-year, 20-year, or even 30-year time horizon," and then actually go and grow this thing. So we've got some capital behind us, but we didn't have to go raise venture or private equity or anything like that. That's kind of how we don't have a ticking time bomb waiting for us to sell in 7 or 10 years at a hundredth valuation.

Shaan Puri

You know, you talked about the Google Analytics. Is this actually a print business, or is it an online media site? A blog that has print as like a vanity piece? Which one? What is the business actually?

Preston Holland

So, when we buy these BD assets, what we have to do is really shift our mindset and product velocity at a lot of these companies. We tend to buy print magazines that happen to have a website, where it's like, "Okay, we take our print content and then we post it online." When you go in and acquire these, you kind of have to level set with everybody and say, "Look, you know, digital is its own product." We split out the P&Ls, right? So, digital has its own P&L and print has its own P&L. We make print a product as opposed to the core business, if that makes sense. Gotcha. The other thing is, and look, when Craig and I came in on day one, we were like, "Alright, we're killing print." I don't know, Sean, Sam, I don't know if you guys have a lot of print magazines, but I don't have a lot of print magazine subscriptions. Let's just say, I'm 30 years old; that's not how I consume media. So, we went in to shut down print, but there's something about being in print that Neil Vogel talks about at Dotdash Meredith as well. He's had a similar experience, so this is not a unique perspective. We're not the only ones thinking this. There's something about having a feeling of longevity and a perception of longevity in having a print product, whether that's with advertisers or with the audience or readers. You just don't get that with a blog. It doesn't feel the same. You think about a brand like Dwell; it's a great example. They have a print magazine, and for some reason, it feels more legitimate than ArchitecturalBlogXYZ.com, right? Because it has a magazine. We use it as kind of a staying power, but we also recognize that the world is going to shift.

Shaan Puri

Yeah, you also mentioned you... like you leave the... You hustled your way to get the magazine in every private chartered plane, right? Just to get the right rich people to be reading the thing because you left it on the table in those planes. Is that right?

Preston Holland

Yeah, exactly. So, we send them unsolicited to a lot of FBOs across the country. Some are solicited, you know. There's about 1,800 or so that are solicited, and we've got an agreement with the distribution company. But the other ones are not solicited. They feel like we've created a product that has so much value that they want to display it on the tables as people go and pick them up. I mean, we've had conversations with some pretty wild folks who were like, "Oh yeah, I was in the FBO and I read your magazine. I want to collaborate on your real estate project." So, it's like, okay, how do you quantify an ROI on that? It's hard to do last touch attribution, except for like, "Oh yeah, you read about our project in our magazine that we put in the FBO, and now we have really cool partners on the real estate project."

Shaan Puri

Gotcha! Well, Preston, you're the man. This is a crazy business. Thanks for the on-the-spot call in.

Preston Holland

Yeah, man. Long time listener, first time caller. So, it's good to be here.

Sam Parr

**First ever caller we've ever had.**

Shaan Puri

Yeah, first ever caller. Actually, alright man, take care.

Preston Holland

Alright, it's you, man.

Sam Parr

That was awesome.

Shaan Puri

Alright, we changed the show. That was cool. I like them.

Sam Parr

Alright, well, I mean, we got our information. That's awesome! Congratulations to Craig at Preston. I'm happy that he was transparent.

Shaan Puri

Yeah, really cool. Alright, what else have we got?

Sam Parr

You got one.

Shaan Puri

Yeah, let me do one. Okay, let's stick to the print idea but take a different angle. The New York Times... when you think about it, you think of this prestigious newspaper. It's all about the news. They want you to think it's all about the truth—that's their marketing. The New York Times has more in common with Zynga than it does with the truth. The New York Times is a games company, and the numbers behind the New York Times and their gaming products are pretty amazing. So, I don't know, do you ever play their games? I'm a subscriber; I kept paying for a subscription to their games.

Sam Parr

Well, I know they have Wordle, and I played that one. They bought Wordle.

Shaan Puri

The guy had made... like, the guy made Wordle for his girlfriend or something like that. Then it took off, and then they [New York Times] ended up buying it. But I have a 22-day streak going right now on the crossword puzzle, on the mini crossword.

Sam Parr

And how much do you pay?

Shaan Puri

I think it's **$6.99** a month or something like that.

Sam Parr

And what's the revenue on that? Take a guess: $100,000,000.

Shaan Puri

A lot more than that. So, The New York Times, just in Q4, had 289,000 digital-only subscribers, which includes all their games and a little bit of their cooking product as well. But it's mostly their games revenue. So, that's $300 million in the quarter. Their gaming has basically pushed their annual subscriptions over $1 billion a year for the first time ever. They released this chart that was basically about The New York Times bundle. You have the news, their cooking section, The Athletic (which is their sports section they bought), and then you have games. Take a look at that chart right there. You can see that games, a few years ago, accounted for roughly 15% of the time spent. Now, it's over 50% of the time spent in their bundle that is on the games product, which is pretty wild. It's more time spent on games than on news; it has overtaken news. So, you have this thing that is just fascinating. They used to have a little crossword section and a little Sudoku section in the newspaper. What they did was transform the product; they unbundled it and made it a standalone thing. What's cool about it is that almost every game on my phone is just trying to figure out how to take all of your time and all of your money. The New York Times approach works way differently. You have one mini crossword a day, one crossword a day, and one Wordle a day.

Sam Parr

You do that every day.

Shaan Puri

Every day, my daughter and I do it together. We play Wordle, and then I do the crossword on my own. The mini crossword literally takes under 1 minute. My average time is probably 57 seconds to finish this thing, so it's a very short game. I'm able to play a game and have that dopamine hit without it taking away from my life by being like, "Oh great, now I'm spending hours on this."

Sam Parr

Hey baby, what's the... it starts with an "E." What's the disease that brought down Chipotle in 2009? Oh, you're right, Ebola! That's it.

Shaan Puri

Yeah, well, she plays Wordle with me, and she gets to type while I come up with the words. These games are really fun; it's a well-done app. It's shocking to me how successful this thing has been. So, I wanted to just read you a couple of things. A few years ago, The New York Times spun off cooking and crossword offerings into standalone products. This meant you could subscribe to either without being a New York Times subscriber. It seemed like an odd choice because the internet already had millions of games and millions of free recipe apps. But what they did was digitize decades of old crossword puzzles and cooking recipes that they already had. So, it's this kind of remnant inventory that they weren't using. They took that stranded asset and turned it into a viable asset, a live asset. Then, they modernized it, put it in an app, and made it work really well. It's a super simple app, and it basically breathed new life into the company. The company has grown like crazy. Now, between crossword and cooking, check this graph out...

Sam Parr

So, we just start calling The New York Times a gaming company.

Shaan Puri

Yeah, exactly.

Sam Parr

Yeah, you guys wrote those great games. Did you get like a sick blog where you talk about the Trump trial? I love that too.

Shaan Puri

Side hustle? Yeah, I love it.

Sam Parr

That little blog you guys have going.

Shaan Puri

They have over... this is in 2020, so this is years ago. They had 1,300,000 paying subscribers that paid on average, you know, $40+ a year on the games and cooking product, which is mostly games. And they're not alone. So that's the New York Times. Then I saw... you know, I opened up the YouTube app. I don't... do you use the YouTube app? Because I opened it up and I saw some very...

Sam Parr

New use that, yeah.

Shaan Puri

Did you see their new games product?

Sam Parr

Do you?

Preston Holland

See this.

Shaan Puri

If I open up YouTube, these are games that say "Play Now," and you don't have to download anything. So, I click play, and now I'm just going to be in this game. This is a popular mobile game called "States." It's like a little Risk-type of game. They have about 20 of these games labeled as instant games—no downloads required. YouTube is doing it now, and then LinkedIn the other day announced LinkedIn Games. They have three games on top of LinkedIn. There's a Wordle variant, and there's another game. They took popular games and just kind of made their remix of it. If anybody needs engagement—like real engagement—it's LinkedIn. LinkedIn has a billion users, but there isn't a lot of good content on LinkedIn. This is cool because they basically made it where they have Sudoku, trivia, and a word game. You can see how other people in your company do. They already have the social graph of who's in your company and who you're connected to. So when you play the game, you can see how you compare to people you already know because they have that social layer built in, allowing you to compete among your colleagues.

Preston Holland

Who do?

Sam Parr

You think they stole this from... Because imagine the meeting where they're bringing this up: "Hey Sharon, you got any ideas?" "What if we call it LinkedIn Influencers and we get famous people to post?" "Been there, done that." And then this other person is like, "Hey Charlie, what do you got?" "What if we just put, like, risk in the feed of LinkedIn?"

Preston Holland

Do you?

Sam Parr

Know what I mean? Like, how would you justify doing that?

Shaan Puri

So, I don't know if they acquired a company that was doing this or if there was just, like, I imagine some product manager that looks like he's just got back from 'Nam. He's like, "I had an idea, and I got it through. I got my manager to approve, my manager's manager. I went all the way up to the product org and went through the committee, and it happened. They all said yes. I get to launch this thing, and like in 6 months, it's gonna die." But I actually think there's a good opportunity here. I think that if somebody built a third-party LinkedIn games app... I don't know fully; I haven't explored the LinkedIn API and what's all possible. But if you can hook in and build a game on top of LinkedIn, that's just like a total greenfield opportunity. LinkedIn will buy it if you do a good job. If you build the actual games product that's getting engagement there, you don't have to invent the games; just steal the games. You're basically saying, "Proven game and new social graph." Yep, and that's the whole business model here.

Sam Parr

That's pretty insane. I did not see that they were doing this, and that is actually quite smart. LinkedIn is the behemoth that somehow always works, so it's quite wise that they're doing this.

Shaan Puri

Yeah, the one that I don't believe in is Netflix doing games. I don't know if you've ever seen it, but they have a games section. There's a trivia game you can play on Netflix. Also, if you go to the app store and search for Netflix as the game producer, they have like 50 game titles. It's pretty insane how many mobile games they have. I don't understand this. I don't think it's going to work. I don't understand the tie between this, but you know, basically, the secret's out. It's like, "Yo, games make a lot of money, and people use them all the time. Maybe we too should be in the games market."

Sam Parr

That's wild.

Shaan Puri

And you know, that's what they're trying to do.

Sam Parr

That's awesome! Kudos to those guys. I've not seen that. Let me do a quick thrill of the show. I want to promote something. I'm going to try and make it extra thrilling. Have you ever thought, while you're building stuff, "Am I doing this right?" I remember being in San Francisco and thinking, "Well, you know, Sean's got a fancy office, therefore we have to have a fancy office." Or, you know, this particular CEO said, "You have to focus on this one thing," so I have to focus on this one thing. To grow Hampton, we came up with this podcast called **Moneywise**. Moneywise is basically like a personal finance podcast but for high-net-worth individuals. I've done 8 or 9 of the episodes as the temporary host, and I want to share my biggest takeaway: to get wealthy, or even to spend the money once you're wealthy, there's no one way that people are doing it. There are a lot of different ways that people are doing it. I've already recorded, I think, 12 or 15 of these, and I had to do 9 already for the first season. Dude, it's insane that people reveal all this information! So basically, what we do is have people come on and reveal their income, their expenses, and exactly what their portfolio looks like. Then, we'll dive deep on one topic, like parenting.

Shaan Puri

Are they anonymous, or do they put their name on it? I haven't listened to it.

Sam Parr

Half and half. So sometimes they're anonymous, and what we do is we change the name and we actually change the voice. There are a bunch of people who you know of that have been on, but they've changed the voice. Then sometimes, like the guy from Simple Modern, came on and he's completely open about it. He'll say, "Here's exactly how much I have in my bank account. Here's what we have in my index or in my portfolio. Here's how much income I have." It's insane that people reveal this amount of information; it's almost scary. So my big takeaways are: 1. There's no one way to do it. 2. I'm shocked that people reveal all this information. 3. The more money you get, the more intentional you have to be. Because these people will make literally $100,000,000 and they don't spend any of it. They're like, "I don't even know what to do with this money."

Shaan Puri

What's been a lesson learned, either in the spending side? What is something somebody said about how they spend that you were like, "Oh, that's a good idea. That's a cool, intentional way of going about this." We talked about giving money away last time. You can't use that one; use a different one.

Sam Parr

I firmly believe that owning more than one home is a massive pain in the ass. That's a dream that people want to have. They want to have a second, third, or sometimes even a fourth home. A lot of these people have that dream, but I think it is a huge pain in the ass.

Shaan Puri

I replaced the word "home" with "problem." It's like I have a second problem in Tahoe. I have a third problem in Florida that I go visit once a year. Nice problems.

Sam Parr

Dude, it's such a pain in the ass to have that. Unilaterally, people seem to regret having multiple homes. So, being intentional about spending money seems like a huge deal. One rich person, one of the very few I think is totally worth it, is flying private. I think that is the one thing where it actually might live up to the hype. When people talk about buying a plane—sorry, Preston, I don't know if that's worth it—but I think chartering a jet as much as you can would be absolutely worth it. So, we're doing this podcast, whatever it's called, *Moneywise*. You guys should look it up. I'll tell you quickly, I had this premise: to make a hit podcast, I think you need one or more of the following. You either need great production, great delivery, or a unique perspective. A unique perspective is like LeBron James talking. Great delivery is typically like comedians, and great production is like *Serial* or whatever, like those *Wondry* things. My gap in the market that I wanted to exploit was the first one. I think you and I do number two and number three, and I wanted to do number one. So far, it appears to be working. If you're a creator, those are the three ways I think to do a podcast. That's my little pitch on *Moneywise*. Congrats!

Shaan Puri

That's a good thriller show. I liked it. Alright, let's do some other ones. Do you have another good one, or can I do my AI camera one real quick?

Sam Parr

Do your AI camera one because I have something funny to tell you.

Shaan Puri

Alright, AI cameras. So, I play in this basketball league in San Francisco. Shout out to Ruben Thorenberg, who hosts this league. He's been hosting it for like 10 years. It's basically called SF Tech Hoops, I think. It's a league for people from the tech industry who like to play basketball. For a long time, Ruben has run the league with real heart, and I really appreciate that. He makes the teams, manages the league, and there are the table stakes: what you expect—teams, jerseys, referees, scoreboard—great. But then, what he does is every week he writes an email recap with GIFs and whatever. He details how Team 1 took on Team 3, led by Sam Parr, who scored 13 points and had a great buzzer beater. He writes these great updates from the commissioner, essentially creating his own internal newsletter for the league. The second thing he does is film the games. He used to set up two tripods with iPhones on each side and would try to cut a highlight reel afterward. "Highlight" is a really generous term because you're talking about out-of-shape tech dudes. I made a game-winning shot last week, and in my head, if you asked anybody I talked to afterward, it felt like Jordan against the Cavs in '89. I was flying through the air, hitting the shot at the buzzer—it was amazing. Then I watched the clip and realized you couldn't even fit a book under my feet where I jumped. It looked ridiculous, slow, and terrible. It was like a game loser, not a game winner. So, "highlight" is a little bit generous, but either way, he puts a lot of TLC into running this league. He just bought this new thing that is a game changer: an AI-based camera called Veo. There are a bunch of companies doing this, but check this out. Basically, it's one smart camera that you post on a tripod. It does a couple of very basic things that sound trivial but make a huge difference. He used to have two iPhones because he needed to record both sides of the court. Half the time, when everybody runs to the other side, one iPhone would just capture empty space. He could never get a full video of the game because he couldn't get the camera to follow the action. He'd have to hire someone to manually swivel their head and do this. But now, with AI, it's one camera that tracks the ball at all times. This works in soccer, basketball, and football. It keeps everything in the center of the frame without needing a human to do it. The second thing it does is upload everything to the cloud. The third thing is it live streams the games, which is cool because now friends and family can watch. The fourth thing is it tries to cut highlights by identifying cool moments and keeping track of stats. It's just getting better and better with software updates. The hardware is just a camera with enough processing power to connect to the internet and the AI software. These companies are crushing it. Ruben bought one of these cameras.

Sam Parr

It raised over $100 million in funding.

Shaan Puri

And it's like some European company. There are four or five competitors, all of whom have raised a bunch of money, and I think they're all doing really well. I noticed this at our game, and then my brother-in-law, who has a kid that plays competitive soccer—she's like seven years old—said, "Dude, have you seen this thing?" He's like, "Bro, it's on every field! You can't go to youth soccer now without seeing one of these on every single field." I think the same way that, you know, Steve Jobs had the vision— I think it was Jobs, or maybe it was Bill Gates—but it was like, "A computer on every desk." I think it was Gates. The goal was a personal computer on every desk. Now, I think it's going to be basically a camera on every field. Every single high school, every single middle school, every AAU game, every travel team—they're going to use these things. Because why not? Someone's going to make the investment one time.

Sam Parr

They're really... it's not a one-time expense. Alright, so for the most popular version, it's a **$1,000** one-time expense and then it's **$130** per month.

Shaan Puri

Yeah, the most expensive one... I think there are cheaper options than that. I don't think you have to get the crazy one. But yeah, that price is going to go down. The $1,000 hardware is going to decrease, but the $100 a month is going to stay the same. If you're like a team, or really, you don't even have to buy it per team. It's like the league needs to have it, right? So, the venue needs to have it. I predict that every venue is going to have these. Whoever wins is going to get these into every single field, every single court, and it'll just be that way. Tennis, wrestling, like every fringe sport... There are people who want to watch. It's the family, the friends, the athletes themselves, and their coaches. There's enough motivation to do this.

Sam Parr

Their website is so good that it makes me want to play soccer. It's sort of like GoPro, where the footage is so awesome that I feel like I've got to get into snowboarding right now, just so I can go and live a life worth recording.

Shaan Puri

Dude, that's how it felt when you were talking about the magazine stuff. I was like, "Yeah, the wind blowing through my hair as I'm on this boat." Yeah, maybe I do want that lifestyle.

Sam Parr

Yeah, do I want to be a boater? That's how I feel when I go to their website. This is awesome! I'm shocked at how large this is. I guess it sounds like it's not a surprise, but it's sort of a surprise that there are multiple companies that have raised nine figures to build this.

Shaan Puri

I think these are doing, you know, **$50,000,000+** a year in revenue minimum. You know, the leaders of this space... I don't know the exact numbers, but like ballparking, I would be surprised if it was under that.

Sam Parr

This is absolutely insane! I never in a million years would have thought that this would become a thing.

Shaan Puri

Well, I have the opposite opinion, which is that this is an obvious idea.

Sam Parr

It's obvious that it's working, but it's not obvious that...

Shaan Puri

I know I did obvious before, dude. When you should be starting, well, because this idea has been around for a long time. For example, in NBA stadiums, there's an enterprise version of this called **Second Spectrum**. There's also a company called **Synergy Sports** that basically installs cameras in the NBA venue to track all the players and their motion. It keeps track of certain specific advanced stats for the teams. So this idea of, "Oh wow, couldn't you either install cameras or use computer vision to track stats?" That's interesting. Then there was **Flow Sports**, which is basically live streaming niche sports like jujitsu competitions and wrestling competitions. They were doing tens of millions a year in revenue.

Sam Parr

Yeah, their office is here in Austin, and I've been to it. It's sick! It's really cool. It's a big company.

Shaan Puri

And you, for those, those are for more official competitions, like, you know, the Texas State Karate Championships or whatever. Not like, you know, little Susie's soccer game, which, like, you know, Susie's parents and grandma and whatever want to be able to watch. Back in college, I remember my roommate Trevor. He would always watch his little sister's basketball games. He'd be on his computer, watching this grainy footage. I'm like, "Who the hell's streaming this 9th grade girls' Wyoming basketball regular season game?" And he's like, "I pay for this thing because we pay, and then this guy films it, and then he uploads it later." It's not live-streamed, but he uploads it later, and I watch the crappy footage. But, like, I really want to see my sister play. That matters to me. I'm willing to pay, like, the equivalent of a Netflix monthly subscription. But instead of giving me, like, all the world's best content, I get my niece's games. There's an emotional reason to do that. So this idea has been around for a long time. I've noticed this, but it needed a technology inflection. It needed the AI camera, where you don't have to hire somebody. The quality is now good enough where it's actually fun to watch. You can live-stream it, record it, cut highlights, all that stuff. So now I feel like the idea is an idea whose time has come. I was talking to my buddy Luke about the AI wave. He's in my AI tutoring group, where we learn about AI together every week, once a week. He's like, "You know, whenever there's a new technology shift, I always think back to what I asked: What are the restaurant menus on the internet of this wave?" I asked, "Menus on the internet? What do you mean?" He goes, "Well, when the internet first came out, the very first obvious startup idea was, like, let's just take restaurant menus and put them on the internet." He's like, "Before we could do DoorDash and online ordering, like, all the next-gen stuff, the first thing you do is just put the menus on the internet. Just a picture of the menu." And he's like, "For every tech wave, there's always, like, the very obvious, it's kind of not where the thing is going to go, but it's, like, immediate value add, no-brainer. Like, wave one of what people do on these apps." It's like, for the iPhone, remember it was, like, the beer app, the flashlight app, the calculator app? That was the menus on the internet. And now, with AI, there are some things like this that are, like, the menus on the internet version of what you can do with AI.

Sam Parr

So, your AI tutoring person has now morphed into a study group.

Shaan Puri

Oh yeah, bro, it's growing.

Sam Parr

What is it?

Shaan Puri

I'm... I don't even want to tell you. It's like *Fight Club*. It's like *Fight Club* with no fighting, just screen sharing on Zoom.

Sam Parr

But is it like a group of you who meet and you just come with the homework and questions?

Shaan Puri

It's three of us who I think are awesome, and I wanted an excuse to hang out with them. So, it's me, Matt Nazzio, and my buddy Luke. I wanted to hang out with these people more anyway. They're also in AI; they're investing and maybe starting companies in the space, whatever. It was like, "Hey, let's just do this together." That way, it's a little study group where you see something, and then one person says something. The other person pushes back, saying, "Well, I don't know, what about this?" Everyone gets a little smarter for doing it.

Sam Parr

What are your biggest takeaways now with AI? I don't know much about it.

Shaan Puri

So Sam Altman recently said something. He goes: > "There's two types of companies in AI: there's the companies that can't wait for us to release a new model, and there's these companies that can't sleep at night knowing we're gonna release a new model." Meaning...

Sam Parr

He’s like, “We’re gonna crush you.”

Shaan Puri

They're not saying this, but the way they've architected their business is: if we make GPT-5 better than GPT-4 and we improve a bunch of capabilities, the model gets smarter. It gets better at doing all the things it's doing, which he's like, "By the way, that's exactly what's gonna happen. Duh!" It's insane to bet against that. He's like, "They risk being blown up... they become obsolete when that happens."

Sam Parr

I'm pretty sure he goes, "We're gonna steamroll them."

Preston Holland

Yeah.

Shaan Puri

He goes, "Well, they will... those companies will get steamrolled."

Preston Holland

True, which is not a...

Shaan Puri

Good thing I'm like that! That is amazing. So then the other companies, he's like, "The other companies are begging us. They can't wait for the next model to come out because it's just gonna make their product better." So what's an example? The group we were talking through was like, "Okay, what does that really mean? Who are the companies that fall into group A and fall into group B?" There was an interesting discussion around that, but I'll just give you a simple example. Let's say you're a company that does transcription and translation, you know, for companies like Rev.com, but not Rev.com. Rev.com says, "Pay us." Rev.com is a good example of the steamroll type company. It's basically like, "Got it, pay us. We do transcription really well. We have human transcribers; they're great." But guess what? It's gonna be better than the human transcribers. GPT-5 is gonna be awesome, and it's gonna be way cheaper than Rev.com. It's gonna drive your price to $0 and be better. So that's like Rev.com is in trouble. Then you have a company that's like, "Cool, we do transcription and translation in the context of this certain healthcare workflow where doctors need to transcribe their notes on the go, and it needs to be really high fidelity." Today, that transcription is done by a human, but whatever. They have a full enterprise workflow, and if the transcription capabilities get better, they're like, "Awesome, our product got better." But the product was like, OpenAI is never gonna build a thing that integrates with the doctors' healthcare record system that they use. They embed themselves in a workflow, and that's like 90% of the product. The 10% improvements to the AI, the transcription, the translation, whatever it is, if those get better, great! Our product got more effective, but it didn't make our product obsolete because we have this 90% that we've built around it that is really specific to a certain use case and workflow. So we can't wait for the next model to come out versus maybe other companies like Rev.com or companies that are like OpenAI but are better at, you know, here's an example of a company I think is at risk. You know, these companies that do voice-to-text and text-to-voice, like 11 Labs is one, PlayHT is another. It's like basically they're like, "We're better than... we can do AI. You type in a thing, and we can create a human-sounding AI, and we're gonna fine-tune our model to do that." But then OpenAI releases, like, every month they just release a new thing. It's like, "Yeah, we have text-to-voice now. Check it out! Here's the demo." The demo's awesome. It's only gonna get better, and then it's just gonna become a standard API for anybody to use for text-to-voice. I think those companies that are trying to be like, "We have our own proprietary model, our own fine-tuned use case," they're gonna really struggle because they can't compete with the behemoth.

Sam Parr

How are you taking advantage of this then from a business perspective? Or are you?

Shaan Puri

I would say on the investing side, I'm much more "measure twice, cut once" right now. This means I'm not springing and printing a bunch of checks into a bunch of random AI companies. I think it's really hard to figure out which companies actually have value right now. Also, they're all really overpriced. So, I have this combination of really high prices and really low traction. The product may be really good in a demo, but not really good in production. I don't know if they're going to become obsolete due to OpenAI, so there are a bunch of problems there. It's like, actually, a better bet would be just to invest in the stock market. Just buy companies that have a massive advantage when it comes to AI. So, go buy Nvidia, buy Facebook, buy a bunch of stocks that are going to benefit from AI, rather than just investing in one random startup that I'm hoping is the one out of a thousand startups that becomes enormous.

Sam Parr

Well, that's what Morgan Stanley put in their report. They said AI is going to be a big deal. Unfortunately, we think that it's going to impact big companies that are already established. It's just going to make them better. There’s going to be more value in improving those companies than in starting new ones. Exactly. They actually mentioned marketing, and the reason I thought it was cool is because I own stock in a marketing technology company. They said they think that marketing technology—like Salesforce, HubSpot, and others—is going to be the biggest sector that will use this technology to grow.

Shaan Puri

Well, I think it's good. I think it's a safer bet and it's a more obvious bet. I don't think that investing in startups right now is a bad idea; I just mean it's really hard right now and it's unclear to me. I haven't put in the time to get a lot of clarity on which startups I should focus on. I don't have a bunch of startups that I'm like, "These are going to be winners in this space." I just haven't been able to get that level of clarity yet. So it's like "measure twice, cut once." Meaning, first I'm like, "Let me just learn this in more depth." Let me use all these tools, which is what we do. In these sessions, we will just be like, "Cool, here's a tool that could do X." Then he says, "You drive," and I go and start trying to build a thing that's going to be useful in one of my businesses.

Sam Parr

Are you paying this person? Yeah, still. Dude, this is so smart.

Shaan Puri

Because we did it as a group, the sessions are more fun, and it's a pretty valuable network of people to be really tight with. Which is ultimately what you want, right? You want the thing to be so mutually beneficial that the financial outcomes are secondary. The primary focus should be: 1. The session is fun 2. These people are awesome 3. I get to hang with these people 4. I get to "iron sharpens iron" with these people That's what I wanted this to get to, and so I feel really good about that.

Sam Parr

Dude, that's so smart! More people should do this. I mean, I used to do this with book clubs, but if I had a very specific interest like you have right now, and even if it's just a temporary thing that lasts 6 or 12 months, that's the way to go. It's so smart! That's such a smart thing for you to do.

Shaan Puri

Well, the smartest people, I think, always did this. I think crypto... I know people were doing this early on. You know, I remember hearing these sessions about South by Southwest. I forgot whose room it was, but it was like everybody used to go up to Garrett Camp's room. At South by Southwest, there were about 15 people who were all kind of like loose friends, but there was a lot of mutual respect. It wasn't like a paid party or some event with sponsors. It was like, "No dude, we're here to basically talk about where we think the puck is going." Then they would debate. That's how Matt Mazzio actually got in with Chris Sacca. Sacca was like, "Who's this motherfucker that has really interesting things to say?" It turns out he was the agent at CAA in Hollywood. Sacca thought this guy should be in the tech world, and he recruited him from there. This is where, you know, a lot of the guys who invested in Uber early on, like Garrett and Travis, were in the room. They were talking about Uber at the time, and Gary V was in the room too. This is a legendary story. I have no idea what actually happened, but I remember hearing these stories and thinking, "I need to get into rooms like that. What is a room like that? How do I make a room like that if I either need to get in or I need to create a room like that?"

Sam Parr

What was the story of the room?

Shaan Puri

Well, I just told you.

Sam Parr

Yeah, Ari, was that the second time this episode Sean copped an attitude with me?

Preston Holland

Well, yeah, I'm like... I told.

Shaan Puri

You’re like, “Well, so what happened?” I’m like, “Well, that’s the thing. I told you everything I know, bro. I don’t know anything else.”

Sam Parr

Does Zoom have like a "bitch slap" animation that I could use? I know they've got a thumbs up.

Shaan Puri

Yeah, you know what I mean? Thumbs up, and it like starts bubbling hearts behind you.

Preston Holland

Do they have a middle finger on?

Shaan Puri

One of those... let's see what happens.

Sam Parr

Yes, does that work? That's our second time.

Shaan Puri

I apologize, I'm a little sassy today. I can be catty on Wednesdays. I know, my bad.

Preston Holland

I apologize.

Sam Parr

Is that the pod? Do we wrap up there?

Shaan Puri

I guess I think I need to go work on myself. I think I'll meditate and chill out.

Sam Parr

Alright, that's the...

Preston Holland

Pod.