How Kid Rock Makes +$30M/Year Using Redneck Business Strategies

Sean, I want to show you 3 things, things that I've read in the past week or 2 that have inspired me. You want me to start with this? I'm going to start with the strangest one. I'm going to get it out the way. Do you listen to Theo Von's podcast?

Not the full, I listen to clips. Do you listen to the full thing?

I listen to the full thing sometimes, and there was one that happened the other day that I sat and watched the entire thing. I think it was 2 hours long. You're gonna laugh when I tell you who it is, but his episode with Kid Rock was awesome. So do you know anything about Kid Rock?

I'm gonna say I don't know anywhere near as much as you know about Kid Rock. I could safely assume that, uh, hands down, I bet my life savings on that.

I have been a fan of Kid Rock's forever. I've been a Kid Rock fan for a very long time, and Kid Rock is a very fascinating guy. So he's like born in Detroit, had this whole like rap thing. It's kind of rap, whatever it was, whatever you want to call that genre. Uh, but the reason he's fascinating is the guys who sold a lot of records in the late '90s are some of the richest musicians out there because CDs were like $22. How much, how much were CDs when we were kids? Like $20, right?

Yeah, CDs were like really expensive, really expensive, and they cost like a dollar.

They cost like a dollar to make. And so Kid Rock has sold something like 40 million albums, which is a shitload of albums. And he went on Theo Von's podcast, and about halfway through, he starts talking all about business, and he's done some amazing things. So let me tell you a few amazing things that Kid Rock has done. Kid Rock at this point He's kind of like Nickelback where people make fun of him or they make fun of you for even kind of liking him. And it's kind of a joke, dude. He's a super savvy guy. So listen to a few things that he's done. Have you ever heard of the Kid Rock cruise?

No.

So Kid Rock has a cruise that he does every year and you pay like, you pay like $3,000 and you go on a cruise for like 4 or 5 days. And he goes on the cruise with you and he plays music every day for the cruise. It's an amazing, like, thing.

You butchered the name. It's the Kid Rock Chillin' the Most Cruise. I feel like you needed to say that.

It's so funny what he does. And so he's been doing this for like 10 years now or 15 years now, I think since 2010 or so. And so that kills it. Listen to a few other things he's got going on. He has the Kid Rock Rodeo. That's his new thing. And so do you know anything about rodeo?

I mean, you're just embarrassing me at this point. No, I don't know anything about— I don't know anything about Kid Rock. I don't know about his cruise. I don't know about his rodeo. You can— you can skip the questions of do I know about Kid Rock's extensive business portfolio? I do not.

You've never been to a rodeo, but you've never been?

I lived in Texas for 10 years and I did not know.

I used to go to them in California at the Cow Palace. Do you remember the Cow Palace? I was like, that's a great name, by the way, dude. The Cow Palace is this venue like literally 2 miles outside of the city of San Francisco. And you go just 2 miles outside of San Francisco and you're at the rodeo for the night and you're in redneck heaven. And so I used to go there, go to it all the time. It's so fun. I used to go to dog shows there. They have dog shows. I used to go and watch like the dog shows and just look at all the Swiss mountain dogs and shit. It was so fun. And so anyway, Kid Rock now has the Kid Rock Rodeo, which freaking kills it because rodeo is up and coming. You know who owns the PBR? It's the same company that owns Endeavor, because it kills it. Well, Kid Rock has started his own rodeo and it has like teams, which is like kind of a new aspect of rodeo, and it's also killing it. And he starts talking about the business of this rodeo. This guy is super, super savvy. He talks about how an owner came to him and was like, "Hey, we're going to start this new rodeo. Do you want to buy a team?" It costs $20 million to buy into the league and to start a rodeo team. And he goes, "No, I don't want to do that." But what if I just help you start the whole league and I own the league with you? And that's what he's done. And now he has the Kid Rock Rodeo where he goes and he performs at the rodeo. It's very, very fascinating. And then finally, have you ever been to Nashville? Nope. Okay. 4 for 4. So in Nashville, in downtown Nashville where I used to live, there's a street called Broadway and that's where all of the honky tonks are. Honky tonks are basically like these kind of crappy dirty bars with bright lights and they call it Nash Vegas. It like looks like it's Las Vegas. I, we used to go on Saturday and Sunday nights and try to like meet all the bachelorette parties. It was like a thing when you're in college. And so Kid Rock about 10 years ago started this thing called the Kid Rock Honky Tonk. And at this point that bar, it sells something like 15,000 beers a night. Yes. Yes.

I don't know how many beers a normal bar sells, but that number sounds like a lot.

It's a huge amount, man. And the business is doing, I was reading about it. The business does something like this one bar, this one location, $30 million a year in revenue. It's insane. It's like a 3-story bar in this main strip of Nashville.

Is Kid Rock our Billy of the Week actually?

Dude, Kid Rock is so fascinating. And on this podcast, he breaks down a bunch of the businesses and he's like, a lot of people think that I'm party and stuff like that. He goes, I don't even drink that much. I wake up at 4 AM, I do a cold plunge, I do a sauna, I do a workout. I swear to God, this is what Kid Rock is saying.

He goes, my morning gratitude journal. He's like, then I do the next thing.

Dude, he's so much more put together than a lot of people give him credit to, give him credit for. And this podcast with Theo Von with Kid Rock, it's so good. You have to listen to it. It's hilarious.

Does he talk about all these business things on the pod or you look those up?

No, he talks about a bunch of them. He talks about— he's like a really savvy business guy. And Austin Reef, our friend Austin Reef, Kid Rock and his like— I guess he has a family office. If I had to guess, I bet you Kid Rock is worth about $300 million. Austin Reef went to Kid Rock's house in Nashville because he was organizing a thing for startup entrepreneurs because he wants to find cool companies to invest in. Listen to this, his home, his home in Tennessee is a replica of the White House. This guy is basically like a redneck with all this money doing exactly what they want to do. It's hilarious. And he talks about his White House home in Nashville. And I'll tell you one last thing. So I'm such a Kid Rock fan that I heard a rumor that his— when I went to Belmont University from 2008 to 2012, I heard a rumor that his son went there. And so I did a little Googling and I find out what his son looks like. And so I spent months on campus just looking for Bobby Jr. That was his name. Uh, because Kid Rock's name is Bob, Bobby Jr. And I, I spent months, I'm like, I gotta find this kid. As soon as I see him, I'm gonna go up and I'm just gonna shake his hand and tell him hi. Just the most, the lamest thing you could imagine. Well, I finally see him on a Friday night when I'm just blackout drunk. Like I barely even remember it. And I see him, I go, Bobby, huge fan. And I'm slurring my words. I love your father. I put my arm on his like shoulder and I go, here, take my number. And I grab his phone and I, and I type my number in his phone and I text myself. And then I just try to like force myself to, on this kid to be his friend. I think I was like a junior. He was a freshman and I just felt like the biggest asshole. And I just try to force myself on him and shockingly it didn't work. But I've been a big Kid Rock fan for years and this podcast was awesome with Theo Von. You have to listen to it.

Okay. That was a great sales pitch. Also, I like take my number. I think take my number is just a very underutilized way of forcing a connection with anybody. Here, here, here. Do you have a phone?

Take my number. It's because I grabbed his phone so I could text myself to to make sure that I got his.

Yeah. The real number. Yeah.

It was so embarrassing that I did this, but yeah, that's my Kid Rock story.

All right. Amazing. I'm tempted to just end the podcast right there and just go try to book Kid Rock as a guest, but I'll give you a couple things that I'm into. Nowhere near as entertaining as that right now. But you, you know, my understanding was kind of like what you're saying is I'm watching some different content, weird content, new info diet. And I wanted to tell you some of the things I'm doing with my info diet. So I'm gonna give you the, the chapter titles of this, and then you get to pick which one you want me to explain. So here's the chapter titles of how, how I'm consuming content. Number 1, Older Is Better. Number 2, look to the left. Number 3, More with Less. And number 4, oh, I actually have 5, 4, Pay for Learning, and 5, early arbitrage exploit. Which one do you want me to talk about?

Number 1, number 5, number 4.

All right. Number 1 is older is better. Okay. So older is better. In general, I'm trying to get away from the newsfeed, right? The newsfeed is in many ways like the actual, like, news. I don't watch the news for the same reason, which is, you know, the news is an entertainment program designed to basically just like find random problems in the world and then just shove them in your face. And Twitter, Facebook, Instagram, these are all kind of the same way where people are like, here, here's my life. And you just throw, you know, here's what I'm thinking right now. And it's useful to a degree, but it's more addictive than it is useful. And my solution is not to just go detox and be like, oh, I just put my phone on silent and leave it in the other room. And I just, you know, enjoy nature. That's not really me either. I got to substitute it with something else, right? And so my substitute is I've found, uh, I was like, what do I want to read that's shorter than a book that's as informational as like, you know, reading an annual, um, like an S-1 or like an annual report for some company, like, like an investor would, like a Warren Buffett would, but still has some juice, still has some story. And I found that annual letters, annual shareholder letters or annual reviews of people is just a really fascinating place to go look. I get—

what's the difference between an annual review and an annual letter?

So one is typically when you have shareholders or LPs, that's when you're writing an annual shareholder letter, right? Because you have your, your investors or you have your shareholders that you are looking out for. So this is like Buffett's letters, Jeff Bezos' letters. I'll give you a really good one that I found, the Nick Sleep letters. You've probably never heard of this guy.

Who's this guy?

Fascinating guy. Uh, when I, when I did the podcast with Mohnish Pabrai, he mentioned Nick Sleep and like, I don't know the full story. I just started looking because I found like 10 years of this guy's annual letters. But the short story is him and his, him and his buddy basically started buying stocks, started investing on behalf of other people, did so well over like a 10 to 15 year period that they ended up just like retiring. And his portfolio at the end was like Amazon, Costco, and Berkshire Hathaway. He had 3 stocks by the end. And I just love somebody who can absolutely crush the market. He absolutely crushed in terms of performance and did it without like going, like working really hard or going into some obscure rabbit hole. He just identified correctly early on that Amazon, Costco, and Berkshire were good bets to be in. And he just stayed with those, rode those ponies till the end. It's pretty, pretty insane. He did other things, but like that was where he ended. I found that fascinating.

How big was the portfolio?

Dude, these guys got filthy rich. I don't know exactly how much, how much in assets they have off the top of my head, but, you know, basically in a very short period of time, you know, got filthy rich. So I just started these letters. I just read the first one last night. So I'm pretty fresh right now.

I like Nick Sleep. When you Google him, the first thing that comes up, by the way, is his legendary letters.

Exactly. The letters is what— and I think some people have like maybe bound it into a Kindle book as well. Like, And you know, whenever it's something like that, like the last time it was like this, it was the Boron Letters. It's like, who's the Boron Letters? Well, this guy was like one of the best copywriters. He wrote a bunch of letters from jail to his son. It's like, dude, I'm in. This sounds like, you know, season 2 of Prison Break mixed with, you know, my copywriting course. I'm in, you know, like give me that. And so I'm really into these annual shareholders or annual reviews. So we have a few friends. Saeed Balki does this every year. He posts an annual review on his blog. And he just goes back and he just says, here's what I did this year. Here's some of the highlights. Here's some of the lowlights, whatever. Nathan Barry from ConvertKit does the same thing. He posts this on his blog. He'll be like, you know, thing one, my family. Thing two, ConvertKit. Thing three, I bought some Airbnbs. Here's the occupancy of my Airbnbs. Here's how much money I made. All bad. But this was a pain in the ass. And I just feel like people who are sharing that type of information is just very interesting to me. And it's a very quick read. And to me, I'm like, I'd rather spend 30 minutes reading that than 30 minutes aimlessly scrolling on Twitter. So that's my older is better. That was my number 1.

All right. What's number 5?

You said the last one, early arbitrage exploit. So I tried to put all my power words in there to hook you because I wanted to talk about this. Have you seen AirChat?

Uh, I don't know exactly what it is. So all I know is that Naval has some type of new social media thing and it's invite only. That's all I know.

It's not invite-only anymore. So as of, I don't know, 2 days ago, they just opened it up to everybody and they pivoted it. They've had a kind of AirChat in beta for a few months. I checked it out. I was like, this is okay. It wasn't super engaging. Like it was kind of confusing UX and it was just a little bit slow to consume.

Is it like Twitter but better?

Okay. So the new one, I'll tell you about the new one because forget the old one. It's gone anyways. The new one is basically like Imagine Twitter, but it's voice first. So you, to post, you just talk into your phone, right? So you don't type, you just talk, but it auto transcribes it using AI and it speeds it up like 1.3x or something like that. So when you like, when you're scrolling the timeline, it just starts to play somebody's audio or you could read it, but it plays it a little bit faster. So it's actually, it's like you're almost listening as fast as you could read in a way, which is kind of interesting. And you get to hear their voice and then people reply or whatever. So it's the generous version of it would be, oh, this is a really cool new, like, social media format. And new formats are interesting, right? Twitter was a short-form format. TikTok was a, you know, or Vine was a 6-second looping format. TikTok was a different short video format. Like, formats mean things. And that's where the big breakthroughs come from. So maybe it's one of those. The other side of it is like, it's kind of like if you turned on Accessibility mode on your phone and then open Twitter. It's like, hey, can you just voice to text? Like, can you just read me my timeline? Which is not great. So I'm not sure if it's going to be a hit or not, but here's what I do know. Just like in the early days of Clubhouse, when an interesting person in Silicon Valley starts a new interesting thing and they invite only their interesting friends, that place is a very interesting place for like the first 90 days.

For the first 90 days.

Who knows if it's going to be successful or not? You get a call option on that. And so I'm like, fuck it. I'm all in on AirChat for the next like 7 days. Let me just go. Let me just throw full force. Let me completely ignore Twitter, completely ignore YouTube, podcasting, et cetera. And let me just AirChat the hell out of myself. Why? Because it's Naval's friends, which is probably the most interesting group of human beings in my world, in the business and tech world. That's who's using it. So all the content is interesting because the people are interesting. And there's not that many people on there. So if I'm even remotely interesting, I'm like in the top 0.1% of interesting people on this app. And the same thing happened when Clubhouse came out. I didn't think Clubhouse was going to be there forever, but I had told my buddy Jason, who I always thought Jason's an interesting guy, and I was like, Jason, quit your job and just be on Clubhouse like 10 hours a day for the next 30 days.

Watch. Didn't he work at your company?

We had gotten acquired. So I was like, just check out. You're at Twitch. Just check out now. Who cares? Nobody will. Nobody will know. Trust me. There's 2,000 people in this place. Nobody does anything. Just stop doing work and just get on Clubhouse 24/7. And he's like, well, you know, like, I got to— no, no, no, trust me, you'll get more value out of this than you will your job. And that's exactly what happened. He went there, he was on it all the time. He's an interesting guy. So he made a bunch of friends. He ended up raising like a $4 million crypto fund out of it, made a couple million bucks doing it, returned their money. And like, none of that would have been possible. Like, he raised money from a bunch of Clubhouse friends and he made like, you know, lifelong friends. They go on trips together in real life now. And it's these early arbitrages when somebody awesome curates something. In many ways, Hampton was like this. You're an interesting guy. You had an interesting idea. And then you curated an early group of people and you were like hellbent, like, I'm going to make this a great experience for them. And so that those first 100 days were going to be like the best 100 days of this whole product forever, just because of what happened, that early day exploit.

Well, I hope not.

I mean, no, it's okay. It's just like in dating. Like there is a honeymoon period. For products, for people, for relationships where, you know, let me get that door for you. Let me take out the trash for you. Let me— it's Wednesday. Let me send you a little gift, right? You behave a little bit differently at the beginning of a relationship than you do 7 years in.

You think AirChat's going to be better than Clubhouse and it's actually going to work?

Too early to say. I've only been on it for like 2 hours. So let me not do a hot take conclusion just yet. But It's interesting for sure. Hey, real quick, as you know, we're big on ideas here. We love bringing new ideas, business ideas, brainstorming ideas for the podcast. Well, a lot of people ask, what do you do with all those ideas? Can we go find them? Is there a list somewhere? The great people at HubSpot have put together a business ideas database. It's totally free. If you just click the link in the description below, you can go download a collection of over 50+ business ideas that are from the archive listed out for you, curated. And so, uh, what are you waiting for? Go download it. It's free.

Check it out.

It's in the description below. All right, back to the show.

What's the fourth thing?

Pay for learning. I don't know if I said this one. Pay for learning. So this is instead of me going out there and trying to get smarter about something, in this case AI, I was like, wait, why is it that as adults we don't ever go to school, go to class, or have tutors? And so I told you this before, I hired an AI tutor.

Yeah.

And the guy, you know, people were like, what, what is an AI tutor? And I was like, dude, AI is changing so fast. Literally every 3 weeks, there's a new mind-blowing paradigm shift in AI. Okay, great. There's thousands of companies getting funded. I can't even keep track of them. There's new models being released. There's a new talk that drops, a new interview that drops where Sam Altman says this interesting thing. I couldn't possibly keep up with it. It's a full-time job to keep up with it. So one way is you go read a newsletter or you join maybe a group chat or something like that. That's good. But what I decided to do was like, how do I use— how do I spend money in an interesting way here? How do I— I basically pay this guy $500 an hour. And I say, your job is every week, you're going to come to the table and you're going to tell me, here's the 4 most interesting things that blew my mind. I live in AI world. He lives in AI world. He has to bring to me 3 or 4 of the most interesting things he's seen. And then I usually ask him a question like, hey, I saw people talking about this. What is it? Or Chamath said this thing. I didn't even really understand it. What the hell is he talking about? Or, hey, in my business, I have this problem. Is there an AI tool that could actually solve this? And then he'll go do the research and he'll come back to me and he'll, he'll answer it. And so this has been just like such a hack to be smart about AI, but shave my time commitment. Like, you know, yes, I'm paying this guy $500 for 1 hour of his time, but I'm kind of saving 8 to 10 hours of my time because I now literally don't have to think about it. I put it out of my brain. I'm gonna have a focused 60 to 90 minutes with him, and he'll tell me everything I need to know.

Have you ever used GLG? Do you know what GLG is?

I know what GLG is. Yeah, I was, I was on GLG. I was on the other side of GLG.

You're an expert. I did it too. I remember basically GLG originally was started because it was like bankers who were going to either take a company public or wanted to invest a large sum into like, let's just say, let's just say Mailchimp. Mailchimp is going to get acquired by Intuit and they're hearing rumors about it. So they go, they would go and find people like me who use Mailchimp-like services and ask us questions like if Mailchimp raise the prices, what would you do? Right. Uh, how would you react? Just so they can get like an idea for the market. Well, there's GLG. Now there's Teegis. There's also Intro. And I also have been an expert on those and you could charge like $2,000 or $3,000 or sometimes $5,000 an hour, like crazy amounts of money to be an expert. Dude, I've been using it on the other end where I've been paying money to like get insights. Yeah. It, it kind of feels like it's cheating. So like you can, you can tell GLG or Teegis or whoever, that you want to talk to your competitor or someone who works at, or worked at your competitor. And you can get so much information from them. I read this, I think I told you about Steve Cohen. I read this book about Steve Cohen. He basically is one of the largest hedge fund guys out there. And one of his guys went to jail, went to prison for many years because what they would do is they would use GLG so much that they would befriend the experts and fly out to the expert's home and get them to reveal a bunch of confidential information that they weren't allowed to reveal. And then they would go and trade assets on that information, which is insider trading. It's so powerful that I've been able to do this. It, it's like been really amazing to be on the other end of paying these people. I'm shocked I haven't done this for years. Have you ever paid money?

I had never done, I've never done it on one of those networks. Cause to me, I'm like paying somebody $2,000 an hour, right? Like it makes sense for most of those customers cause they're making very large investment decisions. So if I can get better alpha, better information for, you know, $2,000, $5,000, $10,000, $20,000, doesn't matter when I'm taking a $10 million position or an $80 million position on a company. I've never been in that position where I needed to do that. That's not what I do. It's not the scale I play at. So like, how do you justify paying, you know, for yourself? Like, what are you paying for? And how are you justifying paying that much money?

I'll give you an example. So let's just say that, let's just say, all right, so Hampton, Hampton's a peer business, a community business. There's like 5 competitors out there. A couple of 'em are quite huge. I'm curious how they're acquiring users. So you could just sign up and say, I wanna talk to the director of marketing at this company. And they go and find a former marketing executive or a marketing leader at these companies and be like, so, you know how, and you don't have to, you don't tell them your background or what you're doing. And you'd be like, so how are you guys, how are you guys acquiring customers? Like, could you just do LinkedIn ads? Oh, LinkedIn ads didn't really work. So instead we did X, Y, and Z. And you can just ask all these questions and hopefully save yourself a year of time of making the same mistakes that other people in your industry. So for e-com, you could be like, um, well, I'm not well versed in e-com, but I guess it could be like, you know, what about, uh, shipping from your own warehouse versus hiring another person's warehouse? You know, things like that. Uh, you could just ask them all these questions and it's made my life so much easier.

Right. Yeah. I think it's more of like a scalpel than it is like a blunt force hammer where it's like, You really, it's a, it's a very precise instrument. You only wanna use it for very specific types of questions where the, the trade-off makes sense. And there's many jobs where that makes sense. And then there's many, like in the e-com example, you'd almost never do that realistically as an e-com person. But if you are, like, I've been on there and people would be like, hey, you use Triple Whale and we're looking to talk to an expert who uses Triple Whale and we wanna know, did you evaluate 3 or 4 other competitors and why did you choose Triple Whale over the competitors? And it's like, yep, I did that. I used Shabla, I evaluated the competitors. Here's, here's the difference, blah, blah, blah. They really couldn't do that because they're not an operator. So when they're making a big investment decision, they have to, they want to, they want to go in with like real information versus random theories on their side where they, they weren't actually an operator in the space. Right. All right, let's do another one. You have anything else?

I've got a book that I think you should read. So I read this book years ago and I just recently reread it because it's so good. And I bet you've never heard of this person. I'm gonna ask, but I know the answer is no. Kirk Kerkorian. That doesn't ring a bell, Kirk Kerkorian, does it?

That kind of does ring a bell. Who is Kirk Kerkorian?

All right, so Kirk Kerkorian, he's born in the early 1900s, like 1920 or something. He's an Armenian immigrant, or born into an Armenian family where he, like, he's born in Fresno, California, but spoke Armenian, didn't even speak English. He eventually drops out of like 8th grade, so he's like this, like, you know, He's not the richest yet, but he's the rags part of the story where he comes from nothing. I think his parents were like farmers or something, grew up poor, learns how to fly a plane because World War II is coming up and he doesn't want to be shooting guns. So he goes into the Air Force and learns how to fly planes and he spends the war flying planes. After the war, he's able to save up enough money to buy a Cessna, one plane for $5,000. I think he saved up like $2,000. He buys a plane. His first business is flying people from California to Las Vegas. This is in the '50s and '60s. Las Vegas is not really a thing yet, but gambling is legal there, and all these rich Hollywood folks want to go to Vegas for the weekend. He's their guy. He flies them out there. So he flies them out there and he starts getting into gambling while he is there as well. And so through his gambling, as well as his very small business of flying people out there, he starts buying more and more planes. And over the course of 15 years, he kind of has a meaningful business to the point where he's like 43 or 44 years old and he's making the equivalent of like $2 million a year in profit. And so he's got a good business. Well, he sells this airline business for $10 million, which is like the equivalent of $90 million today. He sells it in his forties and that's really where things start taking off. With that money, he buys a plot of land and he turns it into the Pink Flamingo Hotel, which is one of the first big epic gambling hotels in Las Vegas. Then using the— What's so funny?

Just the Flamingo. That's hilarious.

Yeah. That's his thing. And by the way, while there, one of the waiters who worked for him has a son and Kirk always treated this waiter really nicely. And so he eventually names his son Kirk Agassi, his first name being Andre. So Andre Kirk Agassi, the famous tennis player is named after Yeah, it's Kirk Kerkorian because he's known as like a— he's a good employer. He's a good guy. Takes his small little casino, parlays it and keeps on growing. And by the time he's in his 50s and 60s, he starts buying other companies. So he buys MGM, which at the time was a lot. It was a production studio, movie studio. And then after years and years of doing this, he just parlays all of this to eventually he's like 85 years old and he buys 10% of GM. And then at 88 years old, he tries to buy the entire Chrysler company. And he almost gets it done at like $30 billion. But what's interesting about this guy, Kirk Kerkorian, never had formal education. So he's, I guess he's a Wall Street guy who's not actually on Wall Street. He's a banker type, but he buys all these companies with no education. He's very private. So there's like 3 or 4 interviews ever about this guy. And he's got balls of steel. He's a nice guy, but he's a hard negotiator and he's just puts his money where his mouth is. And he does this until the age of like 94 when he dies. To the day he dies, he's making deals. And he's really low-key, but he dies with like a net worth of like $15 billion. And if you like, you know, you and I have kind of been into the whole capital allocation type of thing. This is the guy, and he's done it without any background, no pedigree. Very fascinating guy.

I have to apologize to Kid Rock. I thought you were the Billy of the Week. Actually, it's this guy. This guy is the Billy of the Week. Wow, this is an incredible story. The Andre Agassi thing just was the cherry on top for me, I gotta say. Uh, thank you for adding that one in. It seems almost impossible to me when it's— by the way, I'm clearly wrong, but it seems almost impossible that a guy could just like start chartering flights for people. He's like a pilot, pilot turned billionaire. That sounds So like the amount of capital he had to amass to end up owning 10% of GM, try to buy Chrysler for $5 billion. Like how the hell did this guy compound at that rate for that long? That's so insane.

The book is called The Gambler. It's a really good book, but basically he's like, I'm a gambler at heart. I love gambling. He's like, I'm in it for the thrill. But basically he caught a couple trends. The first being obviously airlines weren't popular. And so like his airline was kind of rinky-dink. And he just bootstrapped it for 15 years. And so it's inspiring. He started the airline when he was 32, right when he got out of the war. It wasn't really a hit until '44, and it wasn't that big of a hit. It was a good business, but it wasn't like some epic, epic thing. But he sells it for $10 million, and then 2 years later, he buys it back, runs it for 3 more years, and then sells it again, this time for $100 million. And the trend that he caught was that airlines just weren't a thing. And so they were kind of bootstrap things. They weren't, they didn't have these massive barrier to entries like you would think of today where you have to have tens of billions of dollars. I mean, starting an airline today seems just like insane. It wasn't like that. And then the same thing with Las Vegas where gambling, it wasn't exactly like that where it wasn't like that big of a thing. Las Vegas was, I think he, the plot of land he paid for, I think it was $800,000. And then he spent another like couple million dollars to build the Pink Flamingo. And he just got these hits early on where he caught these trends, you know, Vegas, airlines, things like that. And he caught 'em all early on. But here's the inspirational part, in my opinion, he wasn't really a baller until his mid to upper 40s. And he was in the game for literally 95 years when he died.

Yeah, I think that, you know, Mohnish Pabrai, when I was talking to him, he was like, you know, there's 3 variables that matter when it comes to wealth. He's like, it's all about compounding. So he's like, it's either the rate that you're compounding. So the percentage gain every year, it's the length of the runway, or it's the amount you started with. And you could pull any of those three levers. You either start with a huge amount, then you don't have to have a high rate or a long time. If you start with a low amount, which is where most people start, then you need a high rate and a long time. Um, or you need to like explosive high rate and not that long time. Those are your variables to play with. And you know, if you look at Buffett, Buffett's thing is that he compounded for the longest time. So he basically, you know, bought his first stock when he was 11 years old. And yes, at 95 now he's, you know, if he hadn't given his money away, he'd be the wealthiest man in the world. Well, you know, what, number 1, number 2, number 3, somewhere up there. And it's because he had an 80-year runway. So it's not that his rate was that absurd, it's that the rate was consistent and it was 80 years. And so it's like, you know, one of those things for compounding is like how How long of a runway do you get? And for most people, you know, like for Buffett and for others, it's like the bulk of their wealth is always kind of in the last, the last 2 or 3 turns of compounding because that's just how compounding works. If you're doubling every 10 years, then doubling, you know, went from 70 to 90 is going to be doubling a huge number at that stage.

And people say that, and, and you're right when you say that, but it almost discredits Buffett. If you read his biography or read any of his early reports or his annual letters, man, even when he was like 35 or 38, he had something like $50 million in assets. And people are like, well, he didn't actually make— the billions didn't come until his 50s or 60s. He was killing it for a long time. Like, he started—

can be true, right? $50 million is still killing it. And $50 million is not the same thing as $90 billion.

Yeah, yeah, yeah, that's for sure. But if you like read about him, he was like, I think he said when he graduated college, I think he had $100,000 of his own portfolio, which in the '40s, that's like having like $2 million. And he was killing it from a, like a really early age. And then his early compounding was like 30 to 50% for like 6 or 8 years in a row. I mean, he was kind of the man. From the beginning. If you ever read about him, when that episode comes out, you'll like it.

That guy, uh, Mohnish is basically like a Buffett historian and a Munger historian. He knows year by year what he was doing, what he was investing in, how much he had. He like has charted it out. He gave me like an oral history of Warren Buffett in a way that I've really never seen. And I loved it because I've met a lot of people who are super successful and then they, it's like, they're not kind of like students of the game in the same way that I am, where I'm like, oh, did you ever go back and read all the letters and kind of deconstruct them? They're like, no, I was just doing my thing. Right? Or like, I know great investors, I'm like, do you do like detailed kind of models? Or like, do you write memos that like, did you go back and review them? You track your hit rate, like nerdy stuff that I like to do. And often, very often, I would say more often than not, the answer is actually no, I don't do any of that shit. I just like, let's focus on what's in front of me. And I just do that thing. So it's really nice when I see somebody who wins with the same play style I have, where they, they kind of are a nerd about it and they do like to go back and kind of chart things out and break things down and, and kind of analyze it a little bit themselves and other people and, and try to use that to kind of reverse engineer, you know, some lessons. Um, so it was pretty cool to see that.

What was your takeaway?

Uh, after he said that, like I said, I think it was reassuring in a way. It sounds silly to say, but it's true. Like whenever I meet a more successful person than me who does things the way I do them, I feel good inside, right? Like I, I feel a little reassured, like, oh, that's cool. Like this person, like, it reassures me that my method can work, right? I already believed it could work, otherwise why, why, why else would I be doing it? But it's even more conviction that this works. I don't need to shift what I'm doing in order to make it work. When you see somebody who's very similar to you, maybe similar demeanor, similar philosophy, similar approach, similar work habits, you know, I, I like finding people who, who have a match because it's very hard for me to change my nature or to change my work style or change my habits So it's actually better for me to double down, make them super strengths and find other people who've won, use it with those same strengths and look and learn from them and what they did versus try to become some different guy playing some other play style that I'm not familiar with, that I'm not good at, that I haven't done for 15 years already.

Let me wrap up by telling you one last thing, and this one is gonna be short cuz I'm not terribly well versed on it. You would know this guy better than I would actually. What's his name? Mike Novogratz. The crypto guy, what's his name?

Mike Novogratz.

Novogratz. So I think he started or helped start Fortress, which is a massive hedge fund, right?

Yeah.

He's got this new podcast called Business Untitled right now on YouTube. I think it has 3,000 subscribers even though they're like 30 or 15 episodes in. His podcast is so good. It's him, dude. It's so good. It's him and this other guy named Mike Barry. Mike Barry, I believe. Is a real estate guy and he owns a chain of hotels or something like that. Really high-end hotels. It's sort of like the All In podcast where it's like billionaires talking about stuff. And that's one of the reasons why it's exciting. But these guys have like a little, like All In is not even remotely, I wouldn't even use the word blue collar at all to describe those guys or what they think of themselves. This podcast, they kind of do have that vibe where they're like born, they weren't born wealthy and they still remember where they came from. And they're talking like they're small business owners except the numbers are absolutely massive. It's a beautiful, wonderful podcast. You gotta listen to a few episodes.

I'm so jealous of this thumbnail style. Oh man, I see this and I just wish this was our thumbnail style. This is so—

is it like dollar bills?

It's just fucking awesome, dude.

It's great, man. It's a really—

I wish you hadn't said this. I wish I could just steal, I wish I could have just, you could have just shown this to me and I'd be like, let's steal this. 'Cause this is so, so damn good of a, of a thumbnail style.

Well, they only have like 3,000 or 4,000 subscribers. How many subscribers do they have on their YouTube? I think it's like 3,800 or something like that.

Yeah. So you're saying we can steal it. Nobody will know.

Yeah, we could steal it. It's really good. This podcast is so good. Like, and they have amazing guests. Like they even had, they've had Snoop Dogg on recently, or they'll have the founder of Equinox or a bunch of like really big names and they just shoot the shit and it's wonderful. It's so good. And they tell stories about starting Fortress Capital and I guess Wes Eden who started Fortress, I think he eventually like bought railroads or something like that. And they tell the stories, but they have this weird blue collar down to earth kind of style that I've been digging. It's really good.

All right. That's a big endorsement. I like that. I gotta ask you, what do you think about the fact that so many people have podcasts? Like it's pretty remarkable. When we started, this was 4 years ago, roughly 4 years ago, I think. And we were not early to the podcasting game. We were like a decade plus late to the game.

Felt late.

Felt late at the time. But I would say since we started, it's now like incredibly common. If you're anybody, like the number of people who start a podcast is, is that are kind of like interesting people from other, other walks of life, right? Like investors, business people, athletes, whatever. Um, it's kind of amazing. Like one of the content, when I was going to talk about was Chasey Riddick has a new pod with LeBron James.

You seen this? I saw that. It's awesome, right?

It's like LeBron is podcasting. This is amazing. What the hell is going on?

I love the athlete ones. A lot of the UFC guys are doing them now too. Kamaru Usman has one. I love them.

So what's your take on this? Like what, what, where does this kind of like, where does this go? Or like what, what do you think is gonna happen with like everybody starting a podcast now?

A, I love it as a fan. Like I enjoy listening to them. B, I don't think they're gonna last that long. I think it's a lot harder than people realize to do it for a really long time. I think when you and I, or when you first started this, the common thing was you guys are going to run out of stuff to say. I hadn't really felt like that much. There's some times where I'm like, what else can we talk about? But in general, that's all— that's only happened 10% of the time. And I don't think they're going to run out of things to say, but I do think that it's, it could be a lot harder work. I mean, you're signing up for something. I'm shocked that Tim Ferriss has done it for 10, 10 years. I think that it's, it's a lot harder to do it for many years than people understand. Do you agree with that?

Yes and no. I think that, uh, I think there's a problem with it. I don't think that's the problem. I'll tell you what it is. But, but on the running out of things to say, I think most people will choose interview, which is a kind of infinite runway format. It's like, oh, you just bring somebody on, then you talk to them, then you ask them questions, then you bring another person on, you ask them. What we do when we don't have guests on is a lot harder for to, to have longevity with. Cause it's like, how many interesting things are me and Sam going to be able to say of original content versus an interview or reacting to news? So I think reacting to news and interview or reacting to TV shows, like that's always going to be a format that has like infinite runway. So I think most people will do those and they won't run out of content. I think the problem is that how many podcasts on average are you listening to at any given month?

5.

And you're a power user of podcasts.

That's funny. Yeah. I mean, maybe less, 3 to 5, right? And not, not a lot.

Shelf space is just really goddamn small. I don't think, I don't think most people realize this. I, I think they think it, I don't even think it's a discovery problem. I think it's a discovery problem because people cannot consume that many podcasts. So for example, I think what a lot of people do is they're like, oh yeah, I use Twitter, I use Instagram. Oh, TikTok comes out, I'll, I'll use TikTok. Like they kind of think everything's social media and your, if your experience before was, Well, if I'm just interesting, like, people can— people will follow me. But it's like, I can follow literally like 5,000 people on Instagram. I can scroll through in one Instagram sitting and I can see content from 200 people in that, like, you know, that 30 minutes. But my shelf— so the shelf space is huge on every other social media. But the shelf space is tiny on podcasts. People listen to 1, 2, 3 on average in rotation. And so The question is, can you break into enough people's top 1, 2, or 3 podcasts? And you're going up against a habit they might have had with other podcasts for 5 years. The hope would be they expand the market, that new people start listening to podcasts. And I'm sure that's gonna happen to some extent. But I think just like the supply demand is so off, the demand is so small of the number of podcasts somebody will regularly listen to that it doesn't matter how many new people create a podcast. It's gonna be very hard because the shelf space is too small.

But you do realize that it's over 2 times the amount of people listen to radio than podcasts. I mean, if you go to where I'm from and you talk to some certain people, they don't, they're like, what's a podcast? Like, it's still like, yeah, but you're listening to music, dude. Yeah. But like, it's not like AM radio, but there's still a lot of market penetration for podcasts, particularly amongst like a general population, like someone who cares about LeBron. Like I bet an athlete will get significantly more new.

But what I'm saying is I think the best podcasts in every category are going to grow like you're saying, like there's still 10x more headroom for them to grow, let's say. However, it's just that there's like the number of winners is very small in podcasting versus on Instagram. There's so many winners, so many people who have followings, either small, like just enough to keep you hooked, enough to keep you engaged. It's very hard to be a winner in any category. Like, let's say I wanna start a true crime podcast or a business podcast or a sports podcast. The, the ones at the top are gonna keep getting more and more and more and more and more downloads because like you, you have an audience now, so it's easier for you to do it.

To do it from scratch when you don't have an audience, I think it's basically impossible. Yeah.

Even people who have an audience, look at like even people who are, who are successful or have some audience, it's very hard to, to boot a, boot a podcast up. I don't know. I think, I think it's the shelf space problem is, is my, my take of like, what, what the limiting factor here is. It's just that there's only so many number of humans who listen to podcasts. That number's growing. But the number that's not growing is how many different podcasts they're going to regularly listen to because they only have so much ear time that they're going to dedicate to ear entertainment. Right.

Is it good? The JJ and LeBron one?

I would say it's amazing. And I mean that in the literal definition of the word, not like the content is amazing. It's just like, I am amazed that this is happening. I am amazed that LeBron James is sitting down and explaining to me like the, the Marcin Gortat screen. It's like, oh, what's the Gortat screen? And he's explaining what this is, what, how it works, whatever. I think they really need to work on getting the, uh, like, like they need overlay. It's like way too X's and O's. Like they need the overlays where you're going to be able to see an actual clip of what they're talking about. Cause it's like so abstract. That the average person's not going to be able to follow. The other thing is I think it's going to be hard for them to resist. So what's happening now already you could see is the clips where it's just LeBron talking about the turning point where he, you know, when they, before winning his first championship, it's a storytime with LeBron. Storytime with LeBron is always going to get 10 to 100x more views than LeBron and JJ Redick explaining this defensive coverage and how to, how to, how they make adjustments to it. Right. Cause it's like, one is just a juicy story. And the other is like really hard math that you need to learn, the basketball equivalent of math. And so I think what's going to be hard is their editors are going to be like, all right, cool. We should just like, hey, ask LeBron like if he thinks he's better than Jordan because that's going to get 10 million views. Like it's just so there for them. And it's going to be interesting to me to see, do they stick to the spirit of what they wanted to start with, which is X's and O's, real basketball talk, no hot takes, no, no, it's not an interview with LeBron James, which would always do well. It's like them talking about, you know, spacing on the wing, you know, like random, like basketball X's and O's tactics. It'll be very interesting to me to see like 6 months from now what's happening. But you know what? Even if it's just a miniseries, even if they just did like 12 of these, still phenomenal. Amazing for JJ Redick. Amazing for LeBron's brand. Because I watch this, I'm like, oh shit, I get why they say this guy's got crazy basketball IQ. Like JJ Redick will bring up some play that happened 4 years ago. 4 years ago and LeBron's like, I remember.

James the man too, right?

He's such a, he's so good. But he'll bring up something and LeBron will have like perfect photographic memory recall of the play 4 years ago on a Tuesday night in Orlando. And that's just kind of amazing. So for his brand, it's like what The Last Dance kind of did for Jordan where it's like, oh man, Jordan's just amazing. LeBron is also like playing the legacy game where he's building his brand of like, dude, LeBron just knows his shit, man. His basketball IQ is the greatest of all time. He's trying to be the greatest of all time in other ways. And so even if they only do 10 episodes and never do it again, mission accomplished, dude.

But what I liked about Jordan was that he didn't give a shit. Like, he cared. Like, you know, if you asked Jordan to come on the podcast, he'd be like, dog, that's beneath me. Like, not a chance. And I kind of like that.

Yeah, but that's because podcasts weren't good at the time. He went on Oprah and he's smiling and he's, you know, giving away stuff on Oprah. Like, he did the things that were the equivalent of podcasts at the time, right? Like, he was very image conscious. You know, my favorite quote about Jordan, the, the, the, uh, they're like, will you take a stand politically? Like, you know, who do you support for this election? And he said, Republicans buy shoes too.

Yeah.

And so he's like, I'm not gonna comment jack shit about this because I'm here to sell sneakers. And it's like, all right, you know, the guy was very image conscious.

I don't give a shit about sports, but anything LeBron is part of, honestly, I would listen to it. I appreciate like the best talking.

Exactly. There's appreciate greatness. Also, it's just fascinating to see, oh, that's interesting. What would you do if you got the A-list, A++ star in there, still active in their game, to sit down and do a podcast with you? What would you do and how would you do it? How would you set the vibe? Oh, they're popping wine, they're drinking wine because they're both into that, but that gives a different casual feel. They film it in a certain way. As a content nerd, there's a lot to pull from it.

Who's producing it? Do they own it?

Uh, Tommy Alter and, uh, Jason Gallagher, I think, is the, the producer of it. Yeah, they, uh, it's like a collab between JJ's media company that he does with Tommy and LeBron's media company Uninterrupted. And so they came together to create that.

I mean, that's a huge pull for JJ, right?

Oh dude, that's like, yeah, it's like Travis Kelce dating Taylor Swift or something. It's like, Travis Kelce is great, you're one of the great tight ends, JJ Redick was a great basketball player. But goddamn, that's a great pull still.

Yeah, that's a good pull. Um, all right, is that it? Is that the pod?

Yeah, that's the pod.

All right, that's the pod.