Sam opens by breaking down Kid Rock’s surprisingly sophisticated business portfolio — the cruise, the rodeo league, and a Nashville honky-tonk bar doing $30M/year in revenue — as a case study in redneck capitalism done right. Shaan shares what he’s been doing with his information diet: reading annual shareholder letters (Nick Sleep, Buffett), experimenting with AirChat as an early-mover opportunity, paying $500/hour for a dedicated AI tutor, and using expert networks like GLG for competitive intelligence. The episode closes with a discussion of Kirk Kerkorian’s wild billionaire arc (from Cessna pilot to nearly buying Chrysler) and a broader conversation about the podcast market, shelf space economics, and the JJ Redick/LeBron James show.
Speakers: Sam Parr (host), Shaan Puri (host)
Kid Rock’s Business Empire [00:00:00]
Sam: Shaan, I want to show you three things I’ve read in the past week or two that have inspired me. I’m going to start with the strangest one — I’m going to get it out of the way.
Do you listen to Theo Von’s podcast?
Shaan: Not the full episodes — I listen to clips.
Sam: I listen to the full thing sometimes. There was one the other day where I sat and watched the entire thing — I think it was two hours long. You’re going to laugh when I tell you who it is, but his episode with Kid Rock was awesome.
Do you know anything about Kid Rock?
Shaan: I’m going to say I don’t know anywhere near as much as you know about Kid Rock. I could safely assume that. Hands down. I’d bet my life savings on that.
Sam: I have been a Kid Rock fan forever, and Kid Rock is a very fascinating guy. He’s born in Detroit, had this whole rap thing — whatever you want to call that genre. The reason he’s fascinating is that the guys who sold a lot of records in the late nineties are some of the richest musicians out there because CDs were like twenty-two dollars.
How much were CDs when we were kids? Like twenty bucks, right?
Shaan: Yeah, CDs were really expensive.
Sam: Really expensive. And they cost like a dollar to make. So Kid Rock has sold something like forty million albums — which is a shitload of albums. He went on Theo Von’s podcast and about halfway through he starts talking all about business. He’s done some amazing things.
Kid Rock is kind of like Nickelback at this point, where people make fun of him or make fun of you for even liking him. It’s kind of a joke. But dude, he’s a super savvy guy. Let me tell you a few things he’s done.
Have you ever heard of the Kid Rock cruise?
Shaan: No.
Sam: So Kid Rock has a cruise he does every year. You pay like three thousand dollars and you go on a cruise for four or five days. He goes on the cruise with you and plays music every day. It’s an amazing thing.
Shaan: You butchered the name. It’s the “Kid Rock Chillin’ the Most Cruise.” You needed to say that. It’s so funny.
Sam: He’s been doing this for like ten or fifteen years now — since around 2010 or so. And that kills it. But listen to a few other things he’s got going on.
He has the Kid Rock Rodeo. That’s his new thing. Do you know anything about rodeo?
Shaan: You’re just embarrassing me at this point. No, I don’t know anything about Kid Rock. I don’t know about his cruise. I don’t know about his rodeo. You can skip the questions about whether I know Kid Rock’s extensive business portfolio. I do not.
Sam: You’ve never been to a rodeo?
Shaan: I lived in Texas for ten years and I did not go.
Sam: I used to go to them in California at the Cow Palace. You remember the Cow Palace? It’s literally two miles outside of San Francisco — you go just two miles outside of the city and you’re at the rodeo for the night. You’re in Redneck Heaven. I used to go there all the time, it’s so fun. I used to go to dog shows there. I’d watch the Swiss mountain dogs and it was great.
Anyway — Kid Rock now has the Kid Rock Rodeo, which is killing it. Rodeo is up and coming. You know who owns the PBR? It’s the same company that owns Endeavor. Because it kills it.
Kid Rock has started his own rodeo and it has teams, which is a new aspect of rodeo, and it’s also killing it. He talks about the business of this rodeo. He said an owner came to him and was like, “Hey, we’re gonna start this new rodeo — do you want to buy a team? It costs twenty million dollars to buy in.” And Kid Rock said, “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. Now he has the Kid Rock Rodeo where he goes and performs at the rodeo. Very, very fascinating.
Kid Rock’s Nashville Honky-Tonk Doing $30M/Year [00:04:30]
Sam: And then finally — have you ever been to Nashville?
Shaan: Nope.
Sam: In downtown Nashville there’s a street called Broadway. That’s where all the honky-tonks are. Honky-tonks are basically like these kind of crappy dirty bars with bright lights. They call it Nash Vegas — it looks like Las Vegas. I used to go on Saturday and Sunday nights and try to meet all the bachelorette parties. It was like a thing in college.
So Kid Rock, about ten years ago, started something called the Kid Rock Honky Tonk. At this point, that bar sells something like fifteen thousand beers a night.
Shaan: I don’t know how many beers a normal bar sells, but that number sounds like a lot.
Sam: It’s a huge amount. The business does — I was reading about it — this one bar, this one location, thirty million dollars a year in revenue. Insane. It’s a three-story bar in the main strip of Nashville.
Shaan: Is Kid Rock our Billy of the Week?
Sam: Dude, Kid Rock is so fascinating. And on this podcast he breaks down a bunch of the businesses. He says a lot of people think he’s partying all the time. He goes, “I don’t even drink that much. I wake up at four a.m., 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, “I write my morning gratitude journal, then I do the next thing.” He’s so much more put together than a lot of people give him credit for.
This podcast with Theo Von is so good. You have to listen to it. It’s hilarious.
Shaan: Does he talk about all these business things on the pod, or did you look those up?
Sam: No, he talks about a bunch of it. He’s like a really savvy business guy. Our friend Austin Rief — Kid Rock has a family office if I had to guess. I bet Kid Rock is worth about three hundred million dollars.
Austin Rief went to Kid Rock’s house in Nashville because he was organizing a thing for startup entrepreneurs — Kid Rock wants to find cool companies to invest in. And listen to this: his home in Tennessee is a replica of the White House. This guy is basically a redneck with all this money doing exactly what he wants to do. It’s hilarious.
Sam: I’ll tell you one last thing. I’m such a Kid Rock fan that I heard a rumor when I went to Belmont University from 2008 to 2012 that his son went there. So I did a little Googling, found out what his son looks like, and spent months on campus just looking for Bobby Jr. — that was his name, because Kid Rock’s name is Bob, so Bobby Jr.
Months. I’m like, “I got to find this kid. As soon as I see him, I’m going to shake his hand and tell him hi.” The lamest thing you could imagine.
Well, I finally see him on a Friday night when I’m just blackout drunk — I barely remember it. I see him, I go, “Bobby! Huge fan!” I’m slurring my words. “I love your father.” I put my arm on his shoulder, I go, “Here, take my number,” and I grab his phone, type my number in, text myself to make sure I got the right number, and then just tried to force myself on this kid to be his friend. I think I was a junior, he was a freshman. I looked like the biggest idiot. Shockingly, it didn’t work.
Shaan: That was a great sales pitch. Also, “take my number” is a very underutilized way of forcing a connection with anybody. Here — do you have a phone? Take my number.
Sam: It’s because I grabbed his phone so I could text myself to make sure I had the right number.
Shaan: The real number. Yeah.
Sam: It was so embarrassing. But yeah, that’s my Kid Rock story. This podcast with Theo Von — you have to listen to it.
Shaan’s Info Diet: Older Is Better [00:10:00]
Shaan: All right, amazing. I’m tempted to just end the podcast right there and go try to book Kid Rock as a guest. But I’ll give you a couple of things I’m into — nowhere near as entertaining as that.
My understanding was kind of like what you’re saying: I’m watching some different content, a weird new info diet, and I want to tell you some things I’m doing with it. I’ll give you the chapter titles, and then you get to pick which one you want me to explain.
Here are the chapter titles of how I’m consuming content. Number one: older is better. Number two: look to the left. Number three: more with less. Number four: pay for learning. Number five: early arbitrage exploit. Which one do you want?
Sam: Number one. Number five. Number four.
Shaan: All right, number one is “older is better.”
In general, I’m trying to get away from the news feed. The news feed — and actual news — is in many ways an entertainment program designed to find random problems in the world and shove them in your face. Twitter, Facebook, Instagram are kind of the same way. Here’s my life, here’s what I’m thinking right now. It’s useful to a degree, but it’s more addictive than it is useful.
My solution is not to detox — not to just put my phone on silent and leave it in the other room and enjoy nature. That’s not really me either. I have to substitute it with something else.
So I was like: what do I want to read that’s shorter than a book, as informational as reading an S-1 or an annual report like Warren Buffett would, but still has some juice, still has some story?
I found that annual letters — annual shareholder letters, or annual reviews that people post — is a really fascinating place.
Sam: What’s the difference between an annual review and an annual letter?
Shaan: An annual letter is typically when you have shareholders or LPs you’re writing to — your investors, your shareholders. So that’s Buffett’s letters, Jeff Bezos’s letters. I’ll give you a really good one I found: the Nick Sleep letters. You’ve probably never heard of this guy.
Sam: Who’s this guy?
Shaan: Fascinating guy. When I did the podcast with Mohnish Pabrai he mentioned Nick Sleep, and I started looking into it. I found like ten years of this guy’s annual letters.
The short story: him and his buddy started buying stocks — investing on behalf of other people — did so well over like a ten to fifteen year period that they basically just retired. His portfolio at the end was Amazon, Costco, and Berkshire Hathaway. Three stocks. And I just love somebody who can absolutely crush the market without going down some obscure rabbit hole. He just identified correctly early on that Amazon, Costco, and Berkshire were good bets to be in and stayed with those. Rode those ponies till the end.
Sam: How big was the portfolio?
Shaan: These guys got filthy rich. I don’t know exactly the AUM off the top of my head, but in a very short period of time they got very wealthy. I just started the letters — I read the first one last night — so I’m pretty fresh on it.
Sam: I like Nick Sleep. When you Google him, the first thing that comes up is his legendary letters.
Shaan: And I think some people have bound them into a Kindle book.
Sam: Whenever it’s something like that — last time it was like this it was the Boron letters.
Shaan: What’s the Boron letters?
Sam: This guy was one of the best copywriters. He wrote a bunch of letters from jail to his son. It’s like, dude — this sounds like season two of Prison Break mixed with my copywriting course. I’m in. Give me that.
Shaan: So I’m really into these annual shareholder letters and annual reviews. We have a few friends — Sahil Bloom does this every year. He posts an annual review on his blog, goes back and says here’s what I did this year, here are some highlights, here are some low lights. Nathan Barry from ConvertKit does the same thing. He’ll be like: thing one, my family; thing two, ConvertKit; thing three, I bought some Airbnbs — here’s the occupancy, here’s how much money I made, here’s what was a pain in the ass.
People who share that type of information are just very interesting to me. It’s a quick read. I’d rather spend thirty minutes reading that than thirty minutes aimlessly scrolling Twitter.
That’s my number one.
Early Arbitrage: Getting on AirChat [00:17:30]
Sam: All right, what’s the last one? Early arbitrage exploit.
Shaan: I tried to put all my power words in there to hook you. I wanted to talk about this.
Have you seen AirChat?
Sam: I know Naval has some kind of new social media thing and it’s invite only. That’s all I know.
Shaan: It’s not invite-only anymore. As of like two days ago they opened it up to everybody. They pivoted it — AirChat had been in beta for a few months. I checked it out before, I was like this is okay, wasn’t super engaging, kind of confusing UX, a little slow to consume.
Sam: Is it like Twitter but better?
Shaan: So the new version — forget the old one, it’s gone anyway. The new one is basically like: imagine Twitter but voice-first. To post, you just talk into your phone. You don’t type — you just talk. But it auto-transcribes using AI, and it speeds it up like 1.3x. So when you’re scrolling the timeline it just starts playing somebody’s audio, or you can read the transcript. But it plays a little faster, so you’re almost listening as fast as you could read, which is kind of interesting. And you get to hear their voice.
The generous version of this is: it’s a really cool new social media format. New formats matter, right? Twitter was a short-form format. Vine was a six-second looping format. TikTok was a different short video format. Formats mean things — that’s where the big breakthroughs come from.
The other side of it is: it’s kind of like if you turned on accessibility mode on your phone and opened Twitter. Like, hey, 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 invites only their interesting friends, that place is a very interesting place for the first ninety days. Who knows if it’s going to be successful — you get a call option on it. So I’m like, screw it, I’m all in on AirChat for the next like seven days. I’m going to completely ignore Twitter, YouTube, podcasting, whatever, and just go hard on AirChat.
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. 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.
The same thing happened when Clubhouse came out. I didn’t think Clubhouse was going to last forever, but I told my buddy Jason — I always thought Jason was interesting — and I was like, “Jason, quit your job and just be on Clubhouse ten hours a day for the next thirty days. Watch — you’re going to build your company.”
We had gotten acquired so I was like, “Just check out. You’re at Twitch, check out now. Nobody will know. Trust me — there are two thousand people in this place and nobody does anything. Just stop doing work and get on Clubhouse 24/7.” He was like, “Well, you know, I gotta—” No, no, trust me. You’ll get more value out of this than 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 million-dollar crypto fund out of it, made a couple million bucks, returned their money. Made lifelong friends who go on trips together in real life now. None of that would have been possible without Clubhouse.
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 you curated an early group of people and were hellbent on making it a great experience for them. So the first hundred days were the best hundred days of that whole product forever, just because of what the early group was.
Sam: Well, I hope not. I mean — no, it’s okay. It’s like in dating. There is a honeymoon period for products, for people, for relationships. “Let me get the door for you, let me take out the trash, let me send you a little gift on a Wednesday.” You behave a little differently at the beginning of a relationship than you do seven years in.
Do you think AirChat is going to be better than Clubhouse and actually work?
Shaan: Too early to say. I’ve only been on it for like two hours, so let me not do a hot take conclusion just yet. But it’s interesting for sure.
Paying $500/Hour for an AI Tutor [00:24:00]
Sam: What’s the fourth one? Pay for learning?
Shaan: Pay for learning. This is instead of going out there and trying to get smarter about something — in this case AI — I was like, why is it that as adults we never go to school, take a class, or have tutors?
So I hired an AI tutor.
People were like, “What is an AI tutor?” And I was like, dude, AI is changing so fast. Literally every three weeks there’s a new mind-blowing paradigm shift. There’s thousands of companies getting funded, new models being released, a new talk or interview dropping where Sam Altman says something interesting. I couldn’t possibly keep up with it all — it’s a full-time job.
One way to stay current is to read a newsletter or join a group chat. That’s good. But what I decided was: how do I spend money in an interesting way here?
I basically pay this guy five hundred bucks an hour, and his job is every week to come to the table and tell me the three or four most interesting things he’s seen. He lives in AI world full-time. He has to bring me three or four of the most interesting things he’s seen. And then I usually ask him a question: “Hey, I saw people talking about this — what is it?” or “Chamath said this thing I didn’t understand — what the hell is he talking about?” or “In my business I have this problem — is there an AI tool that could actually solve this?” He does the research and comes back with an answer.
This has been such a hack to stay smart about AI while shaving my time commitment. Yes, I’m paying him five hundred dollars for one hour, but I’m saving eight to ten hours of my own time. I put it out of my brain. I have a focused sixty to ninety minutes with him and he tells me everything I need to know.
Sam: Have you ever used GLG? Do you know what GLG is?
Shaan: I know what GLG is. I was on the other side — I was an expert on GLG.
Sam: I did it too. Basically GLG originally started because bankers who were going to take a company public, or wanted to invest a large sum — let’s say MailChimp is going to get acquired by Intuit — would go find people like me who use MailChimp-type services and ask us questions. Like: “If MailChimp raised prices, what would you do? How would you react?” So they could get a read on the market.
Now there’s GLG, there’s Tegus, there’s also Intro, and you can charge like two, three, sometimes five thousand dollars an hour to be an expert.
Shaan: Dude, I’ve been using it on the paying side — paying money to get insights. It kind of feels like cheating. You can tell GLG or Tegus that you want to talk to someone who works at or worked at your competitor, and you can get so much information from them.
I read — I think I told you about this — the Stevie Cohen book. He’s one of the largest hedge fund guys out there. One of his guys went to prison for many years because what they would do is use GLG so much that they would befriend the experts, fly out to the expert’s home, get them to reveal confidential information they weren’t allowed to reveal, and then trade on that information. Which is insider trading. It’s so powerful — I’ve been able to use it on the paying side and it’s been really amazing. I’m shocked I haven’t done this for years.
Sam: Have you ever paid money on one of those networks?
Shaan: I’d never done it before because I’m like, paying somebody two thousand dollars an hour — it makes sense for most customers because they’re making very large investment decisions. If I can get better information for two thousand, five thousand, ten thousand, twenty thousand dollars — it doesn’t matter when I’m taking a ten-million or eighty-million-dollar position on a company. I’ve never been in that position.
Sam: So how do you justify paying that much for yourself? What are you paying for and how do you justify it?
Shaan: I’ll give you an example. Let’s say Hampton — a peer business, a community business, there are like five competitors out there. A couple of them are quite big. I’m curious how they’re acquiring users. So you just sign up and say, “I want to talk to the director of marketing at this company.” They go find a former marketing executive at that company, and you can just ask: “So, how are you guys acquiring customers? Did LinkedIn ads work?” And they go, “LinkedIn ads didn’t really work, so instead we did X, Y, and Z.” You can ask all these questions and hopefully save yourself a year of making the same mistakes other people already made in your industry.
Sam: Yeah, I think it’s more of a scalpel than a blunt-force hammer. It’s a very precise instrument. You only want to use it for very specific types of questions where the tradeoff makes sense.
Shaan: Right. And on the Ecom example, I’ve been on there and people would be like, “Hey, you use Triple Whale — we’re looking to talk to an expert who uses Triple Whale. We want to know: did you evaluate three or four other competitors? Why did you choose Triple Whale?” And it’s like, yep, I evaluated the competitors, here’s the difference.
They really couldn’t do that any other way, because they’re not operators. When they’re making a big investment decision, they want to go in with real information versus theories.
Kirk Kerkorian: Pilot to Billionaire [00:32:00]
Sam: All right, let’s do another one. You have anything else?
Shaan: I’ve got a book I think you should read. I read this years ago and just recently reread it because it’s so good. I bet you’ve never heard of this person.
Kirk Kerkorian. Does that ring a bell?
Sam: That kind of does ring a bell.
Shaan: All right — Kirk Kerkorian. Born in the early nineteen hundreds, like 1920 or so. Armenian immigrant family. Born in Fresno, California. Spoke Armenian, didn’t even speak English. Eventually drops out around eighth grade. Not exactly the rich part of the rags-to-riches story yet — he comes from nothing, parents were farmers, grew up poor.
Learns how to fly a plane because World War II is coming and he doesn’t want to be shooting guns. Goes into the Air Force, learns to fly. After the war, he saves up enough money to buy a Cessna — one plane, for five thousand dollars. And his first business is flying people from California to Las Vegas.
This is in the fifties and sixties. 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. He starts getting into gambling while he’s there as well. Through his gambling and his small charter business he starts buying more and more planes.
Over about fifteen years he builds a meaningful business. By the time he’s forty-three or forty-four years old, he’s making the equivalent of like two million dollars a year in profit. He sells this airline business for ten million dollars, which is the equivalent of about ninety million dollars today. He sells it in his forties.
And that’s really where things start taking off.
Sam: Then what?
Shaan: With that money he buys a plot of land and turns it into the Pink Flamingo Hotel — one of the first big epic gambling hotels in Las Vegas.
Sam: Wait, the Flamingo? Just — that’s hilarious.
Shaan: Yeah, that’s his thing. And by the way, while he’s there, one of the waiters who works for him has a son. Kirk always treated this waiter really nicely. The waiter eventually names his son Kirk — first name Andre. So Andre Kirk Agassi — the famous tennis player — is named after Kirk Kerkorian.
Sam: No way.
Shaan: Yeah. Because he’s known as a good employer, a good guy. He takes his little casino, parlays it, keeps growing. By the time he’s in his fifties and sixties he starts buying other companies. He buys MGM, which at the time was a movie production studio. And after years and years of doing this, he eventually parlays all of it until, at eighty-five years old, he buys ten percent of GM. And at eighty-eight years old he tries to buy the entire Chrysler company — almost gets it done at around thirty billion dollars.
What’s interesting about this guy: Kirk Kerkorian never had formal education. He’s a Wall Street type who’s not actually on Wall Street. He buys all these companies with no education. He’s very private — there are like three or four interviews ever about this guy. He has balls of steel. He’s a nice guy but a hard negotiator. He puts his money where his mouth is. And he does this until the age of ninety-four when he dies. To the day he dies, he’s making deals.
He’s really low-key, dies with a net worth of about five billion dollars. If you’re into capital allocation, this is your guy.
Sam: I have to apologize to Kid Rock — I thought you were going to be the Billy of the Week, but actually it’s this guy. The Andre Agassi thing was just the cherry on top for me.
This seems almost impossible to me — though I’m clearly wrong. A pilot who starts chartering flights turns into someone who buys ten percent of GM and tries to buy Chrysler for thirty billion dollars. How did he compound at that rate for that long? That’s insane.
Shaan: The book is called The Gambler. Really good book. Basically he’s like, “I’m a gambler at heart — I love gambling. I’m in it for the thrill.” But he caught a couple of trends. The first being Airlines — his airline was kind of rinky-dink and he just bootstrapped it for fifteen years. He started the airline when he was around thirty-two, right when he got out of the war. Wasn’t really a hit until he was forty-four. Good business, but not an epic thing. But he sells it for ten million, then two years later buys it back, runs it three more years, then sells it again — this time for a hundred million.
The trend he caught was that airlines weren’t a big deal yet. They didn’t have these massive barriers to entry like you’d think of today where you need tens of billions of dollars. Starting an airline today seems insane — it wasn’t like that then.
Same thing with Las Vegas. The plot of land he paid for — I think it was eight hundred thousand dollars. Then he spent a couple million more to build the Pink Flamingo. He just got these early hits by catching these trends — Vegas, airlines — and he caught them all early.
But here’s the inspirational part: he wasn’t really a baller until his mid-to-upper forties. And he was in the game for literally ninety-five years when he died.
Compounding, Buffett, and Runway [00:40:00]
Sam: Yeah. Mohnish Pabrai said when I talked to him — there are three variables that matter when it comes to wealth. He said it’s all about compounding, and it’s either the rate you’re compounding, the length of the runway, or the amount you started with. You can pull any of those three levers. If you start with a huge amount you don’t need a high rate or a long time. If you start with a low amount — which is where most people start — you need a high rate and a long time, or an explosive high rate and not that long.
Shaan: And if you look at Buffett, his thing is that he compounded for the longest time. Bought his first stock at eleven years old. At ninety-five now — if he hadn’t given his money away he’d be the wealthiest man in the world. Because he had an eighty-year runway. It’s not that his rate was absurd, it’s that the rate was consistent and it was eighty years. In compounding, the bulk of the wealth is always in the last two or three turns because that’s just how compounding works.
Sam: People say that, and you’re right when you say it, but it almost discredits Buffett. If you read his biography or his early annual reports — even when he was like thirty-five or thirty-eight, he had something like fifty million dollars in assets. He was killing it for a long time.
Shaan: Both can be true. Fifty million is still killing it, and fifty million is not the same as ninety billion.
Sam: Yeah, for sure. But if you read about him — I think he said when he graduated college he had a hundred thousand dollars of his own portfolio. In the forties, that’s like having two million dollars. And his early compounding was like thirty to fifty percent for six or eight years in a row. He was kind of the man from the beginning.
Shaan: When that episode comes out you’ll like it. Mohnish is basically a Buffett historian and a Munger historian. He knows year by year what Buffett was doing, what he was investing in, how much he had. He charted it out. He gave me an oral history of Warren Buffett in a way I’ve really never seen. And I loved it because I’ve met a lot of people who are very successful, and then it’s like they’re not students of the game the same way I am. I’m like, “Did you ever go back and read all the letters and deconstruct them?” They’re like, “No, I was just doing my thing.”
Or I’ll meet great investors and I’m like, “Do you write memos? Did you go back and review them? Do you track your hit rate?” The nerdy stuff I like to do. And more often than not the answer is actually no — “I just focus on what’s in front of me and do that thing.”
So it’s really nice when I see somebody who wins with the same play style I have, where they’re a nerd about it, they go back and chart things out and break things down and analyze it, try to reverse engineer lessons from it.
Sam: What was your takeaway after talking to Mohnish?
Shaan: It was reassuring. It sounds silly to say but it’s true — whenever I meet a more successful person than me who does things the way I do them, I feel good inside. I feel reassured like, oh, that’s cool — this person’s method can work. I already believed it could work, why else would I be doing it? But it’s more conviction that it 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 — similar demeanor, similar philosophy, similar approach, similar work habits — I like finding people who have a match. Because it’s very hard for me to change my nature, my work style, my habits. It’s actually better for me to double down, make them super strengths, and find other people who’ve won using those same strengths and learn from them — versus trying to become some different guy playing some other style I’m not familiar with or haven’t done for fifteen years.
Mike Novogratz’s “Business Untitled” Podcast [00:47:00]
Sam: Let me wrap up by telling you one last thing. This one’s going to be short because I’m not terribly well-versed on it — you’d know this guy better than I would. Mike — what’s his name? The crypto guy?
Shaan: Mike Novogratz?
Sam: Novogratz. So I think he started or helped start Fortress, which is a massive hedge fund. He’s got a new podcast called Business Untitled. Right now on YouTube I think it has about thirty-eight hundred subscribers, even though they’re like fifteen or thirty episodes in. His podcast is so good.
It’s him and this other guy named Mike Barry. Mike Barry is a real estate guy — owns a chain of really high-end hotels. It’s sort of like the All-In podcast, where it’s like billionaires talking about stuff. But these guys have a weird blue-collar, down-to-earth vibe where they’re like, “We weren’t born wealthy and we still remember where we came from.” They’re talking like they’re small business owners except the numbers are absolutely massive.
It’s a beautiful, wonderful podcast. You’ve got to listen to a few episodes.
Shaan: I’m so jealous of their thumbnail style. It’s just like dollar bills — it’s freaking awesome.
Sam: I wish you hadn’t said that. I wish you could have just shown this to me and I’d have been like, “Let’s steal this.” Because it’s such a good thumbnail style.
Shaan: They only have like thirty-eight hundred subscribers. So you’re saying we can steal it — nobody will know?
Sam: Yeah, we can steal it. The podcast is so good. They have amazing guests — they’ve had Snoop Dogg on recently, the founder of Equinox, a bunch of really big names. They just shoot the shit. And they tell stories about starting Fortress Capital and Wes Edens — who started Fortress — eventually buying railroads or something. They tell the stories with this weird blue-collar, down-to-earth style. I’ve been digging it.
Shaan: That’s a big endorsement. I like that.
The Podcast Market: Shelf Space Is Tiny [00:51:00]
Sam: I’ve got to ask you — what do you think about the fact that so many people have podcasts now? When we started this — four years ago roughly — we were not early to the podcasting game. We were a decade-plus late. Felt late at the time. But since we started it’s now incredibly common. If you’re anybody, you start a podcast. Investors, business people, athletes — it’s kind of amazing.
One of the ones I was going to mention is Jay Redick has a new pod with LeBron James. Did you see this?
Shaan: I saw that. It’s awesome. LeBron is podcasting. What the hell is going on.
Sam: I love the athlete ones. A lot of the UFC guys are doing them now too. Kamar Usman has one. What’s your take on where this goes? Where does everybody starting a podcast end up?
Shaan: A: I love it as a fan. I enjoy listening to them. B: I don’t think they’re going to last that long. I think it’s a lot harder than people realize to do it for a really long time.
When you first started this the common thing was, “You guys are going to run out of stuff to say.” I haven’t really felt that much — there are some times where I’m like, what else can we talk about, but that’s only happened ten percent of the time. I don’t think they’re going to run out of things to say. But I do think it could be a lot harder work. I’m shocked Tim Ferriss has done it for ten years. It’s a lot harder to do this for many years than people understand.
Sam: Do you agree with that?
Shaan: Yes and no. I think there’s a different problem. On the running-out-of-content thing — most people will choose the interview format, which has an infinite runway. You just bring someone on, ask them questions, bring another person, ask more questions. What we do when we don’t have a guest is a lot harder to sustain long-term, because it’s like: how many interesting things are me and Sam going to generate of original content? Reacting to news, doing interviews, reacting to TV shows — those formats always have infinite runway. I think most people will do those and won’t run out of content.
The problem is something different. How many podcasts on average are you listening to at any given month?
Sam: Five. And I’m a power user.
Shaan: Maybe three to five. Not a lot. The shelf space is just really goddamn small.
I don’t think people realize this. I think they think it’s like social media — like, “Oh yeah I use Twitter, I use Instagram, oh TikTok comes out, I’ll use TikTok too.” On social media, if your content is even remotely interesting, people can follow you and see it. I can follow five thousand people on Instagram and scroll through content from two hundred people in thirty minutes.
But the shelf space on podcasts is tiny. People listen to one, two, three in rotation on average. So the question is: can you break into enough people’s top one, two, or three podcasts? And you’re going up against a habit they might have had with other podcasts for five years.
The hope is they expand the market — new people start listening to podcasts. I’m sure that’s going to happen to some extent. But the supply-demand is so off. The demand is so small — the number of podcasts somebody will regularly listen to — that it doesn’t matter how many new people create a podcast. The shelf space is too small.
Sam: You do realize it’s over twice as many people listen to radio than podcasts? If you go where I’m from and talk to some people, they’re like, “What’s a podcast?” There’s still a lot of market penetration left, particularly among a general population. Like someone who cares about LeBron — an athlete is going to get significantly more new listeners.
Shaan: What I’m saying is I think the best podcasts in every category are going to grow. There’s still ten times more headroom for them. However, the number of winners is very small in podcasting versus on Instagram. On Instagram there are so many winners — so many people who have followings, even small ones, just enough to keep you engaged. It’s very hard to be a winner in any category in podcasting. Let’s say you want to start a true crime podcast or a business podcast or a sports podcast — the ones at the top are going to keep getting more and more downloads. Because you have an audience now, so it’s easier for you to do it. To do it from scratch without an audience, I think it’s basically impossible.
Sam: Even people who have some audience — it’s very hard to boot a podcast up.
Shaan: The shelf space problem is my take on the limiting factor. There are only so many humans who listen to podcasts, that number is growing, but what’s not growing is how many different podcasts they’re going to regularly listen to. They only have so much ear time.
JJ Redick and LeBron’s Basketball Pod [00:58:00]
Sam: Is the JJ Redick and LeBron one good?
Shaan: I would say it’s amazing — and I mean that in the literal definition of the word, not like the content is amazing. I am amazed that this is happening. I am amazed that LeBron James is sitting down and explaining to me the Gortat screen. Like, what’s the Gortat screen, and he’s explaining how it works. I think they really need to work on overlays though — it’s way too X’s and O’s. They need actual clips of what they’re talking about, because it’s so abstract that the average person is not going to be able to follow.
The other thing is I think it’s going to be hard for them to resist the easy clip. What’s happening already — you can see it in the clips — is it’s just LeBron talking about the turning point before winning his first championship. Story time with LeBron is always going to get ten to a hundred times more views than LeBron and JJ explaining this defensive coverage. Because one is a juicy story and the other is basketball math you have to actually learn.
So what’s going to be hard is their editors are going to be like, “All right, cool — hey, ask LeBron if he thinks he’s better than Jordan, because that’s going to get ten million views.” That’s just so there for them. It’s going to be interesting 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, not an interview with LeBron James, but them actually talking about spacing on the wing. We’ll see what happens in six months.
Sam: You know what — even if it’s just a miniseries. Even if they only did twelve episodes, still phenomenal. Amazing for JJ Redick, amazing for LeBron’s brand. Because I watch this and I’m like, oh shit — I get why they say this guy has crazy basketball IQ. JJ will bring up some play from four years ago and LeBron will have like perfect photographic recall of that Tuesday night in Orlando. That’s just kind of amazing.
For his brand it’s like what The Last Dance did for Jordan — oh man, Jordan was just amazing. LeBron is playing the legacy game where he’s building this brand of: dude, LeBron just knows his shit. His basketball IQ is the greatest of all time.
Shaan: But what I liked about Jordan was that he didn’t give a damn. Not about his legacy — he cared — but he would never do something like this. You ask Jordan to come on a podcast and he’d be like, “Dog, that’s beneath me. Not a chance.” He did the things that were the equivalent of podcasts at the time — he went on Oprah, he was smiling, he was giving away stuff. He was very image conscious.
You know the great Jordan quote? They asked him, “Will you take a stand politically, who do you support for this election?” And he said, “Republicans buy shoes too.” He’s like, I’m not going to comment on any of this because I’m here to sell sneakers. The guy was very image conscious.
Sam: I don’t give a damn about sports, but anything LeBron is part of I would listen to. I appreciate greatness.
Shaan: Exactly. Also it’s just fascinating — what would you do if you got an A-list, A++ who’s still active in their game to sit down and do a podcast with you? How would you set the vibe?
Sam: They’re popping wine — they’re drinking wine because they’re both into that. That gives it a different, casual feel.
Shaan: They film in a certain way. As a content nerd, there’s a lot to pull from it. Who’s producing it?
Sam: Tommy Alter and Jason Gallagher, I think. It’s a collab between JJ’s media company that he does with Tommy, and LeBron’s media company Uninterrupted. They came together to create it. That’s a huge pull for JJ.
Shaan: Oh dude, that’s like Travis Kelce dating Taylor Swift. Travis Kelce is great — he’s one of the great tight ends. JJ Redick was a great basketball player. But God damn, that’s a great pull.
Sam: Still. That’s a good pull.
Shaan: All right, is that it? That the pod?
Sam: Yeah, that’s the pod.
Shaan: All right. That’s the pod for today.