EPISODE
744

The man who made a billion off blueberries

Sep 12, 2025·78:00·Sam & Shaan·Listen·AppleSpotify
0:0039:0078:00
14 moments · 273 paragraphs · synced to the second
SHAAN

This guy's story is kind of amazing. So this is basically a farmer billionaire.

SAM

Love it.

SHAAN

In. In. I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel. Never look back. Okay, let me give you this one. This is kind of a crazy story. So do the words John Bragg mean anything to you?

SAM

No.

SHAAN

They don't. Didn't mean anything to me either. Shout out to, uh, Shane Parrish over at Farnam Street. He did a great podcast with this guy that caught my attention. Um, this guy's story is kind of amazing. So this is basically a farmer billionaire.

SAM

Love it.

SHAAN

In, in. Like, there was only two sources for this. Farnam Street and the Van Trump Report had written about this guy. There's only things I could find. Yeah, he's got a biography as well. But, um, all right, so So here's this guy's story. I just think there's a bunch of factoids about this guy that I just think you're gonna love. You're gonna love this guy's whole aura, his vibe. He is the Billy of the Week. Cue the music. A million dollars isn't cool.

SAM

You know what's cool? A billion dollars.

SHAAN

John Bragg. This guy grows up on a family farm, like a sawmill or something like that. And when he's in high school, you know, what do teenagers do? They start to experiment. They start to dabble. Maybe a little bit of, maybe girls, maybe weed. No, no, blueberries. He tries to harvest blueberries for the first time at 13, 14 years old. You know, he starts to, he gets the itch and then he goes to a local blueberry farmer. He decides, hey, can I pick blueberries for you? And he picks blueberries all year. His last year of high school, him and 4 or 5 other blueberry pickers end up making $4,000 each picking blueberries, which was a lot of money at the time because this guy's very old. And he realizes, oh wait, I can pay for college if I just pick blueberries every year. And so he's making— college was like $10,000 or $12,000. He's making $4,000. He realizes, oh, I can do this. My parents otherwise weren't really going to be able to send me, but I could do this. And so he makes more money the next year and the next year picking blueberries. Finally, when he graduates, he's got a couple options on the table. Uh, you know, plan A was going to be to become a teacher, and he was going to make, I think, like $3,800 or something like that, being a teacher, an extra $100 if he coaches like the, the, the basketball team or something. And plan B was, let me go work on the family business, maybe over time buy out my dad on the sawmill. But he decides to go plan C. He's like, I think this blueberry thing, there's something to it. And he decides to start his own blueberry farm. So he buys a little piece of land and he starts trying to harvest blueberries. And it goes pretty well the first couple of years. He's doing all right. But a couple years in, he— there's a problem in the blueberry industry, which was that one year there was just huge supply glut. So there was way too many blueberries, not enough buyers, and prices crashed. And so he's like, shit, you know, could have quit. But he's like, no, no, no, I'm just going to figure out what I should have done differently. He's like, I need basically like a backup plan, a sort of, you know, an insurance. And he wasn't doing financial insurance, but he's like, I need another way to make money in case this ever happens again. Never again will I let this happen to me where I'm at the mercy of the prices. And so he decides, I think I need to build a packaging and freezing plant for blueberries. Now he's got no money, but he's like, uh, I'm gonna try to do this. So he goes to the other blueberry farmers. He says, hey guys, we all just got whipped. Let's put some money in together and I'm gonna build this plant and then you can use the plant too. You could freeze and package your stuff too if it ever, if we ever have oversupply. And so they do that. He borrows money from the bank. He gets money from the other farmers. He starts to build this thing. Never, no experience, by the way. No manufacturing, no factory experience, but he's like, I can do this. So he builds this plant, and in the first year that they build the plant, he's ready for 2 million, uh, like a capacity of 2 million, but they only produce 100,000 because there's this crazy frost that kills all the blueberry production that year., and he's like, oh my God, I owe so much money. And I, and like, we came in at like 5% of the, like, the estimated, like, freezing capacity. This is terrible. I have this empty factory now. I owe a lot of money. And basically it's like, dude, you gotta just let this go, declare bankruptcy, move on with your life. Instead, he calls another guy, uh, who he knows, this guy, uh, McCain, and he's like, McCain, he's like, yo. What's something you need to make, but you don't want to make? Is there anything? Give me the last thing you want to do, but you should do it. And the guy's like, all right, I got you. Onion rings. He's like, onion rings? Okay. He's like, I, he's like, can you send me like a file? Like about, so he gets like a little book on how to make onion rings. And he's like, all right, say less. I'm never going to ask you another question. I will figure this out from here. And so he, he's got an empty factory, but he turns it into like just for that one season or whatever. He makes onion rings for this guy. It just tides him over enough to continue. And so he carries on and he ends up building something called Oxford Frozen Foods, which today controls about 40 to 50% of the global supply of blueberries. It's like 70 million pounds of blueberries they're making every year.

SAM

Do they still have onion rings and blueberries and onion rings and mozzarella sticks on their website?

SHAAN

You never forget. You never forget who got you there. And so he builds this absolute juggernaut over time and they become bigger and bigger and bigger. His brother invents this like blueberry picker that can do the work of 35 like humans doing this. And he's like, oh, amazing. And then what he does is he actually like gives it out, basically like freely shares it with other blueberry farms too. He's like, he's like, what's good for one is good for all. Here we go. And so he wants the entire blueberry industry to grow because he's like, the more the blueberry industry grows, the better we all do. I don't want to be the biggest fish in the smallest pond. I want the pond to get bigger., and we're competing with all the other fruits out there. So if we can up our production and we can have more blueberries, we can build more innovative products. This is going to be good for everybody. And so he's got this very interesting business philosophy. He ends up then going into a new business. So it's, um, many years later, uh, actually, I, actually, I think he kind of did this around the same time. I shouldn't say many years later. I don't know the exact date on this, but it wasn't like once he is already like huge. It was like somewhere, somewhere around that same time. TV was picking up and cable, cable TV was picking up. And this guy's from Nova Scotia, population 9,000. And so they held a, like, an auction. They were like, hey, all right, who wants to buy the cable TV rights for Nova Scotia? Nobody shows up. He's the only guy there. And so he picks up the cable TV rights for that area and he's like, all right, I don't even know what to do with this. Like, I guess I'll put like some old recorded programming on here. There's like no programming basically. But he's like, whatever, let's do this. And so he's in that business and he's losing money the first couple of years. And his dad's like, bro, you got to figure this out. Like this, you can't just keep bleeding money over here. And so he cuts his costs. He tries to figure this out. He finally gets it to like kind of a, like a break-even point or whatever. He ends up over the next, you know, couple of decades building the largest private telecom company in the country. And he owns cable TV networks, you know, everywhere. He does a bunch of acquisitions. He takes on a bunch of debt and he ends up buying up Others, and he goes down, uh, he goes like sort of down, uh, the stack. So whereas most TV companies want to do the sexy fun stuff, they get into original programming and content and they're like, content is king. He's like, yeah, no, yeah, you know what's king?

SAM

Fiber.

SHAAN

Like, I'm going to go own the underlying infrastructure for, for cable TV. And he ends up building this juggernaut. And so this guy ends up now, he's like, whatever. Uh, like, you know, much older now in his 80s or something like that. And he's worth $1 billion. He built the largest farm, uh, fruit farm basically in the world. And he's built the largest, largest private telecom company in the country. Isn't this kind of amazing?

SAM

This is amazing. I've, I'm, as you're telling me this, I'm, I've noticed there's a trend amongst this era of people. Was this, was he doing it right when cable was getting started? Yeah, man. There's, uh, there's a trend. So Ted Turner, who eventually went on to start CNN, He owned a billboard company, which he parlayed into a radio station and then eventually a cable news network, CNN, Cable News Network. Do you know another guy named Jim Pattison? Have you heard of Jim Pattison?

SHAAN

No.

SAM

Who's that dude? Google Jim Pattison. Another Canadian guy. Look at what he looks like.

SHAAN

He's like, oh, yeah, yeah, yeah. I've seen this guy before. He's like one of the richest guys in Canada, right?

SAM

Yeah. He's like, he's like one of these guys who is like, he's like an Energizer Bunny. Like, he, like, he is like a wind-up toy. Like, he just can't stop. Like, moving, but he— I think his story was he, at a young age, opened up a car dealership and within 3 years he bought like a plastic manufacturer or something very like out of left field. And then another thing and another thing. Now he owns a telecommunications business, but he also owns like Ripley's Believe It or Not. And I think that like the Pattison Group, which he owns the whole thing, I think has 100,000 employees or something insane like that. And then another one is, his name's John Cat. His last name is crazy. I'm gonna butcher it.

SHAAN

Cat, uh, Katzman— Katzmanzeditis?

SAM

Yes. Is that it?

SHAAN

He's got a condition. Katzmanzeditis.

SAM

Do you know him? Do you know him? No. So he started a grocery store. Uh, I think it was called Apple Foods.

SHAAN

Dude, lemme just tell you this. Any guy who looks like this, if I just showed you this photo and I said rich or poor?

SAM

Yeah. You already know everything about him just by looking at him.

SHAAN

One photo.

SAM

Yeah. Like when he, this guy, when he gives you a handshake, he's pulling you in. Do you know what I mean? You can just look at him and you know what he's going to do. He's going to pull you in. He's going to smack you really hard on the back shoulder. Yeah.

SHAAN

And no chance this guy has one wife, by the way. Let me just look this up. I bet you, I'll bet you anything right now. Let's just Wikipedia.

SAM

If you Google his kids, they're beautiful. First wife, divorce.

SHAAN

Yeah. New wife, Margot.

SAM

Uh, this guy started, um, Apple grocery store. It's like a 20—

SHAAN

what?

SAM

It's a 20-store chain in New York City. Like, it's tiny. But then he bought a radio station, and then, uh, that's like how he got extra rich. And then I think he also bought a cable news network as well. And so my point being is there's this refining company, and then he owns an energy company, like an airline. I think he owns like a small private airline. He owns everything. There's this type of entrepreneur where they're kind of cowboys, where they start in one thing and they get into media eventually. And a lot of it happened in the '80s, the late '70s and the early '80s when cable was getting popular. And it was sort of like the first version of, of a, of a SaaS business. You know, it was recurring revenue, huge TAM, kind of weird and unknown. People weren't sure what to do. And I believe that a lot of the cable news networks they were regulated by, uh, the FCC and you had a certain satellite, like you could only own X amount of satellites. Like there was some type of like limiting blocker where only a certain amount of cable companies could even exist. And so if you were able to like get in on that, it was almost a near monopoly. Ted Turner came along and he was one of the first guys that were like, uh, petitioned Congress and was like, this is nonsense, we need more competition. And that's when CNN came about.

SHAAN

But this whole era, it's like, I like how sometimes when we explain these things, it's kind of like when I explain stuff to my kids, like they're like, How does, um, like, how does the picture come on the TV? Like, where is this coming from? And I'm like, oh, um, satellites. And they, and they're like, but how does it get from a satellite to our TV? I'm like, it shoots it. It's shooting Gabby Dollhouse at our, at that tower. I think, I think that's what the cables are for, or maybe that's electricity. I'm not sure exactly what's going on. It doesn't matter though, just go. But you're like they ran, there was only so many satellites. You had to buy these letters, but they only had so many letters. No one had the letters, okay? The fibers were in limited supply.

SAM

I do know that it is true.

SHAAN

There's some spectrum available.

SAM

There's like a, yeah, yeah, we know a lot about spectrums. Uh, there was, I do, I do know there was a famous like, um, like hearing where Ted Turner like made this passionate speech to like politicians to convince them that they have to change the rules to allow small upstarts to, to get a satellite. Uh, but anyway, that's cool. I like this blueberry guy. All right. So a lot of people will talk about how you need a million dollars and 3 years of experience to start a business. Nonsense. If you listen to at least one episode on this podcast, you know, that is completely not true. My last company, The Hustle, we grew it to something like $17 or $18 million in revenue. I started it with like $300. My current company, Hampton, does over $10 million in revenue. Started it with actually no money, maybe $29 or something like that. Nothing. And so you don't actually need investors to start a company. You don't need a fancy business plan, but what you do need is systems that actually work. And so my old company, The Hustle, they put together 5 proven business models that you could start right now today with under $1,000. These are models that if you do it correctly, it can make money this week. You can get it right now. You can scan the QR code or click the link in the description. Now back to the show.

SHAAN

Let me give you some of his, uh, his little business-isms, his philosophies. Okay. So. And this is again, some of this from, uh, from, from Shane Parrish's stuff.

SAM

And I can just tell this guy is he Canadians are in Midwestern people where I'm from. They're the same, the same people, aren't they?

SHAAN

Yeah. It's like a species in its own. So here's a great line by him. I have no reverse gear. I just thought that's an amazing line. Um, which is like, he's like, yeah, you know, when things got hard and the blueberry crop died and then the factory is empty, like I just didn't consider going backwards. I did not consider— like, it was just not a gear I have to either stop or reverse course. Like, I just decided I have to find a way through, and the onion rings are the way through. Um, another thing that I thought was interesting, which was kind of counter to conventional advice. So, you know, most people who are in, uh, the business, the game of business— Buffett and all the real estate guys— the famous phrase they all say is You make your money on the buy. You don't make your money when you sell. If you buy it right, then you're going to make money.

SAM

Dude, I read that line like after I bought 3 real estate projects that I totally lost money on. I was like, shit, I'm being serious.

SHAAN

Like, it's not like the fine print, by the way. This is like the first thing you learn.

SAM

Like, I was like reading a Warren Buffett book and I read that quote and I remember thinking like, That was literally the exact opposite of what I thought it was.

SHAAN

You were just doing the John Bragg. So here's John Bragg's philosophy. Intentionally overpay.

SAM

Wow.

SHAAN

Okay. I'm in. So he goes, he goes, early on, I intentionally overpaid for acquisitions and word spread fast. If you want to sell, sell to John Bragg. You'll get a fair price, a quick close, no games. Which I love that. Like, if I'm, I'm going to put that on my, uh, on our like little mini private equity shop, uh, website.

SAM

I feel like that advice typically isn't right though.

SHAAN

Well, typically not. So here's the caveats. Here's the caveats of, you know, they say like, you know, the amateurs learn the rules or the amateurs don't know the rules. Professionals know the rules and then masters know when to break the rules or whatever that thing is. This is kind of when to break it. So he goes, I will overpay as long as it's something that's only available once, because when opportunities are scarce, you need to pay what it takes. I know many people who tried to nickel and dime and then spent the rest of their life regretting not getting that key asset. So I think in the, in the, in the realm of buying the TV rights, when there's only— they're only going to be up once and whoever gets it's going to own it. Those are— that's like a time to overpay. Or if it's a key asset that locks down, you know, a certain competitive advantage, don't quibble on price. In fact, come in over so that you make sure you secure that asset and you develop a reputation. He, he said something like, you can't buy a reputation. I was like, I think that actually what you're saying is you can buy a reputation. It's like, oh, but here's the reputation. I will overpay, right? Like, it's like SoftBank in the venture game right now. It's like, oh, you want a bunch of money and at a huge crazy valuation? Go to SoftBank first, right? And there's actually like some merit to that strategy when you have these like, you know, this, this, if you can get the things that have huge upside.

SAM

So was he, uh, like an M&A guy? Like, or, or was it?

SHAAN

It was a lot of building the empire through M&A.

SAM

And what was he buying? Other cable companies or other farms?

SHAAN

Both. Here's another banger of a line. So he has 40 to 50% of the global supply, and about half of that is like stuff that he owns and operates his farms, and half his farms he's buying or owns like a, you know, big stake in. And he's like, he goes, here's the exact line. He goes, we don't want to have 100% of the industry. That wouldn't be good politics. Dude, that's like, imagine having the choice to have 100% market share and they'd be like, uh. That's, that's not polite.

SAM

Well, what a baller.

SHAAN

Here's, here's some Sam porn for you. So focus is absolutely critical. Probably the biggest single principle you can have in business. Here's a big mistake people make. They make their first million and they think, now I can succeed in any business, even ones I know nothing about.

SAM

I've been there.

SHAAN

Sam buying the ranch.

SAM

Yeah.

SHAAN

And then, and then he goes, I just wanted to He goes, I wanted to just stick to my knitting, figure out what I could do well, and then just do more of it. You know, everybody else who came into this industry wanted to make a buck. I was this young guy who said, I'm here to play this game for a long, long time.

SAM

This guy's awesome.

SHAAN

This guy's awesome, right?

SAM

I think he's my uncle.

SHAAN

Then he goes, here's a couple other great, great quotes. The guy who asked the question to me looks better than the guy who knows the answers. I like that. Done.

SAM

Did you get all this from Shane's podcast with him?

SHAAN

Uh, Shane's, and then there's like a couple other people that have written about him, but a lot of this is from Shane's podcast, which I didn't even get to watch because I was doing that, like, I discovered this guy this morning. It was like on my list of like things to check out. And as soon as I checked it out, I was like, oh man, this is amazing. I gotta, I gotta go watch this later. So I've actually only like skimmed the transcript and stuff for this. Um, so I might be getting some of the details wrong.

SAM

A couple other things.

SHAAN

He's one of these like Buffett types where it's like, He's a billionaire, but the vast majority of wealth came like after the age of 70. So it's like, you know, just same, same way for Buffett where they just, they keep compounding. Um, he had some other things I thought were pretty interesting.

SAM

So I would have thought he'd be richer if you own all half the blueberries in the world. Wouldn't you be richer than $1.5 billion?

SHAAN

Yeah.

SAM

Punk.

SHAAN

Yeah. Weak shit.

SAM

He better be a huge, like, philanthropist and have given it a lot away because I definitely would have thought he'd be richer, right?

SHAAN

I mean, I guess. I don't know. I'm not going to— I'm not going to knock him. All right. So he believes in Buffett a lot. He loves Buffett. And so he— Buffett has this great quote, which is, I'm a better investor because I'm a businessman and I'm a better businessman because I'm an investor. Yeah. So at age 70, He was worth, you know, hundreds of millions of dollars. So he goes to each of the executives at his companies and he says, today you're just businessmen, you're not investors. He gives them $10 million each, not as a bonus, but as an investment portfolio that they get to run. And he said, I want them to see how strong companies operate and how weak ones fail. There was no penalty for losing the money and no bonus for the gains. It was pure education. Isn't that like pretty wild to do?

SAM

So he gave— how many managers did he have?

SHAAN

I don't know. 6 teams. So $60 million.

SAM

He gave them what, like a stock portfolio or he gave them $10 million in total?

SHAAN

$10 million to go invest, go buy businesses.

SAM

Oh, within their portfolio. Sure. Wow. Okay. That's badass.

SHAAN

That's crazy. He said— and this was at age 70. And then he's like, most people stop learning once they become successful. But the outliers, Never stop being students. Love that. Resonated with me. All right. What else resonated with me? Let me give you one more.

SAM

How about the fact that, like, I just Googled— I Googled the Shane podcast. Shane went to his office, which is really cool, and he's 84 years old doing a podcast. Like, that's, that's amazing that he's with it and he's sharp and he's had this pod.

SHAAN

Dude, when I'm 84, I'm going to be in the metaverse. I'm going to be so just like plugged into what everybody's doing in the future.

SAM

I hope.

SHAAN

All right. You want to do one or you want me to go?

SAM

Have you read about United Fruit? If we're going to talk about fruits, have you read about United Fruit?

SHAAN

United Fruit? Is that the Banana King guy?

SAM

Man, that's a great book. I'm in the middle of reading it and it's the story of United Fruit, which is basically centered around bananas. So like—

SHAAN

You want to do the quick story? I think we've talked about it before, but it's, it's on theme. It's on trend.

SAM

In the late 1800s, I think bananas were discovered, I think in Nicaragua. Or somewhere in Central America, and they brought 'em to America. Americans were like, yeah, we, we want every banana we can get our hands on. We love it. It even got to the point where like, I think in the 1920s when immigrants would land at Ellis Island, we gave 'em a banana and that was like, you're here now. This is Amer— this American thing.

SHAAN

And it's sort of American because like when you get to Hawaii and they give you the lei and like a drink.

SAM

Yeah, it was like a banana. And this, the banana company, United Fruit, it became so big that it was basically a monopoly. And they did the same thing where they tried to hide that they weren't a monopoly for years and years and years. And Sam the Banana Man, I think his name's Samuel Zamuri. He was, I think, a Ukrainian immigrant. And he started out like, uh, with like a fruit cart, like walking the streets. And his whole thing was he would sell ripes. And so the way it worked is a banana train would start in one part of the country, I believe Louisiana, and it would slowly make its way up over 7 or 8 days to the northern part of America. And along the way, it would drop off that bananas at different markets. And his whole shtick was he was gonna sell ripes, meaning bananas that were already becoming a little bit brown that they previously thought were throwaway bananas. And he was like, oh, I'll buy 'em for a fraction of the price and I'll just be really fast at getting them to where they need to go. And he eventually becomes so big that by the time he's in his 60s, he takes over United Fruit and it's a big deal.

SHAAN

Well, he starts with $150 and by the time he is 21, he's got $100,000. And this is way back in the day, right? So this is like a lot. That's a lot of money.

SAM

And it keeps on going and it gets to be so—

SHAAN

and that's— you're saying he's basically— he starts as just like a dude on the dock or whatever, like a dude on the side of the road taking their discarded trash and going and hustling and selling it. And by the time he reaches his peak, he buys the— he buys the whole company where he was initially just like taking their discarded trash.

SAM

And the book is called The Fish That Ate the Whale because he was the fish and he eventually ate the whale. But it gets even crazier. So Samuel Zamora, he has a lot of admirable qualities. You know, he's this, like, hardworking immigrant. He's pretty quiet and he's like a stoic guy, but he's kind of a warlord because, because at one point, Nicaragua, like, they have like some type of meltdown and a new president or dictator comes in charge and they won't sell them bananas. And so he funds a coup. So he basically gets like a small unit of like 10 or 20 people. To like help this other guy assassinate the current leader and take over. And that leader was like, all right, thanks for getting our back. Now you can have some more bananas. And, uh, so that's kind of like the story of Sam— Samuel Zumwalt. It's pretty badass.

SHAAN

Got that killer instinct. Let's go. Um, yeah, that's— this is— it's pretty wild, right? Like, imagine a story like that today.

SAM

Is there such a thing? Uh, I can't think of, uh, I mean, what Elon does in rockets is like pretty, like, you're kind of like dominating another planet, like, potentially.

SHAAN

I mean, that's like pretty crazy of like the Republican Party this year, like, going to the point of like actual, like, funding a militia.

SAM

I guess like Donald Trump is doing this, like, where he's like, for shits and giggles, I'm gonna like play a joke and run for president, and just kind of starts to work. But yeah, I mean, it's a pretty crazy story. Yeah. So it's been great. So I did something this weekend and I thought about you and I've been holding this in me, like waiting to like talk to you about this, but like a, like a man in Lent or, or, or November holding it in. Yeah. Oh man. Yeah. If you know, you know. So I saw a Broadway play for the first time ever this weekend. Phenomenal. Wow. Phenomenal. It's called Oh Mary. It's basically about Mary Todd, who was Lincoln's wife, and it's just like a comedy. It was fantastic. Never been to a— never really been to a play, honestly, my whole life.

SHAAN

Because you judged it or just happened to not go? What's the deal?

SAM

Yeah, I don't know. Like, you know, it just wasn't on the list of things to do. It just didn't— it just didn't— it didn't make its way into my life. And I finally went. The first thing is I thought of you because you had made an offhanded comment a while ago that you cared about like writing a show.

SHAAN

Yeah, I just thought it'd be cool. I went and saw one and I was like, oh, that would be kind of a fun, fun thing to work on.

SAM

Yeah. So you had the same thing I did, which is like, it was like a new art form that you hadn't previously experienced, and then you go to it and you're like, I understand the appeal now. Is that right?

SHAAN

Yeah.

SAM

Yeah.

SHAAN

I had gone to a bunch when I was a kid, and so I think I liked it from that. Like, I was a theater kid when I grew up, so I liked it.

SAM

Now, how's it related to this podcast? Well, for one, if you Google O'Mary revenue, you can see there's a website called BroadwayWorld.com where they estimate the revenue of each show. I guess they look at like if they're selling out and the average ticket price online. And this thing, Oh Mary, I think it's been live for June of '24. It came out and it's been making $1 million a week. So it's doing quite well. And it started off with about $4 million in funding to get going. And it all reminded me of this podcast that we did about 2.5 years ago. You didn't make it, but we had this guy named Michael Harris. Did you ever look into who Michael Harris was?

SHAAN

What was it, Death Row? Which, which record label was he the guy?

SAM

Yes. Yeah. So the short of it is some people call him Harry O because his name's Michael. Michael Harris. They call him Harry O, like Harry OG Gangster. So Harry was famous because in his early 20s, He was basically a drug kingpin and he made a lot of money selling cocaine. And at one point in the podcast with him, I said, yeah, you know, try to be nice. I was like, you know, instead of saying you are a drug dealer, I said, I read an article saying that the article said that you were selling $1 million. Yeah, the article said you were selling $1 million a day in cocaine. And he goes, I think that article said $2 million a day.

SHAAN

He's like, I told that journalist it was $2 million.

SAM

I was like, yes, sir. And eventually at the age of like 32, I think he gets sentenced to life in prison, one for attempted murder, one for drug conspiracy, which basically is like the RICO kingpin law. And he had a life sentence. And recently, I think like 10 years ago, Trump commuted his sentence and that's how he got out of prison. And when he was 32 years old, he founded Death Row Records with Dr. Dre and Suge Knight while he was serving a life sentence in San Quentin. And that's like how Death Row got started. And one of the reasons why it's called Death Row is because he was—

SHAAN

they co-founded it with him while he was in prison. And what did they— what did they want from— what was he able to offer them while he was in prison for life?

SAM

Money. Money. So his wife, his, his wife was on the outside. Okay. And she somehow had funds to fund Death Row Records, you know?

SHAAN

Right.

SAM

Now, how does this relate to Broadway? Well, on the podcast that I did with him, he said something that I didn't pounce on because I wasn't— I didn't know anything about it. It, but he made this comment to me where when he was 29, I think, he was the first ever Black producer of a Broadway musical or Broadway show. And he kind of told the story, but basically somehow he got in cahoots. You know, he was, he was considered, uh, like well-known for being like a drug guy.

SHAAN

And I hope you said cahoots to him.

SAM

Right after I said, okay, okay, okay, how do you end the podcast?

SHAAN

Which button ends this podcast?

SAM

Yeah, I was like, holy moly, Harry.

SHAAN

Oh, you dog.

SAM

Holy moly, Harry. So somehow he got in the loop with this, but he funded Denzel Washington, an early Denzel Washington, his first ever play. Damn. Michael Harris. Harry O was the fund— he was the investor that funded the show with $1 million. I think this was in '93 or '92 when Denzel, he was just getting going and he starts telling the story. And while, while I was at this play, I was like, holy crap, this guy got his way into being the first ever producer of Broadway. Like, while I was there, I'm like, oh my God. Like, he was so much cooler than I even realized.

SHAAN

I invested in Denzel before he became Denzel. That's like, you know, Jason Calacanis is like always saying he's the fourth investor at Uber. I would never shut up about it.

SAM

Google Michael Harris, Denzel Washington. You'll see a photo of them together. And Michael Harris looks like a, like a well-to-do guy. He's wearing a suit. Turns out he was only, I think, 29 or 28 in these photos, and he was a drug kingpin. Kind of amazing, right?

SHAAN

Yeah, that's, that's incredible. When he was 26 or something.

SAM

Was he 26?

SHAAN

Like, I think he was pretty young.

SAM

Yeah, very young. And like allegedly had made something like $100 million selling drugs. Pretty crazy. And when I was like sitting there in this play, I was like, obviously, what do you and I do when we do everything? We go to the play and you type in like, oh, Mary revenue on Google.

SHAAN

And I started seeing the numbers and I'm like, it's like the play's going on in front of you. You're turned around counting how many seats are in the upper bleachers and they're like, are you, are you watching the show? What are you doing here?

SAM

And this is how I remembered, uh, Michael Harris saying that, where it all like clicked together, where I was like, oh my God, do you know how much revenue these shows generate? I'm looking at it, it's astounding.

SHAAN

It's astounding. The number one— this, I'm just gonna give you the top, top 5, top 5 highest grossing Broadway musicals of all time. You have number 1, Lion King, grossed over $2 billion in just, just the ticket sales. Wicked, $1.7 billion. Phantom of the Opera, $1.3 billion. Hamilton, which is newer, already crossed a billion.

SAM

Insane, right?

SHAAN

And of course, our guys from South Park.

SAM

Are they number one?

SHAAN

They're number five. Book of Mormon, number five, $850 million on their second. That could be us, dude.

SAM

Could be us. Dude.

SHAAN

Just need to be talented and hardworking. That's all we're missing.

SAM

They are so talented. When I was at the show, I was like, this is just They're oozing with talent. One of the guys, Abe Lincoln, the character was played by, what's the guy from Silicon Valley, Kunal? Is that his name?

SHAAN

Oh, he's in the play?

SAM

Yeah, he's in the play. And it's like, it was like famous actors and actresses were like in the plays.

SHAAN

He's like a jacked Indian Abe Lincoln? Like, what do you mean he played Abe Lincoln?

SAM

It sounds crazy. And honestly, it is crazy. The guy who played Mary Todd was a guy. So like, it's all types of crazy. Yeah, it's a whole thing. Uh, but I just had to like nerd out with you about this.

SHAAN

So I looked into this pretty hardcore. Um, so it's definitely an outlier hits business, just like most angel investing is. Yeah, it's angel investing because, uh, and then I was looking at the venues. I was like, should I own the best venue in San Francisco? Like, can I go buy the San Francisco, like, you know, uh, I forgot what it's called, like the, the, uh, the theater or the opera house, whatever. There's like a bunch of, there's like 3 or 4 different, um, theaters for this. And I was looking at them because the theaters make money either way because the shows have to pay rent. They got to be like, hey, we want to do 60 days on stage. They're like, great, we'll take your money, right? Whether that show becomes a hit or not, they paid the money up front. So I thought that was kind of interesting. Then I was looking at the shows and I was looking at how much it costs to produce the shows, uh, because I just seen the one about Lehman Brothers, which I recommend, by the way. It's like a—

SAM

it's too long.

SHAAN

First of all, it's way too long.

SAM

It's like, dude, the one that I went to, we only went to it because it was 90 minutes. I can't sit there for more than 90 minutes.

SHAAN

Yeah, less is more, guys. Less is more here in the theater. But, but it was great. And it was, it was business entertainment, which is what I consider to be my genre. And I was like, damn, if they could take— I wasn't even interested in learning about the Lehman Brothers. If they took an uninteresting subject to me, but they made it great and I remember the story because of it. This is cool. This is a really cool format. And so, yeah, definitely, definitely interested in that. If somebody actually knows how to do these things, I would love to to talk to you. Email me, maybe we can make something, make something.

SAM

We were, I got a story in mind, but, uh, we had, um, Tim Ferriss on the pod and like the top comment on YouTube was like, rich guys finally discover board games.

SHAAN

And like, like that's what we all like paying attention to the rich guys part. I was like, yeah, hell yeah.

SAM

Thank you. No, no, this one's gonna be like the bros discover plays.

SHAAN

Uh, like, like Sam, they were singing in the middle of that. You're talking one second, then they're singing. It's incredible.

SAM

But it's all part of the story.

SHAAN

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SAM

A little bit. Like, I went last year and like I kind of watched a little bit on TV. The, the Russian gal, she's, she's an athlete, man. She's a freak. What's her name?

SHAAN

Sabalenka, I think.

SAM

She looks like a Terminator.

SHAAN

So I follow, uh, I've, I've gone in and out of tennis, right? There's many years where I won't even pay attention, then there's like, oh my God, Nadal, he's amazing, and I'm watching these guys and the a great tennis match is up there. It's like very thrilling to watch a great tennis match. It's like a great UFC fight. Like, there's some sports where, um, you know, the median game is like really good. I put like, you know, NFL in that category. But then there's some sports where just the peak is just like peak drama, right? Yeah. Boxing and UFC are like that, where like the average thing's not that good, but the peak, the biggest personalities, when it's all on the line and it's just two guys going in there and they're trying to take each other's head off. Like, it's hard for a basketball game to match that. Okay. So tennis, um, tennis is kind of up there in that sense. So there's the new, the new wave, uh, of tennis players. So this guy Alcaraz and, um, this guy Sinner.

SAM

Did that happen? Did the men's final happen?

SHAAN

It just happened. Yeah. And so, um, so I really wanted Sinner to win because I just like went down the rabbit hole of this guy's YouTube highlights and he's unreal. And, um, and the other guy is also unreal, but he's he's unreal when it's in the sense of like, you know, a guy who just like does all the right things. It's like he eats right, he works out right. Like he just does it. He just like prepares really hard. He's very talented. He's maximizing his potential. He's not like, there's not a lot of like flaws to like attach with there. You know, there's not a lot of like, it's like, oh, so you work hard and do all the right things. Great. Yeah, that's fantastic. In fact, they showed the warmup right before, because I think Trump showed up at the US Open. So it was delayed like half an hour or an hour or something like that. And so the guys were just in their locker room, like, supposed to be warming up. And Alcaraz is like, you know, doing a side plank in midair with his trainer and like activating his core to get ready. And the other guy was playing dodgeball with his trainer and like running around the gym, like just throwing balls at each other.

SAM

Like, yeah.

SHAAN

So I was like, I was like, I kind of like this other guy. Anyways, they go out there, Sinner loses, and he just keeps losing to Alcaraz. He's, he's, he's ranked number one because he beats everybody else. But Alcaraz has beat him, I don't know, 4 out of the 5 last times that they've faced each other. And he's like, I, and so he had this great quote that I thought, like, forget tennis. This is just like a great, like, mindset quote. So they were talking about, like, you know, hey, you know, it must be tough. You're at the top and then you, you're ranked number 1, but this guy seems to, you know, you've had some tough matches. This guy's got your number a little bit. And here's what he said. He goes, I was very predictable on the court today. He changed up his game and the style of how he plays. And now it's on me if I want to make changes or not. I'm definitely going to work on this. You know, for example, I didn't use a lot of drop shots. I didn't do one serve and volley. You know, you arrive at a point where you're going to play this guy. I got to go out of my comfort zone. So here's what I'm going to do. I need to start playing more unpredictably. I might even lose some matches, but I'm going to have to do it. I'm going to have to make some changes. I'm going to have to try to become more unpredictable as a player. That's what I have to do to become better at tennis. And at the end of the day, that's my main goal. And I really just love this mindset from the number one ranked guy who's beating everybody else. And he's like, you know what? I'm here, but the top of the mountain is still a little higher. But this path I'm on doesn't get me to the summit. I got to go back down for a bit and I got to find a new trail. And that is so hard to do in life. It is so hard to go back to the bottom and reinvent yourself.

SAM

He's like, I'm going to, I'm going to learn how to play tennis, but I'm really learning how to play the game of life. It's like one of those. Type of moment.

SHAAN

Totally, totally. Like, and to be like, I'm going to lose. I'm going to probably lose some more matches because I'm going to have to learn this. I'm going to have to experiment with this new style and that's going to suck, but I'm going to do it. And like, I— whatever you're doing in life, that analogy probably holds for you right now, whether it's you as a parent, it's you on the book that you're writing, it's you at your job, it's you and your business, like whatever it is. I guarantee you there's an element of like, if I want to get to the next level, What I've been doing doesn't probably get me there. And I need to like be willing when the time comes, when the, when I recognize the moment, I need to be willing to go back down the mountain for a little bit and then come back up a new way.

SAM

I, uh, have you ever heard of this guy named Meb Kurfleski? If you Googled him, that's a hard name to make up names. I know. Yeah. That's a, that's a hard last name to Google, but if you Google marathon Meb, M-E-B, you might recognize his face.

SHAAN

Marathon.

SAM

Meb. M-E-B. You see Meb?

SHAAN

I don't recognize this guy.

SAM

He's 50. Yeah. So I think in 2004, he was the gold medalist in the Olympics in the marathon for America. But he's an immigrant. And so when he won, it was sort of one of these things where everyone got behind him because he's a nice guy and it was like the American dream type of energy. And I think it got to the point where he like spoke at Obama's— a bunch of Obama events and whatever. He's a big deal. He's, he's great. His brother listens to MFM, his brother Howie, and he reached out to me when he heard that I liked running. And I've been friendly with him for a couple of years now. And this past weekend was this thing in New York called the Fifth Avenue Mile. And so they get all these guys, these Olympian milers, and they get them to run 1 mile down Fifth Avenue. Which is basically a huge street and it's slightly shut down or they shut it down. No, no, no. They shut it down. It's a big event. It's like a huge event. And there's tens of thousands of people there. And so I went with Howie and I got to, like, be like his, like, sidekick. So in Howie, who he runs a management company, who he originally— Howie was managing his brother Meb. Now he manages other runners because Meb was like, can you do— can you help me make more money? And he was like, yeah, fine, I'll do it. And then eventually now he manages, I don't know, 40 runners or something. And a lot of his athletes were running at this race. And so I got to be his, like, assistant, basically. And he, like, took me in. Like, I got to meet all these cool people, whatever. And these guys are flying, by the way. I think the guy who won ran 3 minutes and 46 seconds for the mile, which is, which is crazy. And the guy who won—

SHAAN

What's your mile time?

SAM

Dude, back in high school, a minute slower, 4 minutes and 47 seconds.

SHAAN

Okay, Ted Bundy. Now, what's your mile time now? What's your mile time?

SAM

18 years ago?

SHAAN

That was not my question.

SAM

7 minutes. Not good. I mean, 7 minutes, like, very, like, recreationally, like, average.

SHAAN

So, wait, did you run it or you just hung out with Howie and Frank?

SAM

Hell no, I didn't run it. I was watching. I was watching. I was just sitting on the sidelines watching. And we got to watch these guys run and they look like gazelles. They look like animals. It's like crazy. And I was asking them, I was like, what separates? So, like, because when I was watching the race, the winner and the guy who got third, they're really close. Like, it doesn't seem very far when you see them, but like, it's like a second is only— it's not that much, but it is a lot when you're running. And I was like, what separates Ngoose, the guy who won, what separates him from the guy who got last? Because they kind of look the same. They're tall and they're skinny and they look like freaks. Like, what's going on? And he was like, it's mindset. He's like, once you get to this level and you're already a 9 out of 10, What separates the guys that get first versus last in these big races is when they step on the lines, they're killers. He wants to kill you and he acts like a nice guy. But when they, when they step there, they think, I am here to win. I am built to win. I am not trying to finish second. I'm trying to be the best and I'm trying to win no matter what. And I was like, well, your brother was like a happy-go-lucky guy. Like, he looks like really kind. And he was like, yeah, he is. But he would sit down for hours and envision winning the New York Marathon. And then when he got to the starting line, you couldn't talk to him. He was an animal. He was out to win. And I thought that was really fascinating. And I always find it fascinating, particularly in sports, particularly in these individual sports, tennis, swimming, track and field, cycling. I think we had Lance on and like we talked a little about this, what separates these, the freaks of the freaks, what makes you a freak among freaks? And it appears as though it is not physical. It is absolutely mental. Running my company, Hampton, it gives me the chance to meet with hundreds of different businesses, and I'm always surprised by how many of them still use spreadsheets, emails, and clunky tools that do not talk to each other. It's like watching someone build a house with duct tape. So here's my take. Custom software that actually fits your needs isn't just convenient. It's a competitive advantage to transform the way you do business. And that's why you need to know about a no-code platform called Bubble. With Bubble, you can build powerful web and mobile apps by literally dragging and dropping different elements on the screen. No coding required. By the way, I use Bubble on a ton of different apps, including Hampton. And if you want help building something complex on Bubble, you have to bring in Xerocode. They're the top Bubble agency out there and literally the biggest plugin creator for the platform. They can build anything— custom portals, SaaS products— and they do it about 10 times faster and cheaper than traditional development. Zero Code is also all about AI business automation, transforming manual and slow processes into efficient automated ones. So stop cobbling together different tools and solutions and head to zerocode.com. That's zero code as in the word zero and then code, Q-O-D-E. Again, code is with a Q. And tell them that Sam sent you.

SHAAN

Have you heard this phrase? You probably heard it because you're like into running, but I don't run. I don't do it. It's not a— it's like motorcycles. I just don't get on that. So one of the guys who was filming for us, he was talking about this. He wants to film this documentary about this woman and she's like this amazing long-distance runner. I don't know her name. You probably do. But the point is she was talking about this phrase called the pain cave.

SAM

Yeah, we go to the pain cave.

SHAAN

You go to the pain cave. Yeah. And I was like, like, not into running, but I'll just take that phrase out. That was a cool phrase. He's like, he's like, so the pain cave describes like when you're in these like ultra long races, 100-mile race or whatever, and it's like mile 60 or 70, you hit this just like extreme level of like physical, mental, spiritual exhaustion and pain. And you go to the pain cave. And I'm like, but what do you mean? What does that mean? You go to the pain cave. He's like, you go to the pain cave mentally, okay? And you basically, I mean, you probably describe it better than I can, but my understanding was you accept that there's going to be this stretch where you're going to be in pain. You go to the pain cave, you know you're there. You become comfortable. You become not comfortable, but you become acclimated to the pain cave and you're able to stay there where others want to quit and you even want to quit. Others would quit. And then you push through and you end up getting, you know, to the, to the second, to the, you get your second wind, you get out of there and you get, get to the end. Um, did I, did I butcher the pain cave or did I describe it right?

SAM

No, no, no. And a lot of athletes—

SHAAN

Have you been?

SAM

You visited? Well, I've been on vacation a couple times. No, I, I was training for an ultra before and it was miserable and I hated it. And I remember going out for a 3-hour run and it just is, it's, it's horrible. It's not a fun experience. And like, you get to a certain point and what's— it's crazy to do a sport or an activity where even if you are winning, you go through hell. So we had Brendan Schaub on the, on the pod, who is a former UFC fighter, and he said that one time he was fighting on a, on a card and the guy who was fighting above him, Cro Cop, who was the main guy afterwards, Brendan saw Cro Cop like on a stretcher and Krokop had just won the championship, but Krokop still had gotten hurt and he was sitting on a stretcher holding ice on his head or something like that. And he looked horrible, like he just got beat up really badly, even though he won. And Krokop was like, give him a thumbs up. And Brennan was like, these animals think that this is winning. And that's why I'm not going to be the best, is because even when you win, you are beat down and broken and they still are giving you a thumbs up of like, yes, we did it. And that's what separates the winners from the losers, is the guys who, like, are willing to go through the pain cave. Because in a lot of sports, I think it's so fascinating. And I honestly, I think this way about business or anything really in life, that when you win and you get everything you wanted, you still have to go through hell. And that's kind of fascinating and interesting to me is like the mindset of, of, of these winners who can just eat so much shit. And honestly, business is the same way. It's not as physical, but it's still emotional where even if you think that you're on top of the world or things are going well, I don't know if you've experienced this where, but where everyone on the outside thinks like, oh, you're the man, you must be killing it. I'm like, dude, it's really, really hard and it feels like it's going to fall apart all the time.

SHAAN

Yeah, I find that these phrases like pain cave or whatever, there's some— there's a lot of power in just having like a label to put on a thing. So that when you're feeling it, you don't feel like this is, this is a bad thing, that you don't panic. Um, and you don't feel like it's forever. You realize it's like a temporary phenomenon. And so I know that one of the things that people brought up to me is that, um, this analogy that's been very useful and is like, if you're going to be an entrepreneur, um, you know, intellectually there's going to be these ups and downs. If I told you that, nobody would be surprised at that idea. Yet when it's happening, you're like, oh, you got that feeling in your stomach when you're going up and down a roller coaster and it does not feel good and you want it to stop and you don't like it and you think this is bad. And then you're like, but the thing we talked on the podcast is like, you got in line for the roller coaster. Like, what did you think was going to happen? You stood in line, you waited, you chose this first. You knew this is the nature of roller coasters and that there are no— there are no ups without downs and no downs without ups. Like, this has to be it's a necessary condition of doing this activity. So don't complain and don't be surprised and don't feel like, woe is me, and don't victimize yourself and don't think this is forever because it's not. And so, like, that's been a very helpful metaphor for people is just remembering, like, you got in line for the roller coaster, baby. Like, you— there was going to be ups and downs. Don't be surprised when they come. And then a tactical thing that's helped me is I have this Slack channel I've told people about. It's called Highs and Lows. And anytime there's an extreme high or an extreme low, I go immediately, I put it in that channel and I put my exec team in there as well. And the beautiful thing about it is when you go in there, you see something from like 4 to 6 months ago that was like an extreme low in the moment or an extreme high in the moment. And now it has like no effect. You're like, yeah, obviously if it was a low, it's like, obviously we survived, it was fine. And even if it was a high, it was like, doesn't have that same pull. And so it keeps you from in this moment going too high and too low because you could just scroll back and see all the other moments that in the heat of the moment you thought were such a, you know, such an extreme and now are like, whatever, you know, just random, random things in the past.

SAM

How often are you adding stuff to that?

SHAAN

All right. So last one was 4 months ago and it was, oh cool, Trump just tariffed all of our goods 150%. So like, imagine a thing used to cost us $10. Now we pay the $10, but then we pay an extra $15. That same item costs us $25. That's the full sales price of some items. You know what I mean? Like, oh cool, we make no money now. Oh, got it. Cool. Uh, business makes no money, thing out of our control. Like, got it. The, and then there was another one and then there's a high 2 months before that when, you know, this celebrity with 6 million followers is posting about our brand. And it's like, oh, that's awesome. But like, now that I look at it, I'm like, who cares? I don't care. Nothing. Like, nothing. My life didn't change for either one of those two things. My life didn't change. We got through the, we got through the low, and I already forgot about the high. You know, another one, Rihanna's manager emailed us asking for product. Like, you know, Rihanna wants our shit. That's cool. That's exciting.

SAM

Wait, hold on. Was Rihanna asking for free stuff?

SHAAN

Yeah. Yeah. They always ask for free stuff. Really? Yeah. Rich people don't pay for things.

SAM

That's insane to me.

SHAAN

You thought rich people buy things? They request things and you gladly give it to them.

SAM

Have you DM'd? I think I've done it maybe twice. Have you DM'd people asking for free stuff?

SHAAN

Asking for free stuff? Uh, no, I've never DM'd anyone. I think I've been like, yo, this is a great product. If anybody wants to send me one, I'm happy to take it. Like, that's the, I think that's the lowest I've stooped. I don't think, maybe I have, I don't, I can't remember ever DMing asking for free stuff. In fact, like we usually, we go the other way, which is like, if it's like a friend's product or somebody we know's product, we want to be their like first customer and we want to like purchase it to like show, cause you know, like, I don't know, it feels good and seems like the right thing to do. Another one, Christmas Eve. On Christmas Eve this last year, the Mexican president blocked all imports. So like, hey, that's cool. Our warehouses in Mexico and on Christmas Eve, all the ports are blocked with no notice and no, there's no other thing you could do.

SAM

But dude, I think you—

SHAAN

cool the shit at the port.

SAM

Do you have a coup staging team?

SHAAN

This is just in one business. This is just in the e-com business. This is not even like, I have 5 other businesses. So imagine like if this is probably, there's a high or low every 2 months. 3 months maybe, but now you multiply by 6 businesses. That means every single month you're getting hit with a high and a low in one of the businesses.

SAM

I think it was, um, cool. You said something actually that was quite good, which is, uh, it feels nice to label certain emotions because it makes it feel better. I went through a period, it's sort of, what's that, that's, we always reference that meme where like, Midway. Yeah, this is like the opposite of that, which is like when I was really young and not very successful, I consumed tons of motivational stuff And then I started like doing some stuff and I'm like, oh, that's for weaklings.

SHAAN

Yeah, I'll bullshit.

SAM

Now I'm like, no, I actually do like reading about like other success stories and—

SHAAN

Love me a good quote nowadays.

SAM

Yeah, like I actually do love that stuff because it feels nice to like label something. It's sort of like when you read a book and you're like, well, that was— the best books, they— people say the same thing about them. They go, everything they said was obvious, but it felt nice for them to say it out loud, for me to read it. And to be told what to do and remind me of the right things to do. And that has helped me all the time. That's like, I pretty much read like lots of like, or it's actually my YouTube page is like only motivational shit.

SHAAN

Here's the trick. So I've rebranded it because liking motivation, that's a pretty low-class thing to do.

SAM

Okay. That's, that's, you know, very low status.

SHAAN

Low status shit. Oh, I need motivation. I'm so So weak. I mean, it's like I need a blood transfusion. It's basically what you're saying. You don't need motivation. You don't like motivation. You like wisdom. Yeah.

SAM

Oh my God.

SHAAN

High-class thing to like. All right. There. I helped you out.

SAM

I listen to tons of wisdom and it gets me fired up. Yeah. My favorite wisdom channel. I'm a wisdom speaker. Yeah. There's this YouTube channel called Motivation 4 U. Best, the best wisdom.

SHAAN

Yeah, exactly. I'll give you another little label. So I was reading this book, uh, another high-class thing to do. I found this like old book out of print, had to like call a guy to get this book. And it's like, it's amazing. It is such a, such a thin book and it's, it's really amazing. I'm not even gonna tell anybody about it. It's my secret gem. And so in it though, he talks about, so it's a book about, um, how to have better ideas. So he's like this, this is great advertising exec who's basically like He's like, you know, and somebody asked me this and I laughed when they asked me the question. And then I realized I didn't have a good answer for it. He's like, and then I started thinking about it. I couldn't get this question out of my head. And he's like, I have now come to the realization that producing great ideas can be as reliable of a process as Ford producing Model Ts on the assembly line. And here's how the assembly line works to produce great ideas. And one of the things he says in the book, he goes, this is just a great quote. He goes, the brain, much like the body, has a second wind. And because he's talking about like, there's going to be this point, like pain cave, there's a point in the process where you kind of fatigue out. He's like, just, I need you to hang in there for like, give it, there's going to be another, you have a little like 10, 15% left. You're just going to give yourself a chance for the brain to have a second wind, much like the body. And literally like for the last 2 weeks as I've been working, I've hit this point where I'm like ready to like stop the thing, go be distracted. I'll go, I want to open up Twitter or I want to go like, go eat some food or do something. And I just, the brain, the brain has a second wind. Let me just give it a second here. And then I push through for like another 15 minutes and it's actually like been like very, very productive. This little, the one, one little simple idea.

SAM

Can I make a guess as to who wrote that? And ignore this if it gives away too much. It was by a copywriter if I had to guess. Is that right?

SHAAN

It was by an ad man.

SAM

Yeah.

SHAAN

So he copyrights.

SAM

It's crazy copywriters. Like there's this weird underground world. I don't know. I don't know if you ever have noticed this. There's copywriters out there where they sort of have a weird mystical, like wizardry about them and they end up learning about copywriting. But in order to be a great copywriter, you have to understand how humans think. And then if you could, if you could be a master copywriter, you're basically a master at learning about what motivates human beings and thus you can teach all about life. But I've come across all these guys that are like old school internet marketers, but also people who are around even before the internet. And they often have these weird auras around them that if you find a bunch of their old landing pages, they explain some of the things that you're talking about and you get on their webpages and you're like, I have to give you my money. And there's not even a buy now button. I have to track you down. But I've come across a bunch of these guys. One of 'em is, um, Bill Bonner, the guy who started Agora. So Agora Publishing is like the billion dollar a year, um, newsletter business that is quite shady. But another one is Mark Ford. Do you know who Mark Ford is?

SHAAN

No.

SAM

Who's that? So he has this book called Ready, Fire, Aim on business, and he's pretty under-the-radar guy. I think he's probably in his 70s at this point, but he helped make Agora really popular. There's Eben Pagan. Do you know who Eben Pagan is?

SHAAN

Yeah. That we were dating.

SAM

Yeah. That we were dating. From, uh, Eben Pagan was a guy who was one of the one of the first internet marketers because he got going in the '90s when the internet was just getting going. And he had an ebook called Double Your Dating, and he wrote it under a pseudonym called David D'Angelo. And Eben Pagan is another guy where if you Google Eben Pagan and come across his courses or books on copywriting, you get entranced and it sort of becomes like a moment where you're like, I used to think this way, then I read this, now my life has just changed. Eben Pagan was one of those guys. A lot of old Russell Brunson stuff is like this. Um, but there's a copywriting world that like you come across these old guys or they're not old. Russell Brunson is not old.

SHAAN

These guys our age.

SAM

No. Yeah. I mean like underground. I don't know how to explain it.

SHAAN

No. Yeah. It's like almost like they ruled the world, but they're not, it, it, today they're less, uh, relevant and on the forefront and up in, in the center of attention as they were 15 years ago, 30 years ago, 40 years ago. There's a bunch of people like that.

SAM

Yeah. And what happens, and, and a lot of people don't realize it, is you can just copy exactly what they do and it still works and you don't have to invent anything. So I'll give you an example. There's this guy named Dan Kennedy. We talked about Alex Hormozi, and a lot of people say this to Alex as if it's an insult. I don't think it's an insult at all, but they'll say, you just ripped off Dan Kennedy. And so I started reading a bunch of, it's not an insult at all. It's totally okay to steal from the, the greats. But if you read a lot of Dan Kennedy's stuff, first of all, if you Google Dan Kennedy, you're gonna see what he looks like and you're probably, you, you'd probably dismiss him. You're like, oh, what does this this person know about business? Because he literally looks like a cowboy. But you read their books and their advice is beautiful, so long as you come with an open mind. And it's incredibly effective. But it's sort of like, um, we talked about, uh, books that where you say phrases like, oh, it's banned in prison because it's too powerful. Yeah, they all have catchphrases like that.

SHAAN

I love copyright. I think there's certain professions where it's almost like, um, Darwinian, right? So like, the only way to survive as a copywriter let's say that was your goal. And a copywriter, then we'll kind of extend that to like an ad man, right? Like the Ogilvies of the world. And the only way to survive is to have these breakthrough ideas and be super persuasive with the written word. So it's like an animal that was, that was on an island, and the animal had to develop this shell if it needed, if it was going to survive. That was the only way to survive in that climate. And so if you want to get great at persuasion, you want to get great at the written word, You could learn from a bunch of people. You can learn from an Elon Musk or Steve Jobs, but those guys, in order to do what they did, they grew up in a— they had to have other disciplines that they were great at, and they could be good or maybe even really good at copywriting. But there's people who that was the only way that they could make it. And so those people like sharpen that. And you see this with a bunch of different things. So you see this with a lot of investors when we have them on the podcast, we're like, Wow. Like, I wanted to ask you about, like, stocks and, like, you know, analysis. But 95% of things you thought— you think about and talk about is like mastering your own, like, your own psychology and disciplining yourself and, like, learning, like, impulse control and learning how to, like, be a little, you know, to think for yourself and be comfortable in your own skin. And it's like, yeah, that's actually what— that's the thing that was required in order to be great in the investment world. Combination of like independent thinking and then like self-control and, uh, playing the long game and patience, right? And then you talk to people who are, you know, maybe comedians, and comedians are like, wow, you're actually like kind of a truth teller. It's like, well, yeah, like that's kind of what comedy is. It's like basically like seeing things for what it is that nobody's saying out loud, and then we say it out loud, and then everybody laughs because everybody knew it. Um, and so you realize like, oh, these comedians are actually like pretty wise and pretty like spot on at spotting, like, the truth, the underlying truth inside. He's like, yeah, because if they don't do that, they don't make anyone laugh and they get booed off the stage and it's horrible. And so the ones who survive are the ones who figure out how to do that one thing at a world-class level. And so you could study different disciplines where, like, the Darwinian, you know, pressure had the natural selection force them to become, like, A++ at a certain thing.

SAM

Who, who do you think falls in that category where you learn about them and they've done the same thing to you? Where you went to them for like, let's say writing, uh, and they changed your life?

SHAAN

Seinfeld. Seinfeld is the easiest example. So I, I wanted this year, I was like, oh, like, could you like make yourself funnier? I just sort of assumed that like, you know, growing up it's like you either are funny or you're not. And in my house, like my sister's really funny. And so it was always like, she's the funny one and she's the great storyteller. And I was like the nice kid. And so I always had this probably like, from a young age desire to be more like her. And like, today is so funny. People would be like, from the podcast, they'd be like, oh yeah, you're a great storyteller. I'm like, you haven't seen my sister. My sister's amazing at this. I'm just okay. But over time, as I've grown up, I've realized like a lot of these things that seem like you either have it or you don't— creativity, humor, storytelling— like, no, these are just skills you can develop. Like, if you just try, you can get way better at it. And so humor was one. This, this year I went into and I was like, All right, let me just take 2 weeks and be like, let me just learn what there is to learn. Let me just see if I can make myself funnier. So I went and studied Seinfeld. So I went for the jokes and then I came out being like, this man is wise and has some of the best sort of like, he has this incredible creative process. Like the way he works has changed the way I work, like completely, like night and day difference.

SAM

In what way?

SHAAN

So Seinfeld does this thing in the morning. You know about this, but like maybe other people don't. Seinfeld, for the last 45 years, has a morning routine. Seinfeld's morning routine is very simple. He's like, if you want to be a comedian and you want to write, you want to, you know, tell great jokes, you've got to write jokes every day. So he wakes up in the morning, he sits down with a yellow legal pad, a pen, and a coffee. And he has 2 hours where before he's pre-input, pre-everything. Nobody, no meetings. Nobody can call him. He doesn't read the newspaper. He doesn't check social media. He doesn't do anything else. He's like, I'm going to do 2 hours of this and then I can do whatever I want for the rest of the day. And he sits down, he does his 2-hour morning block, it's 2-hour morning routine. He's done that every day for 45 years to the point where there's a photo where he took the pages from his yellow legal pads over the 40 years and he laid it out on the street, I think in New York.

SAM

No way.

SHAAN

You haven't seen this? No.

SAM

I'm going to go look.

SHAAN

It literally becomes the yellow brick road.

SAM

This is awesome. Are you kidding me? This is so cool.

SHAAN

So he, to promote his book, so he published a book basically of like all of his like scrap jokes that he didn't put into his standup. It's called Is This Anything, I think is the name of the book. But to promote it, he did this yellow brick road of all his yellow pages. And, you know, like, for example, you know, how did I work before this, right? I'd wake up, I check Slack, I check my email, I'd then start to think about what I'm gonna do, but then I got kind of hungry, then I go do this, then, oh, I had this meeting scheduled at 9, so I'm gonna get to my main thing at 11. And just Seinfeld's like keeping it sacred of like, yo, what's your main thing? You spend 2— if you're gonna be creative, you're gonna spend 2 hours in the morning creating. That's it. Tim Urban from Wait But Why told me the same thing. He goes, if— he goes, all I have to do in life is wake up and spend the first 2 hours writing. And if I do that, life is amazing. And if I don't do that, my life sucks. He's like, and by the way, it's only 2 hours. It's not 8 hours. It's not 10 hours. I don't have to keep grinding all day. 2 hours is more than enough if I actually do it. So Seinfeld does that, and he talks about writer's block where they're like, but Jerry, like, what do you do on days where you don't know what to write? He's like, like, what do you do with writer's block? He goes, oh, You know, it's funny you ask because there is no writer's block. And they're like, what do you mean, Jerry? Like, of course, like, we have all felt it. There's writer's block. He goes, no, no, no. There's lazy, there's afraid, there's, um, having too high of expectations, but there's no writer's block. Let's be clear. And he's like, here's the cure to writer's block. You ready? Accept your own mediocrity. Don't sit down and think, today I'm going to make this great thing. It's going to be so amazing. The words are going to flow. I'm going to make this funny joke. He goes, That's what stops you. What you need to do is almost an anti-affirmation. You need to sit down and say, today I'm going to sit down. It's going to be hard to write. The thing I'm going to come up with is going to pretty much suck. I'm going to look at it and I'm going to hate it. I'm going to want to crumble it up and throw it in the trash. It's going to be that bad. But you know what? I'm going to put it down on paper anyways, because every once in a while there'll be a little nugget of something good. And then after I find a little nugget of something good, I might be able to polish it with a ton of work later and make it great. And he's like, this sort of like anti-affirmation, right? So like, I have taken that and completely stolen that as my daily process. From this guy I went to to learn about, like, how to make people laugh.

SAM

And I'm like, that's awesome.

SHAAN

I learned how to work, how to live. Like, he talks about— he does Transcendental Meditation. They're like, ooh, is that— that's really great. You love meditation? He goes, no, I just want to write great jokes. He's like, but you have to whip the mind. You have to whip the body. He's like, so why do I work out? To be a better comedian. Why do I meditate? To recharge my battery so I can be a better comedian. He's like, all this stuff I do is to be a better comedian. He's like, he's like, you'll learn pretty quick if you don't work out, You're leaving, you know, some of you on the table from being able to do your best work. If you don't do something like a meditation or something to recharge your mental battery, you're going to do worse work. Like, it's just as simple as that, right? He's got a ton of stuff on that.

SAM

I've been— that's so great. Jerry, I listened to— I listened to a lot of his YouTube videos, his interviews, because it's the same thing where I learn more about life than anything. You know, there's a famous one where he talks about like consultants, like, and comedian— comedians and making jokes. McKinsey. What's he say about that?

SHAAN

So the joke is, uh, he's getting interviewed by, I think, like, Harvard Business Review, and they go, um, you and Larry David famously wrote Seinfeld together with no writer's room, just the two of you guys. You wrote every single season, every episode, and burnout was one of the reasons you stopped the show in the end. Like, you know, was there— and he goes, the Harvard Business Review goes, was there a more sustainable way to do it? Could McKinsey have helped you find a better model? And he goes, who's McKinsey?

SAM

Wait, did they really ask that?

SHAAN

Yeah. He goes, who's McKinsey? And they go, it's a consulting firm. He goes, are they funny? He goes, they go, no. He goes, then I don't need them. If you're efficient, if you're efficient, you're doing it the wrong way. The right way is the hard way. The show is successful because I micromanaged it. Every word, every line, every take, every edit, every casting. That is my way of life.

SAM

Did you have this up right now?

SHAAN

Dude, I have like a dossier of Seinfeld. Like I told, I studied this man. Like I went deep on this.

SAM

That's awesome. Um, have you ever seen him live?

SHAAN

Yeah, I've seen Seinfeld live. Honestly, wasn't that funny.

SAM

I was going to say the same thing. I was going to say the same thing.

SHAAN

Love the guy. Don't love his comedy actually.

SAM

His, his standup is meh. His writing is the best, but his standup for some reason is just fine.

SHAAN

Yeah. It's like just okay.

SAM

I've been obsessed with it.

SHAAN

But actually, it's in part why I really love this guy, right? Because he's been touring for 50 years as a comedian. 50 years. This is unbelievable. Like, LeBron James is jealous of Jerry Seinfeld's longevity. There's like 50 years of unbelievable longevity as a touring comedian. And he's also, I think it was remarkable, he's one of the, he's the first and only billionaire comedian, mostly because of Seinfeld the show, but also like, you know, comedians in cars doing coffee. He sold for like $100 million.

SAM

Like, did he really?

SHAAN

Touring for a long time. Yeah, Netflix picked up for $100 million. He's a super— he's outlier. But the great thing about Seinfeld is if you see him, he's not like naturally just oozing charisma and like talent. Like there's some guys, they could do amazing impressions. You're like, I could never do that, right? Or there's other guys that are just like, they have just this knack, this gift for gab, and you can just see it. Like the way they grew up, like this guy's just so funny. And Seinfeld is like a he looks like an HR manager, right? Like, he doesn't look like he's the most naturally talented guy. And that's kind of why I love it. Like, the guy's the most successful comedian. He's because he's just this craftsman. He like, yeah, squeezed everything out of his natural talent. And I think how often does that really happen? Like, how often do people really maximize their potential? Very rare.

SAM

I remember when I was starting The Hustle, Scott Belsky, like, I cold emailed him and asked him to invest and he didn't want to invest. But then I just like added him to The Hustle and I started writing like extra good emails., and he eventually replied. He's like, this is so good. Can I invest like a very small sum? But I just want to let you know, like, this is like, you're fantastic. This is great. And he let me hang out with him. So for anyone listening, Scott Belsky, at this point he's known as like a legendary investor. But before he was this amazing investor, he had started Behance, which he had sold for, I think, $175 million. Now he, he was nearly the CEO of Adobe, which is one of the largest companies in the world. I think now he works at A24, is that right? Like the big shot Hollywood, uh, production company.

SHAAN

He's the, like, chief strategy officer and something else.

SAM

And I didn't listen to his advice when I, when I met with him. And I always regretted that I didn't listen to his, his advice. And I didn't understand it until now. He basically was saying the exact opposite of scale, scale, scale. I was like, I need to automate this. I need to hire more people. I need to get away from writing this email every day and making it great. I need to add more revenue. I need to get more advertisers. And he was basically like, you need to go in a room and just not have anyone around and you just need to write this email every single day for about 4 or 5 years and be— he used the— I'd never heard anyone use the word steward. He was like, you need to be a steward of greatness and a steward of taste for your audience. And I didn't understand what that entirely meant. But what I thought in my head, I was like, but you're wanting me to act like I'm a small business owner. You're wanting me to act like a craftsman. I was like, I'm not trying to be some garage band. I'm trying to be Lady Gaga. Like, I'm trying to sell out stadiums. What are you talking about being a craftsman? Do you know what I mean? Like, I don't understand what you're saying. Why am I going to stay small? I want to sell out. I don't want to— like, that's the whole goal. And it took me years to understand what he meant, which was you can become this like huge successful person and also be a craftsman. You know who honestly does a great job at this? And it seems silly, is Dave Portnoy. Dave Portnoy has had it, and I don't even like the comedy anymore, but he's had his hands in it and he's been consistent now for 25 years. And he's ridiculous. He's a ridiculous person. He's sort of obnoxious. But you know what? He's done it. He's done exactly what Scott Belsky has said, which is you need to be in the thick of it and you need to be focused purely on creative and you need to be a steward for taste. And I didn't understand what that meant until I was about 32 years old. I think he told me this when I was 26, and I was like, Scott, how are you so successful? You don't know anything about business. You're telling me not to, like, focus on scaling and all this.

SHAAN

Gaga, Scott, gaga.

SAM

But now that I know, like, some of these people who are actually making the most money are actually still craftsmen and like, and so like, I distinctly remember I'm like, I want to sell at stadiums. I'm trying to sell out. I'm not trying to be a small little, like, Korean family-owned bodega. Like, I'm trying to take over the world, baby.

SHAAN

You, uh, you said Dave Portnoy. Uh, there's another guy who's like that, Bill Simmons. And, uh, he's probably, you know, he's probably the reason I'm doing a podcast today is because I was back in college and I don't know what, what that was, 2007, listening to his, to the BS Report. You know, I used to like fall asleep listening to the BS Report. Like, it was like that. It was that like And at the time, podcasts were nothing. And he, he had been a blogger before that, then he was an ESPN columnist, then he did the podcast, then he did 30 for 30 documentaries. Then he went— he gets fired from ESPN because he does the, he does The Ringer.

SAM

Why'd he get fired?

SHAAN

Um, he was pretty outspoken against Roger Goodell, the NFL commissioner. He's like, this guy's like kind of covering shit up and like not— like he doesn't care.

SAM

It could be contained.

SHAAN

That was like a domestic violence thing. There was like the concussion stuff. And he was basically like, he would make jokes, but like the NFL's ESPN's biggest partner. And so he was, he got suspended a couple times and then they were just like, this guy's too hard to work with. And so they, um, they killed his project Grantland and they fired him. And so he comes back after licking his wounds a little bit and he comes back with The Ringer, which is just the Grantland again. Um, and he'd been doing this now for like a long time, but he ends up selling to Spotify for $200 million. And there's a great tweet that was going on the other day. So The tweet was basically a video of Simmons, and he's walking through the office. He's carrying like a chair, like a school chair, and he's carrying a chair and a microphone, and he's like, um, and they're like, they're like, Bill, what are you doing? He's like, a trade had just happened in the NFL. The Micah Parsons trade had just happened. And it's like kind of like a, you know, in the grand scheme of things, not like a big story, but like, you know, it was like the biggest story that week. And his company has like 15 other podcasts. And so there's like this NFL podcast going on. And he's like, I got to go talk about this. So he's just carrying a chair through the hallway and there's a guy behind him, like, filming him. Like, Bill, what are you doing? And he just barges in and he, like, puts down his chair with his microphone and he wants to, like, talk about it with the guys. And there— and somebody tweeted, they're like, honestly, respect. This guy's been doing this for like 20 years. He's got— he's worth like $200 million. And yet on a, like, Thursday, he can't wait. He's literally carrying his chair, his microphone, and wants to sit with his friends and do a podcast about this trade. Like, that's kind of goals, you know what I mean? Like, that's actually like career goals. And, um, that really, like, I don't know, that, that kind of like stuck with me. Like, that is really what you want is like a job that's so fun and so like, so you, that it doesn't matter what's the money in the bank. Like, you really just want to do it. You just want to do the thing to the point where you're just going to carry your chair down the hallway and try to find a podcast to go do about it. You know, I thought that was great.

SAM

Where is he now? So is Grantland still a thing?

SHAAN

Grantland died with ESPN. He creates The Ringer. Ringer sold to Spotify. And so it's part of Spotify. Um, and he's been, you know, making bank, uh, ever since.

SAM

Why haven't we been able to get him on here? You've talked about him like 4 or 5 times as like your number one.

SHAAN

He's like that girl at the dance I don't want to approach.

SAM

Yeah.

SHAAN

I'm like, hold on, I just gotta like, I'm gonna fix my shirt real quick. I gotta tuck in my shirt. I gotta go, I gotta go get some punch. I'm thirsty. Yeah, I got to do— I'll do everything else except for ask him.

SAM

Yeah. I mean, he looks pretty awesome. I don't know really anything about him. I would love to talk to this dude. He seems great. And you've talked about him like—

SHAAN

He's prolific. Yeah.

SAM

Is he?

SHAAN

Is he? I mean, to go from a dude who couldn't even get hired by like a local paper, basically. So he starts blogging early on on the internet, parlays that blog into like getting his own section and being the highest paid sportswriter at ESPN. But the thing is, it's not just that he was the highest, it's not just that he was successful. He did it his way. Like, he created an entire style of writing on, on like a publication like ESPN. He basically wrote like a blogger on ESPN. Nobody did that. He wasn't impartial. He was like, no, I love the Red Sox. I love the Patriots. I'm from Boston. What are you talking about? I'm going to write like a fan. Like, I'm going to write like a fan. And sometimes I'll be pissed at what my team is doing. Sometimes I'll be excited about it. I'm going to make a bunch of references to like, MTV Road Rules, The Challenge. Like, I'm going to do what I'm interested in, even though that makes none of it is like by the book. And then he does podcasting early on. Then he does the documentary series, builds the most successful sports documentary series.

SAM

What, 30 for 30?

SHAAN

30 for 30. He like, it was his brainchild. He conceived it. He created it inside of ESPN. Like, nobody believed in it basically. And he, you know, he kind of fought for it, got it done. It became super successful. I mean, he's epic, dude, what he's done. And still on the podcast, he, um, you would never know. So he'll never reference the fact that like, he's basically richer than like a lot of the athletes he covers at this point. And he's super well connected to them, but he's tried to like, never really, he doesn't let that sort of creep into his content. Also, he didn't really rub it in ESPN's face, um, which he very much could have because they like literally kicked him to the curb and didn't believe in him and told him like, Grantland, the idea is a failure. Like that, that's a money loser. Doesn't work. And he replicated the same business and sold it for $200 million. So, you know, like he, he could have done a victory lap and never did.

SAM

That's awesome. I'm a, I'm a Bill Simmons fan now. There you go. Should I interview him without you?

SHAAN

Yeah, I think you should.

SAM

I would love that actually. So, Sean's not here today, but he says you're his, you're his inspiration and he would do anything for you.

SHAAN

But he's not here. There's been a couple of these guests where you fangirl. That would be one where I'd be, I'd be too much of a fangirl and, uh, it really would be counterproductive to the podcast.

SAM

That would be great to get you rattled. You're not normally, uh, someone who gets rattled. Um, all right. That was a good episode. I enjoyed that. But, uh, that's, that's the pod.

SHAAN

I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back. All right, let's take a quick break because as you know, we are on the HubSpot Podcast Network, but we're not the only ones. There's other podcasts on this network too, and maybe you like them. Maybe you should check 'em out. One of them that I want to draw your attention to is called Nudge by Phil Agnew. And whether you're a marketer or a salesperson and you're looking for the small changes you can make, the new habits you could do, the small decisions you could make that will make a big difference, that's what that podcast is all about. Check it out. It's called Nudge and you can get it wherever you get your podcasts.