Sam reveals that MFM producer Ben Wilson has been consulting a wealthy finance executive for free, using lessons from history drawn from his podcast. The hosts coach Ben on how to monetize this skill — from consulting rates to corporate speaking gigs — then pivot to Shaan’s angel investing strategy (long-term orientation, thematic bets, compounding reputation), Sam’s deep dive into the short-term rental world, and a fascinating story about Tailgate Guys, a business that built a monopoly by becoming the exclusive tailgate provider at college campuses. The episode closes with a look at Mystery Science, which reached 50% of U.S. elementary schools before selling for $140 million.
Speakers: Sam Parr (host, co-founder of The Hustle), Shaan Puri (host, founder of Milk Road), Ben Wilson (guest, producer, host of How to Take Over the World podcast)
Opening — Ben’s Secret History Advisory Retainer [00:00:00]
Sam: I think you should go hard on this. You have 100,000 listeners a month and you’re making single-digit thousands of dollars. You would make six figures a year for sure doing this.
Shaan: All right. So, what’s good? What’s going on?
Sam: You got Ben still on the line?
Shaan: What’s up, what’s up?
Sam: Normally you’re like, “Turn off your video, we need to focus.” I’m going to tell you why. So, Ben made a comment to me — maybe to you too, I think you were here — like a month or two months ago. I’ve been thinking a lot about it. He kind of made it not a big deal, but it’s kind of a big deal to me.
Ben, I’m not going to — I’m only going to kind of mention the thing, and then you can explain how you want to. But basically, Ben Wilson has this podcast called How to Take Over the World, and you said that a very wealthy person — like a hundreds-of-millions-of-dollars person — has you on retainer, and basically tells you the strategy they’re going to do in business, and you tell him stories from history to let him know what you predict will happen. Is that right?
Ben: What? Yes. Yes, he made — is that crazy?
Sam: He didn’t explain it that way, but that’s exactly what happened.
Shaan: It’s like a sugar daddy, but it’s like a history daddy.
Ben: Like a history baby, I guess?
Sam: Sugar baby. Okay, that’s true. Did I explain that accurately?
Ben: Yeah. So here’s the full story. I get a lot of people who reach out to me at this point. Basically any fan who’s like, “Hey, can I talk to you for a little bit?” — I’m just like, yeah, I’m not that big yet. That’s starting to change a little bit. A lot of people want my time now, but this was a while ago.
So I said yes. He’s like, “I’m thinking of starting something, I want to talk to you about it.” I was like, okay, this guy’s probably a joker, but whatever, he reached out to me, I’ll talk to him. So we hop on a Zoom, and first thing — he’s got a glass wall behind him, and you can tell he’s in a very, very high rise in New York City. You can see the whole skyline behind him. So immediately I was like, this is not what I thought it was going to be.
He was like, “Yeah, I’m a managing director at XYZ bank — one of the biggest banks in the world — and I lead their X division.” Very big financial division at this big bank. He’s like, “I just randomly found your podcast, and you don’t know this, but I’ve been listening to you. You’re my guru now. So I want to talk to you about what I’m thinking of starting and just bounce it off you.”
So he gets to call me whenever he wants to.
Sam: That sounds more normal. But you were saying he specifically wants you to tell him — based on history — what’s going to happen?
Ben: That’s what’s going on. He wants me to tell him, like, “How would Julius Caesar handle this?” or “How did Julius Caesar handle this? Tell me what to do.” That’s basically the angle he’s going for. Because he knows me from How to Take Over the World.
Shaan: Oh my god. That is amazing.
Sam: Isn’t that awesome?
Shaan: Well, first of all, hopefully me laughing about it doesn’t blow this for you. But wow, okay. I want to ask you more questions about this, man.
Sam: I had the same reaction, Shaan. I was like, what? That sounds like a scam. But I’ve been thinking a lot about this and I actually think that’s a great idea. What do they say — history may not repeat itself, but it definitely rhymes. If you’re going to tell people what behaviors to avoid, or how other people had the same move and what happened, I think that’s great.
How much is he paying you?
Ben: Zero.
Sam: What? I thought you were like on a retainer?
Ben: No, no, no. He offered to pay me. So, he didn’t offer explicitly, but he said people who do what you do — who consult people like me — often make upwards of five thousand dollars an hour. I don’t think he would pay me that because I’ve never done it before, I’m not like a high-level coach. But I was like, well, that’s a pay range I was not considering, I must admit.
He said he will pay me, but I ended up telling him no, don’t worry about it. I just think it’s better to have the connection and have him think he owes me at this point.
Sam: Okay, that’s fine. But I actually think there’s something interesting here. Like Alex Fridman or these thinker types — they definitely could get paid five or ten grand an hour.
Ben’s Advisory Model and What He’s Actually Delivering [00:05:30]
Shaan: To me, the way you described it — it’s more like, you know, in Billions or whatever, there’s that guy who goes and gets dominated by some shaking woman in a mask with a whip. To me it’s more like that, where it’s like some rich guy is just like, “Hey, when I call you, I need you to tell me I’m a huge screw-up and I suck, and that’s going to motivate me to go into this meeting and prove myself daily — and I will pay you two thousand dollars an hour if you are someone who tells me I suck and spits on the webcam.” That’s more where the opportunity is to me than, like, telling me about lessons from history.
Sam: No, this is good. Because it’s like, let’s say he goes, “I’m working on this thing, my opinion of it is this, this, and this,” and Ben goes, “Well, you know, the Rothschilds — the reason why they did really well is because they just got information a little bit faster, and they did this, this, and this.” Business is so context dependent.
Shaan: It’s not like you actually need the strategies of the Rothschilds or Julius Caesar. I think it’s motivational to hear these stories.
Sam: Well, that’s actually accurate. Because you’ve got to know — what am I delivering? What am I actually selling this person? Am I selling them strategies from the 1830s, or am I selling them something motivational?
Ben: Here’s an anecdote I use from How to Take Over the World: Edison used to — he was amazing, he’d done so much by the age of 25 — and he was like, “But Nikola Tesla had already done XYZ by this age, I’m so behind.” Even though he was the greatest inventor of his age, he personally felt behind because he was comparing himself to someone.
And then I read that Julius Caesar used to go look at a statue of Alexander the Great and think, “What the hell am I doing with my life? Alexander the Great already ruled the world by now.” To me, the lesson is: a lot of people feel like they’re behind, or they compare themselves to others doing better. But there’s no end to that. Julius Caesar did that. So you know — that’s a trap. You know there’s no amount where you’ll stop feeling that way, so you might as well just let it go.
Shaan: But that’s kind of the same thing — you’re just talking about life strategy.
Sam: I’ll tell you how it actually went. Because what you said, Shaan, actually plays into it. He said, “I’m thinking about starting this thing. It’s a higher possible outcome, but if I stay where I am right now, it’s just more steady. I can go from where I am to hopefully 500 — but I’m not going to become a billionaire.” But if he goes and starts his own thing, he could lose a lot of money.
Shaan: What does 220 mean?
Sam: 220 million. Oh, that’s what he’s worth? I’m saying a number, I’m not going to tell you what he’s worth. But he is in the hundreds of millions.
Shaan: Sounded pretty specific to me.
Sam: All right. So he was essentially like, “Should I do this thing?” So I — I talked about the concept of exactly what you’re saying. There was so much pressure on me to say something that wasn’t stupid. I was literally as he was saying this going, “Why the hell is he talking to me?” It was so funny to me. But he loved the podcast, he thought I’d have something interesting to say, so I was literally just grasping in my head, panicking a little bit.
I said, “Okay, well, have you heard of loss aversion?” And I brought up loss aversion, which I’m sure you’ve heard of. He hadn’t heard of it. So I explained to him what loss aversion was.
Shaan: Explain it for somebody who’s listening.
Ben: Loss aversion is the idea that you value not losing your money more than you value gaining money — you put more emphasis on losses. So I essentially said, “You need to make loss aversion work for you. If you believe that you’re going to be successful, you need to visualize that success and realize that every day you delay starting your new thing, you’re losing millions of dollars because you’re failing to act.”
He was like, “That was amazing, that’s changed my whole perspective.” He was blown away.
Sam: I think you’re doing something that’s so common — you’re putting too low a value on yourself. You’re playing way too small.
The Awkward Ending and Pricing Strategy [00:10:00]
Ben: Let me tell you how it ends, though. So it was like a month later, I was in New York City. I said, “Let’s meet up, let’s get lunch.” We went to a really nice restaurant, he bought me lunch, which was very nice. And I was like, “So, when are you starting the thing?” And he’s like, “Well, I’m not actually doing it.” And he gave his reasons why he’s not starting it yet.
Sam: Your spit is watered-down, drink it.
Shaan: Exactly. That’s when you need to go dominatrix, dude.
Sam: Yin and yang, good cop bad cop sort of thing.
By the way, I think the loss aversion ratio — the numbers are two to one, meaning you’d have to make two dollars to feel the same as losing one. You’d have to make two thousand to feel the same emotional hit as losing a thousand would cause. I don’t know if that’s exactly right, but I’ve read that that’s the ratio of how much we value losses more than gains.
Shaan: Do you get asked to consult and do this type of stuff?
Ben: I get asked. I’d never consult anymore, but I basically run a simple filter: would I do this for free? That doesn’t mean I’m going to do it for free — it just means, would I? For Ben’s case, Ben’s like, “Oh, this sounds like a super interesting guy.” He did do it for free. I’m going to learn as much from this guy as he’s going to learn from me, if not more. So I’m happy to do this with my time.
Shaan: Dude, you get paid crazy money for doing this type of thing. Sam, you do GLG calls — have you done any of those?
Sam: I used to. I think I was getting paid a thousand dollars an hour.
Shaan: Exactly. I set my rate at the max they let me, which is two thousand. And dude, I’ll get paid two thousand bucks to do like a forty-minute call with some — first of all, it’s kind of funny because it is this weird underground thing where they’re like, “I’m a hedge fund manager. I can’t tell you what fund, I can’t tell you what I’m looking at, I can’t tell you my name.” It’s like a one-way transaction. I’m the masseuse and they’re laying face-down. I can’t see who they are. And then they’re like, “Okay, say the word ‘metaverse.’” And I’m like, “Metaverse.” “Tell me — who’s going to, which stock’s going to go up because of the metaverse?” And I’m like, “Dude, I don’t know.” They’re like, “What?” And I’m like, “Yeah, but I could tell you some things I think…”
Sam: Whenever I do those things, I talk really slowly.
Shaan: Yeah, because you just need an hour to pass.
Sam: I always talk really slowly. I’d be like, “Wait, hang on, let me get my headphones in so I can hear you better…”
Ben: I can’t talk slowly. It’s like — like I said with this guy, you feel a tremendous amount of pressure. It doesn’t really matter how much money you have. When somebody’s paying you something — I would never pay someone two grand for a phone call, even though I’m sure there’s an economic case where it makes sense. It’s just a big number to me to pay just for somebody to talk to me. So when I’m on the other side getting paid, I’m like, I need to deliver this guy some insane insight that they’ve never heard before. I put this weird pressure on myself that’s just unachievable.
I’ll say my point, and I really only have one point, and I’ll be like, “Another way of thinking about it is…” and I’ll repackage the same idea with some metaphor or analogy just to fill air space. Because in reality it’s one idea that’s worth it to them, or not. I don’t have ten amazing ideas. I have one, around one topic.
Shaan: But there’s a reason Ben’s shtick is amazing. You can only consult on your life experience, and you can’t live that interesting of a life all the time. Whereas Ben can just steal — he can read a book a week and he’s going to have fifty-two new ideas a year.
Sam: The thing that this guy was trying to sell me on was that I should come and speak to his bank. He’s like, “You could get paid like fifty grand a pop to come give a speech.”
Shaan: Sure. That’s the point. I do ten grand for a Zoom at home to give a speech to somebody now. And I’m like, why am I not doubling my price? The pricing strategy is: unless half the people are saying no, you’re priced way too low. Right now everybody’s saying yes — why not price double?
Sam: I did one recently, it was twenty-five thousand, but it was in person.
Shaan: How many zooms a month do you do?
Sam: Not even one a month. One every two months, probably.
Shaan: That’s pretty sick to me.
Sam: Oh, it’s great. And there’s this other thing, Ben — I don’t know what the history or psychology will tell us about this, but there’s extra joy in making money when you can assign what that money gets to go to, versus just generally making money going into a general bank account. Versus like, “Oh, ten grand — I do these two speeches this month, I’ll go buy that car” or “I’ll get my wife this gift.”
Coaching Ben: How to Monetize the Consulting Angle [00:15:00]
Sam: Can you tell me if there’s ever a moment — the reason I’m not doing any of this stuff is I just feel fraudulent going up there and saying…
Shaan: That’s normal.
Sam: Maybe I just need to get over it?
Shaan: One hundred percent you need to get over it. The way you should think about things is: most of your life you’re basically underpaid. You’re underpaid and underappreciated. The universe has this way of evening itself out — Sam will make more money off some random investment he thought about for five minutes than he would from grinding some apartment-finder business he ran for two or three years. The inputs don’t always match the outputs in life.
Once you acknowledge that, you accept it. The level of difficulty for you is not what dictates the value for somebody else.
Sam: The effort is not in proportion to the output. It’s irrelevant. All that matters is the output. The fact that you know the input — that’s actually a liability for you. A weird psychological liability. You would be better off not knowing how hard it was to say that one thing to that guy at that moment.
Shaan: The second thing is, Mr. Market will decide what it’s worth. You might get lucky once, you might get lucky twice, but if people consistently pay you for something, it’s because that’s what it’s worth to them. They need a positive ROI on that interaction. So just let the market decide. Over time it’ll balance itself out.
Sam: I think you should lean into this hardcore. How much money are you making on ads for your podcast?
Ben: I have one sponsor right now. I’m making four digits per month — low four digits.
Sam: Okay, so one to five thousand a month.
By the way, the hack when somebody says “how many digits” — just take the bottom three numbers of that range. So if I say I make seven figures, I’m saying one to three million. When The Hustle sold for eight figures, it’s ten to thirty million. Once you cross fifty million, you would say “over fifty million,” not eight figures.
I think you should go hard on this. You have 100,000 listeners a month. You’re making single-digit thousands. You’d make six figures a year for sure doing this. Do your own ad read that basically says: “Look, yes, people who listen to this tell me they got a bunch of inspiration, they got some strategies, they filled in the gaps of something they didn’t know about history, and they can see their place in the world today through that. But what actually ended up happening is companies started hiring me to come in and talk to them about lessons from the greatest figures in history. It’s motivational for the executive team, it’s a great addition to any off-site.” And basically say, “This actually ends up making me more money than the ads. So if you’re interested, contact me.”
I bet if you do that, you’ll get one of these a month, and it will quadruple your current ad revenue.
Ben: Dude, you’ve got to do this.
Shaan: Okay, next month we’ll do another segment in Ben’s First Million.
Sam: You can make it as simple as my best friend Neville Medhora. He has what he calls consults. If you go to his blog — CopywritingCourse.com — there’s just a checkout page, it’s a thousand dollars, and you book one hour with him. You just pay and then select on Calendly. Every Tuesday and Thursday from nine to one, he just knows that’s his call time. He makes a lot of money from it a year. You could do it as simple as that.
The other thing you need to do is like a profile piece — maybe for How to Take Over the World — something like “Here’s Pixar’s creativity process. Here’s how Pixar consistently has creative hits in storytelling.” That opens the door for you to basically teach the Pixar way to a bunch of companies that want to be more creative or better storytellers. Replace Pixar with any company that has excellence in X category.
Ben: Yeah. So you select the companies by who would listen to this, and then pay me to consult.
Sam: Work backwards from that. I always, whenever I give advice, explain it this way: I’m going to say some things that make you feel uncomfortable — either because you personally would feel nervous saying this to a customer, or quoting that price to a customer. I’m just telling you: if you crank the commercialization knob to twelve, here’s what you could do. And then you could decide to dial it back to nine or eight — wherever you feel comfortable.
I always say it differently: do you want your future kids to have braces or not? Do you know what an orthodontist costs? Get to work.
Ben: That’s too good.
Shaan: All right, let’s do some other topics. Thank you, Ben. Good luck.
Ben: I really do appreciate the advice. Thanks, guys.
Sam: That’s amazing, right? I was thinking about that for about a week.
Shaan: That’s hilarious. I had no idea that was going on. He mentioned it to us but didn’t make a big deal out of it.
Shaan’s Angel Investing Is on a Tear [00:22:00]
Sam: What do you want to talk about?
Shaan: I know what I want to talk about.
Sam: I’ve noticed that your angel investing is on a tear. Our friend Suli just said — whatever, Shaan joke. He was like, “Oh, I got this new brilliant investment strategy. Shaan invests in something, and then he tells me about it two weeks to two months later, and then I pay ten times the price for the same company.” He was joking, obviously. But that’s literally what’s happened in like six or eight deals now — I’ll even tell him about it, but he just delays responding for a couple weeks, or I forget to tell him. And then he tells me about the company a few months later and I’m like, “Oh yeah, I invested in that.” He’s like, “Awesome, can you make an intro?” And I make the intro, but the price has gone up dramatically because the company has more traction.
I put you on an email list for my friends where I’m sending you everything. Are you getting those?
Shaan: No, I didn’t see anything.
Sam: I sent you two of them so far. I’ll forward them to you — one of them I’ll send you after this. But anyway, so I’m starting it off where I’m sending them to you, so you gotta hopefully if you find something that interests me, send it back. But how are you getting such good deals?
Shaan: I don’t know. I feel like there’s the easy answer: oh cool, I do this podcast, and because of this podcast people come inbound. The bigger this podcast gets, the more people want you to invest.
There’s this great thing my buddy Vishal taught me: startups are the only asset class like this. Real estate — if you want to buy it, you go buy it. Stock market — if you want to buy it, you go buy it. Startups are the only thing where even if you want in, you don’t just get in. The asset selects you just as much as you’re selecting the asset. And that one insight is pretty important. It basically means you need to build your brand and your reputation so that people want you in deals, because the best deals are all super competitive to get into.
You want people, when they’re first thinking of an idea, to reach out to you, because they know — like, for example, I did a great deal recently. And it’s so funny, you’re gonna hate this, it’s gonna piss you off so much.
Sam: You’ve been talking about short-term rentals.
Shaan: Somebody came to me with a short-term rental startup idea because they thought I was you or something. The subject line she reached out with was “Last one in.” It was like, “Hey, I have the smallest bit of allocation left in this — this is a company called Hostfully. You’ll love it because it’s literally exactly what you’re doing.”
Basically what they’re doing is — if you own a bunch of Airbnbs, which is kind of a new market, you’re more than just renting out your home. You have multiple properties, but you’re not a traditional property manager who owns a multi-family building of thirty-two units. This is for people who run multiple Airbnbs, and it just makes your life way easier as the owner. They have a few million dollars in recurring revenue, the valuation was great, the founder was really impressive. So I was like, yeah, great — SaaS software for people who manage multiple vacation rentals.
And then you’re over here building the Short-Term Rental Club, building this community, doing this thing. And I got the benefit because people thought I was you.
Sam: That’s ridiculous. That is a piss-me-off answer. Whatever. Send me — what’s the company called?
Shaan: Hostfully.
Sam: Well then I can just email her.
Shaan’s Investing Framework: Long-Term Orientation and Thematic Bets [00:28:00]
Shaan: Here’s some of the things that have been working. One: when I share deals with you, you share deals with me. My buddy Julian Shapiro shares some of the best deals. He’s very active, very consistent — like every week he’s sending me some good stuff. That’s probably forty to fifty percent of the portfolio.
Relationships with friends who are themselves experts in one specific niche. For example, we’ve been doing a bunch of sales-person software because we have a relationship with Craft Ventures — started by David Sacks. He’s kind of the enterprise SaaS guy. He built Yammer, sold it for a billion dollars. His fund specifically just focuses on SaaS companies. So when they’re seeing something good, they’re just trading notes with my partner Romine, and we’re getting to get in on a lot of their deals.
Sam: Are they giving you the deal because they like Shaan, or do they like Romine?
Shaan: In this case it’s Romine. He has that relationship — catching up with that guy every two weeks, getting coffee. But then I do the same with my guys in India or Southeast Asia, because I think that’s where a lot of opportunity is and that’s where I have the right relationships. We’re sharing stuff amongst that network.
The other thing is themes. Once I decide a theme is correct — worth betting on — what I learned from Suli is the level of aggression you need once you decide X is a good idea. You need to go invest in that company and then the five other companies that are adjacent to it. For example, there’s this trend of neo-banks.
So this started several years ago where people were basically like, “Look, banks are something everybody uses but has super low customer satisfaction scores — their apps sucked, their marketing sucked.” So people were like, “We can create a digital-first bank.” Nubank is probably the best example of this, in Brazil. They’re about to go public. It’s a ten-billion-dollar company with millions of customers in Brazil. The same thing happened in the UK with Revolut and Monzo.
Neo-banking basically: can you make a super slick app for customers, digitally market to get customers, and basically you’re building the customer relationship, but under the hood you’ve partnered with some bank like BBVA?
Sam: So you decide that’s a good idea, and then…
Shaan: You go find every version of it. So, for example, Brex and Ramp — Brex, I think, was the fastest-growing YC company in the last few years. What are they actually doing? They’re giving credit cards to a group of people dissatisfied with current credit card providers. Brex did it for startups and they get a portion of every card swipe — a piece of the interchange fee.
So if a million people are spending a thousand dollars a year and they’re keeping 1.3% of the interchange, you can do the math. This company’s going to get big pretty fast. So we did the math on neo-banks — how much is the neo-bank customer worth, how much is a credit card customer worth — and then we went and did it in every niche we could think of. We invested in Keep, which is doing this for Canada. We invested in Pluto, which is doing this in the Middle East.
Sam: Did you holler at them?
Shaan: Then we go search-and-destroy basically. How do you go hunt for the best companies doing this in either this geography or this customer base?
Sam: And you just DM them on Twitter, probably?
Shaan: Exactly. Cold DM and say, “Hey, I’m a believer in this for this reason. What you’re doing looks super interesting, would love to invest.” And sometimes it comes inbound — sometimes you got a hundred things inbound but you know what you’re looking for, so you quickly pounce on the four that fit your thesis.
Sam: Aren’t you out of money at this point from the fund, though?
Shaan: I raised more money. Before, I thought — will I get a million dollars’ worth of deals every quarter that are good deals? I’m not just trying to invest in crap. So I was like, I don’t know how many high-quality deals I’ll have. And now I realized that whatever I had before was too low. So now we’re doing almost two million a quarter. We raised more money because we just had better deals, man.
Sam: Because I’m starting — I started angel investing almost one year ago. I did five or eight companies personally before that. A couple of them have turned out to be like meaningful — like turning twenty grand into three, four, five hundred thousand, and I’m like, holy crap, this is how it works.
But it sucks for a while, right? You just invest it, you’re like, well, that money’s gone. You don’t hear anything. And then you’re like, oh nice, it works. So I’m in some of those cases with huge markups, and other cases I’m just now experiencing two and three and four X markups, and I’m like, that’s awesome.
What would have happened if I’d invested at a ten-million-dollar valuation instead of a fifty-million-dollar valuation? That would have been wild. How do I do that?
Shaan: I hated startup investing for a while because I was like, is this the best use of time and money? It feels like an expensive hobby. I’m just spending money and not getting anything in return. Then I realized two things.
Bezos has this quote: one of the biggest competitive advantages you can have is being long-term oriented. If you have a ten-year view and the other guy is trying to maximize quarterly earnings, you can make bets they can’t make. Amazon was basically like: we’re willing to lose money to invest so that we provide two-day shipping instead of seven-day shipping, or a larger selection that’s going to cost us more inventory. Their strategy was long-term. Short-term, they got punished by the market because their quarterly earnings didn’t look great. But that turned out to be the magic — the biggest competitive advantage Amazon had was their ability to be long-term oriented.
I think this is true just in general: if you’re competing against somebody who needs a result in one year and you’re willing to be patient and get the result in five, seven, ten years, you can make bets they can’t make. Lower-priced bets that will pay off bigger over a longer time horizon. That’s how startup investing works: if you need money or need to see positive growth in one year, startup investing sucks. If you’re willing to play a ten-year game, this can be an awesome game.
Sam: Do you think you’ll earn more from the ecom thing or from angel investing?
Shaan: Probably for me personally the ecom thing, because I own the majority of that company. If it sells for fifty or a hundred million dollars, I own the majority of it. Whereas with startup investing, my fund invests a hundred thousand dollars, we own point-eight percent of this startup, I personally have twenty percent of the carry, but then I share with Romine and Ben and Zach. So I personally own like fourteen-point-something percent of the carry. It’s a slice of a slice of something big, versus owning the majority of something that sells for a decent chunk. That’s just better financially. So much better.
Sam: Whenever people raise money, I’m like, “Are you sure, man?” You might be able to sell this for fifty million dollars and make more money than if you raise money and sell for five hundred.
Shaan: Yeah. But I have to operate that other business, whereas startup investing — you just read about cool ideas, you meet awesome founders, you say yes, you write the check, and then they go do the hard work. It’s just a different thing.
The second reason is that you want to do things that compound. If I wanted to beat the market in the stock market, I need to have proprietary insight — I need to be smarter than anybody else about something. Being smarter at a game where money’s on the line is just really hard to do.
Whereas if you basically say, “Hey, my advantage comes from my reputation or my network” — that’s just going to compound every year. The more deals I share with you, the more deals you share with me. The more companies I have that are winners, the easier it is for me to get into the next winner, or for founders to come reach out to me because they’ll say, “Oh, I saw you did these five Indian unicorns, I want to be the next one, can you invest in me?” Compounding happens in a way that doesn’t happen in the stock market, and doesn’t even really happen in real estate — not in the same way as how fast your reputation can compound in startup investing.
Short-Term Rentals: What Sam Is Learning [00:38:00]
Sam: You brought up STRs — short-term rentals. Have you researched that at all? So I joined your club, but it’s crazy, right?
Shaan: Did you — you used to review it, yeah?
Sam: I’ve been looking at some of these posts, dude. It’s like techy guys — like people who have hundred-million-dollar companies. By the way, I don’t know how you founded Facebook, but every time I open Facebook, whatever you’re working on is always the top post on my feed.
Shaan: I don’t know if Facebook just knows that I love you.
Sam: I’ve always been like that. It’s always been that way for some reason. I mastered Facebook. And that sucks, because it’s the least valuable platform.
Shaan: I figured out what you’re talking about.
Sam: Yeah, because I can only have five thousand friends on Facebook. But your groups are big, okay. So tell me — what is that group? It’s sick, right?
Shaan: How many people are in it? A thousand people in this group. And people are basically posting, “Hey guys, here’s the properties I own,” and they show a bunch of cool photos.
My strategy — for example, my family owns five big short-term rentals in Kissimmee, Florida, which is five miles from Disney World. His strategy is basically Airbnb near Disney World. He has a full-time job, he’s a PhD student, and they’re showing these Disney-themed rentals and people are asking questions in the comments. Everybody’s comfortable telling you how much money they’re making and sharing a bunch of good info.
So here’s what I wanted to hear from you: give me the top two most interesting stories you’ve learned.
Sam: I’ve gotta be a little subliminal about this. In that group of a thousand people, I met one person who’s got thirty-five million dollars in homes — he owns about twenty of them — and he’s currently making close to a million dollars a month in profit.
Shaan: Was this person wealthy before this? How do you get to thirty-five million dollars in real estate?
Sam: They were mildly wealthy — worth probably fifteen million, they had a business they sold. Not poor. They invested a lot of it into short-term rentals, and now they have a staff of a couple people who are full-time. His take is about eight hundred grand a month.
I met another guy who worked at a hedge fund — his name’s Richard, if you Google “Richard short-term rentals” he has a story in there. He eventually quit his hedge fund. Now he owns fifty million dollars’ worth of short-term rentals.
The themes I’m seeing: one, institutional capital has not come into short-term rentals in a significant amount. Two, the numbers might be inflated because the economy is crushing it, but I’m not entirely sure. Three, a couple years ago people were just buying places without doing much math and making twenty-five percent returns — it was crazy. Now it’s a little more challenging, but it’s still a lot of opportunity.
Shaan: Of all the things you’ve read in here, what seemed like the smartest “small ball” strategy? Not the guy who had fifteen million bucks and built this big thing — who did something small, started small, grew it in some niche?
Sam: Is a million dollars considered small? If you buy a property for a million dollars, you’re going to put down like one-fifty.
There’s a guy in there — search the word “coconut” in the group. There’s a guy who bought a plot of land on a coconut farm in Mexico and put four — I think four — tiny homes on it. He rents them for about a hundred fifty dollars a day. He did really nice landscaping but not complicated stuff. It looks beautiful.
Shaan: Is it Safa Farms?
Sam: Yeah, Safa Farms. Six cabins, one house, an in-ground fire pit, a pool in Mexico. It looks cool — a bunch of wooden cabins that look really small, like one-person, two-person kind of stays, and then a really cool outdoor area with hammocks and pools and common areas and places to go do yoga with like chickens running around. Is that wild?
The Airbnb Opportunity and Content-Driven Property Thinking [00:44:00]
Sam: How cool is Airbnb, that it created this opportunity for anybody to say: if you can create an awesome experience for people, a great and unique place to stay, we will give you the ability to make money just by creating this cool little farm-and-huts setup in Villa Corona, Mexico?
And on the other side, it’s like: here’s the buffet of dope experiences that’s not just a cookie-cutter hotel that you can stay at. How sick is Airbnb in that respect?
Shaan: It’s amazing.
Sam: What I’m learning is — it’s just like content. It’s just like scrolling through YouTube. If you look at it through that lens, you can make a lot of money.
When you’re buying a property, you go on Zillow and look at their thumbnail pictures. You’re like, what catches my eye? And then sometimes you see a place that took a bad picture, but if they changed the angle here and made the light at sunset — this will look beautiful. So you’re basically shopping for thumbnails.
Then the second thing: you’re not shopping in any place where you have to create demand. You use AirDNA, which shows you who has the highest booking rate.
The third thing is: you pick a very specific niche and you have one unique thing about the property. For example, you call it a “zen retreat” because you’ve got a little pond on the front. Or: has a fancy gym. Has a putt-putt course. Has a deck with a view of the sunset. One unique thing.
And that’s the same way content works — it lets you reimagine. Okay, if this home was not for a family of four to live in every day, then maybe this space instead of just two couches and a TV, it’s actually where companies are going to come for their retreats. Different groups of twenty-five at a time. They need a big sauna in one area, a pool area, a barbecue pit. I’ll over-invest on these things and not worry about the daily utility functional things a normal house would need.
It’s just been so fascinating, because I didn’t realize how many tech nerds are into this stuff. That group is so cool.
Shaan: Rohan from Priceonomics — it appears as though Priceonomics is on the back burner and all of his time is on short-term rentals. He owns like seven of them. It’s badass.
Sam: I just want to give money to this group and be like, “Hey — anybody who wants to trick out their place or buy their next property, I’ll just finance it with you and share cash flow if you want. Some preferred return, that’s fine.”
There’s no such thing — or there aren’t many funds — for short-term rentals. Like, you and I have invested in Blackrock-style investment funds that buy five hundred Walgreens and make five percent. There should be one of those for short-term rentals — a REIT or some way to have passive skin in the game.
Shaan: Wild.
The Tailgate Guys: Campus Monopoly Playbook [00:48:00]
Sam: Okay, let’s do one other thing. Let me give you two quick ones.
Tailgate Guys — have you ever heard of this business? So this came up at FarmCon. I go to this dinner with this guy who listens to the pod, and he was telling me — I was trying to make small talk at this dinner and I hate normal small talk. I also don’t know anything about farming, so I can’t contribute that way. So I tried an icebreaker: “Did you have a side hustle in college?” I went around the table. Everybody was doing something different when they were in college, and everybody had an interesting one.
So one guy tells a story. He goes, “Yeah, I went to Ole Miss” — or Alabama, one of these southern football colleges — “and I created a tailgate in a box.” He’s like, yeah, tailgating is huge before the football game. People go to the parking lot and they want to grill and drink and play beer pong.
His family used to tailgate, and it was so competitive that you had to go wait almost overnight to get your spot. So they would send him down to — I think it’s called the Grove at Ole Miss — and he’d have to wait in the parking lot and hold his family’s spot.
Then they started being like, “Okay, you got the spot. Well, you gotta set up the tailgate for us too. We need tables for beer pong and this and that.” So he’s like, okay, I’ll get the stuff every week. And he would create a good setup. Then the space next to him was like, “Hey dude, next week — will you set ours up?” And he’s like, “All right, you give me two hundred bucks, I’ll get you guys some stuff.” Yeah, sure. And then the price goes up.
He’s like, I can basically charge each little tailgating group five hundred dollars just to set up a cool tailgate spot, turnkey tailgating. So he did this at his college and was making thousands of dollars every semester.
Shaan: Is it — I Googled “Tailgate Guys.” Did it get acquired?
Sam: So that was their competitor. There was a nationwide version of this. He was doing it at small scale as a college side hustle. I was like, who’s Tailgate Guys? He’s like, “Oh, these guys basically took this idea and started doing it nationwide.”
Shaan: That’s really smart. How does it work? You just hire college kids?
Sam: You say, “We’ll give you fifty-fifty — three hours on Saturday, you get fifty, we get fifty.” The kids go to Walmart and buy the supplies, or you give them supplies in bulk. You tell them, “You need this table, these bowls, this beer” — whatever — and you use a company credit card.
And here’s the key: they would partner with the school. They would say, “Hey, we’d like to be the exclusive tailgate provider for the school.” The school would give them the license, so they had a monopoly. It’s pretty common — schools will basically pick one vendor provider. They sell you the license rights. You become the official, you know, “Tar Heel Tailgate.” They link to you, it’s their thing. You pay them a fee or a revenue share, but in exchange you get a monopoly.
And it’s super viral — because you’re like, “Wow, that setup looks legit. What is that? Oh, they use Tailgate Guys. Okay cool, we should use them next time.”
Tailgate Guys apparently — I think they got bought out by private equity — were doing like thirty to fifty million dollars a year doing this.
Shaan: What?
Sam: I thought, what a great example of a college hustle that you then scale up. If this works at my college, it’s going to work at every college that has a football program with tailgating. And then there’s this repeatable sales model of going to the university and saying, “These other eight universities partnered with us. We’d like to partner with you. You get extra income, and we will provide a safe, convenient way for your fans to do this.”
Then I started thinking — what are the other businesses that use the same tactic of partnering with the school and becoming the exclusive provider?
Shaan: We had a little mini-brainstorm about this. He said this is also happening with scooters. When Bird and Lime came out, companies decided: oh shoot, we should become the exclusive scooter provider on campus. We’ll drop scooters everywhere, branded with the school. The school gets a revenue share for every ride that happens, and we get a captive market that nobody can compete with.
What else could be done today that doesn’t even have a market yet — where you’re creating the market?
Sam: The hard thing now is that schools have gotten wise to it. They won’t give the license up super easily. They want to make sure they get a fair shake. So once you come to them with the idea, they’re like, “Great — hold on, ninety-day proposal period. We’re going to talk to five companies before we just say yes to you.” But in the good old days, you used to be like, “I have this idea,” and they’d be like, “Sure, you came to us, you get the deal.”
Kira Cubby and Selling to Schools [00:55:00]
Sam: I’ve learned a little bit about selling to schools. I sent you this company — it’s called Kira Cubby. Kind of a bad name, but basically this guy Stephen had an autistic kid, got diagnosed with autism, and he didn’t feel like sending him to a normal school. So he started a school. Like twenty kids in the neighborhood went to it. He was like, man, managing this school is a pain in the ass. He found another parent — he lives in Oakland, so the other parents are tech guys — who sent his kid to his school. They decided to build software together that basically makes it really easy to collect tuition payment and also pay your bills. So it’s like a Bill.com plus QuickBooks plus Eventbrite — you can check kids into after-school programs and stuff like that.
They’re crushing it. It’s just four guys, they’ve gotten it up to 2.4 million in recurring revenue. And he’s been telling me all about selling into schools, and it sounds like a nightmare.
Shaan: Yeah, I think it is. The company I think has done the best at this is Mystery Science. Have you seen them?
Sam: Is that like a TV show?
Shaan: Kind of, okay. So Mystery Science — oh wow, they got acquired. I didn’t realize this. They got acquired last year for one hundred forty million dollars. Good for them.
What Mystery Science was doing was — how do we make entertaining videos, sort of like Blues Clues or Magic School Bus, on every topic? If you’re like, “Why are plants green?” or “How hot is the sun?” — they would make the definitive most entertaining, simple answer to that question.
It turns into something like a game. The teacher can just pick one of those questions and be like, “Hey class, today here’s the question: who wants to know the answer?” And everyone’s like, “Yeah, I want to know the answer.” So there’s a worksheet and a video that teases part of it, and then the class has to go figure out the next bit before they watch the rest. It makes it easy for teachers to teach around a question that kids are genuinely curious about.
They reached like four and a half million teachers countrywide. At one point, thirty or forty percent of all elementary schools were using them.
Sam: How did they only sell for a hundred and fifty million with that kind of penetration? That’s crazy to me.
Shaan: I know. Wild. They basically raised very little money and were super profitable. So I think the guys made over a hundred million dollars off this deal. They raised I think only four million dollars lifetime. They started in 2014, so about seven years.
Charging money to schools is always hard. But these guys were super smart — they talked to the guy Keith, and I just really respected what they’d built. What a cool product. Amazing that they got to that level of saturation.
The way they sold was kind of bottoms-up. Teachers couldn’t help but talk about it to other teachers because they were like, “Oh, this is amazing.” Normally when I wheel out the TV, it’s like, “We’re watching a movie today.” This was different — it’s interactive, it’s based on questions, it’s based on science. And they were like, “We’re just going to teach science this way.”
Sam: That’s so good.
Shaan: They reached fifty percent of the U.S. elementary school market.
Sam: How much revenue were they making? Wild.
Shaan: I don’t know at the time I was talking to them, but they were doing somewhere between ten and twenty million in revenue, profitably.
Sam: How do you reach that many teachers but only sell for a hundred and forty? That’s crazy to me.
Shaan: I don’t know. Just wild.
Closing and Contest Winner [01:01:00]
Sam: Anyways, I gotta run, dude. I got a call with this crazy crypto thing that I’m trying to get into, so I want to see if I can do that.
Shaan: All right, we’ll talk soon.
Sam: All right, Shaan — if you want to leave, you can leave. I think Ben — do I got to read out some names?
Ben: Yes, actually just one name.
Sam: All right. We did this thing where we gave sixty minutes of Shaan’s and my time. What did the person have to do to win?
Ben: They had to rate and review us on Apple Podcasts.
Sam: Great. And the winner is — is it SS? Yes. Spencer Scott — you are the winner. Has Spencer — he follows me on Twitter, he always replies to my stuff. Does he know that he won, other than right now?
Ben: Yeah, I told him.
Sam: Nice. All right, Spencer Scott’s a winner.
Last week we gave the winner for the TikTok thing — so we did this TikTok thing where if you made videos on any platform and used the MFM clip hashtag, you could win five grand. We gave three — did we get three or two? And before that we did a contest where if you rated and reviewed us, you won sixty minutes with Shaan and me. So we gave that one to Spencer Scott. We’re going to keep doing these.
That’s the episode. That’s the winner. Check it out.