Intro: Picking Topics [00:00:00]
Shaan: All right, let’s do some topics. What do you got?
Sam: I got a couple.
Shaan: What? Dude, I got a bunch of good stuff.
Sam: All right, let’s pick one of yours. Let’s do the Satoshi and the Paul Le Roux thing, because they’re both really interesting. Which one do you want to do first?
Shaan: I don’t know who Paul Le Roux is.
Sam: You don’t know who Paul Le Roux is?
Shaan: Great name though, dude. Listen to this — how much more would I be worth if my name was Shaan Le Roux? At least triple, right? And how much respect would I get? He’s also African — South Africa, I think.
Shaan: Ben, you’re nodding a little bit. You know who this is?
Ben: Yeah, I know who Paul Le Roux is. He’s kind of like — who’s the guy we were talking about that you knew? Ross? He’s kind of like if Ross had been as crazy as everyone thought, but actually ten times crazier. That’s Paul Le Roux.
Shaan: Whoa. Yeah, yeah.
Sam: I don’t know him. Fill me in — who is this?
Paul Le Roux: The Origin Story [00:01:00]
Sam: All right, so Paul Le Roux — he’s this big, fat, disgusting guy. Imagine… have you seen South Park where they’re playing video games and there’s that fat guy on the computer eating Cheetos? He kind of looks like that. He’s just a total slob but he’s this computer whiz. Google him. He’s like disgusting, and that kind of fits the personality of the whole story.
There’s this great book I’m reading called Mastermind. It’s about him. Basically, this guy always had grandiose thinking — he thought he owed it to the world to run it. Around 2002, 2003, 2004 he started a company called RX Limited, which sold Viagra and a couple other Schedule II drugs. Things that are considered Schedule II — just one below Schedule I. And in like three or four years it netted him hundreds of millions of dollars in profit.
Sam: Do you remember years ago when you’d get an email that said “hey, we sell prescriptions, click here”? Years and years ago when you were in high school?
Shaan: Not really, but go on. Let me say yes — go ahead.
Sam: And then maybe you remember going to websites that just showed a ton of drugs, and you’d get a text that said “buy drugs online.” Basically, he created RX Limited. Eventually he started creating so many domain names that he built his own domain registration system. His network got so big he created his own email system because he didn’t want anyone to hack into his stuff.
At one point he had two or three thousand employees — mostly Filipinos working in call centers in the Philippines, and Israelis. He said the Israeli guys were the hardest working for the cheapest rate.
Sam: The way it worked: he would somehow convince a doctor that he was doing everything by the book, and technically he kind of was — at first. He had doctors all over America in places like Minnesota, Kentucky, Florida. Small practices. He’d say, “Hey, we’re a telemedicine service. Can you fill the prescriptions we’re sending you? It’s all legal — we’ll send them to a pharmacy.”
So he’d send them to a pharmacy, and the local mom-and-pop pharmacist would be like, “Oh, Dr. X just called in this prescription. I’ll ship it to the patient. No big deal.” Both the doctors and the pharmacists thought they were mostly following the law. The pharmacist is thinking, “This is a little weird — I’m a mom-and-pop shop and I’m shipping out 2,000 orders a week — but I have no reason to believe this is illegal.”
Eventually it became highly illegal. He didn’t require any doctor to actually see patients. At one point he was selling something like 80% of all online drugs in America.
Sam: Ben, am I missing anything?
Ben: Throughout all of this, the story gets even crazier.
Sam: Yeah, it made — I believe — $400 million in profit in four years. One employee went to his apartment in Manila and said he saw $10 million in cash in the house. This guy didn’t want the IRS to see anything, so he’d just transfer everything into gold. This was before Bitcoin was really around.
He lived in the Philippines. He was born in Cambodia — or maybe Zimbabwe — moved to South Africa, then moved to the Philippines. He had this grandiose thinking where he was like, “I owe it to the world to run the world.”
The Arms Dealing and African Nation Plans [00:06:00]
Sam: So he hires ex-Israeli guys to run call centers. Eventually he hires ex-Israeli army guys as bodyguards. Through them he starts learning about arms dealing. He buys thousands of acres of land in Zimbabwe and Somalia. He’s like, “I’m going to raid an African nation, set up my own country, and be the leader.” Crazy stuff.
It expands to the point where he’s now an actual arms dealer — selling guns to different parts of Africa. He gets in trouble for selling missiles to Iran. He’s killing people along the way. He makes relationships with Colombian drug lords and trades pills for cocaine. He’s selling hundreds of millions of dollars worth of cocaine. And he was doing almost all of it from behind a computer.
Eventually he gets caught. He was sentenced to 25 years in prison, and that doesn’t include what he’s convicted for in the Philippines. So after he gets out — if he gets out — he goes straight from the US to the Philippines.
Because he’s essentially a drug lord, they won’t say where he’s being held. Online you can barely find any pictures of him other than one mug shot — the one where he looks really big. That’s the only recent picture I’ve seen. It’s one of the craziest books I’ve ever read.
Sam: The reason I started talking about Satoshi is because a lot of people think Le Roux might be Satoshi Nakamoto. There’s not a ton of hard evidence, but he was talking about creating a digital currency early on. When he was arrested, Satoshi quit blogging. You can read a lot of Le Roux’s emails — and that’s how I got interested in the Satoshi angle, where you can read all his old blog posts.
This guy would have been an amazing businessperson had he not gone the wrong route. It’s a crazy book.
Shaan: What was in the emails?
Sam: You can just see him commenting with people. He was actually a pretty good writer for a while. He wrote guest posts — I believe for the Washington Post — under a pseudonym, talking about the future of money and economic stuff. He was somewhat eloquent. But in person he was brutish and disgusting. He’d go to McDonald’s and wouldn’t even talk to his employees — he’d kind of tell them to f*** off. He wasn’t pleasant to be around. But in the emails he wrote pretty nicely.
Ben: What are you going to say?
Ben: They found 500 pounds of cocaine on his yacht when it crashed. That was worth something like $100 million. He also owned a logging business in Somalia at one point. He was like, “I’m going to create a business — Western countries driving through Somalia, if they want the pirates not to bother them, I’m going to be the go-between. I’ll pay the pirates off and take a little profit.” He owned that business. He was also in mining. At one point the district attorney of — I believe — New York said, “We think this is the most dangerous and powerful man in the world.” And all of it was done on a computer.
He was very early in all this — kind of in the same ballpark as a lot of the crypto guys. Some of his ideas, even though he was a criminal, were totally on point with the Bitcoin stuff. It’s super fascinating.
The Satoshi Connection [00:12:00]
Shaan: There’s an article about the case for why he might be Satoshi. I haven’t read it yet but I just pulled it up while you were talking.
You say he did it all behind a computer — my research on this is old, but didn’t I remember a story about him throwing someone off his yacht and having people shot in the water?
Sam: Yeah, but in that particular story he wasn’t there. But there are a few occasions where people think he actually fired the bullet himself. He had hitmen — some of them are arrested now and spilling the beans — but he did travel. He’d go to Africa. He’d go places.
The thing is, the guy had 3,000 employees and most of them had no idea who he was. He had two Israeli brothers running a call center in Israel with like 300 employees who had never met Paul. He’d talk to them via email just like a regular employee. Anonymous work is something we’ve talked about, and that’s pretty much how it worked. So some of his employees had no idea who he was.
Sam: This article I pulled up says he’s “the Jeff Bezos of organized crime” and “the digital El Chapo,” because he was moving so much weight. He was given up for adoption by his birth parents — that rejection haunted him. He transformed himself into a programming genius who developed encryption software like E4M in the 90s. He founded RX Limited, which became the black market for pharmaceuticals. He was raking in $250 million a year selling drugs, weapons, and murder-for-hire.
Sam: The “dark web” thing is actually a little misleading, because a lot of what he was doing was before Tor was even around. The email spamming — he was one of the originators of that. He hacked into a pharmaceutical company and stole hundreds of millions of email addresses. The reason he bought all those domain names is that when one domain got banned he’d just switch. It was incredibly complex what he built.
Before he turned to the dark side, he built a small open-source product that helped encrypt things. It eventually turned into something called TrueCrypt, which is actually a big deal.
Sam: His first murder: he told his head of security, “Come to my house in the Philippines and dig a hole — I’m going to bury a safe filled with millions of dollars.” The guy dug the hole. Then he shot him with a machine gun. That was his first taste of murder.
Another story: they took a guy out on his yacht, threw him in the ocean, and started to drive away. The guy freaks out, they come back, and he fires shots next to the guy in the water and says, “Don’t worry — I didn’t miss. I’m just keeping the sharks away because I need to talk to you. Are you stealing from me? If you tell me quickly I’ll kill you now. If you don’t tell me, I’m going to shoot you in the leg and drive off.”
Shaan: Wow. This guy makes the Wolf of Wall Street look like a small puppy. He’s insane.
Sam: Never heard of him either, right? How’d you hear about him?
Sam: When I tweeted that I love crime books, someone suggested this book called Mastermind — it’s by a journalist who worked at Wired Magazine. I’ve been reading it and it’s freaking crazy. Even though what he did was obviously wrong, it does inspire me to want to live a more adventurous life. I’m reading it and I’m like, “Why am I so fascinated by this?”
Shaan: I’m the same way. It’s like — why does this excite me? I’m beginning to normalize this in my head and think it’s okay. I can’t watch this anymore. But I do think there’s something about needing a little more adventure in your life. You could use it for good, you know.
Sam: I read it and I’m just intoxicated by it. Do you get that way?
Shaan: Yeah. I think that’s why people love movies about prison breaks and bank heists, and why people play video games with violence. There’s definitely a part of us that this stuff appeals to. And if you can get that outlet just by reading the book or watching the movie or playing a video game — good. Because it doesn’t have to translate into your actual life. You don’t have to let that deep-rooted desire for adventure, thrill, and power spill into your normal life.
Sam: It inspires me a little bit in the sense of — man, living life on the edge is crazy. I don’t want to go to prison, but still. You should just add that to your bio: “Top inspirations: Pablo Escobar, Paul Le Roux.”
Shaan: Heroes.
Satoshi’s Bitcoin Forum Posts [00:18:00]
Sam: One of the reasons this story is interesting is that you can read criminals’ correspondence from this era. When they arrested Le Roux, his computer was open, so they were able to see a bunch of stuff. And that’s what I really love about this era of online crime — you can see it happening. That got me interested in Satoshi’s posts.
If you just Google “Satoshi blog posts” — the guy who created Bitcoin — the forum is still up and you can read all of it. I spent about an hour looking at all the people commenting on his original post, Googling them, seeing what they’re doing now. You can see them reply back and forth.
Sam: The first few comments — it’s not like this thread blew up and people were instantly like “Genius! This is a breakthrough!” That’s not what happened.
Shaan: No, it was like “this is cute,” right?
Sam: Literally. The first commenter — Sepp Hasslberger or someone — says, “Great stuff. This is the first real innovation in money since the Bank of England started issuing promissory notes for gold, which became banknotes. I believe an open-source currency has great potential — a bit like Google has become the default search engine for many of us.” So this guy recognized it for what it is.
Then there are some people who have questions about how it works. And then there’s Hal Finney, who I think got the first transaction — Satoshi sent it to him. He had the most questions, which is why some people think Hal Finney was Satoshi Nakamoto. I think he was also the first to write out the total addressable market for it — he broke down why each coin could eventually be worth over a million dollars.
Sam: Imagine: it’s 2009, somebody posts this thing about creating “the new world money,” and you’re like, “Well, that means this random thing I could go mine on my computer could each be worth a million dollars?” Yeah. And to me, the people who saw it for what it was — a true innovation, something great, something that could catch on — I’m blown away by them.
Shaan: Me too. I think it’s amazing. When I read it I feel inspired. And I think that’s why I got a little obsessed with Paul Le Roux too — just these people who have this self-belief and vision, even if it’s a horrible vision, and just go out and do it. It’s really interesting.
Sam: You can read these forum posts, click on people’s profiles — they’re wearing fedoras and crocodile Dundee hats. They’re the nerdy guys I would have dismissed. But you read this and they’re incredibly thoughtful. They’re taking it seriously right off the bat. I admire that. It’s a really fun thing to read.
Shaan: The forum, I think it was called the P2P Foundation or something like that — just a Ning forum. The people who hung out in these types of forums were obviously pretty hardcore into peer-to-peer, cryptography, these different subjects. Hanging out at the fringes.
Finding Fringe Thinkers Early [00:23:00]
Shaan: I gave a talk recently for a bunch of people in the Midwest — they Zoomed me in — and one of them asked, “You said something about surrounding yourself with interesting people. How do you actually do that?” And I basically told him: I’m a pretty normal person. I like catchy songs by Katy Perry. I don’t have some sophisticated nose for the next big thing. But there are people who do have that as their superpower.
I used to make fun of those people because every time they’d do something weird I’d point out how weird it was. I remember in college, the guy who lived next to me — this guy Toji — I walked in and he was playing a video game, but the game kept going while he turned to talk to me. I was like, “Are you even playing?” And he said, “No, I’m watching a match from last night in Korea.” And I’m like, “What? You’re watching somebody else play video games?” This was like 2006.
I said something like, “Say five more lame things. Tell me you’re a virgin without telling me you’re a virgin.” I was just — never coming in this room again.
Then fast forward ten years. We sell our company, it gets acquired by Twitch, and all of a sudden my title is like “Director of Esports” or something. He calls me: “You [bleep]! Mr. Esports now, huh?” And I’m like, “Yeah, dude. It’s a big thing. You were on top of it.” I was so embarrassed because it was so true. I was making fun of that behavior, and then sure enough it becomes a multi-billion dollar industry.
Shaan: I kind of learned the hard way, many times, making a fool of myself. Now when I hear something weird I’m immediately like, “Let me pull up a chair. Tell me — why do you do this? Do other people do this? How often do you do it?” And the weirder it is, the more I want to lean into it. Because I know it’s just a matter of time before I discover this is totally normal behavior.
“Oh, you only drink Soylent for all your meals? Interesting. Is there a community? People who do this?” “Yeah, we’re called biohackers. There’s a subreddit with tens of thousands of us.” “Oh, interesting.” You start to see that the future is already here — it’s just not everywhere. And how do you get closer to the future? Find people who already live in the future, doing weird stuff, and don’t judge them.
Sam: Reading these old blog posts does exactly that. You’re seeing the pattern: this thing sounds silly at first, and then it worked. So what does that look like? How do I not make that same mistake again?
Shaan: The guy that owned the forum — at the very bottom of the forum page it says “about,” and you could read who the owner is. He’s just a professor in Berlin. Just a guy. All these people were there when this historic thing was announced and they saw it for what it was. It’s kind of weird to say, but they were like — they were around when Jesus was around. They saw this thing that potentially changes the next thousand years of history.
The Milk Road / Bitcoin Conference [00:29:00]
Shaan: I put this in the Milk Road — did you see the thing about Peter Thiel? The big Bitcoin conference just happened in Miami.
Sam: Yeah, that was really good. You did a piece on Friday — that one killed it.
Shaan: But did you see the clip I linked to? So Peter Thiel goes and gives his talk at the Bitcoin conference in 2022. Before he comes out, they play on the big screen a video I had seen before — I think I even talked about it on here once. It’s a video of him giving a talk in 1999, and he’s talking about the idea of a currency not owned by the government. Basically a two-minute clip of Peter essentially describing Bitcoin without saying the word Bitcoin. He didn’t know how it would work. But he’s like, “The world needs a currency that’s not controlled by the central banks of different countries.”
Shaan: He mentioned that PayPal’s original vision was to create a global virtual currency. They used to have shirts that said “one currency to rule them all” or something like that. Then they shifted away from it toward something more practical. At the 2022 conference, he goes, “Yeah, we wanted to create our own financial system, we tried really hard, and we settled on — oh, PayPal. It’s a payments network that works with your existing bank and existing dollar currency.” You could tell he kind of regretted it. Like, before we wanted to build this huge idea, and Bitcoin proved that was the big idea.
Sam: Him giving that talk in 1999 — that’s one of the greatest calls I’ve ever seen. Predicting what’s going to happen and why. He predicted smartphones too. He said, “This currency will live on your cell phone outside of a bank. Smartphones are going to be a thing.” He mentioned he was already seeing the adoption of smartphones in Finland. He gave a five-year timeline, and it took ten years, but he got it right. A billion devices. There was never a billion-user product before smartphones. There weren’t a billion people who had computers. The cell phone was the first thing where a billion people had the product.
Sam: Of course, if you launch an app today, your addressable market is a billion people who can download it immediately. That’s an overlooked fact about why mobile was so big. Your restaurant could never serve a billion people. McDonald’s couldn’t serve a billion people no matter how many locations they open. The cell phone was really the first thing able to do that.
Shaan: He’s paying attention to what’s happening in Finland — who even pays attention to Finland? If I asked you right now to point to Finland on a map, could you?
Sam: Me neither. Finland, Denmark, Holland, Sweden — they’re all the same thing to me. That’s where white people are clean and nice. I don’t know, dude.
Shaan: No wonder people who were hanging out with Peter Thiel went on to do amazing things. The PayPal Mafia — people who worked at PayPal went on to create YouTube, LinkedIn, Tesla, SpaceX, Yelp, Affirm. I think there’s like over ten billion-dollar companies that came out of the PayPal Mafia. Kiva, one of the best nonprofits, came out of that. You’re hanging out with people who are already thinking about the future, living in the future. They’re all weird nerds.
Peter Thiel’s Contrarian Thinking [00:36:00]
Sam: Dude, this gets me inspired. How do you think guys like Peter Thiel — I think his background was pretty modest — how are people like him right so often? Or do they just make a ton of guesses and are only right a couple times but I just don’t understand how you think that big?
Shaan: When you hear him talk, it’s like when you’re in a plane that takes off and the houses start to look like little toys, the people look like ants, the cars look like little specks. That’s how my brain feels listening to Peter Thiel. I am a small simpleton. I’m a single-cell organism compared to this guy — in terms of where my brain goes and how much conviction I have around my original thoughts.
That’s his thing, right? Being a contrarian. Jeff Bezos said something about Thiel — he goes, “Yeah, that’s the thing about contrarians. They’re usually wrong.” And somebody else said Peter’s constantly predicting sort of the end of the world, the market crash. You just remember the two times he was right in twenty years, and the four times he was wrong it seemed like he was just a little early on his prediction.
Shaan: But there’s something to it. When you’re right, you’re right in a major way. He was right about PayPal in a major way. He was right about Facebook in a major way — he was the first investor, bought a 10% stake for $500,000. Best investment of the decade. He was right about Trump in a major way — the only guy in Silicon Valley publicly supporting Trump, speaking at the convention. Thiel picked that horse pretty early. And the Thiel Fellowship.
Sam: He basically went on stage and announced he would pay people $100,000 to drop out of college. It was like, “Keep this man away from my children.” He was calling out college at a time when a hundred out of a hundred politicians, parents, anybody was pro-education. He said college education is a bubble — the greatest bubble since the housing crisis. He explained why: people go for this certificate, this insurance product. Parents buy it so their kids don’t fall through the cracks of society. You don’t go to learn; you go to get the certificate.
Then he put up — I think $2 million at the start — but that $2 million was like $200 million of free publicity because he made it bold. Not “here’s an alternative to college for people who don’t want to go.” He said: “I will pay you $100,000 to drop out.”
Shaan: And then how did he get his money back? I think he invested in the projects.
Sam: Ethereum came out of the Thiel Fellowship. That’s a $300 billion product. Which is kind of ironic because he kind of crapped on Ethereum at the Bitcoin conference, which is a bit weird. Vitalik Buterin being a Thiel Fellow was total validation. But also Figma came out of it, and owner.com. I’ve invested in about three of the Thiel Fellowship companies.
Shaan: I heard mixed things about the program itself, but there’s no doubt good stuff came from it. If just Figma came out of it, the program was a win. Ten billion dollars came out of it.
Sam: So this guy has been contrarian and right many many times. That’s more impressive to me than just being successful. If you showed me one person who’s very successful and another person who is an original thinker who’s right when they go against the grain — I have a lot more respect and admiration for the person who had an original thought that was right.
Going Big: Jared Kushner and the Question of Ambition [00:43:00]
Sam: I was reading today — weird tangent — about Jared Kushner. You know Jared Kushner?
Shaan: Yeah.
Sam: So there’s Jared and Josh. Josh is the younger one, maybe 35. He runs Thrive, which is a very successful VC thing. His brother is Jared, who was Trump’s right-hand man in the White House. A lot of people think he’s kind of evil. He has this like Skeletor vibe.
But he just announced that a few months after leaving the White House, he founded a $3 billion private equity fund. And regardless of politics — it’s just crazy that that’s just your next thing. When I end a job, I take a three-week vacation and then start another job that’s 20% higher salary and a slightly better title. He just goes, “I’ve got some free time now. I’m going to do this thing.” And it’s a $3 billion fund. I find that incredibly inspiring and also makes me feel like an ant.
Shaan: Yeah, exactly. It does beg the question — why don’t you go bigger? Is there a reason, Sam, that you don’t go create a $3 billion private equity fund?
Sam: There are two reasons. The first is fear. It is scary — raising outside money and screwing it up, that’s bad. But number two, I do think — I don’t know if Peter Thiel has this — but Elon Musk for sure has this. Did you read that article in the New York Times where he describes his life? He’s talking to the interviewer and he starts to cry. He’s like, “You don’t want to be me.” He said he missed his brother’s wedding — or almost missed it, flew in at the last minute, saw it, immediately got back on the plane. A few weeks ago for five days he didn’t leave the factory, didn’t see sunlight, didn’t see his children. He had a birthday and no friends came to say happy birthday because he was running around the factory. He said, “I’m lonely and pretty sad. Frankly, death — I look forward to it as a way of relief.”
Shaan: Jesus Christ.
Sam: Take a nap. Just try it. Little advice.
Shaan: And it’s like, on one hand, I don’t want to be a slave to a computer and a machine. But I do think — and I haven’t fully formulated this thought — there’s a world where you can go big and have some work-life balance.
Sam: Yeah, of course it’s true. You just have to decide your terms. And as soon as you decide those terms, watch — you’ll figure out a way to make it happen, or you’ll find people who help make it happen.
I am so anti-”there’s one way to win.” That’s the one thing I’m most against. Because I used to fall into that trap. I’d see somebody doing something one way, hear advice that makes sense, and just accept it. But in life I’ve always found the counterfactual — wait, but this guy doesn’t do that. Wait, this lady did both. So if both is an option, I’m taking both every time. It’s only when I accept that both is not an option that I fall into misery, picking one or the other.
Shaan: I play two games about any project I’m doing.
The first: if I met up with you twelve months from now, grabbing a beer, and you said, “Hey, what happened with that thing?” — what’s the most likely thing I’m going to say went wrong? What did I think we had figured out that we turned out to be wrong about? That question helps you identify the riskiest assumption you’re making, the thing you need to validate, the risky path where you’re cutting off other options. I ask it that way because if you just ask “what’s the biggest risk?” people answer differently. But framing it as — let’s presume it already went wrong, what was the cause of death? — people can actually answer that.
The second game we played yesterday with the Milk Road: “Why the f*** aren’t you?” It’s like, if I were an objective observer looking at what we’re doing, what would I say — “Why the f*** are you guys doing this?” or “Why aren’t you doing that?” Why are you doing something that takes you five hours a day that you could hire someone for? Why aren’t you at this Bitcoin conference if you’re building a crypto product? There’s just this series of obvious good ideas we’re not doing and obvious bad ideas we are doing, and you distill it down fast.
Shaan: So — why aren’t you going bigger? Assuming you’re not going big, for the sake of discussion.
Sam: I wouldn’t say I’m not going big. But the Jared Kushner question — I want to know what enough is. I want my vision of success to be bigger than just what’s going on in my business. If you said “paint a picture of winning,” it’s not just a number in an account or a number in my sales dashboard. It’s a perfect Tuesday. My normal day is perfect for what I want.
Right after this I’m going to go work out with my trainer in my home gym — that’s part of my perfect Tuesday. If my business requires me to not have time for that, or doesn’t provide enough money to afford that, that’s not winning. Being able to take my daughter to swim class — those things are part of winning. I’m only going to deviate from that if I need to update the picture. The only thing I question is: is this picture the picture I actually still want, or is it outdated?
Ben: I tweeted something like “it’s a superpower to know what you really want.” What made you tweet that?
Ben: I’ve had a bunch of people reaching out recently. The people who say “hey, I’d love to connect” — I get so annoyed. You just dumped something on my plate for me to figure out. Whereas the people who say, “Hey, I love what you do. I’m also a podcaster, my podcast is this size, I want to get it to this size, I’m having trouble in these two areas, and I’d love to talk” — great. You know exactly what you want and I’ll gladly help.
It applies almost everywhere. The guy who walks up and says “do you have any spare change?” — no. The guy who says “I need $2.50 to get a ride home on the bus, do you have that?” — all right, I guess I’ve got $2.50. It’s a superpower in every way.
Real Estate Twitter and Building Trust Through Content [00:54:00]
Shaan: My cousin put out a tweet yesterday — he’s on Twitter and according to his updates he’s killing it. He just bought like 20,000 square feet of something, he’s on top of the game. He put out a thing on how he does due diligence on properties — a great checklist. Just putting out great information. It makes me trust him. It makes me think this guy knows what he’s talking about.
Our friend Nick Huber does this too. He’ll send a picture of him smoking a cigar on the golf course at 1 p.m. And you don’t get to do that regularly unless you’re doing really well. It makes me more likely to invest in Nick’s storage company. Some people take it as an anti-signal — why isn’t he working? To me, if you’re able to live well, you’re doing something right.
Sam: And to me that’s one of the coolest things happening on Twitter right now — these real estate people are just crushing it. Some of them have said they bring in tens of millions of dollars in investor money just from people who became fans on Twitter. If you’re in real estate: do what those guys are doing. Up your Twitter game. It will lead to more deals and more investors without knocking on doors.
I have no idea how big Nick Huber’s portfolio is but I wouldn’t be surprised if it’s over nine figures, and I bet most of it came through Twitter.
Shaan: I agree with where you’re headed. Though that’s also one reason I haven’t invested in more of these guys — the fee structure. One thing I don’t love about real estate fees is the acquisition fee model. You buy a $50 million property and bank a million dollars just for buying it. That incentivizes you to accumulate rather than be really discerning between a great property and a good one.
I think Nick actually has a real Playbook — he buys self-storage, cuts labor, adds automations, has a template for adding value. Not every investor says they have that but I think Nick actually does. In general though, I hesitate because of that incentive mismatch. You’re incentivized to take my money and go buy something because you get guaranteed money today that isn’t fully linked to long-term returns. And by the time we know if the deals were good, you’ve already banked acquisition fees fifteen times over.
Sam: By the way, if I were Nick I’d do exactly what he’s doing. Charge the highest fees I can while still delivering a great return. If you can go beat that return somewhere else, I invite you to do it. I don’t knock him for it. It’s what I’d do.
”Copy My Trip” Business Idea [01:00:00]
Shaan: Do you want to do more topics, or save yours for Wednesday?
Sam: Let’s do a couple ideas. People like ideas.
Shaan: All right, let me pitch you two real quick. The first is what I’m calling “Copy My Trip.”
Sam: Great name.
Shaan: Thank you — came up with it myself. So I’m booking a vacation right now, taking the family to Hawaii. I’m on Expedia. Which island? I don’t know. Which resort? Oh God, here we go. And then all the details — do I rent a car? Do I get car seats? Do I take the shuttle? Is this activity age-appropriate?
My wife follows these Mommy influencers on Instagram and when they recommend something she buys it because they have the same taste and a good track record. But those influencers aren’t saying, “Copy my trip.” Like, I want them to literally say: “You want to go to Disneyland? Click this. Here’s the full itinerary — we fly into this airport, take this transportation to this hotel because it’s great for families for these reasons, we buy these things,” and I just get their whole trip that I can copy.
I went on Expedia — miserable experience. Overwhelming list of 100 options ranked five different ways. I don’t know if the reviews are real. The photos are static shots from a plane above the resort. I just want to see someone walk into the room and say, “Oh, this is really nice. The bed’s good. There’s space over here. They give you breakfast every morning.” Like an Instagram story.
Shaan: There should be a thing called “Copy My Trip” where anyone could do it. It creates a profession of professional travelers — people who find the best path to Bali or Hawaii, and you follow someone whose style you align with. You follow the fitness-oriented traveler who went to Thailand and did Muay Thai classes and trained at this gym — that’s the trip I want.
Sam: You could do this for trips and weddings. Whenever I saw my wife working so hard on our wedding planning I was like, “Dude, just find someone else who did the same thing and copy it exactly. No one will know, no one cares.” Birthday parties too. It’s like Pinterest but the whole thing strung together.
Shaan: Someone uploads an itinerary, people rate it, you pay for it. You don’t even have to explicitly buy the trip — just by booking from the itinerary, those people get paid through affiliates. If I book the resort because this person said it was awesome, they get a kickback on everything they recommended. You could even do it where you take the entire pool of affiliate fees and pay out based on whose trip got copied, even if the hotel doesn’t explicitly pay to be promoted.
Sam: And this is not a fictional example — I’m actually trying to book this Hawaii trip right now and I cannot figure it out.
Shaan: I was like, okay, I could tweet it out — but that only works for me because I’ve got a following. How do normal people do this? I went to YouTube. Watched a family vlog at one of the resorts. It’s an 8-minute video covering one aspect and doesn’t tell me about all the other stuff I could do. So elements of this are already happening, but someone should make it an explicit product.
Sam: Jack Smith uses VAs for this constantly. He even had a VA in a different country go to three hotels, take pictures, and report back on which ones were best for a trip he was planning with his wife.
Shaan: I’m calling him Jack Le Roux from now on. That is crazy.
Sam: He just sent me a picture of him and Andrew Wilkinson with their TED Talk badges on. They’re clearly at TED together.
FlightFox and the Travel Concierge Model [01:08:00]
Sam: There’s a company called FlightFox — do you know it?
Shaan: Is it like a travel agent, or like where someone finds you the best deal?
Sam: So you go to FlightFox and you click the button that says you’re traveling for business. Then you say, “I want to go around this date, come back around this time.” You leave notes — “I’ve got a budget of X” or “I only want first class” or “I have to be back for a wedding, so I need backup flights.” And then a real person pops up and says, “Hey, what’s going on? I’m here to help.” They go find five to ten different flights that fit what you want.
You say, “This itinerary looks good” or you reply and say, “Actually I’ve got a change of plans, I need to adjust X, Y, Z” and they go find new flights. They know where to search for the cheapest options. They only get paid after you book, and they take a $50 fee. I have no idea how they make money.
Sam: When I was in Portugal my flight got canceled, so I just logged on and said, “Hey, the flight you booked was canceled, can you address it?” They call for you, wait on hold, and then get back to you. You pay them $50. It’s amazing. I have no idea how this makes money.
Shaan: Get it while it lasts.
Mop Points: Credit Card Optimization [01:11:00]
Sam: Similar to that — did I ever tell you about Mop Points? MopPoints.com. Our good buddy Ramon’s good buddy.
Shaan: Oh yeah, yeah.
Sam: This was one of the best things I’ve done. You go to MopPoints.com — it solves the problem of “what credit card should I get?” You could Google that question and you’ll get the most SEO-optimized blog post in the world because they make so much money referring credit cards. You don’t know if you’re getting the real deal.
So I called this guy for 30 minutes. He said, “All right, tell me what you spend on and what you want. Do you want to travel like a baller?” He said, “Look, I travel first class worldwide just off points. I’m not rich, I just use points. Here’s how.” I said, “Yeah, I want that.” He said, “Cool. Get the Amex Gold. You’re going to get 4x points on all your Facebook ads for your e-commerce. Get one for you and one for your wife — now you’re going to rack up 2 million points in the next year.”
And then for redeeming: “Don’t book within their points portal. That’s what everyone does. You need to transfer to travel partners and use programs like KLM to fly here and here.” He said, “Just call me when you want to book first class.” For now, buy the Amex Gold and start racking up your points.
Sam: Dude, I felt so taken care of. The relief of knowing I’m in good hands — Mop from Mop Points is my real Allstate.
Shaan: I love that model. These things are typically monetized through affiliates, but instead you just pay for honest advice.
Sam: I actually like that idea a lot. People should go sign up if they spend significant money on their business. If you spend $100,000 a month on ads — very common for e-commerce — and you use a Bank of America Platinum Honors cash back card at 2.6% back, that’s $2,600 a month back straight to your bottom line. You can reinvest that. It just makes financial sense to optimize it.
Shaan: What does a big company like BCG do with all the points their employees rack up?
Sam: I asked my previous startup that. I think they just do cash back, which is not the most efficient use. But it’s the fair way — otherwise the question is who gets to keep the points?
I kept the Hustle’s points. I flew first class twice a month. It was sick. When I sold the company I didn’t have that perk anymore. I was like, “Damn, I have to actually pay for a flight for the first time in four years.”
Shaan: That’s how you’ve got to negotiate — keep the points.
Sam: I kept all the points we had — like a million of them. I just didn’t get future points going forward.
Shaan: Gotcha.
Sam: All right, that’s it. I’ll save my other ideas for the next episode.
Shaan: You got a crime baby?
Sam: Yeah, I know. All right, thank you.