Pomp joins Sam and Shaan to share three business ideas he’s actively pursuing or excited about in 2024: a residential real estate media brand (Resi Club), government-facing computer vision enforcement companies, and AI agents for opportunity discovery. Along the way the conversation covers legendary investors Julian Robertson and Bill Miller, the Brad Jacobs roll-up playbook, Nikita Bier’s consumer social experiments, and a debate about whether creators should call themselves content producers.
Speakers: Sam Parr (host), Shaan Puri (host), Anthony Pompliano / Pomp (guest, investor and media entrepreneur)
Cold Open — Who Is Pomp? [00:00:00]
Shaan: Well, I guess we’re live. Pomp — do people ever introduce you by your real full name, or are you just Pomp at all times?
Pomp: Yeah, some people do. But people get offended if I go to a conference and I introduce myself as Anthony and then later they’re like, “Wait, you’re Pomp?” Like, who knows you as Anthony? And I’m like, well, that is my name — my parents didn’t name me Pomp.
Shaan: Well then, we’re going to keep you as Pomp. We have Pomp here. Pomp, you’ve been on the pod a handful of times, we’ve talked about you a handful of times, we’ve been on your pod a handful of times — so it’s nice to have you back. Congratulations on the new family member, and you’re here recently after doing it, so we appreciate that.
Pomp: Yeah, of course. Just three dads hanging out on the internet. Who could have guessed.
Shaan: I had a good joke I didn’t get to use the other day. When Sam Altman was in the news, then Jack Altman comes out and says something, then Max Altman comes out and says something, then his sister Annie Altman comes — I’m like, how many Altmans are there? There are more Altmans than Pomplanos now. What’s happening here? Because I feel like you have brothers coming out of the woodwork as well. Do you feel your sibling dominance is threatened in any way by the Altmans right now?
Pomp: I did see people making that joke. I did Google how many Altmans there are and they are not more Altmans than Pomplanos, so we’re safe for the moment.
Introducing Pomp — From Bitcoin Laser Eyes to Media Empire [00:01:30]
Sam: What I don’t even know how to describe you, so I think a lot of our listeners will know who you are and we don’t have to spend that much time. But you started out as kind of a one-trick pony — you were basically the guy on Twitter who talked about Bitcoin. But now you’ve evolved significantly beyond that. You’ve got the Pomp media empire, but you’ve also started — I don’t even know how many businesses.
Shaan: Hold on, Sam. Can we do an analogy? Pomp going from Bitcoin laser eyes to real estate and all kinds of other stuff he’s doing now — is this Justin Timberlake from *NSYNC going solo? What’s the right analogy? Who has made such a transition, such a life pivot like this — is there anyone that’s done this in Hollywood?
Pomp: Here’s the thing — it’s not really a pivot if you just expand out off of the internet, right? If you think about it: I started my career building companies, then I went and worked at Facebook, then I started investing, and once I was investing that’s really where the Bitcoin stuff happened.
Even the stuff on the internet — I worked directly with Mark Zuckerberg and Sheryl Sandberg for a short period at Facebook when they were trying to figure out how to grow their audiences. I remember early on with the Jerry Instagram account, they were trying to go from Instagram and figure out their Facebook strategy.
I think of someone like Kim Kardashian — she goes from sex tape to reality TV star to entrepreneur billionaire to Criminal Justice Reform, and I think she’s going to be president of the United States one day. And you look at that and you’re like, actually the same thing that makes the sex tape go viral could get you elected president today. In some ways it’s actually the exact same skill set, just packaged up differently with different ambitions.
Networking With Legends — How Pomp Meets Interesting People [00:05:00]
Sam: You have this really good ability to brute-force yourself into interesting networking opportunities. Like, I feel like Sean is actually better at this than I am — I just hang out with a small crew of internet nerds. But you’ve done a really good job of meeting actual big shots. I don’t even know all the people you know. You were telling me how you met Julian Robertson, who started Tiger Management. You just name-dropped Zuck, you’ve worked with Snapchat, hung out with Evan — you’ve done a really good job of meeting all these fascinating people.
Pomp: Yeah, I mean, I think it’s just: if you’re a curious person, other curious people want to be around those types of folks. And also, I probably more so than many of my friends say yes to opportunities — even when it’s not very clear what the purpose of doing it is. If you do that enough times, it’s just shots on goal. You will meet some of these fascinating or successful people.
But each one of them is very different. The Julian Robertson story — Mark Yusko, who started Morgan Creek Capital Management, we did a joint venture with him to raise a couple of venture capital funds. Mark was the former CIO of the UNC Charlotte endowment in the late ’90s, early 2000s, and at that time Julian Robertson was in his heyday. Hedge funds were really getting off the ground, and Mark Yusko had a big hand in getting endowments to invest in them. Julian Robertson was on his board. Eventually Julian was like, “Hey, this kid Chase Coleman who now runs Tiger Global — he’s leaving and I’m going to give him some money.” And he sent him down to talk to Mark, and Mark gave the sixth and seventh million dollars to Chase Coleman to start Tiger Global.
So Mark Yusko and Julian Robertson had known each other for 20 or 30 years, and I think it was 2019 — Mark calls me up one day and says, “Hey, now’s the time. We’re going to go meet a bunch of the legends of Wall Street.” Julian was the first stop.
Meeting Julian Robertson — A Lesson in Curiosity [00:09:00]
Pomp: You feel like you’re going to meet a legend, so more than usual you’re nervous but excited. We walk in and he’s had the same office for a number of years. He had three secretaries — each with different responsibilities — sitting outside his office. I was like, okay, that’s different. Mind you, Julian at this point is definitely in his 80s.
We go in to see him and he sits down in almost like a living room area of his office. He was the single most curious legend of Wall Street I’ve ever met. He sat with us for an hour and just kept barraging me with questions, trying to actually understand Bitcoin and blockchain technology. You’re just like, man, this guy does not have to be here right now. He is rich on rich on rich, and he’s also pretty old. He’s got to know he doesn’t have another 50 years to live. But he’s sitting here trying to learn.
About halfway through the conversation you could see the proverbial light bulb go off in his head. He just sat back in his couch, looked up at the ceiling, and started talking to the ceiling. I remember thinking, am I boring? Did I lose him? And he had a microphone in the ceiling and a speaker so he could talk directly to his three assistants, and he basically started asking, “Hey, send so-and-so in here, go find this, whatever.” I was like, this guy built Jarvis in his office way before anyone else — he is absolutely a legend.
It was a really cool experience. Unfortunately he passed away, but things like that are once-in-a-lifetime opportunities.
Sam: What I know about Julian is he started Tiger Management, which was revolutionary. Why was it revolutionary — did they just make good investments, or did they do something different?
Pomp: He’s one of the very first true hedge funds. He basically said, “I’m not just going to do value investing, I’m a true hedge fund.” He had high conviction and ended up being right, so he was able to gather a lot of assets and drive a pretty good return at a time when the whole concept of hedging — going long and short — wasn’t the traditional way of investing.
I don’t know if they call him the Godfather of hedge funds, but he could be. And then the lore of Julian expanded even more when a bunch of people who worked for him left. He would seed them, and those guys — now known as the Tiger Cubs — became very successful. Tiger Global is probably the most successful.
He was good as an investor, but he was even better as a talent identifier — seeding people to create great firms. Tiger Cubs are like the PayPal Mafia of finance, but bigger. If you Google “Tiger Cubs Finance Wikipedia,” you’ll find sections called Tiger Cubs, Tiger Grand Cubs, and Tiger Great-Grand Cubs. It’s literally 100-plus names, including Chase Coleman, who’s worth north of $20 billion.
Sam: And then you have guys like the one who like, accidentally unplugged Wall Street — Bill Hwang?
Shaan: Yeah, brought down the economy through a couple bad bets.
Sam: And then Chase Coleman with Tiger Global. This guy Julian is prolific, man. He’s like the Gucci of finance.
Shaan: These are all names you’ve only read, never had to say out loud.
Sam: Exactly. I just accelerate through them and hope no one notices I mispronounced it.
What Makes Great Investors — Bill Miller and Conviction [00:17:00]
Sam: What attributes do you think — other than curiosity — did Julian have that spread to all these other guys?
Pomp: So obviously I met Julian, but I’ve met a bunch of other folks over the years who are similar. And usually you’re not in a situation where you can just say, “Hey, let me learn from you” — you’re asking them for money or an introduction, so the power dynamic is off. But in those conversations what you find is: they’re all very, very curious. And two, these guys just have brass balls. They are willing to make insane bets at times when other people are not.
Another person who maybe doesn’t get the same fame as Julian but I put up there as one of the best investors over the last 50 years is Bill Miller. In the late ’90s people were giving him grief because he called himself a value investor but was buying tech stocks. Tech exploded, he was outperforming everybody. He was the only investor to outperform the S&P 500 for 10 years straight in the ’90s.
Amazon was one of his big bets. Amazon crashes 90% in the dot-com crash — Bill just backs up the truck and buys more. I think at one point he was the single largest outside shareholder of Amazon.
So you look at that and you’re like: one, you have to find Amazon. Two, you have to not get scared when it drops 80 or 90%. And three, even if you’re not scared, you still have to hold your nose and put way more money in. That’s a common theme — just conviction and the ability to bet over and over again regardless of what’s happening.
And the last one: these dudes are junkies. They’re obsessed. In the book about Bill Miller, he had seats behind home plate for the Baltimore Orioles and he used to bring research reports and read them in the stands between innings. That’s why you end up owning 15% of Amazon — you did the work.
Shaan: That’s intimidating to hear, right?
Pomp: Yeah. And the hard part is the line between genius and idiot is so thin. Like, am I Bill Miller backing up the truck when Amazon crashed 90%, or am I just an idiot putting all my money into a loser? History is told years later. You have to have not just conviction in the investment — you have to have conviction in yourself that despite market conditions, despite current results, you are able to correctly differentiate between a winner and a loser.
Shaan: You’re basically saying, “I’m smarter than everyone else.” Everyone else is selling this thing and I’m going to buy it.
Pomp: Yeah. And that’s why they call them Masters of the Universe in the hedge fund world. The people who end up making a lot of money actually seem to be smarter than everyone else. How many of those are there? Way less than the number of people who claim to be.
Two Stories About Running Into the Fire [00:23:00]
Shaan: I’ll tell a story like that. My friend was in real estate, making his early fortune in his mid-20s, 2006 to 2007. Then 2008 happens and he described it later — he said, “It was like there was a tunnel and everyone was running out screaming fire. And they were handing me things on the way out. I was like, wow, they’re just giving me this — these prices are fantastic.” He kept marching forward while everybody else was running away screaming fire and handing him their assets. It turns out he should have run away from the fire. He lost everything in the ‘08 crash.
But that same feeling would be there at the dot-com crash — everybody yelling fire, selling things for pennies on the dollar. The difference, I think, comes down to: can you tell yourself why you were buying something when everybody else is selling? You heard somebody else who made a fortune during the dot-com crash and she said, “It was amazing — everything was on sale. Black Friday. Everything was 80% off. I couldn’t believe it. The best companies in the world were 80% off.” She didn’t know if they’d return to where they were, but she knew these were still the best companies in the world.
You’ve got to be careful you don’t want to be the guy running into the fire. You have to have some ground truth you believe in, that you’re willing to stand on, willing to lose on — and you’re okay saying, “I’m okay if I’m wrong on this.”
Sam: When you guys hear those stories, is it like watching a UFC fight when you’re a little drunk and you think you could get a lucky punch — or do you hear this and you’re like, I’m just not in the same league?
Pomp: I think it just depends on your circle of competence. There’s only one time in my life where I’ve had the conviction, felt like I did the work, and really backed up the truck — and that was the Bitcoin stuff. Bitcoin went from $1,000 to $20,000 in 2017, crashed down to around $3,200, and I went on national television and was like, “You guys are idiots. This thing is going to come flying back, we’re buying.” One of my favorite memories that’s kind of gotten lost in the internet archives — we issued a million-dollar bet to anyone on Wall Street. We said, “We’ll take Bitcoin, you take any other asset — just pick anything — over the next 10 years. If you beat us you get a million bucks; if Bitcoin outperforms, we get a million bucks.” And no one took it.
In UFC, you might look at a card and think you know who’s going to win five matches, but on that one match you think you know — you’re just not going to bet against the other person. You sit that one out. That level of conviction exists across markets. Amazon — people knew it was a pretty good company, but no one had the conviction to buy. You have to identify that these bets shouldn’t happen once a month. Maybe once in a decade you see something that is so non-consensus but you believe in.
Sam: Did anybody even consider taking you up on that bet?
Pomp: CNBC wrote an article about it. The people who were even considering it were basically fools who just wanted media coverage. They were trying to come up with these weird aspects of the deal — like, “Okay, I’ll take your bet but we have to take the return divided by two, times the number of times I jump on my head…” And we were just like, “Dude, you’re way too smart for us. We just want a straight-up bet.”
Shaan: They could have perfectly hedged that bet by just buying Bitcoin in addition to making the bet.
Pomp: Exactly. Either somebody would have figured out how to definitely beat us, or we were issuing the bet before the smart people started paying attention.
Were you inspired by the Warren Buffett S&P 500 million-dollar bet?
Sam: Of course. That was one of the smartest things Buffett’s done. A lot of the advice he gives is solid. But also — he’s a master marketer. Warren Buffett was the original finance influencer. If he was in his 30s today, he’d have a Substack, a Twitter account, a podcast, he’d be streaming on TikTok. He understood how to leverage the media tools he had at the time. He didn’t need to do it, but the bet was a great way to continue driving the lore of Warren Buffett.
Creator vs. Producer — The Content Identity Debate [00:32:00]
Pomp: There was a period where I was beating myself up even over this podcast. I was like, am I going to be a content creator or am I going to be a businessman who actually does the damn thing? And I started reading a lot of biographies and started thinking about it differently. A lot of these great people — whether in business or not — actually had newsletters. Warren Buffett’s annual letters were basically newsletters. Ben Franklin had a newspaper. George Washington constantly wrote editorials. Bill Ackman does this — uses Twitter now, but before that had other things. Some of the greats who are great business people are also wonderful content people.
Shaan: I like how you just used “content producer.” That’s nicer than “content creator,” which is better than “influencer.”
Sam: Actually, I think that’s all we need. You laid it out — do you want to be a content creator, an influencer, or a businessman? I think we need to level up the phrase. We just need to be content men. A couple of producers.
Pomp: I remember one time you had a guest on and Shaan asked, “I create courses too, and sometimes I feel like a little — you know — when I do courses. Like, should I be doing something else with my time?” And I think about that. But then you look at Warren Buffett — he taught a Dale Carnegie course. He taught a finance course at a university. It’s actually common that some of these people are teaching and creating, and that’s helped me feel less embarrassed about what I do.
What is all this content stuff, really? People would say, “Oh, he has a podcast,” and I used to cringe — like somebody stabbed me in the stomach and twisted it. I’m like, you are disrespecting all this other work I’ve done. Yes I have a podcast, but I also wear shoes — are you going to introduce me as, “Oh, Pomp wears shoes”?
What you eventually realize is it’s just marketing. Whether it’s Twitter, whether it’s a podcast — the people who tend to be good at it don’t think of it that way. They’re taking a poop and they pull out their phone and start tweeting random things and go viral. At the end of the day, if they could do it they’d do it themselves.
Shaan: To clarify, Sam — I never said “fraud.” Fraud means you’re misrepresenting yourself. I said I feel like a little you-know-what when I do courses. And you have to ask yourself: is that accurate or not? Maybe it’s not the best use of time.
Sam: Sorry, I paraphrased incorrectly. I actually think I made you sound better.
Shaan: I’d rather be honest.
Business Idea #1 — Resi Club: The Dominant Voice in Residential Real Estate [00:40:00]
Shaan: Okay, Pomp, you brought some ideas for us. You know this is the ideas podcast. Let’s rattle them off. Start with number one — what ideas, trends, or opportunities do you see right now?
Pomp: This first one is something we’re actually doing. Housing affordability is the worst it’s been this century. People are worried — should I rent, should I buy, what are interest rates going to do — but there’s no dominant voice in terms of news, commentary, and data. So we started a company called Resi Club. The idea in the beginning is just: go educate people about what’s happening.
I’m not an expert on residential real estate, so we partnered with a guy named Lance Lambert. Lance was the real estate editor at Fortune Magazine — he’s got 75,000 followers on Twitter, a lot of people in the industry follow him. We basically said, “Look, we want to build the dominant platform in residential real estate coverage. Why don’t we do it together? We know how to scale and monetize. You know the content and you’re the expert.”
We got started about two months ago. I love these types of businesses because they look stupid in the beginning. “Oh, you guys just created a newsletter.” Yeah, that’s exactly what we did. And then it turns into a media company. And then it turns into a data product. And then maybe 10 years from now we’re seeding general contractors in different markets to build affordable housing. You start with this small profitable thing and as you grow the business you can increase your ambition over time.
A lot of people start with massive ambition — “Let’s go to Mars.” Sure, for some companies that makes sense. But for businesses like this it’s: hey, there’s a problem, a lot of people aren’t talking about it, we should build a platform around it, and we’ll figure out how big it can get as we earn the right.
Sam: How much did you fund it with?
Pomp: Way less than people would think. We were profitable within the first month, so we actually didn’t even need the money. I think we put in $100,000 and never touched it, because within the first week we were profitable.
Sam: And the market for this — is it brokers, real estate agents, investors, or the average person on Zillow looking for a home?
Pomp: The beauty of residential real estate is it’s the largest asset class in the world, but none of us who are like “we’re so smart, we’re business people, we’re finance people with podcasts” ever think about it that way. We’re like, oh — stocks, crypto, bonds, whatever. What you end up getting is something that’s very niche — residential real estate — but also very big because it’s the largest asset class in the world. Home builders, real estate agents, people who want to buy or sell homes, people doing mortgages — there’s a huge ecosystem. It’s small and specific but also large and broad at the same time.
Sam: I’m looking at your paywall and it says you get access to a regional housing tracker data set. I think that’s smart. But I’ve got to say — your premium Pro Plan is $150 a year. That is so stupid, man. Why aren’t you charging way more?
Pomp: I know, I know. We’ll increase the price. But a lot of times when you’re building these businesses you have a choice: have a high CPM and be okay with not selling out all your ads sometimes, or have a lower CPM and just sell out all the ad inventory and build the muscle. I tend to always go for the latter.
Same thing with the subscription. Starting at $150 is like — if you’re interested and we’re creating something valuable, there is zero friction for you paying $150 a year. If we came out at $1,000 a year, people might say, “It’s valuable, but not worth $1,000.” At least now I know we have something people want, they’re not churning, and I can go do price discovery over the next 12 months. I’d rather start with a lower price, make sure we’ve got the right product, and raise prices later.
Shaan: I like this idea a lot. I think this is a $50 to $100 million outcome bootstrapped. But I’ve got to ask — you’re a guy with a thousand different opportunities. Can you walk me through the idea maze? Why residential? Why not commercial? Why not just pure finance — you’ve got a foothold there?
Pomp: This is actually a great one to talk about because we had a false start. We had partnered with somebody else who cut the market by geography — very focused on South Florida. The idea was we’d go to Tampa, then Orlando, then Atlanta, then just expand through geographies. It didn’t work for a bunch of reasons — probably some our fault, some on the other person who was very focused on the content they’d already been creating. The market wasn’t pulling it into existence. So we were like, hey, rather than bang our heads against the wall for the next 10 years, why don’t you just keep doing your thing and we’ll go back to the drawing board.
Resi Club was the second attempt. A lot of people don’t realize how often there are false starts.
Nikita Bier and the Art of Consumer Social Testing [00:55:00]
Pomp: Nikita Bier — who is friends of all of ours — he’s talked about this a bunch with consumer social apps. He says product-market fit is not a single metric, like you just know. It’s everything exploding. But in both TBH and Gas — which he launched and eventually sold to Facebook and then to Discord — he would launch it, it wouldn’t hit, he’d go back and make a couple changes, launch again. Sometimes he’d launch five, six, seven, eight times. And then eventually there was the right combination of things that worked.
So there are two ways to do entrepreneurship. One is: I’m going to bend the world to my will — here’s the thing that’s going to work regardless of what the market tells me. And then there’s the iterative approach. A lot of what I work on is much more iterative. You just have to be really good at going 100% in, running the test as perfectly as possible, but being willing to cut bait and try a different combination if it’s not exploding the way you want.
Shaan: You’ve got to tell the Nikita story — the one about what happened one time they renamed the app.
Sam: Yeah — one time they renamed it and it took off in the gay market. All he did was change the name of the app and it appealed to only gay people. Then he changed the name back and it reverted. You know, he says the most important thing for a consumer startup is that you develop a machine that lets you launch real high-fidelity tests of your product. That is your most important product at the beginning.
Shaan: I kind of agree with that but kind of disagree too. That’s a great way to do the apps he’s trying to do — where if it doesn’t have a k-factor over one it literally doesn’t work. His apps are: I’m going to get you in, it’ll spam-invite your friends, there’s a paywall, and I need 2% or more of people to buy the in-app purchase. If under 2% this doesn’t make money. If 2% or more, this thing makes a few million dollars of profit in the next 90 days.
But if you look at how some of the great consumer products are built — Pinterest wasn’t sitting around creating a system to launch systematically in high schools until they got it right. Facebook and Snapchat eventually figured out how to grow, but they didn’t have a thousand shots on goal with different variations trying to get virality just right.
What Nikita is doing is awesome because it’s such a different game than anyone else was playing. But his advice is basically how to build a virus, not how to create the next social network. People think of him as the genius consumer social guy when really he’s very good at building viruses that go on teens’ phones.
Pomp: What are you optimizing for, right? If you want to build the next great social network, k-factor matters in the beginning but actually what matters more is 30/60/90-day retention. If you want to just go viral and be on every 14-year-old’s phone in America, the only thing that matters is k-factor.
Both his apps within 100 or 200 days of getting acquired were shut down and written off to zero because they didn’t have retention. But one thing I’d give him a ton of credit for: he went back to the well. Most people don’t do that. They become super knowledgeable about a space and they get so jaded that even though they’re the best-equipped person in the world to go back and build in that space, they’re so turned off they go become a beginner at something else.
The second thing: he was in the world of “build a hit social app, get 100 million users, then make money on ads, raise venture capital.” When he went back the second time he broke down the fourth wall of Silicon Valley. What if I don’t fund this? What if I just charge a little bit of money? What if I just make a few million dollars of profit per month?
The mobile gaming guys were like, “Yeah of course — get a bunch of downloads and charge a small amount.” But the social apps guys don’t build mobile games. He rethought the rules of the consumer social game: I’m going to build a consumer social app but it’s going to have the monetization of a mobile game. In basically a six-month span it made seven or eight million dollars in gross revenue and was very profitable for him.
Sam: There’s a whole group of people trying to rewrite the rules like this. One example I don’t want to name — they created a way to make photos in your Instagram story blurry, and you’d have to pay on Apple Pay to unblur it. Obviously all the OnlyFans girls would put blurry photos in their stories and people would pay $2, $5, $10 to see it. They’re bootstrapping off these massive audiences and just building a little feature on top without raising money. They make a lot of money.
Brad Jacobs — The Billion-Dollar Roll-Up Machine [01:04:00]
Sam: Speaking of folks who go back to the well — do you guys know who Brad Jacobs is?
Shaan: Yeah, he’s created like six billion-dollar companies. The guy’s the GOAT. I’ve been trying to get him on the pod, I can’t get to him.
Sam: He’s got a book coming out. He is 100% going on everyone’s podcast because he’s got a book coming out — that’s always the best time to get these guys. But so about four or five years ago, somebody like a back-alley drug dealer was like, “Check out Brad Jacobs.” I’d never heard of him. Got on Wikipedia and for a week and a half I just didn’t sleep — I was scouring the internet trying to find what obscure podcast this guy had done.
What he essentially does is roll-ups. Wayne Huizenga is another guy famous for this. What Brad did is figure out a business model, figure out a funding mechanism, start winning, and then go around and tell everyone, “I’m going to do the same playbook and I’m going to win again.” And people gave him money.
Shaan: So explain what he did.
Sam: One of the things he did was in the waste industry — Wayne Huizenga had a big one too. He’d go to Podunk towns and buy the landfill. Once he had the landfill, there were like seven companies picking trash in the surrounding area and bringing it there. He’d start buying them one by one. Eventually he’d own all seven companies plus the landfill. He did this across the country, rolled it all up. That was United Waste Systems in the early ’90s — took it public, multi-billion dollar outcome.
He’s done that same thing six or seven times. Then he did United Rentals — renting heavy equipment, dump trucks, bobcats. Then he did XPO Logistics, which is currently publicly traded. Building one billion-dollar company is cool. Building two, you’ve got the golden touch. Do it more than five times and there’s literally one of you.
Shaan: You want to know something funny about how he’s described online? He’s built multiple billion-dollar companies, but on LinkedIn it says “Brad Jacobs is an influencer” because of the categorization. Imagine telling Brad Jacobs: “You’re not really a multi-billion dollar entrepreneur, you’re just an influencer.” He’d blow a gasket.
Sam: That’s so true. His first top link on Google — “Brad Jacobs is an influencer.” Period. Got him.
The reason he’s cool is: he lives in Greenwich, Connecticut, wears a suit and tie, looks like a professional CEO. But if you listen to some of the things he says, he’s way more entrepreneurial than his picture suggests. He’s got that artist vibe. The guy is special. And before his book he’s been really under the radar for how successful he is.
Business Idea #2 — Persistent Patrol: Computer Vision for Government Revenue [01:13:00]
Shaan: What other ideas are interesting to you at the moment?
Pomp: I’ll give you a couple of categories. There’s one the best name I have for is “persistent patrol companies.”
One of the big problems that city governments and the national government are going to have is they need to get more money. They’re broke. If you’re broke you either cut costs or you make more money. They’re not going to cut costs, so they have to make more money.
One of the best examples is in New York City — the congestion tax. The way it works is, I don’t know, 9-to-5 Monday through Friday, if you drive from outside of Lower Manhattan into Lower Manhattan they charge you like $20. Only charged once per day, but imagine all the cars driving from above 59th Street to below 59th Street during that window. It’s a way for the city to raise more money. It’s the first one in the United States, but this has been happening in Europe for a while.
And over the last couple of years in cities like New York, people who were paying a lot in taxes left. There’s the infamous story of David Tepper — he was in New Jersey and was responsible for something like 3% of the state’s budget in taxes he personally paid. He moved to Florida. There were articles saying the state of New Jersey was going to go broke. The story goes that when he moved back he called up the state treasurer and said, “Yo, you’ve got $120 million coming to you next year — put it in your budget. I’m back, baby.”
So wealthy people have been moving. My idea is: how are these governments going to generate more revenue? Right now a lot of it comes from parking tickets and stupid things where they have humans walking around trying to catch people. I think there’s going to be an entire rise of businesses that use computer vision to do the same thing. Anything that can be automated will be automated.
Parking tickets — easy. Fire marshals. How many times have you gone to an event and the Fire Marshal says 220 people can be in here and you think there are a thousand people in the room? Automate that — $500 fine every single time the venue is over capacity. Elevators. You go through this and see over and over that computer vision will just become the persistent eye.
It’s scary. I don’t like the idea of this. But someone is going to build this technology, and it’s not going to be the government. So we’re likely to see a huge rise of businesses that use what is pretty standard technology at this point — counting humans walking into a building — so the government can generate more revenue.
Sam: There’s also in LA the Mansion Tax, right? If you sell a home for more than $5 million there’s just a new tax. And they’re like, “What are these people going to do — live in small homes? They’ll never downsize. We’ve got them.”
Shaan: New York has that too. You want to know what the threshold is to pay it?
Sam: What?
Shaan: Keep in mind the average sale of a New York home is about $800,000. The Mansion Tax starts at a million dollars. So basically you have a two-bedroom — Mansion. I think it’s close to 4% at the higher end. So if you purchase a two-bedroom apartment in New York City you’re basically handing over an additional $40,000. It’s pretty wild.
Pomp: New York gets you in so many different ways. It’s a very challenging place to live.
Sam: You live in New York, right? What will it take for you to move?
Pomp: Basically nothing at this point. I’m not going to move. I’ve come to the realization that I’m willing to pay for the experience. Yes, the taxes are higher, but the money I give on those higher taxes is very much in exchange for the density of New York City — the experience of it. So to some degree it’s like the biggest expense I pay every year, but it’s because of the specific quality of life I want. I’ve come to terms with it and I stroke the check every year.
Compared to other cities, New York does a half-decent job of making it feel like you’re getting what you paid for — you know, good parks, subway system, whatever. But damn, it’s still challenging.
Shaan: I’m in Texas at the moment and when I’m thinking about going to New York I’m like, this changes the math a lot.
Pomp: Just close your eyes and don’t look.
Business Idea #3 — AI Agents for Opportunity Discovery [01:24:00]
Pomp: All right, I’ve got one more idea before we go — AI agents. I don’t know this guy, Jacob Greenfield, but he posts amazing stuff. He posted this yesterday and I was thinking about what we could talk about today.
He basically used AI agents to find opportunities and score them based on how much money you could make and how difficult it would be to execute. He populated this whole list. Then — and here’s the clever part — he created a second AI agent that looks at all the opportunities that are high-earning potential and low difficulty, and has them create a plan to actually execute on each one. And presumably you’d create a third AI agent to carry out the plans from agent two.
Yes, you have to be technical or work with technical people, but the world is changing at a very rapid pace. Everyone was worried about the blue-collar worker getting automated away, and now it sounds like Jacob is automating away My First Million. Nobody needs to listen to the podcast anymore — they’re just going to get an Excel sheet with “how do I get rich without doing a lot of work” and go do those opportunities.
Shaan: This tweet is awesome. I’m looking at it now. Very good.
Sam: They are awesome. But also — I think the demo shows you what’s possible, but the demo is not usable. I feel the same way about VR. Every time a new VR headset comes out I buy it, I put it on, I’m like, “Holy, this is amazing, I can’t wait to show five other people this.” And then I put it on the shelf and don’t touch it for a year. But soon this will solve all the pain points. It’s improving one step at a time.
For example, the things on this list — “clean energy solutions for shipping,” “innovating fuel alternatives” — like, yeah, sure, money-maker, battery that lasts forever. Cool. Pomp, why isn’t real estate blog on here?
Pomp: Not enough money and way too difficult.
Sam: It didn’t make the top 30. So I think the idea is really cool but in practice, if somebody sat down and tried to actually use it to execute — I don’t think any of it is usable at this point.
Shaan: I’ll give you one example that I think is usable right now. Upwork has like $3 or $4 billion of GMV every year — people paying for tasks. I’m pretty sure a huge number of Upwork and Fiverr tasks are automatable right now. Or maybe not 100% automated, but you could take that same person, use AI, and 10x their output — give them way more operational leverage.
If somebody combined private equity and AI, you could go roll up and buy the top profiles on Upwork and Fiverr. Buy the search juice — they’re going to get the top jobs because they’ve been ranked number one since 2013 on Fiverr or whatever. Put them all under one roof and use AI to fulfill a huge number of those tasks. You can make a lot of money because those little properties on top of Fiverr and Upwork are like rental properties — they generate income every month. And now you have a way to get more margin out of that rental income.
Sam: This is the whole idea that Thrasio and the Amazon aggregators had — they were going to buy up Amazon stores. I know somebody who financed a lot of them and his thesis was: if you’re the first search result for a very popular product, that is real estate. Location, location, location. The hard part with Amazon was you’re dealing in physical goods. What you’re talking about is dealing with software.
There is 100% somebody in some obscure place in the world who is the best Fiverr logo designer right now and they’re just a Midjourney power user. They used to design X number of logos per month, now they can do 100x that. And if you want to give feedback, they just change the prompt. They can do it in one-hundredth of the time.
Pomp: That sounds awesome for that person. And frankly, that’s how the world should work. You should pay the same for the result because you’re buying the result, not the amount of work. And that person who figured out how to do it is going to be financially rewarded. We want that economic system to be exactly how business works.
Running 10 Businesses — Time Allocation and Buy vs. Build [01:35:00]
Sam: Of all the companies you’re working on — how do you allocate time, and how many businesses do you have?
Pomp: I don’t know exactly, but let’s call it around 10. I think of it as a 2x2 matrix. Some businesses are young and need lots of time; a lot are older and don’t need as much time. The only thing that changes between them is fires.
If you look at my day, it’s mostly distributed to the companies just getting off the ground — trying to build momentum, get to profitability, figure out the first couple of hires, make sure the product is right. Then maybe 20% or 15% of my day is, “Oh, we just lost a big customer” or there’s some fire to put out with a mature company.
After the first six months or so, the company works or it doesn’t. And if it works, I’m probably doing the company a disservice if I’m still meddling in day-to-day decision-making. We have somebody who runs the company — they should be the ones to sink or swim. They appreciate the autonomy.
The one thing I do consistently is get a weekly update from every company. I read them, give a little bit of feedback here and there. But it’s more so for the people who run the company — it forces them to write down what they got done this week. Nobody ever wants to send an update that says “we got nothing done,” including me.
Sam: How are you balancing buy versus build? Sean and Andrew Wilkinson toy around with that — buying parts of companies or wholly owning companies they buy, versus focusing on the one or two things that could have outsized returns.
Pomp: We’ve bought a couple of businesses and built a lot of them. Right now there’s a sector I’m looking at in the media space — a very specific type of audience. We understand something about this audience that most other people haven’t yet discovered. There are two players in the market that are well-known in that industry, and you’d probably have to pay over $100 million to buy either of them. You probably can’t buy a minority stake.
At this point, given our track record, I probably could go find big institutional investors who want to buy media businesses and put it together. But there’s a lot of work — convincing someone to sell, getting the terms right, integration. And I’m like, dude, I think for $100K we could create a competitor. It’s not going to be worth $100 million within two or three years, but could we take a big dent into their businesses? Probably. When it’s that skewed I obviously lean towards building.
Where buying gets more attractive is when the business is worth $5 million or $10 million and you’re like, that’s two years of progress versus spending the money upfront. That’s where I lean much more towards buying — it’s lower risk and the deal is easier to get done.
Sam: What about the focus thing? I only do one thing.
Pomp: I remember your face seared in my brain last time you asked me this. I was like, I don’t do a lot of things — I do one thing. We provide capital and distribution to businesses. That’s it.
Shaan: I think that’s inspiring. And Sam, I’m slowly buying into other viewpoints —
Sam: Oh no.
Shaan: I’m trying to focus more.
Sam: Wait, hold on. This is a lie. Sam, you have multiple businesses. You’re not just doing one thing. You built out Airbnb short-term rental at the same time you were getting Hampton off the ground. There are all these things where sometimes it’s not “I’m going to raise money and go build this big business” — it could just be projects.
Sam: I call them hobbies. I have a 40-hour-a-week thing which is actually — I’ll disprove my own point — it’s podcasting and Hampton. But so that’s like my nine-to-five. And then I’ve got weekend projects.
Shaan: Meet Sam Parr: he’s a podcaster with weekend hobbies.
Pomp: Podcast influencer. Content man.
Sam: Content producer. I think we’ve done a really good job of rebranding. “Creator” just sounds weak for some reason.
Shaan: It lumps you in with everybody else. That’s the problem. “I’m not like them — that guy’s just unemployed. I’m a different thing.”
Names Matter — Risk Identifiers and Data Scientists [01:44:00]
Pomp: I met a guy who was one of the early hires at Palantir — basically like the COO in the early days. He said one of the cool things about the culture is you kind of jointly with your boss made up your title. His was “Risk Identifier and Destroyer.” What does that guy do? I want to go work at the company where that could be my title. Names do matter. What the president does at different companies may be different, but the guy whose title is “Risk Identifier and Destroyer” is 100% focused on risk.
Same thing — “content creator” might just be the wrong name. Change the name and all of a sudden everyone’s really excited about it.
Pomp: Chamath has a good story about this. He says when he was at Facebook they were trying to hire a PhD-level math and stats guy. “Cool, you can come be a data analyst.” And the guy was like, “I don’t want to be a data analyst, I’m going to go get my PhD instead.” So Chamath was like, what if I create a new field called data science and you’re one of the first data scientists on Earth? And now data scientist is a prestigious job title in Silicon Valley.
Sam: Is that story true?
Shaan: I believe it. I have no reason not to.
Scaramucci as a Unit of Measurement [01:48:00]
Sam: I love the All-In guys so much, but I was laughing — people were giving them grief about using “scaramucci” as a measuring stick. You guys see that?
Shaan: Yeah. What’s that about?
Sam: Scaramucci was the White House communications director for 11 days, right? The infamous photo with the sunglasses and the finger guns — probably one of the greatest stints in White House history. So whenever someone does a very short tenure people tweet at Scaramucci like, “When Sam Altman’s interim CEO situation happened for 48 hours, how many scaramuccis did she last?” And it’s calculated like 0.2 or whatever.
The All-In guys had been saying it for a while and were like, “We invented that.” They went on Twitter and said, “Give us credit if you’re going to use it.” And of course the internet loves to hate on those guys if you’re not in the tech industry. They started pulling up articles. Man, this is peak internet — somebody wants credit for a term no one’s really clear where it came from, a bunch of people who don’t like that person want to critique them, and everyone’s doing a bunch of work to disprove it.
I was like: we are all wasting our time. We should just get off the internet and go do productive things.
Shaan: It’s kind of like when I say MFM gets credit for making Andrew Huberman and Brian Johnson famous.
Sam: You’re welcome, world. I actually think Kim Kardashian is famous because of you guys — didn’t one of you tweet about her early on?
Shaan: Yeah. You’ve ever heard of Rob Dyrdek? First one to watch her work.
Wrap-Up [01:52:00]
Sam: Pomp, thanks for doing this man. We love hanging out with you.
Pomp: Absolutely. I appreciate you guys very much. Can I plug one thing before I leave?
Sam: Yeah.
Pomp: We have a job board called DreamStartupJob.com. It used to be called Pomp Crypto Jobs — it was just crypto. We’ve expanded it to be crypto and everything else. We’ve helped on average three people a day for now over two years get a new job. There are 10,000 open roles on there. If you want to get a job at your dream startup, go to DreamStartupJob.com.
Sam: Looks good. I remember what it used to be — I think this is a smart move.
Pomp: We’ll figure it out. Appreciate you, fellas. Good to see you.
Sam: That’s the pod.