Entrepreneur and investor, founder of Professional Capital Management and prominent Bitcoin advocate who hosts The Pomp Podcast.
Pompliano tracks his net worth weekly, not every six months like Sam, on the principle that the act of measuring something causes it to move. If you want a metric to grow, measure it often.
“I feel like, uh, things you measure move. And so if you want it to move, then you gotta measure it like often.”
Pompliano recaps how Michael Saylor took MicroStrategy from owning no Bitcoin in July 2020 to more than 210,000 coins, over 1% of all Bitcoin, by repeatedly raising debt and selling equity to buy more.
“And he went from owning zero Bitcoin in July of 2020 to today he has more than 210,000 Bitcoin, which is more than 1% of the Bitcoin network. And it's worth, you know, I don't know, something more than like $10 billion.”
Pompliano's contrarian stance: for a company with a long-term posture that doesn't need the cash for operations, holding dollars is riskier than holding Bitcoin because inflation erodes purchasing power over 10-20 years.
“I think it is riskier for a company to sit with $500 million in US dollar cash on their balance sheet than $500 million worth of Bitcoin. And the reason being that, or maybe the one clarifier is if you have a long-term oriented posture and you don't need that cash for day-to-day operations right now, Bitcoin will definitely do better from protecting your purchasing power over the next 10, 15, 20 years than the dollars will.”
Inspired by a story from the Elon Musk biography where a Tesla self-driving failure was fixed by repainting a road, Pompliano pitches buying road line-striping businesses at ~3x EBITDA. As autonomous driving spreads, governments will mandate more frequent repainting, driving revenue and multiple expansion.
“these like line striping or line painting businesses are going to be exponentially more valuable in the future because as self-driving becomes prevalent on the road, governments are going to mandate that the roads are painted more often so that the cars from a safety perspective can actually drive correctly. And so you probably can go buy these line striping businesses right now for like 3 times EBITDA and you start to scale them.”
Steal thisRoll up line-striping companies now at low EBITDA multiples and ride the self-driving repaint mandate wave.
Pompliano describes the traffic cone and barricade rental business as the greatest real estate business in the world: buy a barricade for about $400, rent it for $5-8 a day, and once it's on a construction site it can't leave until the job is done, sometimes for years.
“They can buy like a hip height, you know, like 4-foot-wide barricade. They buy those for like $400 and then they rent them out for like $5 to $8 a day. And once you're on site, you're not allowed to leave the site with like the equipment can't leave until the job's done.”
Pompliano profiles investor Philip Anschutz, who bought Regal Cinema when theaters were crashing. His aha: the 20 minutes before a movie is a captured audience, so he turned the theater into an ad business, changed the unit economics, and saved the chain. Pompliano then copied the idea, running paid TV commercials in the middle of his own conference.
“And what he realized in his like aha moment was for 20 minutes before the movie starts, you have a captured audience that are just sitting there looking at the screen. And so he started to sell ads and he made the movie theater an ad business. And then all of a sudden he completely changed the unit economics and was able to like save Regal Cinema, became this huge thing, sold it, et cetera.”
Steal thisFind the captured-attention window inside an old business and monetize it as ad inventory.
From over 100 Facebook product-manager interviews, Pompliano says the only instant strong-hire answer to 'traffic is down 50%, what do you do?' was a candidate who said he'd immediately alert the whole team. Communicating the problem before rushing to solve it signals real team experience.
“He goes, I would immediately alert the entire team. We have a problem. Like everyone else would jump to solve the problem, but it was so obvious. Like this guy's worked on teams before.”
Steal thisIn a crisis-scenario interview, listen for whether the candidate communicates the problem to the team before diving into the fix.
Pompliano cites a heuristic for sizing up a startup: look at the competitor it chooses to fight. Figure AI's founder picked Elon Musk as his rival in humanoid robotics, a signal of ambition, fundraising firepower, and conviction.
“one of the best ways to evaluate a company is like what enemies they pick.”
Steal thisWhen judging a startup, ask who it has chosen to compete against; the size of the enemy reveals the size of the ambition.
Pompliano notes Placer.ai, which uses cell-phone location data to sell granular foot-traffic analytics (which aisles you walk, which parking lots you enter) to real estate firms and hedge funds, just announced $100 million in annual revenue at roughly a $1 billion valuation.
“They just publicly announced that they're doing $100 million in annual revenue. And so when you look at that again, like it's for real estate, right? That's where they've seen a lot of people buy.”
Pompliano describes his Solana trade: he bought at $48, and instead of congratulating himself when it rose, he doubled the bet at $55 because the market was confirming his thesis. He kept scaling in and later bought more on a 30% drawdown, riding it to roughly $190.
“Instead, what I did is I bought a little bit of Solana at $48. It started to go up a little bit more. And usually when that happens, people are like, oh cool, I was right. Instead, I doubled the bet at $55. Like the position is going in your favor. And so I doubled down because it's telling me, like the market's telling me I'm right.”
Steal thisWhen a position moves in your favor and the thesis holds, add to it rather than trimming to lock in gains.
Pompliano's takeaway from interviewing Andrew Tate before he was famous: every claim had a kernel of truth wrapped in a bombastic, viral package. People don't become viral and successful without being highly intelligent, and Tate's communication tactics have since become standard internet marketing playbook.
“I think like that was the biggest takeaway was people don't become viral and successful without being highly intelligent. And he very well understood the human psychology and the way the internet worked.”
Hedge-fund legend Julian Robertson seeded employees who left Tiger Management; those proteges (the 'Tiger Cubs', most famously Chase Coleman's Tiger Global) became hugely successful. Pomp argues Robertson was even better as a talent identifier than as an investor.
“And then, you know, the lore of Julian kind of expanded even more when a bunch of people who worked for him left. He would seed them, and when he would seed them to get them off the ground, those guys now known as Tiger Cubs became very successful. Tiger Global probably being the most successful. And so it was like, hey, he was good as an investor, but he was even better at like a talent, you know, kind of identifier and then seeding these people to create these great firms.”
Pomp's common thread among legendary investors: they're obsessed gym-rat types. He cites Bill Miller reading research reports in the stands behind home plate at Orioles games, between innings.
“And then the last one is these dudes are junkies, man. They're obsessed. I almost think of it like a gym rat. They not only are curious, but they do the work. And so in that book about Bill Miller, they talk about he was in Baltimore and he had seats behind home plate for the Baltimore Orioles. And he used to bring research reports and read them in the stands in between innings.”
Pomp's common thread among legendary investors: they're obsessed gym-rat types. He cites Bill Miller reading research reports in the stands behind home plate at Orioles games, between innings.
“And then the last one is these dudes are junkies, man. They're obsessed. I almost think of it like a gym rat. They not only are curious, but they do the work. And so in that book about Bill Miller, they talk about he was in Baltimore and he had seats behind home plate for the Baltimore Orioles. And he used to bring research reports and read them in the stands in between innings.”
After Bitcoin crashed from $20K to ~$3,200 in 2018, Pomp publicly offered $1M to anyone on Wall Street who could pick any asset that would beat Bitcoin over 10 years. No one took the straight-up bet. He treats it as one of the only true high-conviction calls of his decade.
“We actually, one of my favorite memories has kind of gotten like lost in the internet archives is we issued a million-dollar bet to anyone on Wall Street and we were like, we'll take Bitcoin, you take any other asset, like just pick anything over the next 10 years. If you beat us, like you get a million bucks. If Bitcoin outperforms, we get a million bucks and no one took it.”
Pomp argues Buffett mastered marketing as much as investing: his shareholder letters and the public S&P-500 bet were lore-building tools. If a 30-year-old Buffett existed today, he'd run a Substack, Twitter, podcast, and TikTok.
“Like Warren Buffett was the original finance influencer, right? And I've joked a million times that if he was today Buffett in his 30s, he'd have a Substack, a Twitter account, a podcast. He'd be streaming on TikTok, like doing all this stuff.”
Pomp partnered with ex-Fortune real-estate editor Lance Lambert to build Resi Club, a residential-real-estate media/data play tackling housing affordability. The playbook: start small and profitable (a newsletter), then layer on a media site, a data product, and eventually bigger bets, earning the right to expand ambition.
“And then it turns into like a media site and then it turns into a data product and then like I don't know, 10 years from now, are we going to have the information where we can go and seed like, you know, general contractors in different markets to actually build affordable housing? Like maybe. And so you start with this small little thing that you can build profitably and you don't have to raise money or, or kind of do anything where there's these, you know, huge expectations. But as you grow the business, you can increase your ambition over time.”
Steal thisLaunch the smallest profitable version (a newsletter), then expand into media, data, and bigger bets once you've earned the right.
Pomp funded Resi Club with $100,000 but says it was profitable within the first week/month, so they never actually drew down the cash.
“We were profitable within the first month. And so we actually wouldn't have even needed to put money into the bank account, but I think we put $100,000 to get started and never touched it. Because basically, you know, within the first week we were profitable.”
Pomp notes that business and finance people obsess over stocks and crypto but overlook residential real estate, which is the single largest asset class globally and supports a whole ecosystem of builders, agents, lenders, and buyers.
“So the beauty of residential real estate is it's the largest asset class in the world, but none of us who are like, oh, we're so smart. We're like business people. We're finance people. We have podcasts. We never think about residential real estate as like the largest asset class in the world. We're like, oh, stocks or crypto or bonds or whatever.”
Pomp deliberately prices Resi Club's premium tier at just $150/year. The logic: a low price removes friction, sells out all inventory, builds the muscle, and confirms people want the product without churn. You raise prices once you know you have the right product.
“It's like, if you're interested in this and we're actually creating something valuable, there is zero friction for you paying $150 a year. Over time, we will increase the price, but that's much better and gives us a better signal than let's say we came out with like $1,000 a year and people are like, man, this is valuable, but it's not worth $1,000. At least now we know, okay, we have something that people want.”
Steal thisLaunch at a low, frictionless price to confirm demand and zero churn, then run price discovery and raise later.
Pomp contrasts two modes of entrepreneurship: bending the world to your will versus an iterative approach. For most of his businesses he goes 100% into running a clean test, but stays willing to cut bait and try a different combination of inputs if the market doesn't pull the product into existence.
“And so there's two ways to do entrepreneurship. One is like, I'm going to bend the world to my will. And like, here's the thing that's going to work regardless of what the market tells me. I'm going to make it happen. And then there's like this iterative approach and a lot of these The things that I work on are much more iterative. And so you just have to be really good at like, go 100% in, run the test as perfectly as possible, but be willing to cut bait and try a different combination of the inputs if for some reason it's not exploding in the way that you want it to.”
Steal thisGo all-in on a clean test, but pre-commit to killing it and swapping inputs if the market doesn't pull it into existence.
Pomp describes a builder who made a feature to blur photos in Instagram Stories, then charge via Apple Pay to unblur them. OnlyFans creators posted teasing blurred shots, fans paid a few dollars to reveal, and the operator made a lot of money bootstrapping off other people's massive audiences with no fundraising.
“they created like an ability to make photos in your Instagram story blurry. And basically you would have to pay on Apple Pay to like unblur the photo. So obviously like all the OnlyFans girls would put it on their Instagram story and it'd be like just blurry enough where people are like, oh, that looks like something I might really like looking at. And then they'd pay like $2, $5, $10, like whatever it was set at.”
Pomp breaks down Brad Jacobs' repeatable roll-up strategy. In waste, Jacobs went to podunk towns, bought the landfill, then acquired all ~7 trash-pickup companies feeding it, repeating nationwide. United Waste Systems went public for a multi-billion-dollar outcome, and he's run the same playbook 6-7 times.
“He basically went to like podunk towns and was like, I'm gonna buy the landfill. And then once he bought the landfill, he was like, okay, there's like 7 companies that all pick up trash in the surrounding area and they bring to this landfill. And he would just like, would start like snipering off each one of 'em. He'd buy the first one, then he'd buy the second one, the third one, and eventually he'd own all 7 of the companies plus the landfill.”
Steal thisBuy the chokepoint asset (the landfill), then roll up every supplier that depends on it, and repeat the playbook across markets.
Pomp predicts broke cities will replace humans issuing parking tickets, fire-marshal checks, and occupancy fines with computer-vision systems that monitor constantly and automatically levy penalties. He expects private companies, not governments, to build this surveillance-for-revenue layer.
“So like they can just automate, okay, you hit with a $500 fine every single time at this event venue, et cetera. Elevators, like you can just go through this and see over and over again that computer vision will just become like the persistent eye. It's scary. Like, I don't like the idea of this, but I do think someone's going to build this technology and it's not going to be the government.”
Steal thisBuild computer-vision systems that automate municipal enforcement (parking, occupancy, fire-marshal) and sell the revenue lift to cash-strapped cities.
Pomp highlights Jacob Greenfield using chained AI agents: agent one scores opportunities by earning potential vs. difficulty, agent two builds execution plans for the high-upside/low-difficulty ones, and a third would carry out the plans. The point: AI can compress thousands of research hours into an opportunity spreadsheet.
“And so he was like, all right, I'm going to go have an AI agent that finds opportunities and I'm going to score the opportunities based on like how much money could I make and how difficult would it be to execute? And he basically populated this whole list. And then he's like, but haha, I'm going to create a second AI agent that then goes and looks at all of the opportunities that are high earning potential, low difficulty. And I'm going to have them create a plan on how I could actually execute to do that thing.”
Steal thisChain AI agents: one to score opportunities by upside vs. difficulty, one to write execution plans, one to carry them out.
Running ~10 companies, Pomp pulls back to a single persistent ritual: a weekly written update from whoever runs each business. He gives light feedback, but the real value is forcing operators to record what they got done, because no one wants to write 'we got nothing done.'
“The only thing that I do do is every week I get a weekly update and frankly, like I read 'em, I give a little bit of feedback here and there, but it's more so for the people who run the company because it forces them just to write down, what do we get done this week? And no one, including myself, ever wants to send an update. It's like we got nothing done.”
Steal thisRequire a written weekly update from each operator; the forcing function matters more than your feedback.
Pomp's rule for build-vs-buy: when buying would cost ~$100M and you could build a real competitor for ~$100K, lean toward building. But when a target is only worth $5-10M (about two years of progress), buying is lower-risk and the deal is easier to close than acquiring giant assets.
“But then I'm like, dude, I think for $100 grand we could create a competitor and like, it's not going to be worth $100 million, you know, within the first 2 or 3 years. But like, could we like take a big dent into their businesses? Probably. So when it's that skewed, I obviously tend to lean towards building versus buying. I think where it's harder is like, Hey, the business is worth like $10 million or $5 million. And you're like, that's like 2 years of progress versus not spending the money upfront and like maybe you get there. That's where I probably lean much more towards like buying versus building.”
Steal thisWhen buying costs orders of magnitude more than building a credible competitor, build; reserve buying for small targets that just buy you time.
Pomp argues that with $50K-$100K you're more likely to build a business to $1M revenue throwing off $500K-$700K profit per year than to win at angel investing in others. The edge: pair your capital and distribution with a decent idea and a killer operator.
“but actually you're much more likely to be able to take, you know, $50,000, $100,000, start a business and get to like $1 million in revenue and throw off $500,000 to $700,000 in profit. Year after year after year and do it with like a very high degree of, uh, of, uh, probability of success. And so in some way, like what's better than angel investing in other people's ideas? It may actually be just like angel investing in your own ideas or your own companies.”
Steal thisInstead of writing angel checks, deploy that same capital plus your distribution into starting your own businesses with a strong operator.
Pomp sizes his media empire: 25 million podcast downloads last year and half a million YouTube subscribers, plus a big email list and Twitter following.
“the podcast is 25 million downloads last year. YouTube's half a million subscribers.”
Pomp sizes his media empire: 25 million podcast downloads last year and half a million YouTube subscribers, plus a big email list and Twitter following.
“the podcast is 25 million downloads last year. YouTube's half a million subscribers.”
Pomp's mental model for managing effort over a career: life has a gas pedal, a brake, and coasting. The skill is knowing when to floor it (when it's necessary, not when there's a wall ahead) and pairing bursts with endurance so you can last instead of sprinting all the time.
“Uh, there's kind of gas and brakes in life. And so at certain points you need to hit the gas and other times you can kind of like let your foot off the gas, coast as the car, and then other times you need to hit the brake and knowing when to hit the gas, when to hit the brake, uh, is pretty important actually. You don't want to kind of be hitting the gas when there's a wall in front of you.”
Steal thisHit the gas only when going all-in is necessary; build endurance so you can last instead of sprinting nonstop.
Balaji Srinivasan publicly bet that Bitcoin would hit $1 million within 90 days, putting $2 million on the line. Pomp argues the real point wasn't the money but creating a meme that got millions of people talking about bank failures, hyperinflation, and Bitcoin.
“I think it's important to call out the Balaji's bet is like the best meme of 2023. He was able to essentially create a meme that has caused millions of people to now talk about this idea of hyperinflation, bank failures, and Bitcoin. And I think that's ultimately what he was trying to do.”
Pomp killed millions in podcast ad revenue because reading a finance ad means renting your reputation to a company you don't control. The bigger prize is cutting out the middleman and owning the product or service you push through your distribution.
“They might pay you $1 to read the ad, but they're making $3 to $5 on the backend as their return on advertising. Now, if you can cut out the middleman and you can just own the product or service, that's a way better deal. The reason why most people don't do it is because they don't have the skillset or the interest in actually building the product or the service.”
Steal thisStop reading ads for products you don't own; build or own the product and capture the full $3-$5 instead of the $1 ad fee.
Pomp's read on why Balaji made the bet: no matter how rich you are, you don't put $2 million on a public Twitter bet unless you have real conviction, because your personal reputation is priceless and that's what's actually on the line.
“but like, I don't care how rich you are. Like, you don't go publicly bet people $2 million on, uh, Twitter unless you have some degree of confidence, because in some way, like, $2 million may or may not be a big number, but like, your personal reputation is, you know, quote unquote priceless.”
Pomp's writing philosophy: argue one point of view as hard as you can so both critiques and support come back just as hard. If you stay willing to change your mind on good counterarguments, the ferocious response helps you iterate toward the truth faster than hedging would.
“is just argue ferociously and then you'll get the ferocious response and that will help you get to the truth faster.”
Steal thisArgue one viewpoint as hard as you can to provoke the strongest critiques, then change your mind when a critique lands.
Inspired by Mark Leonard's Constellation Software, which buys vertical-specific software companies across many verticals, Pomp built a holding company (Inflection Points) that owns many products and services within a single vertical (crypto): a job board, a recruiting firm, corporate training, and research.
“I'm fascinated with Mark Leonard. I don't know if you guys know Constellation Software. He basically buys these like vertically, vertical-specific software companies. Well, what happens if you don't have a holding company that ends up buying across the different verticals? What if you just have a holding company within a specific vertical? And so that's basically what we've built.”
Steal thisPick one vertical you have distribution in and stack multiple products and services under one holding company.
Pomp's heuristic for whose disagreement to trust: pay the most attention when someone who agrees with you 95% of the time suddenly disagrees, and when a habitual disagreer suddenly agrees. The signal is the reversion away from their mean, not the raw agree/disagree.
“And what you want to look for is like volatility in agreement. So the more that somebody agrees with you, you pay attention and put weight on when they disagree. And then the more that somebody disagrees with you, that you want to pay attention when they actually agree. So it's that volatility or that kind of reversion away from the mean that ends up being important to pay attention to.”
Steal thisWeight feedback by how unusual it is for that person: a rare disagreement from an ally beats a habitual critic's noise.
Pomp's Crypto Jobs board, a simple job board where companies pay to list roles and his distribution drives traffic, reached $50,000 in monthly revenue within roughly its first four weeks.
“Got it, we launched it, it got to like $50,000 in monthly revenue pretty much in like the first like 4 weeks, uh, and it was like, okay, we have a business here, right?”
Pomp discovered Will Clemente, now his research lead, when Clemente had ~1,000 Twitter followers and was tweeting Bitcoin charts from the Target bathroom on his lunch break. What sold Pomp wasn't experience but the kid's compounding rate of learning: reading a book in 2-3 days and reporting back the lessons.
“He was going into the bathroom at Target and like tweeting like Bitcoin charts and stuff. And so I met him because of the stuff he was tweeting and then was in the bathroom. No, online.”
Silicon Valley Bank's deposits roughly tripled during the money-printing era, from about $60 billion to about $190 billion, leaving it with ~$130 billion of new cash it parked in low-yielding long-dated bonds that later cratered.
“Silicon Valley Bank is a great example. They had about $60 billion of deposits to start. They ended up having about $190 billion of deposits. So kind of 3x growth, $130 billion or so.”
Silicon Valley Bank's deposits roughly tripled during the money-printing era, from about $60 billion to about $190 billion, leaving it with ~$130 billion of new cash it parked in low-yielding long-dated bonds that later cratered.
“Silicon Valley Bank is a great example. They had about $60 billion of deposits to start. They ended up having about $190 billion of deposits. So kind of 3x growth, $130 billion or so.”
In every business Pomp creates upside by taking a portion of revenue or profit, putting it into a pool, and splitting it among the team. When incentives align so that the team's wins are his wins, the capitalistic incentive drives quality and velocity of work.
“And so in every business, what I try to do is I try to create upside where we take a portion of revenue or profit depending on the business. We put it into a pool and then we try to split that among the team. And so if you have a profitable business and you're able to incentivize people and you're like, hey, when you win, I win. And when I win, you win. People will do incredible quality and velocity of work”
Steal thisCarve a fixed slice of revenue or profit into a shared pool and split it among the team so their incentives mirror yours.
Pomp explains the accounting treatment at the heart of the SVB collapse: banks can park bonds in a 'hold to maturity' bucket and count them at purchase price, not market value. It only breaks when all depositors want their money at once, forcing the bank to sell underwater bonds at a loss.
“Hold to maturity basically means we get to count what we bought it for, not what it's worth today. And the reason why they're allowed to do this is because they can hold the bond until the maturity, the 10-year period, and they'll get the principal plus the return. So as long as they don't sell it before it matures, then it ends up being worth what they paid for it. The only time that this does not work is if all of the depositors want their money back at the same time”
Pomp explains the accounting treatment at the heart of the SVB collapse: banks can park bonds in a 'hold to maturity' bucket and count them at purchase price, not market value. It only breaks when all depositors want their money at once, forcing the bank to sell underwater bonds at a loss.
“Hold to maturity basically means we get to count what we bought it for, not what it's worth today. And the reason why they're allowed to do this is because they can hold the bond until the maturity, the 10-year period, and they'll get the principal plus the return. So as long as they don't sell it before it matures, then it ends up being worth what they paid for it. The only time that this does not work is if all of the depositors want their money back at the same time”
Pomp's stance on online hate: the more people attack you, the bigger your audience gets, so the haters are effectively on your team and just haven't realized it. He even uploaded a hostile TV interview to YouTube titled 'Pomp Destroys TV Host on Bitcoin.'
“So I think that the hate, you have to also realize like, oh, like that's the president of my marketing team. That guy, there's a guy yesterday, true story, who created an entire thread of hate. He had videos, he had tweets. He literally filmed himself unfollowing me, right? Like he filmed his phone screen record unfollowing me. And I almost DM'd him and said, thank you.”
Pomp names a concept he expects to recur for decades: a 'digital catastrophe' is a negative real-world event drastically accelerated by the speed of online communication and action. SVB is the prime example — a Wednesday announcement became a dead bank by Friday because the internet weaponized a bank run that once took days of physical effort.
“But the way that I define a digital catastrophe is it's an event that occurs that is negative, usually plays out in the analog world, kind of the real world, but it is drastically accelerated by the speed of communication and action online.”
Pomp's verdict on the Balaji bet: he agrees on direction but not timeline, putting maybe 5% on the 90-day window — higher than most because hyperinflation tends to hit fast. He believes central banks will choose saving the banks over saving the dollar, but wouldn't bet $1M on Bitcoin hitting $1M in 90 days.
“Uh, again, I'm like maybe 5% because I do think there's very systematic, uh, problems and issues currently in the global financial system. I do think that the banks or the central banks, when faced with save the banks, save the dollar, will save the banks, which will lead to inflationary pressures. Uh, but I would not bet $1 million that Bitcoin will be $1 million in 90 days.”
Shaan relays Anthony Pompliano's line for dodging on-the-spot valuation questions: when asked to calculate a number live, just refuse to 'do public math.' Sam and Shaan adopt it as a running bit for the rest of the episode.
“if somebody has 100,000 Bitcoin and Bitcoin goes to 750,000, how much is that worth? And he just goes, I don't do public math. They go, what? They're like, what did you just say? He goes, I don't do public math. You don't do math in public? He's like, yeah. I don't do public math. And I just was like, that's actually a great policy. I don't do public math.”
Sam profiles Blockworks founder Jason, who at 23 relentlessly cold-emailed Bitcoin investor Pomp until Pomp asked for help launching and monetizing his podcast. That relationship became the seed of a bootstrapped, fully-owned crypto media company doing 8-figure revenue.
“So he was like 23 years old and he cold emailed Pomp and said, listen to this podcast I'm working on. Come to this event. Just like he was just like constantly emailing him. Pomp, who's this big Bitcoin guy, but who was less of a big Bitcoin guy years ago, said, all right, you've been emailing me too much. Whatever. You're persistent.”
Steal thisCold-email a rising operator relentlessly until persistence alone earns you a seat next to them.
Sam pitches a crypto news aggregator modeled on Hacker News, with a strict no-price-talk rule so technology and usage discussions aren't drowned out by daily price moves. He suggests a figurehead like Pomp is positioned to own it.
“Hey, I think somebody can create this. I think maybe Pomp or somebody who's like a central figurehead in crypto similar to Paul Graham, maybe Pomp should be creating the Hacker News for crypto that is specifically not about price. I think that would be a smart move. If I was Pomp, I would consider doing that.”
Steal thisLaunch a niche 'Hacker News for X' with one firewall rule that bans the topic everyone defaults to (e.g. price).
Andrew Finn (Wait But Why) told Shaan that to build an audience you need a 'red pill': the truth you've uncovered that people aren't hearing elsewhere, like Pomp hitching his wagon to 'Bitcoin is the way.' Shaan compares it to comedy, where a great joke is just a truth well told.
“What are you handing society that they're not hearing everywhere else? What's the truth that you know that you've uncovered? It's just like comedians. Comedians do the same. A funny joke is just a truth well told. I think that's the same thing for people who want to build an audience. You gotta figure out what is your red pill.”
Steal thisBefore building a following, identify the single contrarian truth you'll be known for repeating.
Shaan argues the old guard (Tim Ferriss, Gary Vee, Seth Godin) massively under-monetized their audiences with just books and ads, while newer creators like Pomp stack rolling funds, paid newsletters, and courses to convert audience trust into value.
“He chose books and ads from a podcast as his two models, and he's so popular that he still made a killing doing those two. But that killing is like— there's people with an audience a fraction of his size that are making as much money, if not more, than he's making off his podcast and books.”
Steal thisDon't rely on books and ads alone; stack a fund, a course, a paid newsletter, and products to monetize the same audience.
Anthony Pompliano says his podcast just passed 10 million downloads for the year so far, having grown largely off the back of his Twitter presence.
“So far this year, we just last week crossed over 10 million downloads for the year.”
Instead of paying to translate its site, Facebook open-sourced the work to bilingual users who volunteered to help, getting translations done faster, cheaper, and more accurately while building a better product for everyone.
“Facebook actually took the opposite, which was they just open sourced it to some degree. They basically said, hey, if you're a user and you speak both like, you know, English and whatever the national language is, like, "Can you help us?" And all of the support poured in and so they were able to basically tap into the user base and get all of the translations done and also get it done much more accurately, faster, kind of more scalably, whatever.”
Steal thisDesign a feature where users do work that improves the product for all users.
Before they had a fund, Pomp and his partner did 8 deals with personal capital, then funded each new check by going back to LPs deal-by-deal: invest your $100K and we match it into the company, plus you get exposure to the rest of the portfolio.
“Like, if you give us $100K, then we're gonna put $100K in this company, plus you get exposure to all the other deals in the fund. And so LPs are like, oh, this is awesome. And they would give us the money and then we would do it. And so like, that's like very like hand-to-hand combat fundraising type stuff. But when you're starting out and literally you'll take like $50,000, $100,000 checks for like a pre-seed fund, it's just the only way that you can is to like build a track record”
Steal thisProve a track record with your own money first, then raise a fund check-by-check off real deals.
Zach Parr was a hired-gun who ran other people's Kickstarters to multi-million-dollar results, then launched his own: Jacket Pets (now Cubcoats), a stuffed animal that unzips into a kid's jacket. He crushed Kickstarter, then layered on licensing deals with sports leagues and Disney/Marvel plus retail and online.
“And so Jacket Pets was, uh, take a stuffed animal, kids don't want to leave it behind, and so like, let's put a zipper in the back, and then when you unzip the stuffed animal, you can like turn it inside out, like press it inside out, and it'll turn into a kid's jacket.”
Pomp's repeatedly-pitched dating app idea: no profiles or texts. You hold the screen, a random question pops up, and you answer it as a selfie video on the spot, then choose to publish or discard. Solves catfishing/false promotion and creates a binge-able feed like American Idol audition tapes.
“Is to create a dating app just called Authentik. And all you do is you hold down the screen, right? So there's no profiles, there's no texts, there's no anything. When you open the app, you just hold down the screen to create your profile and a random question pops down. And it's the selfie video, you've gotta answer it on the spot, just like you would, you know, a date or an event or whatever.”
Steal thisKill static profiles; force live, unedited video answers so what users see is what they get.
Take a category everyone has written off, segment it tightly, and rebuild the same infrastructure with a different skin. Muzmatch did this as a dating app for Muslims, encoding niche details (halal, willingness to relocate) and became the largest Muslim dating app in the world.
“So it's like you could go do that for every single religion. And I think people have done that. You can go, you know, city by city, you can do all these different things. And so you could take an industry and just segment it and then just rebuild the same infrastructure with a different kind of skin on it and, uh, and probably do pretty well.”
Steal thisPick a saturated category, slice off one underserved segment, and rebuild the same product encoding that segment's specific rules.
Pomp's recurring theme: if you ask people which verticals are dead or over, those are often the best to go after. Consumer social was 'over' 18-24 months before TikTok exploded.
“Like, and by the way, this is like a recurring theme is if you go and if you ask a bunch of people like, what are the verticals that are played out? Like those are actually probably the best ones to go after, right?”
Steal thisSurvey what founders call 'dead'; treat the consensus graveyard as your shortlist.
Facebook found that friending 10 people in 7 days predicted ~85% retention. The playbook: identify the single action that predicts a retained user, then re-engineer onboarding so every new user is pushed past that threshold fast. Slack's version was 1,000 messages sent.
“And I was like, well, at Facebook, like, I think if I remember correctly, it's like if you get 10 friends in 7 days or something, right? If you like friend 10 people, then like there's like an 85% chance, whatever the number is.”
Steal thisFind the single action that predicts retention, then re-engineer onboarding so new users can't avoid doing it fast.
Per Chamath's framework, the US optimized for efficiency over resiliency, which COVID exposed. Pomp predicts a swing back: companies will reshore supply chains, and because American labor costs 4-5x Southeast Asia, they'll rely on automation and 3D printing, displacing workers but making reshoring viable.
“And so if you just re— if you just brought back your facility to the United States and tried to use American labor at the cost, you would like 4 to 5x the labor costs that you have compared to Southeast Asia or wherever. So like it almost would be like cost prohibitive to do it. But if you can instead use automation and 3D printing or whatever it is, now you can actually bring it back to the United States, increase your resiliency, and keep some like barrier of efficiency as well.”
Pomp's insight on Cutco and Gartner: people join knowing they won't stay, because the training gives them a skill for life. If you're churning 25% anyway, word spreads that the experience is worth it, making intense training a powerful recruiting tool.
“So I tend to think that like the organizations that spend a lot of time on the training, like word spreads like, hey, working there is good, but the training you get will like serve you for the rest of your career and it helps on the recruiting front.”
Steal thisMake your training so good people join for the skills even knowing they'll leave; let word-of-mouth do recruiting.