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My First Million

3 Business Ideas You Should Start in 2024 (ft. Pomp) (#524)

Episode 524: Shaan Puri and Sam Parr are joined by Anthony Pompliano about what secret sauce makes for the most successful investors, billionaires you’ve probably never heard of, plus three 10/10 business ideas.

Sam ParrhostAnthony PomplianoguestShaan Purihost

Nov 29, 20231h 9mWatch on YouTube

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Chapter summaries

Pomp’s identity, personal updates, and how his brand expanded beyond Bitcoin
Sam and Shaan welcome Anthony Pompliano back and riff on his “Pomp” moniker, family life, and public persona. Pomp explains that what looks like a pivot from “Bitcoin guy” to broader business interests is really an expansion of skills he’s used before—building companies, working at Facebook, investing, and leveraging internet distribution.
- •Sam and Shaan joke about whether anyone calls him Anthony versus “Pomp.”
- •Pomp describes his path: company building, Facebook, investing, then public Bitcoin commentary.
- •He argues the same skill set—distribution/virality—can apply across arenas.
- •He compares the modern “viral skill set” to how fame and influence translate into entrepreneurship and beyond.
Brute-force networking and meeting Julian Robertson through long relationships
Sam tees up Pomp’s knack for getting into rooms with influential people. Pomp explains that curiosity and saying “yes” to unclear opportunities creates luck, then details how a partnership with Mark Yusko ultimately led to meeting Tiger Management founder Julian Robertson.
- •Sam frames Pomp as unusually proactive at getting high-value networking opportunities.
- •Pomp attributes it to curiosity and saying yes often—“shots on goal.”
- •He explains the Mark Yusko connection and the long relationship chain to Robertson.
- •He recounts the day they went to meet “legends of Wall Street,” starting with Robertson.
Inside Julian Robertson’s office: curiosity, relentless questioning, and learning mindset
Pomp recounts the meeting with Julian Robertson in vivid detail, emphasizing how unusually curious Robertson was—even late in life and with nothing to prove. The story highlights a theme that repeats later: sustained curiosity and willingness to learn as a hallmark of enduring success.
- •Robertson’s office setup and presence signaled his stature and habits.
- •Despite being in his 80s, Robertson aggressively questioned Pomp to understand Bitcoin/blockchain.
- •Pomp highlights the contrast: enormous wealth and age, yet intense desire to learn.
- •A humorous moment: Robertson uses built-in office tech to summon assistants mid-thought.
Why Tiger Management mattered: hedge fund innovation and the Tiger Cubs talent factory
They unpack why Julian Robertson became so influential: an early hedge fund approach, high-conviction investing, and a legacy of seeding talent. The hosts compare the “Tiger Cubs” to a finance equivalent of the PayPal Mafia, with an extended lineage of firms and investors.
- •Pomp describes Robertson as among the first “true hedge funds” with long/short hedging style.
- •High conviction and being right helped him gather assets and drive returns.
- •His outsized legacy came from spotting talent and seeding future fund founders.
- •The “Tiger Cubs / Grand Cubs” network is discussed as a massive lineage.
What makes a master investor: curiosity, extreme conviction, and obsessive work ethic
Sam asks what traits spread from Robertson to the broader cohort of legendary investors. Pomp lists recurring attributes: deep curiosity, willingness to make non-consensus bets, and a near-addictive obsession with doing the work—illustrated by stories about Bill Miller and investing behavior during drawdowns.
- •Pomp says many elite investors share intense curiosity and comfort with bold risk.
- •He emphasizes ‘insane bets’ when others won’t—conviction under pressure.
- •Bill Miller is cited as an example of long-term outperformance and concentrated conviction.
- •Obsession shows up in daily habits—reading research constantly, even at leisure activities.
Thin line between genius and idiot: conviction in yourself and buying into ‘the fire’
Shaan reflects on how hard it is in real time to distinguish a brilliant contrarian bet from a disastrous mistake. He shares a real estate story of someone who mistook panic selling for opportunity during 2008, and contrasts it with a different story where an investor bought ‘best companies’ at an 80% discount.
- •Shaan argues the hardest part is trusting your ability to tell winners from losers amid chaos.
- •Story: a real estate fortune evaporates after moving ‘toward the fire’ in 2008.
- •Contrasting story: viewing market crashes as ‘Black Friday’ for top companies.
- •They discuss needing a clear rationale and being willing to accept being wrong.
Pomp’s $1M Bitcoin bet and ‘once-a-decade’ conviction moments
Sam asks how they personally react to legendary-investor stories—confidence versus intimidation. Pomp describes the one time he ‘backed up the truck’: Bitcoin after the 2017 peak and crash, including a public $1M performance bet against any Wall Street taker, and why conviction bets should be rare.
- •Pomp describes Bitcoin falling from the 2017 peak to much lower levels and his public conviction.
- •He recounts a $1M bet: Bitcoin versus any other asset over 10 years—no one took it.
- •He notes many who engaged were seeking media attention and tried to complicate terms.
- •He argues these moments should be rare—maybe once a decade—not a constant posture.
Warren Buffett as ‘finance’s first influencer’ and reframing content as marketing
Pomp credits Buffett’s famous bet as inspiration and calls Buffett an original finance marketer. Sam and Shaan broaden the point: many major business figures produced “content” (letters, newspapers, editorials), and Pomp reframes modern content creation as straightforward marketing and distribution rather than something to be embarrassed about.
- •Pomp says Buffett combined investing ideas with masterful marketing and media leverage.
- •Sam notes many historical business leaders produced frequent written content publicly.
- •Pomp says content is marketing; good marketers often do it naturally rather than via calendars.
- •They discuss stigma around being labeled a podcaster/creator and why it’s misplaced.
Idea 1: ResiClub — building a residential real estate news + data platform from a newsletter
Pomp introduces the first concrete business idea: a dominant platform for residential real estate coverage and data, starting with a newsletter and scaling into a media site and data products. He explains why the category matters—housing affordability concerns and a lack of a central voice—and details how partnering with an established editor made execution viable.
- •Pomp frames a gap: no dominant voice for residential real estate news, commentary, and data.
- •He describes ResiClub as starting small (newsletter) with a path to media and data products.
- •He highlights the partner strategy: teaming with Lance Lampert, described as an expert with industry credibility.
- •He emphasizes starting profitably and increasing ambition only after earning the right to expand.
How ResiClub monetizes: audience breadth, data paywall, and pricing strategy debates
The hosts dig into who would pay for residential real estate coverage and how the business can expand. Sam critiques the initial $150/year pricing as too low; Pomp defends it as a low-friction entry point to validate value, reduce churn, and do price discovery later.
- •Pomp argues residential real estate is both niche and huge, with many stakeholders (builders, agents, buyers, lenders).
- •Sam points out the premium tier includes data access and questions who produces the data.
- •Pomp explains a lean start: one main content operator now, team expansion later after profitability.
- •Pricing debate: Sam wants higher prices; Pomp prefers low initial pricing, then raise later after validation.
Navigating the idea maze: false starts, iteration, and product-market-fit signals
Shaan asks how Pomp chose this specific path among many options. Pomp describes an earlier attempt focused on a South Florida geography strategy that didn’t “pull” hard enough, and explains a broader philosophy: run high-effort tests, watch for explosive traction, and be willing to change inputs rather than force a plan indefinitely.
- •Pomp recounts a prior partnership and strategy centered on one geography that didn’t work out.
- •He stresses that false starts are common and often under-discussed in entrepreneurship.
- •He describes an iterative approach versus “bend the world to your will.”
- •He cites product-market-fit as something you often ‘just know’ when it’s exploding.
How Nikita Bier engineers virality: repeated launches, K-factor focus, and rewriting monetization rules
Shaan explains Nikita Bier’s approach to consumer apps: repeated launches and tweaks until virality hits, optimizing for K-factor. He also critiques the tradeoff—virality without retention—and praises Bier for changing the consumer-social playbook by using mobile-game-like monetization and prioritizing fast profitability rather than traditional venture outcomes.
- •Shaan recounts repeated launches/renames to find the combination that sparks viral growth.
- •He distinguishes building a “virus” (K-factor) from building a long-term social network (retention).
- •He credits Bier for going back to the same domain rather than switching to something new after scars.
- •He highlights the monetization shift: consumer social app mechanics with mobile-game-style revenue thinking.
Brad Jacobs: repeated billion-dollar roll-ups and ‘under-the-radar’ operators
The conversation shifts to business builders who repeatedly create huge outcomes. Shaan and Pomp discuss Brad Jacobs as an example of someone who has built multiple multi-billion-dollar companies, describing a roll-up strategy (including buying landfills and surrounding operators) and noting how many highly successful people remain relatively unknown in internet circles.
- •Shaan describes becoming obsessed with researching Brad Jacobs after a tip.
- •Pomp explains the roll-up mechanics: acquire a key asset, then consolidate surrounding fragmented operators.
- •They discuss Jacobs’ repeated large-scale wins and how rare that pattern is.
- •They reflect on how many major operators are not widely recognized online and how success can come from straightforward asset accumulation.
Idea 2: Persistent Patrol Companies — computer vision as automated enforcement and revenue generation
Pomp outlines a business category he expects to grow: using computer vision to automate enforcement that currently relies on humans, allowing governments to raise more revenue. He ties it to fiscal pressure in cities/states, citing examples like congestion pricing and other fees, while acknowledging the concept feels ‘scary’ even if likely.
- •Pomp argues governments are broke and will prioritize new revenue sources over cost cutting.
- •He uses congestion pricing and other proposed fees as examples of the drive to raise funds.
- •He proposes automation of enforcement: parking, occupancy limits, and other compliance monitoring via computer vision.
- •Shaan agrees the revenue opportunity is real while disliking the “persistent eye” implications.
Idea 3: AI agents — automating opportunity discovery and planning (and what’s actually usable now)
Pomp describes a post showing AI agents generating business opportunities, scoring them, and producing execution plans—suggesting parts of ideation work could be automated. Shaan is skeptical of how usable those outputs are today, but proposes a practical angle: buying high-ranking Upwork/Fiverr profiles and using AI to expand throughput and margins, akin to aggregating search-position ‘real estate.’
- •Pomp describes AI agents that find, score, and plan execution for opportunities.
- •He suggests this could compress research time and threaten human-driven “idea” workflows.
- •Shaan compares the state of AI agents to impressive but not-yet-usable VR demos.
- •Shaan proposes a concrete model: acquire top freelancer profiles as distribution, then use AI to fulfill more work at higher margins; Pomp links it to the Amazon aggregator thesis of search position as real estate.
Pomp’s portfolio management: time allocation, buy vs. build, and a unifying strategy
Sam asks how Pomp runs many businesses at once and how he decides between acquiring versus building. Pomp describes focusing most time on early-stage companies, limiting involvement once a business works and has a leader, using weekly updates for accountability, and evaluating buy/build based on cost and complexity; he also reiterates his umbrella approach as providing capital and distribution.
- •Pomp estimates he’s involved with around 10 businesses and concentrates time on the newest ones.
- •He says older companies should run autonomously; he steps in mainly for occasional ‘fires.’
- •Weekly updates are a consistent mechanism to maintain momentum and accountability.
- •He prefers building when acquisition prices/complexity are extreme, but is more open to buying at smaller scales; he frames his core activity as providing capital and distribution.

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