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My First MillionHow Pomp Makes 8-Figures With A Podcast & Newsletter (434 Part 2)
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Why starting your own businesses can beat angel investing
Anthony Pompliano explains why, for many people, building a small profitable business can be more reliable than hoping for venture-style power-law outcomes. He frames his current focus as “angel investing” in his own ideas by pairing capital and distribution with strong operators.
- •Angel investing can be lucrative, but small businesses can offer a higher probability of steady profit
- •A modest amount of startup capital can potentially create meaningful recurring profit
- •The competitive advantage he leans on is capital plus distribution
- •Success hinges on pairing a decent idea with an exceptional operator
Pomp’s career arc: building companies, Facebook as an "MBA," then investing
Pomp outlines the phases of his career: early company-building, a formative period at Facebook, and then building asset management firms. He contrasts the satisfaction of building with the dynamics of venture capital, which he describes as increasingly driven by access and allocation.
- •Early stage: learning how to build companies and recognizing limits
- •Facebook period as a concentrated learning environment with exposure to top leadership
- •Shift into investing and building two asset management businesses
- •Critique of venture as an access/status game once companies are de-risked
Distribution-first entrepreneurship: build the audience, then build the product
Pomp describes his “aha” that modern creators can identify and gather an audience first, then create products for them afterward. He shares the scale of his media reach and how that becomes a foundation for launching multiple businesses.
- •In the past: build product first, then search for customers; now: find customers first, then build product
- •Media reach spans podcast, YouTube, email, and social
- •He views building online businesses as a game he genuinely enjoys
- •Distribution is positioned as a core 21st-century advantage
Turning off podcast ads: reputation risk and owning the back-end
Pomp explains why he removed advertising from his media business despite it being highly monetized. He highlights reputation risk in finance advertising and argues the larger opportunity is owning the products sold through distribution, even if that means personally covering costs during the transition.
- •Finance ads can mean “renting your reputation,” especially when people entrust money to products
- •Crypto blowups made reputation and control feel even riskier
- •Turning off ads created short-term losses that he chose to personally absorb
- •He believes owning the product/service captures more value than taking ad payments
Asset management decisions: joint venture fund, rolling fund, then returning capital
Pomp distinguishes between two asset management efforts: a joint venture with Morgan Creek Capital and a separate rolling fund. He explains why he returned uninvested capital from the rolling fund and shifted to investing personally, citing economics and time saved from fund management overhead.
- •Joint venture fund invested in opportunities including Bitcoin and companies like Coinbase
- •He was an early adopter of AngelList rolling funds and scaled one near the top of the platform
- •He prefers pre-seed/seed investing over later rounds tied to access dynamics
- •Personal investing can be more attractive than fund economics, plus less time spent on LP management
Inflection Points as a vertical holding company: jobs, recruiting, training, research
Pomp describes Inflection Points as a holding-company-style structure focused on a specific vertical rather than broad acquisitions. He walks through multiple products launched under it, starting with a job board and expanding into recruiting, corporate training, and a subscription research business.
- •Holding company concept inspired by a vertical focus (as opposed to buying across many verticals)
- •Crypto jobs marketplace monetized by companies paying to list roles, with distribution driving traffic
- •The job board scaled quickly, validating demand
- •Expansion into recruiting (Proof of Talent), corporate training, and research subscriptions
Finding young talent online: Will Clemente’s Target bathroom tweets to a research business
Pomp tells the story of discovering Will Clemente through his early Twitter analysis while Will was working at Target during college. He describes how Will’s rapid learning and work ethic led to partnering on Reflexivity Research and early revenue milestones.
- •Discovery through Twitter content rather than traditional credentials
- •Will was working at Target while in college and posting analysis during breaks
- •Pomp evaluated talent through repeated interactions, podcast appearances, and evidence of fast learning
- •They structured a research business and shared early ARR growth expectations
Reflexivity Research product: crypto-native analysts packaged for institutional consumers
Pomp and Sam discuss the pricing and structure of the research subscription and what subscribers receive. Pomp explains how young “crypto native” analysts track communities while he helps shape their work into a format that larger investors can consume, including reports and an analyst call.
- •Subscription includes multiple research reports per week plus a weekly analyst call
- •Analyst team skews young and deeply embedded in crypto communities
- •Pomp emphasizes translating insights into a format usable by family offices, hedge funds, and others
- •Humor about the culture gap between professional investors and internet-native analysts
How to run multiple businesses: Pomp’s focus on capital + distribution + picking operators
Sam challenges why run several initiatives instead of focusing on one, and Pomp reframes it as one core activity repeated. He says his role stays consistent—providing capital, distribution, and partner selection—while operators run day-to-day execution inside each business.
- •He claims he’s effectively doing “one thing” across ventures: capital and distribution
- •He stresses staying in his circle of competence and not trying to operate every business
- •Selecting the right operators is a critical success factor
- •Goal is for products to grow beyond his distribution over time
Clout cycles, criticism, and using conflict as marketing fuel
Sam asks about the fear of losing relevance, and Pomp describes experiencing peaks and valleys tied to market cycles. He explains how he handles criticism, including leaning into tough interviews, reframing “haters” as marketers, and repurposing mainstream attention into his own channels.
- •He distinguishes bull-market virality from personal genius and expects downturn backlash
- •Philosophy: accept praise on the way up and endure criticism on the way down
- •He recounts a contentious TV segment and then uploading it to YouTube with a provocative title
- •He argues online attacks can inadvertently expand reach by amplifying attention
Distribution channel priorities: email ownership vs the intimacy of audio
Asked which distribution channel matters most, Pomp says he wouldn’t give up email, while also praising the intimacy of audio. He emphasizes choosing channels that match a creator’s strengths and warns that without an edge, it’s hard to cut through the noise online.
- •Email is the channel he values most to keep, even if not his main growth focus
- •Audio creates trust through long, intimate listening sessions
- •Different media require different strengths; not every creator fits every medium
- •Cutting through noise requires knowing your advantage
Recruiting ‘action’ young builders: Milk Road stories, Degods, and “weird shit that works”
After a sponsor break, Shaan and Pomp swap stories about young, high-momentum creators and operators, including Milk Road hiring attempts and an NFT founder’s unconventional tactics. They explore why these builders move fast, ignore social risk, and often create outcomes through bold experimentation.
- •Shaan recounts hiring attempts, including a candidate who made a viral “chugging milk” video
- •Story of a prospective hire who became associated with Degods and used provocative mechanics like the “paper hands” tax
- •Pomp shares how young builders’ willingness to do socially risky things can unlock growth
- •They discuss how formal recruiting funnels can attract the wrong “high achiever” type versus off-path builders
“Who’s figured it out?”: internet entrepreneurs they admire and why
Pomp asks Shaan and Sam to name internet entrepreneurs who seem to have “figured it out,” preferably outside the mainstream. Sam cites several operators and low-key builders; Shaan names people he believes will create outsized impact, and Pomp adds perspective on one of the companies mentioned.
- •Sam names Nick Huber and Austin Rief as operators he respects, plus other low-key winners
- •Sam mentions Mark Jenney and Saïd (WordPress plugins) as examples of lifestyle and business wins
- •Shaan cites Amjad from Replit and explains why he thinks it’s bigger than many realize
- •Shaan highlights Daniel Gross as someone he expects to do something “epic,” possibly in a different field
The ‘independent-minded’ archetype: Jack Smith, contrarian habits, and finding interesting people
The conversation shifts to what makes certain people repeatedly successful: independent-mindedness and a willingness to do things differently. Shaan and Sam describe Jack Smith’s unusual experiments, while Pomp reflects on how groups gravitate toward confident contrarian viewpoints and why internet communities seek novelty.
- •Jack Smith is described as perpetually pursuing new “capers” and unconventional experiments
- •They contrast genuine weirdness with performative contrarianism for personal branding
- •Pomp describes how groups often shift opinions toward whichever viewpoint feels magnetized by confidence
- •They discuss why internet life can be an escape from bland local routines and how to find more interesting people
Closing riffs: morning show chaos, sponsor mishaps, and “turn my volume up”
They wrap with jokes about doing longer live shows, including Pomp’s take on why daily streaming is fun but risky. The episode ends with stories about sponsor awkwardness and a Facebook-era moment escorting Flava Flav, culminating in the line “turn my volume up on Instagram.”
- •Pomp calls the morning show both the best and worst thing due to time and unfiltered talk
- •Sam recalls a sponsor-related joke that made Pomp nervous in the moment
- •They banter about podcast styles, blunt questions, and audience analytics
- •Pomp tells the Flava Flav story and the request to “turn my volume up” as a closing punchline
