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My First MillionHow To Grow & Monetize A $10,000,000+ Podcast Business (#440)
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Acquired x My First Million crossover: how both shows evolved
The hosts welcome Ben Gilbert and David Rosenthal from Acquired and reflect on a prior crossover. They recap how Acquired shifted from focusing on tech acquisitions to long, company-wide history and strategy episodes, and how My First Million got started through Hustle publishing.
- •Shaan Puri introduces the crossover and how he first discovered Acquired
- •Ben Gilbert describes Acquired’s evolution from acquisitions-focused to deep company histories
- •Sam Parr recounts how My First Million launched via The Hustle, including Shaan’s improvised pilot story
- •They contrast their different growth journeys while landing at similar per-episode scale
Niche, “flavor,” and earning the right to expand beyond your initial hook
The conversation explores how a specific niche helps a show earn initial attention, but personality and perspective are what let creators broaden topics. They discuss the idea of building a “flagship franchise” first, then launching additional formats once trust is established.
- •Ben says a niche earns you the right to exist, but demeanor/perspective gives license to expand
- •David frames this as “flavor”
- •Shaan shares a Wait But Why model: start with a flagship franchise, then expand into new franchises
- •They discuss how early podcasting’s mainstream adoption made discovery easier than it is now
Growth realities: download numbers, release cadence, and audience quality
Sam asks for candid scale benchmarks and what it takes to grow beyond early milestones. Acquired and My First Million compare reach and cadence, then shift to the idea that audience composition can matter more than raw audience size.
- •Sam shares MFM’s early spike, later dip, and eventual climb in per-episode reach
- •David says Acquired is at a similar scale but with one-to-two long episodes per month and few viral spikes
- •Shaan argues quality and audience type are undervalued compared to simple view/download counts
- •Sam explains why he’d rather saturate a valuable niche than chase millions of listeners
Guests vs host-led format: why Acquired’s biggest episodes aren’t interviews
They discuss what listeners actually show up for and how guest choices can help or hurt. Ben and David describe a consistent pattern in their analytics: their host-only deep dives set records, while guest episodes underperform relative to the prior episode.
- •Shaan outlines four guest types: “like us” contributors, famous, internet-famous, and personal-nerd-out
- •Ben notes “real famous” guests often lack distribution compared to internet-famous creators
- •They observe Acquired’s record episodes are canonical host-only deep dives (e.g., Nintendo, LVMH)
- •Ben says guest episodes are consistently less listened to than the previous episode
Inside the Acquired process: month-long research and “conversational audiobooks”
Sam asks how Acquired prepares episodes, and Ben and David explain their research-heavy workflow. They aim to consume virtually everything about a company and then turn that work into a lively conversation between close friends.
- •David compares their prep to writing a college term paper, then doing a “thesis defense” together
- •Ben describes the goal of consuming every major source: books, talks, podcasts, obscure videos, and citations
- •They want to avoid missing key information listeners might DM them about later
- •Ben calls the output “conversational audio books,” made engaging by their friendship dynamic
Patterns in outlier companies: contrarian bets and “left for dead” assets
Asked about shared traits among exceptional companies, they stress there’s no repeatable formula because each is an extreme outlier. Still, they repeatedly see winners making bold, contrarian moves—often pursuing markets or assets that everyone else abandoned.
- •Ben says success often requires being contrarian and right, but each story is an N-of-one
- •He cites examples of pursuing assets or strategies others dismissed as dead
- •Nintendo is highlighted: entering after the 1983 U.S. video game crash and rebuilding the market
- •They describe these as “nut job bets” with huge upside when correct
Real vs performative contrarianism—and an Alibaba “keys to failure” story
Shaan shares a heuristic for spotting true contrarians: they’re not excited about being contrarian; they’re confused others don’t see what they see. He then tells a detailed story from a visit to Alibaba, emphasizing a framework focused on avoiding common failure modes.
- •Shaan’s tell: performative contrarians are eager to flaunt disagreement; real ones treat their view as obvious
- •Ben adds an analogy: wanting the idea of a relationship more than the relationship itself
- •Shaan recounts meeting an Alibaba leader who argued success models don’t copy, but failure patterns do
- •The story’s “failure keys” are framed as money, plans, and technology—and how the company tried to avoid those traps
Nintendo deep cut: from playing cards and the Yakuza to Disney and toys
They dive into Nintendo’s surprising origins, including its age and early business model. Ben and David describe how Nintendo began with hanafuda cards, ties to illegal gambling distribution, and later diversification through Disney licensing and toy retail leverage.
- •Ben says Nintendo is a 130+ year old company that started making hanafuda cards
- •They describe Japan’s isolationism era context and how cards served gambling demand
- •Nintendo’s early distribution ran through illegal casinos and the Yakuza
- •They discuss a later pivot involving a Disney partnership and pushing Nintendo products through retail channels
Rapid-fire favorites: best company to own, NFL durability, and MLBAM/BAMTech
Sam prompts a rapid-fire segment on companies Acquired has covered. Ben and David pick the NFL as the ultimate durable asset and explain league-wide media-rights negotiation and revenue sharing, then revisit MLBAM/BAMTech’s origins and why it became strategically important.
- •Ben says the NFL is the company he’d most want to own due to entrenched durability
- •They discuss the NFL’s unified negotiation of media rights and equal revenue sharing
- •Shaan summarizes MLBAM/BAMTech as a co-owned baseball tech effort that became critical streaming infrastructure
- •Ben notes MLBAM/BAMTech had an early head start on insights about streaming infrastructure
Who you least want to compete against: Jensen Huang and Bernard Arnault
They debate the CEO archetype you’d least want as a competitor, offering two different “badass” profiles. David champions Jensen Huang’s persistence across multiple company “acts,” while Ben argues Bernard Arnault’s dealmaking and empire-building makes him uniquely formidable.
- •David names Jensen Huang and explains NVIDIA’s shifts from gaming GPUs to AI platform positioning
- •Ben explains NVIDIA’s CUDA bet and how it created a platform moat for AI development
- •David describes Jensen’s personal intensity and brand of leadership as both tough and kind
- •Ben names Bernard Arnault as the most dangerous competitor due to deal prowess and leverage across brands
Founders, leadership, and media narratives: Airbnb, journalism limits, and “toxic” headlines
The conversation shifts into how people evaluate leaders and how media coverage can distort reality. They discuss Airbnb’s durability as a marketplace, praise Brian Chesky’s leadership presence, and critique how journalism can sensationalize normal startup behavior.
- •David frames Airbnb as a business you “cannot kill,” emphasizing its global network effect
- •Ben shares his personal proximity to Airbnb and praises Brian Chesky’s leadership communication
- •They argue podcasting enables more “operators” to speak directly compared to traditional journalism pipelines
- •Sam cites an Away Travel media takedown as an example where the details felt overhyped for the headlines
Business ideas: corporate podcast agency and why companies pay (even if no one listens)
Sam asks for half-baked ideas, and the group proposes a corporate podcast agency serving external or internal shows. The core logic is that podcasts can function as relationship-building, sales enablement, and lead nurturing—regardless of organic audience size.
- •Sam proposes a corporate podcast agency for companies to launch podcasts
- •They argue podcasts are valuable for relationship conversations with customers and prospects
- •Ben describes use cases like sales enablement and lead nurturing content
- •David says the model works because customers can be price-insensitive, but it’s vulnerable when budgets tighten in downturns
Monetization, selling the show, and building businesses off the audience
They discuss whether Acquired would ever sell, what kind of valuation threshold would matter, and how growth has been unusually consistent. The conversation expands into how podcast audiences can drive sponsor value, equity opportunities, investing vehicles, and spinout businesses—without necessarily running a large operating company.
- •David says he wouldn’t entertain sale conversations below “tens of millions,” comparing to deals like The Hustle and Morning Brew
- •Ben says Acquired has doubled annually for years and asks whether to trust their own underwriting vs an acquirer’s
- •David describes managing funds via AngelList enabled by Acquired’s platform and credibility
- •They compare sponsor cash vs equity tradeoffs, and discuss MFM’s HubSpot ownership/performance-fee arrangement and constraints
Podcasting as an operator medium, AI as a rewriting tool, and the “gentleman’s agreement” outro
They argue podcasts lower the barrier for credible experts to publish, unlike writing-heavy or highly produced formats. Ben shares how he uses ChatGPT as an editor/rewriter, then the episode wraps with cross-promotion and the show’s “gentleman’s agreement” call to action.
- •They say podcasting attracts more credible practitioners because it’s easier to speak than write or heavily produce content
- •Ben describes using GPT to rewrite a LinkedIn post for virality and then toning down the output
- •They promote subscribing to both shows and explain the “gentleman’s agreement” as the listener’s way to ‘pay’
- •They close with discussion of YouTube subscriber growth and a proposed YouTube Premium giveaway idea
Publisher timestamps
- 0:00Intro
- 1:07Intro to Acquired
- 2:25What to do when your schtick runs out
- 7:05How to scale to a big podcast
- 14:07How big do you have to be to be at the top of the business category?
- 22:46What commonalities are there between weird companies?
- 27:12How to tell a real from a fake contrarian
- 34:40Nintendo
- 38:15Which company would you most want to own?
- 42:12Who would you least want to compete against?
- 52:42Business ideas
- 58:17Will you ever sell Acquired?
- 1:07:24Best ways to make money as a podcast
