Oct 4, 2022 · 2h 23m · acquired
ACQ Sessions: Jason Calacanis · Acquired
Jason Calacanis · 1h 26m spoken Ben Gilbert · 23m spoken David Rosenthal · 16m spoken Christina Cacioppo · 1m spoken
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In this inaugural Acquired Sessions episode, hosts Ben Gilbert and David Rosenthal sit down with angel investor and media veteran Jason Calacanis for a wide-ranging, unscripted conversation on the mechanics of the All-In podcast, early-stage venture capital frameworks, tech M&A, and the evolution of digital broadcasting.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Ben and David hold 30.9% of the talking time here. How this is scored →
Ben and David as informed peer 3.4 Guest teaching 2.0 Guest disagreement 1.6 Ben and David pushing back 1.4
speaking balance: gold is Ben and David, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 2:00:55 Jason forcefully rejecting a16z's Hall of Fame candidacy
Jason aggressively pushes back against the hosts nominating Andreessen Horowitz, dismissing their strategy as a soulless industrial factory indexing venture capital rather than practicing relationship-driven investing.
Hardest push from Ben and David ▶ 37:23 Ben challenging Jason's meritocracy narrativeBen directly interrupts Jason's idealistic claim that the tech ecosystem is completely fair, insisting the world remains unfair and success requires navigating those asymmetries.
Biggest teaching moment ▶ 1:22:20 Jason coaching Calm on pricing strategyJason walks through how he reframed Calm's original low-cost model by benchmarking digital meditation app subscriptions against real-world in-person class pricing.
Ben and David hold their own ▶ 1:31:40 Ben breaking down Adobe's strategic imperative for FigmaBen articulates a sophisticated structural case for why Adobe had to acquire Figma at a high multiple due to organizational network effects and distribution channel leverage.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Ben and David as informed peer | Guest teaching | Guest disagreement | Ben and David pushing back | Why |
|---|---|---|---|---|---|---|
| Launching the Unscripted Acquired Sessions Format | 3 | 1 | 1 | 1 | The hosts introduce the new unscripted format over wine in a relaxed, convivial atmosphere. The segment includes a brief sponsor interview with Vanta founder Christina Cacioppo explaining trust reports. | |
| Early Origins, Brooklyn Grit, and Silicon Alley Reporter | 4 | 2 | 1 | 1 | Jason recounts his Brooklyn upbringing, laser printer repair hustles, and launching Silicon Alley Reporter. Ben and David show deep familiarity with 1990s venture history, prompting details about Flatiron, Fred Wilson, and GeoCities. | |
| The Conception and Chemistry of the All-In Podcast | 3 | 2 | 1 | 1 | Jason narrates the backstory of All-In, from meeting Chamath at AOL to their private poker game during the pandemic. The tone is highly collaborative and conversational as they reflect on Buckley vs. Vidal style debates. | |
| All-In's Cultural Reach, Roles, and Political Dynamics | 4 | 2 | 2 | 2 | Jason explains crafting on-air archetypes for All-In and coping with political backlash. Ben offers insightful commentary on how two-party coalition dynamics force tribal alignment across unrelated issues. | |
| Silicon Valley Wealth, Opportunity, and the Meritocracy Debate | 5 | 3 | 4 | 4 | Jason passionately defends Silicon Valley as a true meritocracy where anyone can access open knowledge. Ben pushes back, arguing that structural unfairness persists and founders must navigate the practical reality of the game. | |
| Deconstructing What Makes All-In Compelling | 5 | 2 | 1 | 1 | Ben outlines his three-part theory on why All-In succeeds (billionaire intrigue, information asymmetry, and charisma). Jason agrees and adds his inspiration from watching John McLaughlin moderate on TV. | |
| San Francisco Politics, Governance, and Free Market Dynamics | 3 | 3 | 3 | 1 | Jason attacks local San Francisco politicians for driving away founders with taxes and regulation, contrasting it with free-market dynamics raising corporate wages. The hosts contribute tax context and let Jason run. | |
| Sponsor Segment: Brex | 0 | 0 | 0 | 0 | Mid-roll host sponsor read for Brex corporate cards and spend management. | |
| Jason's Daily Media Engine and 506(c) Venture Model | 3 | 3 | 1 | 1 | Jason breaks down his extreme daily media routine, the operations behind his 22-person organization, and raising capital via 506(c) public solicitation. The hosts listen intently while clarifying details. | |
| Institutional LP Ambitions, The Calm Origin Story, and Pure Angel Investing | 3 | 4 | 1 | 1 | Jason reflects on pitch interactions with major university endowments and shares the origin story of leading Calm's early seed round. Ben recognizes the rarity of early angel conviction saving a company before PMF. | |
| Evaluating Seed Investments, Product Velocity, and Public Equities | 4 | 3 | 2 | 2 | Jason explains his criteria for early-stage investments, emphasizing design and product velocity. The conversation moves into public equities where the hosts and guest discuss trading public stocks to understand macro market cycles. | |
| Big Tech M&A: Adobe Acquiring Figma and Weblogs Inc. to AOL | 6 | 2 | 1 | 1 | Ben delivers an incisive analysis of Adobe acquiring Figma, highlighting distribution channels and internal network moats. Jason validates the take by comparing it to AOL acquiring Weblogs Inc. to monetize excess ad inventory. | |
| All-In Valuation, Live Summits, and Howard Stern's Media Playbook | 3 | 2 | 2 | 1 | The discussion covers the standalone valuation of All-In, organizing live summits, Howard Stern's media playbook, and Jason's interest in developing a startup reality series. | |
| Sponsor Segment: Tiny | 0 | 0 | 0 | 0 | Host sponsor read for Tiny, highlighting their permanent equity model for acquiring profitable internet companies. | |
| Debating the Venture Capital Hall of Fame | 5 | 2 | 4 | 3 | The hosts and Jason debate a fictional Venture Capital Hall of Fame. A sharp back-and-forth erupts when David and Ben advocate for Andreessen Horowitz, while Jason forcefully dismisses them as a soulless mega-index fund. | |
| Reflections on Unplugged Podcasting Formats | 4 | 2 | 2 | 2 | They analyze the lineage of conversational long-form media from Charlie Rose and Howard Stern to Joe Rogan, Lex Fridman, and SmartLess. Jason advises against doing tech interviews without deep research. | |
| Studio Heat, Craigslist Furniture, and the First Big Exit | 2 | 1 | 1 | 1 | The episode wraps with comedic banter over David's Craigslist-furnished house, the catharsis of Jason's first big AOL wire exit, and drag racing an early Tesla Roadster against a Corvette. |
Statements from this episode (28)
Calacanis: SoftBank and J.P. Morgan each backed half of Flatiron Partners
“They were half of it, and Masayoshi-san, Softbank, was the other half.”
Calacanis bootstrapped Silicon Alley Reporter to $10M revenue by age 27
“I grew that business to ten million dollars in revenue off my credit cards and Had a, 75 to a hundred people working for me when I was 27 years old, and I didn't know anything about how to run a magazine, how to run Edsels.”
Calacanis: Chamath Palihapitiya invented 'growth hacking' at Facebook
“There is no equivalent of growth. That was, the idea of growth hacking didn't exist as a term until Chamath did what he did.”
Calacanis: I premeditated character arcs on All-In and created 'Sultan of Science'
“In all honesty, I did craft with All In. I was very premeditated in creating some character. I've never really talked about this. But I crafted some character kind of arcs. I, The fights are all real. Trust me, there's nothing scripted about that. But I did sa…”
Calacanis: Only ~5% of my 350 portfolio founders attended Stanford
“I've invested in 350 companies. Like, maybe five percent of the founders went to Stanford.”
Calacanis: Journalists only have between 5% and 35% of any story
“I, now looking back on it, I think we had between five and 35% of a story, and I know that's, like, probably triggering to a lot of journalists that they have that little information.”
Calacanis: California will be damaged for a decade or two
“I think Austin's kind of the future. I think California's gonna be damaged for a decade or two. So I think for the rest of our adult lives, this town.”
Calacanis: Bezos dunked on Sanders and Warren via Amazon's internal policies
“He took the platform that you could never actually enact. And he enacted it inside of Amazon. If it's not perfectly clear what just happened, literally he's dunking on you. You wanted free college and couldn't get it done, he gave it to Amazon employees. You w…”
Calacanis: My syndicate is the world's largest, deploying $50M annually
“The angel syndicate is now the largest syndicate in the world. I've deployed, like, one hundred eighty-five million dollars in my career as an angel investor. I'm doing fifty million a year now.”
Calacanis: SEC accreditation rules will soon allow test- or course-based qualification
“I believe that we're going to have a test For accreditation. And you'll be able to be sophisticated if you take a course. So I think that's coming in the coming years.”
Calacanis: Top endowments cited solo GP status as blocker
“If, you know, I've met with all the top endowments in the world over the years, and they're very kind to me, but it's always been like, solo GP is a blocker, no track record.”
Calacanis: Calm raised at $4M then bootstrapped to $250M valuation
“They had, it was four million dollars, we put 378 K in on six percent, and they didn't raise any money. Until it was a two hundred fifty million dollar valuation, so no dilution.”
Calacanis: I did not change Uber or Robinhood's trajectory
“A, that is not the case with Uber or Robinhood. I was along for the ride, let's be honest. I did not change the trajectory of those companies.”
Rosenthal: The best venture GPs over two decades all trade public stocks
“If you look at the very best People, the best GPs in venture over the past two decades, they all trade public stocks.”
Gilbert: Comparing early-stage startups to public comps is foolish due to market cycles
“And early stage investing, it's almost silly to compare to, like, my opinion is it's very silly to compare to public comps, because the only thing you know for sure is we're going to be at a different place in the cycle by the time this company gets liquid.”
Gilbert: Adobe will not ruin or kill Figma post-acquisition
“And all these people that are like, oh, they're gonna ruin it. They're gonna kill Figma. No, they're not. That's why they paid twenty billion dollars for it and have a gigantic bonus for Dylan to stay on board.”
Calacanis: AOL paid $30M for Weblogs Inc with only $200K in revenue
“And when I sold weblogs to AOL, people were like, oh my God, these people are idiots. They gave thirty million dollars to, you know, for weblogs Inc. They've only got 200 K in revenue.”
Calacanis: Best M&A deals seem overpriced initially, underpriced five years later
“And that's the best M&A. Is when you look like you robbed the bank. And then five years later, it looks like you robbed the founder.”
Calacanis: Inaugural All-In Summit generated millions and turned a small profit
“In the event, did a couple million dollars, had a small profit. But it was the number one tech event of the year by far.”
Calacanis: The All-In podcast is worth $50M to $100M
“It's worth fifty million, to answer your question. 50 to a hundred million. I mean, as a top 40 podcast, it's worth at least fifty million.”
Calacanis: Andreessen Horowitz is a soulless index fund of venture capital
“I think they're just an index adventure. I find it quite soulless, if I'm being honest. Like, I feel like it's a giant index on venture, and I don't think that their hearts are super into it.”
Calacanis: Andreessen Horowitz's long-term returns won't match Benchmark or Sequoia
“I think in the arc, it will not be comparable to benchmark at Sequoia.”
Calacanis: Sequoia offered a 50/50 carry split on early scout deals
“It was like you know, at the time, they carried fifty-fifty. Fifty-fifty at the time. They dropped it down after that.”