Sam Lessin

Note on the episode: the feed title promises an Omaze storytelling interview, but the captions are actually a 20VC roundtable — Harry Stebbings with Jason (likely Jason Lemkin of SaaStr), Rory (likely Rory O’Driscoll of Scale), and Sam (likely Sam Lessin). The spine of the episode: DPI is the only score, most companies “don’t matter,” and AI is repricing every layer of software.

The panel reluctantly sides with Chamath’s “you can’t eat IRR. You can only eat net DPI.” Sam’s sharpening: there are two different games both called venture — actually making people money (a DPI game) and asset gathering, which “is actually a better business” but one he has “no respect for.” Sam’s proof that liquidity gets capital: Thoma Bravo raised a record $34bn fund after $30bn of distributions last year, in a quarter when nobody else could raise $5bn.

Sam’s pushback is the best counterpoint: calling TVPI meaningless is “vaguely right, but not useful” — venture consciously buries money for 5-7 years, so TVPI is a loose proxy with real signal in it. Sam’s machine-learning example compares funds at 2x versus 8x TVPI at year three or four. His alternative scoreboard ignores marks entirely: “just give me the list of four things” that are credible fund returners.

The middle of VC is hollowing out: SVB pegs $200-500M funds as the squeezed zone, Sam calls the billion-dollar fund “the death zone,” and Rory’s implication for founders is blunt — if nobody’s left to write the $20-30M Series A, “get to know folks with five or 10 billion funds before demo day.”

On selling: “you cannot sell the things that matter” — but Harry argues Chime’s seed holders would have wanted to sell into the $25bn round (they’re absent from the S-1 principal-stockholder table), and one panelist would sell Revolut and Chime right now: both sit near 15% market share and “CAC only goes up.” Harry’s counter: Revolut is “quite likely” at least $100bn, likely $150bn — selling at 25 forfeits $125bn of gains.

The “mattering” fight: one panelist says Chime and Box don’t matter, most companies don’t, and even OpenAI only “might matter” in 20 years; the rebuttal — “if Chime is not an important company… I’ve never done anything important in my life.” The panel’s resolution: market cap is a rough proxy for mattering, because “the capitalist system works.”

From the Mary Meeker report: ChatGPT hit 800M users in 17 months, the big six spent $212bn of capex (“they would break Mr. Buffett’s heart… capex hogs”), token costs collapsed 99.7% in two years, and the “$600 billion question is where are the apps.” Rory’s overlay: OpenAI’s revenue tracks Google exactly 20 years later, but projections assume it becomes twice the Google of its day — merely Google-good means missing next year’s number by ~40%, and “public company investors are just mean VCs on steroids.”

MCP is an existential threat to SaaS: agents abstract the app away (“I could become a pipe overnight,” per the Mangomint founder), value accrues to the system of work not the system of record, and the “AI slow roll” is the #1 thing killing B2B. Quickfire bets: the Jony Ive device family gets a screen, Meta ships a closed model (“I wouldn’t bet against Zuck”), and Jason puts 50% on Elon out as Tesla CEO before 2027 — “he can’t scale… with the 58 kids and the 11 companies.”

🔗 Original source & video: Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll