The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20VC: Is Chamath Right: Is DPI The Only Thing That Matters | Does OpenAI Even Matter | Mary Meekers AI Report: The Analysis| IPO Breakdown: Chime, Circle & Thoma Bravo's New Fund

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Jun 5, 2025

Sam Lessin, a venture capitalist and entrepreneur known for his deep expertise in technology, dives into pressing topics in the investment landscape. He questions the relevance of OpenAI and the validity of traditional metrics like TVPI. The conversation highlights challenges faced by mid-tier VC funds and critiques the valuation of startups like Chime. Lessin also addresses the implications of Mary Meeker's AI report and the future of SaaS in an AI-driven world, emphasizing the need for innovation amidst rapidly evolving market dynamics.

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00:00 / 00:00

DPI is the Only True VC Metric

Chamath Palihapitiya argues that DPI (Distributed to Paid-In) is the only metric that truly matters in VC performance.
Rory O'Driscoll agrees, emphasizing that TVPI is often marketing fluff, and actual cash returns (DPI) show if investors made money.

00:00 / 00:00

Capital Concentrates in Few Winners

Only a few companies per generation truly matter and command most capital.
Many capital deployments at Series A are wasteful, but mega funds can profit by deploying large amounts broadly.

00:00 / 00:00

Selling Early for Life Balance

A friend chose to sell a company early for life balance, gaining significant money and personal happiness.
Holding longer might have made more money, but the choice aligned with his life goals and brought fulfillment.

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Agenda:

00:00 – The Most Unfiltered Episode Ever Begins

03:30 – Does OpenAI Even Matter? Sam Lessin Says Maybe Not.

05:45 – TVPI Is Bullshit?

09:20 – Asset Gatherers vs Real Investors: Who Actually Wins?

12:15 – The Death of the Billion-Dollar VC Fund?

16:00 – Mid-Tier VC Funds Are Getting Annihilated

21:00 – Chime: Great Exit or Missed Opportunity?

27:00 – The War on Relevance: What Companies Truly Matter?

33:00 – If You're Not a Billion-Dollar Company, Do You Even Count?

37:10 – Mary Meeker's AI Report: What Everyone Missed

39:50 – $600B in AI CapEx—Where Is the Revenue?!

43:40 – What Could Trigger the First AI Crash?

51:10 – The Existential Dread Missing in Most B2B Startups

58:30 – Will AI Reduce Your Startup to Just a Pipe?

01:01:10 – IPO Market Is Back: What Actually Matters Now?

01:06:50 – YC Startups at $60M Valuations: How Should You Play It?

01:10:00 – Why 3% Ownership Could Still Work—Maybe

01:11:30 – Will Elon Still Be Tesla CEO by 2027? Place Your Bets

01:14:10 – Will Meta Release a Closed AI Model? And Does It Even Matter?

01:17:30 – The Real Challenge of Managing 11 Companies and 58 Kids

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