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Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell

Rory O’Driscoll is a General Partner @ Scale where he has led investments in category leaders such as Bill.com (BILL), Box (BOX), DocuSign (DOCU), and WalkMe (WKME), among others. Jason Lemkin is one of the leading SaaS investors of the last decade with a portfolio including the likes of Algolia, Talkdesk, Owner, RevenueCat, Saleloft and more. ----------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 01:08 Daniel Gross & Nat Friedman: Why Two Legendary VCs Walked Away From $1B to Join Meta 08:07 Meta’s AI Talent Magnet: Will It Actually Work? 15:38 Cursor Is Breaking the Market: Can Anyone Compete? 18:58 OpenAI’s SBC Bombshell: More Stock Comp Than Revenue 23:40 CoreWeave’s Power Play: Buying Their Landlords 27:50 Is Circle Next to Go Shopping with Meme Equity? 30:25 PE Is Back: The Olo Take-Private Explained 37:02 Why Triple, Triple, Double, Double Is No Longer Sexy 47:47 QSBS Hack: The Billionaire’s Tax Loophole You’re Missing 53:02 Microsoft’s AI Layoffs: Salespeople Are Dead, Long Live Engineers 55:54 “If You Need a Week to Learn AI, You Should Be Fired” 59:06 Kalshi Quick-Fire Round ---------------------------------------------------------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZ... Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast... Follow Harry Stebbings on X: / harrystebbings Follow Jason Lemkin on X: / jasonlk Follow Rory O’Driscoll on X: / rodriscoll Follow 20VC on Instagram: / 20vchq Follow 20VC on TikTok: / 20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/con... ----------------------------------------------- #20vc #harrystebbings #roryodriscoll #jasonlemkin #ai #meta #openai #shaunmaguire

Jason LemkinguestRory O’DriscollguestHarry Stebbingshost
Jul 9, 20251h 12mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Meta’s AI Talent Landgrab Reshapes Venture, PE, and Tech Careers

  1. The discussion centers on Meta hiring Daniel Gross and Nat Friedman away from their red‑hot AI fund, unpacking the financial math, LP impact, and what it signals about AI talent wars and venture incentives.
  2. From there, the hosts examine how mega-cap tech and AI companies are overpaying for scarce top-tier talent, how stock-based compensation and meme-valued equities (CoreWeave, Circle) are being used strategically, and why B2B AI recruiting will be a defining constraint by 2026.
  3. They also cover private equity’s role in cleaning up overvalued SaaS (e.g., Thoma Bravo–Olo), retail capital flowing into PE via Vanguard, and how university endowment pressures and tax policy ripple back into venture.
  4. Finally, they debate Microsoft’s shift from generalist sales reps to solutions engineers, the reality of AI-driven role compression, and how companies should force—or gently nudge—their workforces to truly adopt AI.

IDEAS WORTH REMEMBERING

5 ideas

AI’s top-tier talent will be the primary bottleneck in B2B by 2026.

The speakers argue that access to a small inner circle of ‘high priests of AI’ will determine which companies can build differentiated products; everyone else will struggle to recruit and must design businesses where “very good” talent suffices rather than S‑tier research engineers.

Meta’s deal for Gross and Friedman shows incumbents will massively overpay for AI talent and time-to-market.

By buying 49% of their fund and effectively compensating them for walking away from roughly $800M–$1B of future carry, Meta turns capital they would have deployed in a frothy market into secure upside for LPs—and accelerates its own AI push with marquee operators.

For LPs, a clean 2x liquidity outcome can outweigh losing star managers.

Though many LPs are emotionally disappointed to lose Gross and Friedman’s stewardship, getting roughly 2x cash back early while retaining upside in remaining positions is far better than the messy, low-return wind-downs typical when funds fracture.

AI labor costs and stock-based compensation will compress venture returns at scale.

Winning AI companies are handing out huge equity grants—sometimes SBC exceeding current revenue—just to hire and retain core engineers; even if headline valuations look great, future dilution and continuous top-ups are likely to erode investor returns versus prior SaaS vintages.

Using expensive equity as currency is rational in capital-intensive, high-multiple environments.

CoreWeave’s purchase of Core Scientific and Weights & Biases is framed as smart balance-sheet optimization—trading richly valued stock for lower fixed costs and more control over critical infrastructure, slightly de-risking if data-center demand doesn’t grow infinitely.

WORDS WORTH SAVING

5 quotes

It will be the biggest issue of 2026 in B2B AI: just the inability to recruit talent.

Jason

The best and the very best only want to work for the very best. They won’t tolerate anything else.

Jason

No one ever said to Winston Churchill, ‘Did you bring World War II in on budget?’ They just said, ‘Did you win World War II?’

Rory

If you think your answer is to go hire a VP of AI that wears a tie and is ‘studying things,’ just shut the startup down.

Jason

If you don’t want to embrace [AI], you are going to make this ship sink… you fire them.

Harry

Meta’s acquisition of Daniel Gross and Nat Friedman and implications for their AI fund and LPsThe AI talent war: compensation, recruiting constraints, and stock-based compensation dynamicsUse of overvalued equity as currency: CoreWeave, Circle, and data-center betsPrivate equity’s role in SaaS rationalization: Thoma Bravo’s acquisition of OloVenture capital deal slowdown, ‘flight to consensus’ in AI, and triple-triple-double-double tradeoffsRetail and institutional access to private equity/venture via Vanguard and endowment tax policyWorkforce transformation: Microsoft sales layoffs, AI-native roles, and internal AI upskilling

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