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

Jason Lemkin and Rory O’Driscoll on 20VC dissect why Daniel Gross and Nat Friedman abandoned a 4x fund for Meta, OpenAI’s SBC exceeding revenue, and an AI talent war that will define 2026.

• OpenAI paid $4.4B in stock-based comp last year — 119% of GAAP revenue — and won’t hit the projected 45% ratio this year.
• Daniel Gross and Nat Friedman left NFDG (a $1.1B fund 4x’d in ~2 years) for Meta, effectively surrendering an estimated $800M–$1B in future carry.
• AI talent war will be the defining B2B challenge of 2026: Cursor pays amounts most companies structurally cannot match, forcing rivals to give engineers 0.5–1% equity stakes.
• CoreWeave acquired Core Scientific for $9B, using appreciated public stock to convert fixed datacenter lease costs into equity dilution — described as smart de-risking, not a bet against data center demand.
• Microsoft’s 9,000 layoffs replaced generalist salespeople with solutions engineers; framed internally as a talent-quality upgrade, not an AI-automation story.
• QSBS federal capital-gains exemption raised from $10M to $15M per person in the new US tax bill; stackable via trusts to a theoretical $750M in tax-free gains.
• Olo taken private by Thoma Bravo at $2B (6.5x ARR, ~20% growth) — a ‘meat and potatoes’ deal that does not signal broad PE rescue of struggling SaaS unicorns.
• Carta data shows VC deals at an 8-year low as capital concentrates in AI winners; triple-triple-double-double SaaS growth is no longer sufficient to attract top-tier checks.

2025-07-10 · Watch on YouTube