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

20VC: Anthropic vs The Pentagon: Who Wins | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR | Block's 40% Headcount Reduction: AI or Overhiring

March 5, 2026·1 hr 23 min·5 clips

Rory reveals why the state is more powerful than Anthropic in a clash over AI military contracts.

Harry Stebbings hosts Rory O'Driscoll and Jason Lemkin to analyze major tech news, including Anthropic's conflict with the Pentagon over AI military contracts, OpenAI's $110 billion funding round, Block's 40% layoffs, and Cursor's rapid revenue growth. They discuss the power dynamics between tech companies and the state, valuation premiums for AI leaders, and the challenges facing public software companies in the AI era.

As heard by us

A blunt valuation-and-momentum argument about AI, public markets, and the price of scale.

This episode stays on valuations and market consequence, with Rory O'Driscoll and Jason Lemkin tracing a line from Anthropic to OpenAI and SpaceX.

Read the full review in PlayNext →

Why you'd press play

If you want a fast, combative weekly take on AI valuations and tech ruthlessness, start here.

Read the full recommendation in PlayNext →

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