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

2026-03-05 · 83 min · 10 entities

episode page audio

Asserted relationships

→ hosted by Harry Stebbings person

0.55

evidence rules-v4
Feed author/publisher: Harry Stebbings
→ discusses Business concept

0.40

evidence rules-v4
Feed category: Business
→ discusses Investing concept

0.40

evidence rules-v4
Feed category: Investing
→ discusses News concept

0.40

evidence rules-v4
Feed category: News
→ discusses Tech News concept

0.40

evidence rules-v4
Feed category: Tech News

Entities found in this episode

concepts 8

mentioned Business concept

0.50

evidence rules-v4
Feed category: Business
mentioned Investing concept

0.50

evidence rules-v4
Feed category: Investing
mentioned Tech News concept

0.50

evidence rules-v4
Feed category: Tech News
discusses Business concept

0.40

evidence rules-v4
Feed category: Business
discusses Investing concept

0.40

evidence rules-v4
Feed category: Investing
discusses News concept

0.40

evidence rules-v4
Feed category: News
discusses Tech News concept

0.40

evidence rules-v4
Feed category: Tech News
mentioned ARR concept

0.35

evidence rules-v4
ARR

persons 2

mentioned Harry Stebbings person

0.70

evidence rules-v4
Feed author/publisher: Harry Stebbings
hosted by Harry Stebbings person

0.55

evidence rules-v4
Feed author/publisher: Harry Stebbings

Episode description as stored

AGENDA: 04:13 Anthropic vs The Pentagon: Who Wins 13:54 Was Sam Altman Wrong to Take the Deal 24:28 OpenAI's $110BN Mega Round: The Breakdown 28:22 Who Has a Bigger Valuation Premium: Sam Altman or Elon Musk 34:38 Why We Got the SaaS Apocalypse Wrong? 43:24 Why Salesforce Could be the Best Buy in Public Markets 47:46 Block Lays Off 40% of Team: AI or Overhiring 01:00:16 Cursor Hits $2BN in ARR… so not Dead? 01:18:15 How to Pick Winners in AI?