How Many Startups Will Survive OpenAI? | E2288

Watch on YouTube ↗  |  May 14, 2026 at 00:26  |  1:24:35  |  This Week in Startups
Speakers
Jason Calacanis — Angel Investor / Founder, LAUNCH
Sam Lessin — Slow Ventures

Summary

The episode covers Anthropic and OpenAI's crackdown on unauthorized secondary SPV sales, sparking debate on the future of private market liquidity. Panelists discuss the rise of vibes-based investing, the wealth gap, and the existential threat AI poses to SaaS startups. Jason Calacanis advises selling concentrated AI positions into diversified index funds.

  • Anthropic and OpenAI declared unauthorized SPV sales void, naming brokers and platforms.
  • Panelists debate the impact on secondary markets and potential lawsuits.
  • Discussion on wealth inequality: equity owners thrive while non-owners struggle.
  • Jenny Fielding shares a story of a founder returning $15M Series A due to AI disruption.
  • Jason Calacanis recommends diversifying from concentrated AI stocks into index funds.
  • Sam Lessin argues that AI companies' valuations are disconnected from fundamentals.
  • Dave McClure sees the crackdown as cleaning up bad actors in the SPV space.
  • The conversation touches on the difficulty of pivoting late-stage SaaS companies to AI.
Trade Ideas
Jason Calacanis Angel Investor / Founder, LAUNCH 53:05
Diversify from AI into index funds.
Sell concentrated positions in speculative AI private companies (e.g., OpenAI, Anthropic, SpaceX) and reinvest proceeds into diversified index funds because these AI companies trade at extreme multiples (30-50x revenue) and face risks from open-source competition, declining token prices, and potential commoditization of AI, making their future profitability uncertain.
VTI MED
Jason Calacanis Angel Investor / Founder, LAUNCH 53:05
Diversify from AI into index funds.
Sell concentrated positions in speculative AI private companies (e.g., OpenAI, Anthropic, SpaceX) and reinvest proceeds into diversified index funds because these AI companies trade at extreme multiples (30-50x revenue) and face risks from open-source competition, declining token prices, and potential commoditization of AI, making their future profitability uncertain.
Concentrated AI Private Company Stocks MED
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This This Week in Startups video, published May 14, 2026, features Jason Calacanis discussing VTI, Concentrated AI Private Company Stocks. 2 trade ideas extracted by AI with direction and confidence scoring.

Speakers: Jason Calacanis  · Tickers: VTI, Concentrated AI Private Company Stocks