#122 - AI Drama — Sierra, Brett Taylor, and the Biggest Conflict of Interest in AI

#122 - AI Drama — Sierra, Brett Taylor, and the Biggest Conflict of Interest in AI

From The AI Cookbook Show by Malcolm Werchota by Malcolm Werchota

May 21, 2026 · 28 min · Episode 122

About this episode

The episode discusses the implications of AI on jobs and highlights the conflict of interest involving Brett Taylor and Sierra's significant funding.

Manila: Ivan loses his job to AI. Same day, San Francisco: $950M for Sierra at a $16B valuation, 105x revenue multiple, 40% of every Fortune 50 as customers — and 99% of humanity has never heard of them. CEO Brett Taylor is simultaneously Chairman of OpenAI, ex-co-CEO of Salesforce, and takes money from Google. Inside the Sierra Agent OS + why this matters for your business.

People in this episode

Host: Malcolm Werchota

Topics covered

  • AI
  • business conflict
  • technology impact
  • leadership
  • venture capital

Keywords

  • AI
  • Sierra
  • Brett Taylor
  • OpenAI
  • job loss
  • venture capital
  • Fortune 50

Mentioned in this episode

Organizations: Sierra, OpenAI, Salesforce, Google

Places: Manila, San Francisco

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