
#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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