For today's essential Heretics 101 feature, we talk to Casey Woo, founder of Operators Guild, and explore the evolution of elite business operators—generalist executives who transcend traditional titles to solve complex problems at high-growth companies, featuring insights on AI disruption, and community building.

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TIMESTAMPS:

(00:00) Intro

(01:15) WeWork Experience: Working with Adam Neumann

(02:52) Key Lessons from WeWork

(04:18) Current Market Climate & AI Impact

(05:21) The AI Revolution in Customer Support

(07:00) AI Management & the "Iron Man" Approach

(07:31) Sponsors: Planful | Metaview

(10:38) The Unstoppable Nature of AI Adoption

(11:31) The Rise of the Operator: Casey's Personal Journey

(14:02) Operators Guild: From 9 to 900 Members

(14:20) The Four Operator Personas

(15:17) Why Titles Have "Screwed Us"

(15:35) The Navy SEALs Analogy

(16:27) Building Successful Communities

(17:55) Do You Ever Miss Operating?

(18:43) The Future Path: From Operator to Founder

(19:10) Breaking the Retirement Mindset

(19:56) Advice for Operators: Have Confidence

(21:28) The Power of Team Building

(22:00) The Next Level: Capital & Founding

(22:31) Wrap

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