Michael Ovitz co-founded CAA and helped reshape Hollywood, then took the same playbook into tech investing and advising founders.

In this conversation, he breaks down the operating rules that kept CAA from losing clients, and the personal disciplines that kept him grounded when the stakes got massive.

You’ll learn how to build momentum, tell the truth without hesitation, read for context instead of noise, hire people who raise the standard, and package ideas into outcomes.

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Approximate Timestamps:

(00:00) Introduction

(00:58) Appetite For Learning

(03:41) Always Tell The Truth

(05:50) The Loneliest Professions

(08:17) Where Does Hollywood Go Wrong?

(10:16) Importance of Being Well Read

(16:42) Don’t Fight Your Job

(18:28) Managing Relationships

(19:15) Ad Break

(20:46) Hiring Top Performers

(22:35) Creating Depth in Knowledge

(26:47) Staying Grounded

(30:27) What Do You Look For in People?

(33:28) A Meeting with Marc Andreessen

(36:44) Being Fearless

(42:12) Allow People to Keep Their Dignity

(43:42) You Fail, So What?

(47:48) Advice From Michael Crichton

(49:46) What Drives You Today?

(52:49) What This Generation Really Wants to Learn

(57:51) The Woke Culture Influence

(01:01:30) How Do You Keep Up With the Flow of Information?

(01:11:30) What Makes A Good Leader?

(01:14:13) Business Education Curriculum

(01:16:28) How Do You Gain Momentum?

(01:18:16) How Important is Packaging?

(01:24:43) What Would You Tell Your Younger Self?

(01:26:30) How Important is Trust?

(01:29:15) What is Success For You?

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