Life After CEO: Missing Work but Enjoying New Freedoms

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Richard D. Fain led Royal Caribbean Group as CEO from 1988, growing it from a $550 million company into a $90 billion cruise industry giant. A Berkeley and Wharton grad, he's known for pioneering revolutionary ship designs and sustainability initiatives that changed how the world cruises. His culture-driven leadership style built one of the most innovative and successful companies in global travel. He now serves as Chairman of the Board.

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➡️ Talking Points

00:00 – Intro

01:28 – Why Richard Fain Can’t Retire

02:44 – 33 Years as a Cruise Industry CEO

04:55 – The Death of Long-Term Thinking

06:36 – The Inflection Point That Changed Everything

08:18 – Building Culture with Intention

12:35 – Leading Under Pressure Without Losing Culture

15:32 – Vision vs. Intentionality: What’s the Difference?

18:17 – Hiring the Right People for the Mission

21:09 – Alignment Over Consensus

23:46 – Sponsor Break

28:21 – Killing Ego While Leading with Purpose

30:17 – Driving Results Without Burning Out Your Team

35:47 – The CEO’s Decision-Making Framework

38:11 – How to Create True Innovation

42:52 – Inside Royal Caribbean’s ‘Culture of WOW’

46:28 – Sponsor Break

49:21 – Getting Your People to Go the Extra Mile

52:59 – Turning Products into Culture Statements

1:01:35 – Fear Makes People Stupid

1:06:04 – How to Pass the Torch the Right Way

1:12:16 – Lessons from Richard Fain’s Book

1:13:31 – The Most Important Lesson for His Kids