Billion-Dollar Leadership and a Vision for California with Stephen Cloobeck

Today on the Servant Leadership Podcast, we’re joined by Stephen Cloobeck — a dynamic entrepreneur, investor, and leader best known for founding Diamond Resorts and appearing on Undercover Boss. From studying neuroscience and psychology to building one of the largest hospitality brands in the world, Stephen has always looked for ways to solve problems, build strong teams, and lead with both compassion and conviction.

Now he’s bringing that same mindset to his run for Governor of California. In this episode, you’ll hear stories about leadership, risk, public service, and what it looks like to create real value in every room you walk into — whether it’s a boardroom, resort lobby, or the state capitol. Join us for an inspiring and energizing conversation that’ll challenge how you think about leadership, service, and impact.

Timestamps:

00:00 Stephen Cloobeck's Intro

00:44 Welcome Stephen Cloobeck

00:54 Diamond Resorts Background/Journey

02:11 A Life Of "Full Circles"

02:29 Importance Of Mentors and Serving

04:05 Instilling A Service Mentality

07:39 Undercover Boss Experience

09:20 Approach After Diamond Resorts

12:01 Living My Dream In California

13:11 Decision To Run For Governor

15:35 Why Haven't Others Succeeded?

17:28 Talk versus Action - Hope Feels Real

19:37 What Is Exciting About Government?

21:31 Facing Challenges

23:39 Some Simple Truths

24:18 New Book: Facing Hard Truths

27:15 Helping Others To Feel Leadership Confidence

29:56 The Concept Of Listening

31:04 Ten Rapid-Fire Questions

32:38 Why Is Servant Leadership Important?

33:22 Closing

Want to learn more about Stephen? Check out the links:

https://stephenjcloobeck.com/

https://californiagetacloo.com/

https://stephenjcloobeck.com/facing-hard-truths/

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