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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