Stephen Cloobeck didn’t climb the ladder. He built his own. In this episode, we talk about what it really takes to grow a billion-dollar company without a business degree: and why integrity, discipline, and grit beat credentials every time.

We get into his biggest pivots, how mentorship shaped his success, and why EQ always outperforms IQ in business and life. Stephen also opens up about giving away over $63 million, calling out “wokeness as weakness,” and what real leadership looks like when you’re under pressure.

Stephen Cloobeck is the founder and former CEO of Diamond Resorts, which sold for $3.3 billion enterprise value. He’s been on Undercover Boss more than anyone, donated millions, and still believes character is the ultimate ROI.

What We Discuss: 

02:03 - Stephen's $63 million in philanthropic giving

04:02 - Undercover Boss episodes and giving away the most money 

09:30 - Learning business from Mike Milken instead of business school 

12:45 - Harvard Business School case study on his industry disruption 

15:20 - Treating employees like family as competitive advantage 

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Find more from Jen: 

Website: https://www.jennifercohen.com/

Instagram: @therealjencohen  

Books: https://www.jennifercohen.com/books

Speaking: https://www.jennifercohen.com/speaking-engagement

Find more from Stephen Cloobeck: 

Instagram: @stephenjcloobeck 

Website: https://stephenjcloobeck.com/