Habits and Hustle

Episode 500: From Broke to Billionaire: Stephen Cloobeck’s $3.3B Mindset

07 Nov 2025

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Description

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 Thank you to our sponsors: Therasage: Head over to therasage.com and use code Be Bold for 15% off Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. Momentous: Shop this link and use code Jen for 20% off Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift. Amp fits is the perfect balance of tech and training, designed for people who do it all and still want to feel strong doing it. Check it out at joinamp.com/jen 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/

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Episode 500: From Broke to Billionaire: Stephen Cloobeck’s $3.3B Mindset

This episode hasn't been transcribed yet

Other episodes from Habits and Hustle

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