From Broke to Billionaire: Stephen Cloobeck's $3.3B Mindset

<p>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.</p>
<p>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.</p>
<p><strong>Stephen Cloobeck</strong> 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.</p>
<p><strong>What We Discuss:</strong> </p>
<ul>
  <li>
<p>02:03 - Stephen's $63 million in philanthropic giving</p>
</li>
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<p>04:02 - Undercover Boss episodes and giving away the most money </p>
</li>
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<p>09:30 - Learning business from Mike Milken instead of business school </p>
</li>
  <li>
<p>12:45 - Harvard Business School case study on his industry disruption </p>
</li>
  <li>
<p>15:20 - Treating employees like family as competitive advantage </p>
</li>
</ul>
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<p><strong>Find more from Jen: </strong></p>
<p>Website: <a href="https://www.jennifercohen.com/"><u>https://www.jennifercohen.com/</u></a></p>
<p>Instagram: <a href="https://www.instagram.com/therealjencohen/"><u>@therealjencohen  </u></a></p>
<p>Books: <a href="https://www.jennifercohen.com/books"><u>https://www.jennifercohen.com/books</u></a></p>
<p>Speaking: <a href="https://www.jennifercohen.com/speaking-engagement"><u>https://www.jennifercohen.com/speaking-engagement</u></a></p>
<p><strong>Find more from Stephen Cloobeck: </strong></p>
<p>Instagram: <a href="https://www.instagram.com/stephenjcloobeck/"><u>@stephenjcloobeck </u></a></p>
<p>Website: <a href="https://stephenjcloobeck.com/"><u>https://stephenjcloobeck.com/</u></a> </p>
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