Habits and Hustle Episode 500: From Broke to Billionaire: Stephen Cloobeck’s $3.3B Mindset
Nov 7, 2025
Stephen Cloobeck, founder and former CEO of Diamond Resorts, shares his journey from financial struggles to selling his company for $3.3 billion. He emphasizes the value of mentorship over traditional education and reveals his $63 million philanthropic efforts. Cloobeck discusses priorities in business, like treating employees as family and focusing on customer experiences. He also shares insights on leadership challenges and his political motivations, calling for accountability and civic engagement.
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Crisis Forced Him To Learn Construction
- Cloobeck nearly went broke when subcontractors, contractor, and tenants failed during a late-80s project.
- He learned to build and complete projects himself, which enabled him to develop his first hotel at 29.
Relentless Work Ethic
- Get up early, work late, and show up even when you feel unwell to build momentum and resilience.
- Believe in yourself when others say you can't and keep pushing through setbacks.
Integrity As A Competitive Edge
- Prioritize integrity: don't break trust with yourself or others and remove people who lie to you.
- Be honest immediately with partners and lenders to preserve relationships and credibility.
