Podcast Summary: Habits and Hustle

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

Host: Jennifer Cohen
Guest: Stephen Cloobeck
Date: November 7, 2025

Overview

In this milestone 500th episode of Habits and Hustle, host Jennifer Cohen sits down with Stephen Cloobeck, a serial entrepreneur, philanthropist, and founder of Diamond Resorts, which he built into a $3.3B enterprise. The conversation dives into Cloobeck’s journey from nearly broke to billionaire, his core business philosophies, the role of mentorship, his experiences in real estate and hospitality, personal challenges, philanthropic work, and his views on current political and social issues—especially as he prepares to run for governor of California.

Key Discussion Points & Insights

Stephen Cloobeck’s Background and Rise

• Entrepreneurial Roots & Education

  • Cloobeck didn’t attend business school, originally studied to be a surgeon at Cedars Sinai, and ultimately earned a degree in neurobiopsychology from Brandeis ([02:30]–[04:49]).
  • Struggled with undiagnosed dyslexia, forcing him to rely on memorization. Only later, after his son's diagnosis, did he realize he shared the condition.

    “I have no idea how I got through school other than memorizing. Seriously, memorizing everything.” — Stephen ([05:45])

• Early Career Moves

  • Entered shopping center development in Southern California, learning accounting basics at Cal State Northridge and business law at UCLA ([08:14]).
  • Started own company at 24 after a bonus was withheld; his first real estate project was a shopping center on Victory and Magnolia in Burbank ([08:37]).
  • A rough patch in the late ’80s almost bankrupted him but taught him construction skills and resilience ([09:07]).

Building Diamond Resorts

• Transitioned from shopping centers to hotels after overcoming challenges with development projects ([09:27]).
• Acquisition and Expansion:
  • Purchased a failed public company (Sentara), took it private despite not knowing the public company world, and renamed it Diamond Resorts ([11:28]).
  • Grew to 432 properties in 35 countries, with 5 million guests annually ([11:24], [18:00]).
  • Relied heavily on mentorship and learning from others.

    "You cannot succeed without mentors. And that's why I pay it forward now." — Stephen ([12:09])

Essential Habits and Skills for Success

• Work Ethic:

  • “Get up early, stay late, go to work with a runny nose. And when they tell you can't do it, believe in yourself that you can.” — Stephen ([10:40])

• Integrity and Brand:

  • “Integrity is. Don't bust the trust with yourself or with others.” ([10:55])
  • Importance of being truthful, both to oneself and to others.
  • The need to recognize yourself as a brand—consistency, accountability, and collaboration build unbreakable teams ([13:00]–[13:57]).

• Numbers and Cash Flow:

  • “Always know your numbers. Always know your deal.” — Stephen ([12:21])
  • Every bank was always repaid—even during tough times—thanks to clear, immediate, honest communication.

Philanthropy and Giving

• Cloobeck has donated over $63 million to various causes ([01:28]). He approaches philanthropy without a fixed goal, simply wanting to be as generous as possible.

Undercover Boss and Authenticity

• Appeared on many episodes of “Undercover Boss”; notes his significant, unscripted giving on the show ([03:18]).
• Attributes his reputation as a disruptor and giver to authenticity and a drive to “pay it forward.”

Family and Personal Challenges

• Discusses complicated family relationships, including legal and financial conflicts with siblings, prompting him to buy out their shares and sever ties for peace ([17:00]–[17:48]).

Wealth and Lifestyle

• Notes his lifestyle didn't drastically change after becoming a billionaire—besides building a dream home in Beverly Hills designed for large charity and political events ([18:14]).
• Security has always been a necessity due to the nature of his high-profile work ([18:59]).

Mentorship and Giving Back

• Cloobeck mentors dozens of young adults, actively helping them through business challenges ([12:14]).
• Stresses mentorship was essential to his own success and is now part of his legacy.

Political and Social Commentary

Running for Governor of California

• Cloobeck is running for governor after not finding any candidate he’d “trust with my family’s life safety” ([03:33]).
• Ran U.S. tourism under Obama as the creator of Brand USA, and has experience influencing business legislation and policy ([03:44]–[04:13]).

Critique of California Leadership and Policies

• Unaffordability & Homelessness:
  • Sharp criticism of living costs, business-hostile environment, and rise in crime and homelessness:

    “The homelessness is unbelievable… Like I'm living in a nice area, and there's literally homeless people on my street.” — Jen ([22:30])

• Failure of current and past leaders to provide value for taxes or account for spending on issues like wildfires and homelessness ([21:04], [24:04]).
• Advocates eliminating burdensome regulations, reforming HR and employment laws, and relaxing housing restrictions to restore affordability ([24:51]).
• Suggests creating a California Department of Performance and Results (CPR) ([27:02]).

On Political Centrism and Wokeness

• Identifies as a centrist “Reagan Democrat,” and calls out the extremes on both political sides ([19:34]), noting 68% want the “hard center” but lack a clear voice ([19:59]).

• Critiques "wokeness" as weakness and a distraction from problems like affordability and safety:

  “The wokeness is weakness… Woke doesn't pay the bills.” — Stephen ([20:16], [29:56])

• On running for office: Being true, authentic, experienced, and results-driven distinguishes him from political opportunists ([26:36], [27:02]).

Reflections on Other Leaders

• Candid opinions on names like Caruso, Kamala Harris, Trump, and Biden—calls out perceived lack of authenticity, business experience, and public service mentality ([25:38]–[28:46]).

Memorable Quotes & Moments

| Timestamp | Quote | Speaker | |-----------|-------|---------| | 05:45 | "I have no idea how I got through school other than memorizing. Seriously, memorizing everything." | Stephen Cloobeck | | 10:40 | "Get up early, stay late, go to work with a runny nose. And when they tell you can't do it, believe in yourself that you can." | Stephen Cloobeck | | 10:55 | "Integrity... Don't bust the trust with yourself or with others." | Stephen Cloobeck | | 12:09 | "You cannot succeed without mentors. And that's why I pay it forward now." | Stephen Cloobeck | | 13:00 | "Because you are your brand, right? And it takes decades to build a brand." | Stephen Cloobeck | | 18:08 | "You get to give more money away." (on the difference between millionaire and billionaire) | Stephen Cloobeck | | 19:57 | "68% of us want the hard center. We just don’t have voice." | Stephen Cloobeck | | 22:30 | "The homelessness is unbelievable… I’m living in a nice area, and there's literally homeless people on my street. This is a big problem." | Jen Cohen | | 24:04 | "Go find our money. It's our money." | Stephen Cloobeck | | 27:02 | "California Department of Performance and Results. CPR, which we need." | Stephen Cloobeck | | 29:56 | "Enough. Enough. No. Enough. It's weak. No breast balls. WOKE doesn't pay the bills." | Stephen Cloobeck |

Key Timestamps

• Early life, dyslexia, education: [02:30]–[06:34]
• Advice on entrepreneurship and hustle: [08:14]–[10:47]
• Integrity, brand, and mentorship: [10:55]–[13:57]
• Philanthropy and business milestones: [01:28], [11:28], [18:08]
• Family/business conflict stories: [17:00]–[17:48]
• Wealth, lifestyle, security: [18:14]–[19:15]
• Political run and commentary: [03:33], [19:34]–[30:35]

Tone and Style

Conversation is candid, direct, and at times irreverent, reflecting both Cloobeck's unapologetically authentic style and Cohen’s forthright curiosity. The dynamic is insightful, supportive, sometimes humorous, and always actionable—delivering both practical business lessons and a sharp critique of current affairs.

Conclusion

This episode offers a raw, practical, and deeply personal look at what it takes to build lasting success—from grit and integrity to lifelong learning and resilience—while also serving as a passionate call for authentic, accountable leadership in business and politics. Whether you’re a budding entrepreneur, an established professional, or simply seeking inspiration to level up, Cloobeck’s journey from broke to billionaire is packed with actionable advice and hard-earned wisdom.