Habits and Hustle

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

November 7, 2025

Key Takeaways Copied to clipboard!

  • Integrity is the single most essential quality for an entrepreneur, defined as never breaking trust with oneself or others, and surrounding oneself only with truthful people. 
  • Dyslexia, while challenging in traditional schooling, can be a gift that enables multi-dimensional, out-of-the-box thinking essential for business success. 
  • Mentorship is crucial for success, as demonstrated by Stephen Cloobeck learning business from figures like Mike Milken and political strategy from mentors like Harry Reid and Bill Clinton. 

Segments

Sponsor Read and Guest Introduction
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(00:00:01)
  • Key Takeaway: Therasage Tri-Light panel is highlighted as a portable red light therapy tool for healing, inflammation reduction, and anti-aging benefits.
  • Summary: The sponsor, Therasage, is promoted for its portable red light panel used for reducing inflammation and pain in various body parts. The device also offers anti-aging benefits, including reducing fine lines and wrinkles. Listeners can receive 15% off site-wide using the code BOLD.
Cloobeck’s Success and Philanthropy
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(00:01:31)
  • Key Takeaway: Stephen Cloobeck sold his company for a $3.3 billion enterprise value, netting $2.2 billion, and has given away nearly $63 million philanthropically.
  • Summary: Stephen Cloobeck is introduced as the founder of Diamond Resorts, which sold for $3.3 billion enterprise value. He is noted for being exceptionally philanthropic, having given away close to $63 million. His success in business disruption is emphasized as a key reason for his appearance on Habits and Hustle.
Early Life and Education Detour
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(00:03:18)
  • Key Takeaway: Cloobeck initially pursued medicine, working at Cedars Sinai, before pivoting to business after learning from mentors like Mike Milken.
  • Summary: Cloobeck revealed he was originally studying to be a surgeon and worked at Cedars Sinai, holding a degree in heart science. He later attended Brandeis University, earning a degree in neurobiopsychology, but struggled academically due to undiagnosed dyslexia. He credits meeting Mike Milken at age 13 as a formative business education.
Political Ambitions and Experience
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(00:04:07)
  • Key Takeaway: Cloobeck is running for California Governor due to dissatisfaction with current leadership, citing experience running Brand USA and changing business laws in multiple states.
  • Summary: Cloobeck confirmed he is running for Governor of California after interviewing all candidates and finding none trustworthy for safety and policy. He highlights his vast experience, including running Brand USA under President Obama and operating in 35 countries. He grew up in the Valley but left California before returning to address its current state.
Dyslexia and Thinking Style
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(00:06:41)
  • Key Takeaway: Being dyslexic allows Cloobeck to think multi-dimensionally, handling complex scenarios like playing ten games of chess seven levels deep simultaneously.
  • Summary: Cloobeck realized he was dyslexic only when his adult son was diagnosed, noting that the condition prevents linear thinking (A, B, C, D). This cognitive difference allows him to handle multi-dimensional thinking, which he views as a gift to be embraced, not a crutch.
Entrepreneurial Hustle and Risk
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(00:08:12)
  • Key Takeaway: Successful entrepreneurship requires taking significant risks and maintaining the fight even after being beaten down multiple times in one’s career.
  • Summary: The host and guest agree on the necessity of hustle and taking risks, though Cloobeck notes that risk does not always pay off. He emphasizes that when chips were down, he simply kept fighting to overcome setbacks. This resilience is a core component of his success story.
Early Career in Real Estate
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(00:08:50)
  • Key Takeaway: Cloobeck started in shopping center development at age 24 after an employer failed to pay a promised bonus, learning construction by necessity after subcontractors went broke.
  • Summary: Cloobeck began his career in shopping center development after taking accounting and business law courses at Cal State Northridge and UCLA. He started his own company when he was 24, building small centers by buying properties like a Chevron station and developing them. A major project failure in the late 80s forced him to build the project himself, which taught him crucial construction skills.
Transition to Hospitality Empire
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(00:10:12)
  • Key Takeaway: The success of a large Las Vegas shopping plaza, Polo Towers, directly led to Cloobeck building his first hotel, marking his pivot into the hospitality sector.
  • Summary: After weathering a near-bankruptcy in real estate, Cloobeck built a successful shopping plaza in Las Vegas called Polo Plaza, which was followed by the Polo Towers. He financed early projects through savings and loans, requiring him to sign personally and assume bankruptcy risk on every deal. This experience paved the way for his entry into hotel development.
Core Entrepreneurial Skill and Integrity
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(00:11:16)
  • Key Takeaway: The number one essential quality for an entrepreneur is integrity, which involves being truthful with oneself and others and avoiding those who do not tell the truth.
  • Summary: When asked for the number one skill for success, Cloobeck stated unequivocally that it is integrity. Integrity means not busting trust with yourself or others, and actively removing dishonest people from your circle. He also advises entrepreneurs never to read their own press clippings and to keep their heads down.
Building Diamond Resorts
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(00:12:03)
  • Key Takeaway: Cloobeck grew his company to 432 resorts across 35 countries, acquiring a failed public company and navigating complex SEC and Wall Street requirements without formal business training.
  • Summary: The company that became Diamond Resorts was originally a failed public company named Sunera, which Cloobeck took private by securing over 90% stockholder approval. He learned public company finance and SEC compliance through listening to mentors like Mike Milken, as he had no formal training in that area. He emphasizes that mentors are indispensable for success.
Mentorship and Financial Discipline
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(00:12:48)
  • Key Takeaway: Successful leaders must know their deal backwards and forwards better than lenders, and Cloobeck maintained perfect repayment history by always telling banks the truth immediately.
  • Summary: Cloobeck mentors dozens of young adults, teaching them fundamental concepts like cash flow and the necessity of knowing one’s numbers. He stresses that an entrepreneur must know their deal better than any lender or partner. His banks were always paid back, even during difficult times, because he immediately disclosed issues, leading banks to tell him to stop calling with updates.
Brand Value and Team Building
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(00:13:40)
  • Key Takeaway: An individual’s brand is built over decades and must remain true to itself, requiring non-vitriolic communication and collaboration to create an unbreakable team.
  • Summary: Integrity is key because the entrepreneur is their brand, which takes decades to build and must not be compromised or pandered to. Effective collaboration requires explaining one’s position without demanding it, thereby gaining trust. This process creates an unbreakable team, referencing the biblical concept that three sticks tied together are unbreakable.
Sponsor Read: Prolon
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(00:14:46)
  • Key Takeaway: The Prolon five-day fasting-mimicking diet, developed at USC’s Longevity Institute, triggers cellular repair, offers fat-focused weight loss, and improves metabolic health.
  • Summary: Prolon is presented as a science-backed, patented plant-based program that nourishes the body while inducing a fasting state for cellular rejuvenation. Benefits include fat-focused weight loss, improved skin, and reduced biological age in just five days without extreme willpower battles. Listeners can get 30% off plus a $40 bonus gift using the code JENNIFERCOHEN at their website.
Value Delivery and Sales Philosophy
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(00:16:33)
  • Key Takeaway: The core business value, taught by Cloobeck’s father (a ‘Glengarry Glen Ross’ type salesman), is to always deliver equal or greater value to the customer.
  • Summary: Cloobeck emphasizes the concept of delivering equal or greater value to the customer, a principle learned from his father, who was a dynamic salesman. He applies this concept to politics, stating citizens are customers who should receive value for their tax dollars. His father, despite attending finance school, was primarily a ‘cash guy’ who didn’t fully grasp GAAP.
Family Conflict and Financial Separation
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(00:17:41)
  • Key Takeaway: Cloobeck bought out his brother and sister’s interest in the company two decades ago after they sued him and his wife over money, choosing to pay them off to eliminate conflict.
  • Summary: Cloobeck confirmed he has a brother and sister, both younger, with whom he no longer speaks due to a lawsuit over money decades ago. He bought out their interest in the company to make the difficult situation go away, preferring to avoid conflict even if it meant paying them off.
Millionaire vs. Billionaire Lifestyle
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(00:18:47)
  • Key Takeaway: The primary difference between being a millionaire and a billionaire is the ability to give away more money, as Cloobeck maintained a consistent lifestyle, building his dream Beverly Hills home after the sale.
  • Summary: When asked about the difference between millionaire and billionaire status, Cloobeck stated it is simply the ability to give away more money, as his personal lifestyle did not significantly change. Before 2016, he lived in Las Vegas with homes in Cabo and Laguna Beach. He built his dream house in Beverly Hills after the sale to host events for charity and politics.
Security and Political Threats
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(00:19:36)
  • Key Takeaway: Cloobeck requires security due to death threats related to his Jewish identity and his political stance as a hard-center candidate opposing the polarized extremes.
  • Summary: Cloobeck has security due to death threats, including anti-Semitic ones, stemming from his decision to run for governor. He identifies as a Reagan Democrat in the hard center, which draws opposition from both the hard right and hard left, who seek to demolish him. He believes 68% of the population wants the hard center but lacks a voice.
Critique of Wokeness and California Politics
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(00:20:55)
  • Key Takeaway: Cloobeck asserts that ‘wokeness is weakness’ and that current California leaders have forgotten the customer, leading to unaffordability, safety issues, and a lack of accountability.
  • Summary: Cloobeck strongly states that wokeness is weakness and that leaders lack ‘brass balls’ while forgetting about the customer. He notes that most of his friends have left Los Angeles because the state is no longer affordable, livable, or workable, citing car break-ins and dangerous homelessness. He proposes a bounty system to find missing wildfire and homeless relief money.
Policy Solutions for California
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(00:25:15)
  • Key Takeaway: To fix California, leaders must execute, be accountable, enforce the law, and immediately relax regulations like CEQA and the Coastal Commission to improve affordability.
  • Summary: Cloobeck believes leaders must execute, be accountable, and enforce the law with respect. He proposes relaxing regulations like CEQA and the Wildlife Species Act as an emergency measure to allow for survival and thriving. He criticizes Sacramento for spending excessive time debating minor bills while neglecting energy policy.
Critique of Other Candidates
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(00:26:17)
  • Key Takeaway: Rick Caruso is viewed as a talented builder but not a fixer of broken systems, and his recent shift to the Democratic party on abortion is seen as inauthentic pandering.
  • Summary: Cloobeck suggests that only a Democrat has a viable path to win the governorship in the current political map. He criticizes Rick Caruso for being a Republican who changed his stance on abortion to win votes, calling it inauthentic. Cloobeck believes Caruso is a ‘Palm Beach guy’ who wants to win a beauty contest rather than serve.
Critique of National Figures
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(00:28:14)
  • Key Takeaway: Kamala Harris is criticized for having no IQ or EQ and being trapped in an echo chamber, while Donald Trump is criticized for lacking integrity and failing to serve others.
  • Summary: Cloobeck dismissed Kamala Harris as being insular, trapped in an echo chamber, and failing to understand basic economic issues like the cost of eggs and gas. He noted that his young male friends were moving toward Trump, but Cloobeck himself views Trump as lacking integrity and failing to pay contractors. He considers both major candidates pathetic.