How Stephen Cloobeck Sold His Company for $3.3 Billion

Stephen Cloobeck didn’t just build a company — he built a hospitality empire from scratch, sold it to Hilton for billions, then pivoted to public service, now aiming for the governor’s seat in California. His journey, which began with real estate and led to 35 countries, offers a masterclass in brand, leadership, and guts.

Let’s unpack how Stephen went from losing his first shopping center to becoming a billionaire — and why his next mission is transforming the fifth-largest economy in the world.

From $20M in the Red to $3.3 Billion in the Bank

At one point in his hospitality career, Stephen was $20 million in debt. But instead of folding, he built a brand so iconic that Hilton Hotels acquired his company for a staggering $3.3 billion.

First hotel? Polo Towers in Las Vegas, at age 29.
Never built a hotel before? Correct. He learned by doing, fighting through setbacks like bankrupt contractors, missed permits, and budget overruns.
Trademark fight with Ralph Lauren? Yep. Ralph sued him over the name Polo Towers — Stephen won.

This wasn’t just real estate — Stephen saw hospitality as theater. Every detail was meticulously crafted, down to how towels were folded and cards were placed under the bed saying, “Yes, we clean here too.”

What Stephen Offers: The Billionaire Blueprint

Stephen’s rise wasn’t about flashy tech startups or crypto plays — it was old-school, customer-first business. Here’s the billion-dollar playbook he used:

Customer Obsession: He built hotels from a guest’s perspective, not a developer’s.
Brand is Sacred: Integrity is everything — lie once, you’re done.
Mentorship Matters: Stephen credits his success to surrounding himself with great minds and mentors.
Extreme Involvement: He could code his company’s back-end systems, clean rooms, and talk strategy at the boardroom table. No job was beneath him.

Recession, 9/11, and the Power of Transparency

During 9/11, Stephen had to face the unimaginable: hotels with zero guests. No flights. No revenue.

But rather than panic, he called his banks — every single day.

He was so consistent that banks eventually asked him to check in every three days instead. His radical transparency paid off. They stuck with him, even when others didn’t. He later paid them back — early.

“Don’t negotiate with your banks. Be honest. Give your investors a return and they’ll fund you again and again.”

The Secret to Brand Longevity? Respect.

Stephen doesn’t do ego. He doesn’t do spin. He does results.

He once fired his number one salesperson because they lied to a customer, even when everyone told him not to. That decision? The company grew 20% right after.

“You build a brand over decades. You can kill it in a minute. Don’t ever mess with the brand.”

Competing With Giants — and Winning

Stephen studied the best: Ritz-Carlton, Four Seasons, Marriott. But where they became too corporate, too rigid — he stayed nimble.

He wrote the front desk script himself.
He shadowed every department.
He even helped create software for his operations.

His style? Combine a battleship’s scale with a speedboat’s agility.

The ultimate compliment came when Marriott copied his investor deck.

“I told my CFO, that’s not a problem — that’s the greatest trophy I’ve ever gotten.”

Iron Man and Wolverine: The Personal Brand

Stephen’s story isn’t just about boardrooms. He literally survived being hit by a car at 40 mph — walked away from it, 40 stitches later, earning the nickname Iron Man. Why? Because he landed on his feet, bleeding, and told onlookers, “I’m good.”

He now preaches the power of staying present. Past? Depression. Future? Anxiety. Present? Peace, opportunity, clarity.

And for someone who helped build Brand USA (yes, he led the country’s tourism campaign), he knows personal branding better than most.

“You are your brand. Who do you want to become?”

Also Read – How a 17-Year-Old South African Became a Meme Coin Millionaire – And Now Advises Billion-Dollar Hedge Funds

From Boardroom to Ballot: Running for Governor

After selling his company, Stephen could’ve disappeared into a life of luxury. Instead, he’s running for governor of California.

Why?

Because he believes California — once the gold standard — is now “closed for business.” Regulations are crushing growth. Leadership is absent. Customers (aka citizens) are ignored.

“I’ve fixed the most broken businesses. California is broken. I’m going to fix it.”

He’s met with over 300 people across the state and says it boils down to one core issue:

California is no longer affordable, livable, or workable.

His campaign is built on three things:
Respect. Responsibility. Results.

Final Thoughts: The Real Billionaire Mindset

Stephen Cloobeck didn’t just build hotels. He built a culture.

He wasn’t afraid to learn from scratch, lead from the trenches, and hold his team — and himself — to sky-high standards.

He shows that success isn’t just about numbers. It’s about:

Grit during chaos
Candor with partners
Unshakable integrity
And a service-first mindset

“Leadership isn’t about pleasing everyone. It’s about doing what’s right — even when it’s hard.”

Want Mentorship From Billionaires Like Stephen?

The host of this interview, who’s met with over 15 billionaires and 1,000+ millionaires, built a community called The School of Mentors — a weekly mastermind with elite founders, including Stephen himself.

If you want to learn from the best — not theory, but actual battle-tested entrepreneurs — that’s where you start.

👉 Join School of Mentors – Where Billionaires Teach Business