Hospitality entrepreneur Stephen Cloobeck has a new venture: a campaign for California governor.
In an exclusive interview with the Southern California News Group, Cloobeck, an entrepreneur who has worked across the hospitality industry, including in timeshares, said he is concerned by how unaffordable California has become.
Pointing to his background in business, Cloobeck decided, on Tuesday, Nov. 5, to join a fast-growing field of candidates vying to replace Gov. Gavin Newsom, who is term-limited and cannot run for reelection in 2026.
“We need a fresh set of eyes, somebody who understands how to make sure the leaders of this state have each taxpayer’s back, to make sure government’s always off their back and to make sure, most importantly, every taxpayer is treated like a customer so each taxpayer or customer receives equal or greater value to the tax dollars they spent,” Cloobeck said.
“There is no difference between the consumer business and those running a state, but our current leaders have forgotten about that.”
A self-described fiscally conservative, “socially responsible” Democrat, Cloobeck decries what he views as identity politics. California, he said, “needs to move forward to the right because we can’t go any further left.”
For him, that means supporting efforts that he believes would make California more affordable. He wants to see “aspirational dates” for electric vehicles, not mandates that he said, “steal our freedom as Californians.” He has an education political action committee, Save Our Schools PAC, that advocates for every child’s civil right to a quality education. Homeownership plans, he added, should also account for apartment living rather than standalone houses.
“I think public-private partnerships are the secret of success for California’s future,” Cloobeck said.
He’s critical of Newsom, particularly when it comes to crime rates.
“Our current leadership,” Cloobeck said, “does not know how to pivot from mistakes that they’ve made.”
Cloobeck, 63, said he once believed he’d become a doctor, maybe a heart surgeon. But he changed his mind his senior year of college at Brandeis University in Massachusetts, he said, and came back to California after graduation. He took accounting classes at Cal State Northridge and night courses in business at UCLA. He began working for companies in the shopping center development industry and ultimately started his own business.
His father was against him branching out on his own, he said, but a family friend advised, “Let the kid try.”
So he did. Cloobeck built his first shopping center in Burbank. From there, he ventured into the hotel business. His first major development was the Polo Towers in Las Vegas in the early 1990s, according to his website. In 2007, his company, Diamond Resorts, acquired Sunterra Corps., a deal industry analysts described at the time as “one of the largest timeshare industry acquisitions ever.” In 2016, Cloobeck stepped down from Diamond Resorts.
“I’m not a career politician. I’m an activist; I’m a businessman,” Cloobeck said.
“But I know politics and policy because I’ve been trained by the best in politics and finance,” he added. “And I’m always used to crossing aisles.”
Former CEO of Diamond Resorts Stephen Cloobeck appeared in the reality series “Undercover Boss” in this 2011 file photo. Cloobeck) journeys to the frontlines of his luxury resort and time-share company for an unfiltered look inside the inner workings of his corporation. (Photo by CBS ENTERTAINMENT)
Though he hasn’t held elected office, Cloobeck has long been connected to politics. In 2004, he was appointed to serve on Nevada’s Standing Committee on Judicial Ethics and Election Practices. Later, he was chairman of Brand USA, a public-private partnership established under the Obama administration to bolster U.S. tourism around the world. He’s talked in media interviews about golfing with former Democratic presidents and about his connections to politicians, including former House Speaker Nancy Pelosi and Homeland Security Secretary Alejandro Mayorkas.
Cloobeck said his mentor was the late Nevada Sen. Harry Reid, a Democratic leader in the U.S. Senate who died in 2021. Cloobeck was part of the push to rename Las Vegas’ airport after Reid, who he has called a “second dad.”
Cloobeck also is close with Rep. Lou Correa, D-Santa Ana, who called the hotel tycoon “a very close friend.”
“He’s an interesting individual,” Correa said. “The guy is smart. He really knows how to get things done. The only question is how does he get that message to the voters.”
Correa compared Cloobeck to former Gov. Arnold Schwarzenegger. Both were successful outside of politics, Correa said. Both men, too, were bodybuilders.
A Cloobeck campaign was seemingly always in the cards.
The question was whether he would run in California or Nevada.
Cloobeck grew up in Encino, spending his summers in Simi Valley, Sanger and Willits, his biography says. He’s had offices in Orange County and resides now in Los Angeles County.
But he was, as recently as a couple of years ago, living in Nevada, where he served as chairman of the state’s Athletic Commission. He stepped down from that position in late 2022, saying he could not work with Joe Lombardo, a Republican who was set to take over as the state’s governor, the Las Vegas Review-Journal reported at the time.
There were rumors, at one time, that he might run for governor in Nevada.
Cloobeck finished his LA home in 2020, he said, but was living in a hotel while it was being built.
“That’s how great California is,” said Cloobeck, noting that Nevada has no state income tax. In California, on the other hand, residents pay tax rates based on their filing status and income.
“I did not intend to move back here, and get involved like this,” he continued, referencing his new political journey.
“But since I’ve been so involved, and found no one else that had the attributes of fixing broken business, having legislated, changing laws in numerous states, I’ve been a regulator and I’ve been an adjudicator.”
“That’s kind of ‘unicorn-ish,’ to have all those attributes and be successful at those things,” he said.
Cloobeck is a man full of maxims, delivering each with earnestness.
“We’re at the end of a cul-de-sac. Time to turn around and move forward.”
“I’m law and order. In my book, it’s the eighth commandment. We don’t steal. ‘Thou shalt not steal.’
“It’s not $950; it’s zero,” he added, referencing California’s Prop 47, which increased the dollar amount for which property thefts would be treated as a felony.
“I just don’t have opinions; I have solutions — because I’ve done it.”
Cloobeck said he’s also detail-oriented and intentional about his political philosophy and the work he’s already done. And he’s an avid cook and entertainer, boasting about his recipes for osso buco, spicy pasta and fried chicken. He plays pickleball and has appeared on “Undercover Boss,” a reality show that placed executives in low-level jobs in their own companies to interact with their employees.
Cloobeck said he values honesty and, if elected as governor, would be candid with voters.
But he also places a premium on tangible results.
“It’s time to govern with respect, responsibility and results that are meaningful and measurable.”
One way he believes he could measure his success as governor is population. He wants to see the state grow an additional 5 million people, to 44 million. The state Dept. of Finance currently estimates California’s population — which has fallen intermittently in recent years — will peak at about 40.2 million in 2044 and begin to decline after that.
“That’s success. That means we’re bringing people back to our state,” Cloobeck said.
He’s a longtime Democratic donor, listing both California and Nevada as his residence over the last two years. He’s donated to Rep. Adam Schiff’s U.S. Senate campaign as well as to Reps. Katie Porter and Barbara Lee when they, too, were vying for California’s open Senate seat.
Other candidates running for governor in 2026 include state Sen. Toni Atkins, Lt. Gov. Eleni Kounalakis, State Superintendent of Public Instruction Tony Thurmond, former LA Mayor Antonio Villaraigosa and former state Controller Betty Yee. All are Democrats.