What do Republicans and a billionaire Democratic candidate for California governor have in common?

They want to slash regulations to make the state more affordable.

Stephen J. Cloobeck, a one-time timeshare mogul, is one of multiple Democrats seeking to replace termed-out Gov. Gavin Newsom in 2026.

“California is not a affordable, livable nor workable,” Cloobeck said in an interview with The Bee – a campaign slogan he is also seeking to trademark. “We need hard, actual results.”

A longtime donor to Democratic causes and candidates, Cloobeck first earned his fortune developing shopping centers in Southern California and the Central Valley. He built the Polo Towers on the Las Vegas Strip before founding timeshare company Diamond Resorts, which he sold in 2016 for $2.2 billion.

The state is “regulated out,” he argued, pointing to laws such as the California Environmental Quality Act, and insurance and labor regulations like AB 5, which requires companies to offer health care and other benefits to contract workers.

A “loyal Democrat” mentored by the late Sen. Harry Reid, Cloobeck’s deregulation platform echoes talking points by Republicans, who have long blamed a maze of red tape for hampering everything from small business to wildfire mitigation projects and new housing production in a state that sorely needs it.

The average cost of housing, utilities and food has grown in California in recent years. In a recent PPIC survey, affordability, the economy and jobs topped the list of most pressing problems in the state.

Democrats’ affordability crisis

Democrats in the Legislature are pledging to tackle the state’s affordability crisis but so far have released few specifics.

“I think it’s good if Democrats start actually focusing on cost of living and actually doing things to lower people’s costs. That’s what we’ve been fighting for for years,” said Assembly Republican Leader James Gallagher. “I certainly welcome that conversation, but it needs to be followed up with actions.”

After running a business that dealt with regulations in real estate, banking, gaming and insurance, Cloobeck said he’s not opposed to most rules.

“Good regulation is just there to keep bad actors out,” he said. But “we’ve made it so regulated, it’s difficult to operate here in any business.”

Even Newsom has made moves to circumvent CEQA for major infrastructure projects and to expedite rebuilding homes after the Los Angeles fires. Cloobeck wants to go even further.

“If we can abandon CEQA – put a pin in it for the fires – why don’t we just put a pin in CEQA right now for affordability in the state of California,” he said.

The 67-year-old businessman grew up in Encino and spent years running his company from Las Vegas before returning to Southern California in 2019.

He twice donned disguises for the CBS show “Undercover Boss,” to investigate the underpinnings of Diamond properties. In one episode, he paid off the mortgage of a maintenance employee who was working two jobs.

“He represents a more populist, anti-establishment voice that is emergent in both parties,”said Mike Madrid, a Republican consultant advising Cloobeck.

“If we’re serious about making progress and making this a livable, affordable place where there’s genuine opportunity for people, it’s going to have to come from somebody like Stephen,” he said.

Pitfalls for billionaire candidates

In the past, ultra-wealthy candidates have had little success seeking statewide office in the Golden State.

Republican Meg Whitman pumped $144 million of her own money into her 2010 campaign for governor, which she lost to returning Democrat Jerry Brown. The same year, former Hewlett Packard CEO Carly Fiorina also funded her failed U.S. Senate bid. And over a decade before, Al Checchi spent $40 million, only to lose to Gray Davis in the Democratic primary.

Coobeck put $3 million into his own campaign last year, according to financial disclosures.

“California Democratic voters have never had an appetite for unknown millionaires without any government experience to be their gubernatorial nominee,” said Steve Maviglio, a Democratic political strategist. “I don’t see that changing, especially with the backlash against Elon Musk and Silicon Valley oligarchs attempting to run the country.”

“That said, a candidate that focuses on the economy and affordability who has tens of millions to put himself in front of voters might be able to find a lane in a field crowded with progressives,” he said.

Other candidates for governor include Lt. Gov. Eleni Kounalakis, former Los Angeles Mayor Antonio Villaraigosa, former Senate pro Tem Toni Atkins, former Controller Betty Yee, state schools chief Tony Thurmond – all Democrats – and the Republican sheriff of Riverside County, Chad Bianco.

Former Vice President Kamala Harris, former Democratic Rep. Katie Porter, and former U.S. Health and Human Services Secretary Xavier Becerra are also considering bids for the state’s highest office.

Cloobeck said he decided to run for governor after he met with several declared candidates for the post and realized “they don’t have solutions. They talk in word salad.”

He accused Democrats leading California’s state government of no longer listening to their “customers” – the residents and businesses that create jobs and generate tax revenue. He described Newsom as a “red carpet” politician who “has lost his way.”

“He’s forgotten about how to execute the fundamentals, how to be accountable and how to enforce,” Cloobeck said, pointing to $20 billion in unemployment insurance debt and $24 billion in homelessness funding that, according to a 2024 audit, was not clearly tracked for cost-effectiveness.

“We shouldn’t have to do audits” to figure out where taxpayer money was spent and whether it was effective, he said. “Our leaders should know our numbers.”