Stephen Cloobeck’s earliest California politics memory is when actor Ronald Reagan became governor in 1967. He was five at the time. Almost six decades later, the hospitality industry executive writes in a new book that California needs another big shakeup in Sacramento.
In “Facing Hard Truths: How Americans Can Get Real, Pull Together and Turn Our Country Around,” he introduces himself and his plan for California with seven principles, including: “Life is tough — Get a Helmet,” “The Best Economies Benefit Everyone,” “Leadership Is About Competence, not Celebrity,” “True Success Requires Putting ‘We’ before ‘Me.’”
Cloobeck is a lifelong Democrat best known for being the founder and chairman of Diamond Resorts International (he sold the company to Apollo Global Management for $2.2 billion in 2016). He entered the 2026 governor’s race in November 2024. In the book, he questions the judgement of Democratic Gov. Gavin Newsom as much as he goes after the temperament of President Trump. Cloobeck’s business success often invites comparisons to Trump, which he rejects. “I’ve got values. He doesn’t,” Cloobeck said. “I pay my contractors. He doesn’t. I create value. He destroys value.” As for diversity, equity, and inclusion (DEI) policies, Cloobeck says “Mine are discipline, education and integrity. His are Donald Jr., Eric and Ivanka.”
One of the first noticeable things about Cloobeck’s affect is that he’s a clever speaker. His blue campaign hat shows California’s state bear facing right — a nod to what Cloobeck sees as Sacramento veering too far left. One of his proposals, “California Performance and Results” (or CPR), would publish letter grades for all state programs. He is also intent on having cash bounties for any tips that expose missing funds intended for homelessness, COVID relief and other mismanaged state programs. He thinks that California’s population could grow from 39 to 44 million if something is done to address “rising unemployment, failing schools, increasing retail theft, the nation’s highest poverty rate, a health-care crisis and an enormous budget gap in the tens of billions of dollars.”
“Facing Hard Truths” also includes its moments of vulnerability. He recalls dropping a tray of glasses while working as a busboy as a kid, and being told, “You break it, you pay for it.” His father called him a “lard-ass,” and a college advisor said he’d always be “a crappy writer.” Cloobeck writes about owning up to public mistakes, including one during his tenure as chair of Nevada’s State Athletic Commission.
“I regret allowing slap fighting in the state of Nevada, and knowing what I now know, I would decide differently.”
One of Cloobeck’s most personal pages describes caring for his father through Alzheimer’s disease and the lessons he took from their relationship.
“We do ourselves a disservice when we equate discipline with punishment,” Cloobeck writes. “They are not the same. Discipline is about establishing healthy boundaries and useful expectations. And that’s something our parents, our schools, and our society could do more to instill.”
The late U.S. Senator Harry Reid (D-Nev.) remains Cloobeck’s political lodestar. Reid served in the Senate from 1987 to 2017, including eight years as majority leader. During that time, he led the efforts to pass the Affordable Care Act, Dodd–Frank Financial Reform and the 2009 American Recovery and Reinvestment Act. He had earlier served as a U.S. Representative, Nevada Lieutenant Governor, and chair of the State Gaming Commission. Reid died in 2021.
One of the book’s starkest moments involves Cloobeck’s observation of how the nature of politics has changed.
“Back in 1960, just a sliver of the political ads fielded by presidential candidates, 10%, were negative attacks. Fast-forward to 2012, and the situation was reversed: Only a sliver of ads, 14%, were inspiring and positive. All the fanaticism, outrage, and performativity in politics has rendered our governing institutions increasingly dysfunctional. U.S. Congress, for instance, has become notorious for soap-opera dramas, not progress toward helping the American people. When you have extremist members of the Freedom Caucus appealing to their most extremist followers by killing off useful legislation that members of their own party championed, you’re just not going to get much done. And Congress, in recent years, hasn’t: In 1975, our national legislative body passed 649 laws; by 2023, that number had dwindled to just twenty-seven.”
Ultimately, Cloobeck is positioning himself as someone who won’t take criticism personally, but also isn’t afraid to call out problems when he sees them. For example, he took on former Vice President Kamala Harris in our interview. Cloobeck calls her “tone deaf” and attributes her statewide success to being merely “battlefield-promoted.” Harris is also considering running for governor in 2026.
“She called me on May 24th, 2019, I spoke with many candidates [for the Democratic nomination for president in 2020],” Cloobeck said. “I was a donor, and I told her, ‘you’re not ready for prime time.’ She hung up on me. That was the last time I talked to her.” He doesn’t consider that kind of talk to be the discourse he laments, but rather, another set of hard truths to face.
“We must all show integrity, standing up for what is right even when doing so exposes us to discomfort and risk,” Cloobeck writes in the final pages of his book. “We must all collaborate better across political divides, and open ourselves to difficult but honest conversations in which we hear each other out and work through disagreements. We must all uphold the basic rules, laws and conventions that allow for the healthy, stable society we too often take for granted. We must all fight hard for economic inclusivity, knowing that we do well when our neighbors are also prospering.”
Cloobeck mentions that if he were to win in 2026, he would be California’s second Jewish governor — the first was Washington Bartlett in 1887, who was also the first Jewish governor of any U.S. state. Cloobeck grew up in Encino, had his Bar Mitzvah at Stephen Wise Temple, attended Camp Alonim and earned a degree in psychobiology from Brandeis. In 2024 he trademarked the slogan “Don’t F— with the Jews.” It can be seen on hats throughout Los Angeles’ Jewish community over the past year-and-a-half. It’s also the title of a yet-to-be-released song by his friend, comedian Jeff Ross (Ross performed it at “The Roast of Antisemitism” show filmed at The Saban Theater in June 2023). During Rosh Hashanah in 2024, Cloobeck’s synagogue, The Temple of the Arts, renamed the stage at The Saban after his father, Sheldon H. Cloobeck.
During our interview, he was more than happy to weigh in about the news of the day affecting the Jewish community.
“On Iran? Right now you cut off the head of the snake,” he said about Israel’s airstrikes on Iran’s nuclear sites. Cloobeck wrote in his book that when criticizing Israel, “some far-left voices veer into dangerous antisemitism, all while ‘canceling’ those who disagree with them.” On campus debates he writes, “Think of the phenomenon of establishing ‘safe spaces.’ Feeling victimized, young people on college campuses shield themselves from hearing other points of view, which in turn can limit their ability to pose critical questions and stand up for others around them.”
That is the core of his book and his overall message.
“We’ve got to move past the wedge issues, the ‘gotcha’ attacks, the unproductive ‘whataboutism,’ the media-baiting,” Cloobeck writes. “We’ve got to set aside the political theater, face hard truths and make decisions that might not please everybody all the time but that will set us right.”
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