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California’s billionaire midlife crisis: Why voters keep humbling the masters of the universe

June 3, 2026

California has become home to a peculiar and expensive tradition. Every few years, a billionaire wakes up, looks in the mirror, and decides that the only thing missing from an already extraordinary life is elective office.

The names change, but the story rarely does.

Michael Huffington. Al Checchi. Meg Whitman. Rick Caruso. Tom Steyer.

Each arrived with immense wealth, sophisticated organizations, top consultants, endless advertising, and the sincere belief that success in business would naturally translate into success in politics. Each discovered what California voters have been trying to teach wealthy self-funders for decades: you can buy attention, but you cannot buy authenticity.

Tom Steyer is simply the latest example. By some estimates, he spent more than $220 million pursuing public office and political influence. Meg Whitman spent roughly $180 million on a gubernatorial race. Rick Caruso spent $100 million trying to become mayor of Los Angeles. California’s political history is littered with campaigns fueled by fortunes and undone by a simple reality: voters do not care nearly as much about your net worth as you do.

What fascinates me about these campaigns is that most begin with a fundamentally understandable misunderstanding.

In business, success often means making good decisions and producing results. Over time, it becomes easy to believe that competence in one arena naturally translates into competence in another.

Politics has a funny way of exposing that assumption.

Running a company and leading a democracy are not the same thing. One is largely about control. The other is largely about persuasion. One rewards efficiency. The other requires patience. One allows you to hire and fire people. The other requires convincing millions of people who owe you nothing to trust you with power.

To be clear, wealth itself is not disqualifying.

Americans admire success. In fact, some wealthy candidates have succeeded spectacularly in politics. Just not typically in California.

California is the billionaire capital of America, but it may also be the state least impressed by billionaires. The challenge for wealthy candidates in California isn’t proving they succeeded. It’s proving they still remember what life looks like for everyone else.

Too many self-funded candidates approach politics the way they approached business. They see a problem, assemble a team, write a large check, and assume success will follow. Politics rarely works that way because voters are not customers and campaigns are not acquisitions.

Of course, the billionaires are not the only ones responsible for these adventures.

Trust me. I know the other side of the equation.

Whenever a billionaire decides to run for office, an entire industry suddenly appears. Pollsters, media consultants, strategists, and digital consultants all rush to explain why this time will be different.

The billionaire wants validation. The consultants want a budget and a villa in Tuscany.

I say that as someone who has spent a career in the campaign consulting business.

One of the uncomfortable truths I’ve learned is that political consultants are often less like doctors and more like bartenders. We do not always tell clients what they need to hear. We tell them what they want to hear and then send another round. We sell the belief that enough money can overcome almost any obstacle.

Sometimes it works.

Most of the time, voters are smarter than we give them credit for.

That is why California’s political graveyard is filled with campaigns that had every conceivable advantage except the one thing voters were looking for: a sense that the candidate understood life beyond achievement and ambition.

Most self-funded candidates are asking voters to believe they understand lives they have not lived in decades, if ever.

Most Californians are not worrying about capital gains taxes or where to park the Gulfstream. They’re sitting at the kitchen table trying to figure out how to stretch a paycheck. They’re deciding which bill gets paid first and wondering whether they can afford groceries, rent, childcare, a medical copay, or a tank of gas.

They are living at the kitchen table, not in the boardroom.

Politics punishes that disconnect.

Voters want to know that a candidate sees them, understands their struggles, and appreciates that most people’s lives are not measured in stock options and quarterly earnings reports. In fact, leadership is not another trophy to acquire after you’ve conquered the business world.

Real success is not measured the way most of these self-funding candidates think it is.

There is a kind of success that has nothing to do with achievement or acquisition. It follows an inverse logic. You give in order to get. You sacrifice in order to gain. Only in serving others can you discover who you really are.

Perhaps that is why so many self-funded campaigns fail. The candidates are often pursuing one final achievement while voters are searching for something entirely different: Empathy and authenticity.

The leaders our future requires will not be masters of the universe. They will emerge from communities, classrooms, neighborhoods, and lives shaped by struggle, gratitude, and service.

California’s billionaires keep spending fortunes trying to teach voters who they are.

Voters keep teaching them something far more valuable.

Humility.

John Shallman is an award-winning political media strategist and crisis manager. He is the national bestselling author of Return from Siberia and president of Shallman Communications, a Los Angeles-based public affairs firm.

Orange County Register

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California’s billionaire midlife crisis: Why voters keep humbling the masters of the universe

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