Thiel made the $3 million contribution on December 29 to the California Business Roundtable, a powerful Sacramento-based lobbying group that represents large employers and corporate interests. The donation is the first seven-figure check publicly tied to opposition to the billionaire tax proposal and Thiel’s largest disclosed political gift since the 2022 midterm elections, when he spent more than $35 million backing populist conservative candidates.​ The New York Times was first to report on the donation, citing a public disclosure.

While the money is not formally earmarked only for the wealth-tax fight, the Roundtable is expected to serve as a central vehicle for organizing and funding the business community’s push to defeat the measure. Rob Lapsley, the group’s president, has said he is actively courting deep-pocketed donors across the state as part of a broader effort to marshal corporate and elite support against the tax initiative and other proposals viewed as unfriendly to business.​

Inside California’s billionaire wealth tax

The proposed 2026 Billionaire Tax Act would levy a one-time 5% tax on the net worth of California residents whose wealth exceeds $1 billion, targeting assets such as privately held businesses, stocks, bonds, art, collectibles, and intellectual property rather than income. Real estate and certain pensions and retirement accounts would be excluded, but otherwise the measure is designed to capture a broad swath of financial and intangible holdings within ultra-wealthy portfolios.​

If approved by voters, the tax would apply to anyone who is a California resident or part-year resident as of January 1, 2026, with the bill calculated on asset values at the end of 2026 and payable beginning in 2027. Billionaires could choose to spread payments over five years, but would incur an extra 7.5% annual nondeductible charge on the unpaid balance, effectively raising the long-run cost for those who opt to defer.​

Billionaires weigh exit or resistance

News of the proposal has already prompted a wave of soul-searching—and anger—among California’s ultrawealthy, with some high-profile founders and investors exploring moves to other states or further reducing their ties to California. At least several billionaires have already left the state in recent years, and business leaders warn the tax could accelerate an exodus and sap the innovation ecosystem that underpins California’s tech economy.​

Thiel himself acquired a property in Miami years ago but remains deeply intertwined with Silicon Valley through his investments and board roles, and his donation signals a decision to fight the measure politically rather than simply watching from afar. He told Joe Rogan in 2023 that real estate prices in Miami were too expensive, in his opinion. Other tech figures, including investors like Chamath Palihapitiya and Bill Ackman, have publicly criticized the tax, arguing it would chill entrepreneurship and risk-taking in the state.​

A rare point of agreement with Newsom

In an unusual alignment, some billionaire donors and Democratic Gov. Gavin Newsom find themselves on the same side of this fight. Newsom has come out against the billionaire tax, branding it bad policy and warning that even floating the idea has already damaged California’s reputation among the global wealthy.​

The campaign over the tax is still in its early stages: backers must gather nearly 900,000 valid signatures to place the measure on the November ballot, setting up months of high-stakes organizing on both sides. Opponents predict that more than $75 million could ultimately be spent to defeat the initiative, with Thiel’s $3 million check serving as an opening salvo in what is likely to become one of 2026’s most closely watched economic battles.

For this story, Fortune journalists used generative AI as a research tool. An editor verified the accuracy of the information before publishing.

In a recent podcast interview with David Senra, Mackey recalled one of his most challenging moments: firing his father from the Whole Foods board in 1994 after nearly 15 years of advising Mackey on the direction of the company.

“That was the most difficult thing I ever did was firing my dad from that board,” Mackey said. “It took all the courage I had. I love my dad so much, and it hurt him so badly. It was so hard to do, but it was also a pivotal event in my own evolution.”

Mackey, who served as co-CEO of Whole Foods from its 1980 founding until his 2022 retirement, described his younger self as a “shirtless hitchhiking hippie” who dropped out of college. A man of contradictions, Mackey has called for marriage equality and claimed that taking psychedelics helps him find business inspiration, and in the same breath, has touted capitalism as humankind’s greatest invention while ripped labor unions, once comparing them to herpes (“It won’t kill you,” Mackey told the New Yorker in 2010, “but it’s very unpleasant, and will make a lot of people not want to be your lover.”)

In 2022, the business leader claimed “socialists are taking over,” and that young people weren’t willing to work anymore because they want to find meaningful work, something that eludes most people in the early stages of their careers.

His relationship with his father, as it relates to business, is no less complicated. As a younger man, the free-market vegan was looking to take risks to grow his wealth, even if it meant breaking from the guidance of his father, an original investor in Whole Foods. Mackey described his father as always being a man who preferred to conserve his cash, even if it meant sacrificing the growth of his wealth. As he aged, Mackey’s father became more rigid in his beliefs, which Mackey attributed in part to an Alzheimer’s diagnosis, made a couple years after his father’s departure from the board.

These diverging philosophies were most salient during the grocery chain’s 1992 IPO, when Mackey’s father encouraged the cofounder to sell company stock. Mackey, trusting his father, obliged, but later regretted it. He said the growing differences in doctrines around money fractured their relationship, leading Mackey to seek out independence from his father.

“That was when my mentorship was over,” he said. “He still advised me but from that point onward, really I was on my own. I was not going to follow him any longer. Before then, I pretty much did whatever my dad suggested.”

Mackey was largely responsible for transforming a single boutique health food store into a grocery giant. Founded in Austin in 1980, Whole Foods soon expanded across Texas and grew nationally, with 12 locations coast-to-coast at the time of its IPO, when the company was valued at $100 million. In 2017, Mackey sold the grocery giant to Amazon for a cool $13.7 billion. Whole Foods now has more than 500 locations across the U.S. and UK.

Mackey’s evolving business philosophy

At the core of Mackey’s businessperson identity is his doctrine of “conscious capitalism,” the flavor of free enterprise he said should operate with strong ethical foundations with the goal to create more than just profit in service of all business stakeholders, from customers to employees. Mackey first identified this value in 1981, when only a year after opening the first Whole Foods, the store flooded, severely damaging nearly everything inside. He recounted getting help from friends, customers, and suppliers, and was able to operate the business again 28 days after the flood.

Mackey said he internalized some value in making conservative financial decisions from his father, whom he said was a child of the Great Depression. Mackey’s father reached adulthood in the midst of World War II and operated under fear of another financial disaster for most of his life.

“He was always thinking there was going to be another Great Depression,” Mackey said. “So he was always trying to protect himself from that because it was such a traumatic experience for him.”

Mackey himself has admitted that making money isn’t everything. In 2007, the CEO said he felt financially secure and slashed his own salary to $1. (According to Forbes, he has a net worth of more than $75 million.)

However, the cofounder’s “expansive” philosophy of business increasingly diverged from his father, particularly in the way he kept shares of the business. When Mackey asked his father to step away from the board, he encouraged him to sell half his company shares and watch what happens to the other half. Whole Foods doubled in stock price over the next year.

While Mackey and his father were able to reconcile their differences, he recalled 1994 as the moment in which he prioritized his own business tactics over his mentor’s.

“I’m not going to do what you tell me to do any longer, particularly when it comes to growth,”  Mackey recalled telling his father. “We’re going to grow this business.”