Contributions to a Roth IRA are capped at $6,000 per year for most people. But some of the wealthiest Americans found ways to grow their Roth IRAs to millions — or even billions — of dollars, tax-free. Here’s how.
One day in early 1999, a deputy of Thiel’s at the company that would become PayPal walked into the San Francisco office of Pensco Pension Services. It could have been an uneventful appointment. Instead, it changed Thiel’s life.
Thiel, a Stanford law graduate, ran a small hedge fund and hadn’t yet joined the ranks of the ultrawealthy. But he had outsized ambitions for his months-old tech venture, where he served as both chairman and CEO. He envisioned his company creating “a new world currency, free from all government control.”
Influenced by libertarian Ayn Rand and Tolkien’s fantasy trilogy, Thiel, then in his early 30s, carried himself like a contrarian philosopher king. A few years earlier, he had co-authored a jeremiad against multiculturalism that accused the administration of then-President Bill Clinton of waging class warfare. “Taxing the rich seems to have become an end in itself,” he and his co-author wrote.
Pensco was a small firm that allowed its customers to put nearly any investment they wanted into a tax-advantaged retirement account. Thiel was about to become Pensco’s whale.
In an interview with ProPublica, Pensco founder Tom Anderson recalled how Thiel and other PayPal executives had wanted to put startup shares of the company into traditional IRAs.
Anderson dangled something sweeter.
“I said, ‘If you really think this is going to be big, you know, you might want to consider this new Roth,’” recalled Anderson, who is now retired. If the investment ballooned, he remembered saying, “‘you’re not going to pay tax on it when you take it out.’ It’s a no-brainer."
The math was compelling. Thiel wouldn’t get a tax break up front, but he’d avoid an immense tax bill later on if the investment surged in value.
“They immediately grasped that,” Anderson said. “And they did it.”
What happened next deprived the U.S. government of untold millions in tax revenue. Perhaps billions. Thiel used his new Roth IRA to purchase shares of his startup.
In 1999, single taxpayers were only allowed to contribute to a Roth if they made less than $110,000. Like many startups, PayPal offered its top executives low initial salaries and large stock grants. Thiel’s income that year was $73,263, the IRS records show.
Thiel also had an advantage over most Americans with IRAs, who typically use them to purchase publicly traded stocks, bonds, mutual funds and certificates of deposit. Since Thiel used his Roth to buy shares of a private company, the value wasn’t set on a public stock exchange.
Although the details of such purchases are not usually public, Thiel’s financial assistant later disclosed them in a letter included in the entrepreneur’s application for residency in New Zealand: “Mr. Thiel purchased his founders’ shares in PayPal through his Roth IRA during PayPal’s formation.”
While SEC filings describing that time don’t mention Thiel’s Roth, they show that he bought his first slice of the company in January 1999. Thiel paid $0.001 per share — yes, just a tenth of a penny — for 1.7 million shares. At that price, he was able to buy a large stake for just $1,700.
In 1999, $2,000 was the maximum amount you could put into a Roth in a year.
Thiel’s unusual stock purchase risked running afoul of rules designed to prevent IRAs from becoming illegal tax shelters. Investors aren’t allowed to buy assets for less than their true value through an IRA. The practice is sometimes known as “stuffing” because it gets around the strict limits imposed by Congress on how much money can be put in a Roth.
PayPal later disclosed details about the early history of the company in an SEC filing before its initial public offering. The filing reveals that Thiel’s founders’ shares were among those the company sold to employees at “below fair value.”
Victor Fleischer, a tax law professor at the University of California, Irvine who has written about the valuation of founders’ shares, read the PayPal filings at ProPublica’s request. Buying startup shares at a discounted $0.001 price with a Roth, he asserts, would be indefensible.
“That’s a huge scandal,” Fleischer said, adding, “How greedy can you get?”
Warren Baker, a Seattle tax attorney who specializes in IRAs, said he would advise clients who are top executives working at a startup not to purchase founders’ shares with a Roth to avoid accusations by the IRS that they got a special deal and undervalued the shares. Baker was speaking generally, not about Thiel.
“I would be concerned about the fact that you can’t support the valuation number as being reasonable,” he said.
At the time Thiel bought his founders’ shares, his own hedge fund had already loaned the new startup $100,000, California and SEC records show.
And soon after the company sold him the shares, millions of dollars poured in from investors, securities filings show. In just a month’s time, the company sold a slice of itself to investors for $500,000. That June and August, another $4.5 million poured in from the venture fund arm of telecom giant Nokia and other investors, those records show.
The dot-com boom was in full swing. “We’re definitely on to something big,” Thiel told employees in late 1999, predicting that PayPal would become “the Microsoft of payments,” according to “The PayPal Wars,” a book by a former employee recounting those heady early years.
But when it came time for Pensco, the custodian of Thiel’s Roth, to report the value of the account to the IRS at the close of 1999, none of the investor enthusiasm was apparent. Pensco told the IRS that Thiel’s Roth was worth just $1,664 at the end of 1999, tax records show.
In an interview, Anderson said Pensco relied on the companies whose shares were in a Roth to say what they were worth. He didn’t know how PayPal came up with its market value, but he said Thiel’s purchase of those shares was “very legitimate.”
From there, nothing would stop Thiel’s Roth. In a Silicon Valley equivalent of Tolkien alchemy, his Roth would transform those PayPal shares into a tax-free fortune — one that would be safer than all the gems, gold and silver in the dragon Smaug’s mountain.
Thiel’s Roth IRA Balloons Into Billions of Tax-Free Dollars
Congress created the Roth IRA as a tax-free account for ordinary Americans to save for retirement. Peter Thiel has turned his Roth into a behemoth investment vehicle that grew to $5 billion in 20 years.