Want to Avoid Taxes the Peter Thiel Way? Don't Even Try

If Peter Thiel could use a special retirement account to accumulate $5 billion tax free, why can't you?

It's only natural to wonder after a ProPublica report last month detailing how the venture capitalist turned a humdrum retirement savings vehicle into a shelter for spectacular capital gains.

Thiel used what's called a self-directed Roth Individual Retirement Account, according to the report.

A self-directed account is one that can invest in alternative holdings such as startups, real estate or partnerships, unlike a traditional account, which typically holds stocks and bonds. IRAs can be self-directed, as can Roths, where tax is paid upfront so withdrawals are tax-free.

According to ProPublica, Thiel was able to put 1.7 million shares of then-private Paypal into a self-directed Roth IRA in 1999.

There are contribution limits for Roth IRAs, but the total value of the Paypal shares was below the $2,000 threshold at the time. Those shares have since exploded in value, along with other investments Thiel has made, but since they're in the Roth, they aren't subject to tax.

Buyers Beware

It sounds too good to be true — and for most investors, it is. From fees to severe penalties for missteps, a self-directed retirement account is something most savers should steer clear of.

First, the fees a custodian will charge for holding and administering alternative investments are generally steep.

Traditional retirement-account custodians like Fidelity and Schwab have to stay competitive with each other, but with alternatives, there are fewer players and less transparency and competitive fee pressure. And self-directed retirement custodians generally charge fees for administering the alternative, liquidating it, and reporting a value for it, as the IRS requires periodically.

Also, if you have a self-directed IRA and are required to take distributions from it, you'll probably want to keep some cash in the account. It's difficult to liquidate part of a building, and you probably won't want to take funds away from an expanding company.

Keep in mind that if you want to convert your self-directed IRA to a self-directed Roth IRA, you'll need to figure out how to calculate the account's value to pay the tax on the conversion.

In addition, custodians of self-directed accounts tend to be pretty hands-off when it comes to telling investors what's acceptable (or not) with respect to activity within the account. Even worse, the Internal Revenue Service rules regarding what's off-limits are complex and sometimes unclear.

Potential Tax Troubles

The IRS says investors will face a substantial tax hit if they use assets in self-directed accounts for their own benefit or to help family members. That means, for example, that the investor couldn't live in a house that's inside the self-directed account.

Since the IRS doesn't explicitly say that siblings fall under the rule, there could be gray areas to exploit. But that's a dangerous game.

It's especially easy to trip over IRS rules, even inadvertently, with real estate assets in a self-directed IRA. If you personally guarantee a mortgage for a real estate investment in your self-directed account, for example, the IRS considers that to be a no-no too, according to Ed Slott, a certified public accountant who specializes in IRAs.

Even something as mundane as personally repairing something at a rental house or apartment held in a self-directed account can get an investor into trouble, said Jeffrey Levine, a CPA and certified financial planner at Buckingham Wealth Partners.

PTE Penalties

The penalty is harsh. A single prohibited transaction turns the entire retirement account balance into a taxable distribution starting Jan. 1 of the year when the penalty occurred. Those under 59 1/2 also face a 10% early withdrawal penalty.

Investors in startup businesses via self-directed accounts can easily blunder into costly missteps. People who own close to 50% of a business need to be careful when adding more shares in a self-directed account.

If they cross that threshold, which could be squishy when purchasing difficult-to-value shares in a round of funding, they'll be in hot water.

Don't assume that because the IRS didn't challenge Thiel, they won't go after you. First, it's unclear whether Thiel engaged in any prohibited transactions — and he has ample resources to hire lawyers to argue the point with the IRS. For almost everyone else, the resources spent are likely to outweigh any benefit.

Despite the caveats, a self-directed retirement account could be suitable for professional real estate investors or venture capitalists, who are in a position to be confident that certain investments stand to earn huge gains.

But remember, if there's any chance of incurring a real-estate investment loss, it's safer to take advantage of straightforward tax breaks that are always available than to play with IRA fire.

See: Peter Thiel's $5 Billion Roth IRA: Tax Pro Jeff Levine Weighs In

(Photographer: Kiyoshi Ota/Bloomberg)