Retirement Hacks: How to invest in a Roth IRA like — and unlike — PayPal co-founder Peter Thiel


The average retirement saver may not be able to mimic the growth of PayPal co-founder Peter Thiel’s Roth individual retirement account, but they could try a few of his and other billionaires’ investing strategies. 

Thiel’s Roth IRA grew from less than $2,000 in 1999 to $5 billion today, thanks in large part to private security investments. Thiel had used his Roth IRA to buy 1.7 million shares of PayPal

in 1999, three years before the company went public when it was worth $1,700, according to a ProPublica report. When the price of those shares skyrocketed after going public, so too did his IRA’s balance. 

Retirement Tip of the Week: Investing in private securities and alternative investments might not be easily accessible to the everyday retirement saver, but there are key lessons to take away from the tech giant’s Roth IRA success. 

See: To Roth or not to Roth

The first: Knowing what to put in your Roth IRA. These accounts are funded with after-tax dollars, as opposed to traditional IRAs, where contributions are pretax. Because of this tax nature, investing in more volatile, growth-oriented options could make sense — if those investments grow substantially, the money they make won’t be taxed at distribution. 

“People should be thinking about alternative asset investment opportunities for purposes of retirement,” said Eric Satz, chief executive officer of Alto IRA, a website for investing retirement accounts in alternative assets. 

Of course, investors should proceed with caution — one goal may be to grow their investments significantly during their career, but they don’t want to erode the money they put in either. 

Typically, for people to trade nonpublic investments, they must be accredited investors. In order to qualify as an accredited investor you must either be an individual earning $200,000 annually (or $300,000 if joint) for the last two years, or that person must have a net worth of more than $1 million. These rules are barriers for many Americans, but there are ways to work around them, such as investing platforms that provide access to these private securities. 

Have a question about your own retirement concerns? Check out MarketWatch’s column “Help Me Retire” 

A few platforms that allow people to invest in startups include Republic and SeedInvest. With these services, investors can use their IRAs to invest in private equity. There are also investing sites that allow retirement savers to own an interest in high-worth paintings, such as a Picasso or a Banksy. “Up to now, you’d have to write a 5- or 6-figure check in order to diversify your interest in art, but because of fractionalizing you can do it at the $500 or $5,000 level,” Satz said. 

There are also plenty of options to invest in real estate within a self-directed IRA, and now, cryptocurrencies as well. 

These investments could be valuable in an IRA, but they should be pursued with extreme caution. Investors may want to avoid making these investments a majority stake in their retirement accounts too. Although these accounts likely have a longer time horizon than a savings account or other investment portfolio earmarked for a near-term goal, which means they can handle volatility, they are meant to amass a nest egg for the future so they should be treated carefully.

How an IRA should be allocated is highly personal to each individual, and is based on age, health, retirement goals and expected lifestyle in an investor’s old age. Typically, these highly volatile investments should be kept to a minimum, however. 

“It is icing on the cake, not the cake itself,” said Jason Flurry, a certified financial planner and president of Legacy Partners Financial Group. The good news — if these investments do particularly well, account balances can jump, but the opposite is also possible, where these investments lose the account money. 

Also see: Talk to your parents about their retirement plans — sooner rather than later 

There’s one other strategy billionaires reportedly used to grow their Roth accounts substantially, ProPublic found — Roth conversions. Roth IRAs have income limits, which restrict some high earners from contributing. Because of this, workers may want to invest through a traditional IRA. 

Investors can choose to fund part of their traditional IRAs with nondeductible, after-tax dollars, which can then be moved over to a Roth IRA. There is a formula that breaks down what portion of the account is taxable and what is not. If an investor has a traditional IRA with pretax dollars, as many do, they can still convert those funds to a Roth IRA but will have to pay taxes on it. Some high net-worth individuals are currently mulling over Roth strategies more now, in response to what investors expect to be increased tax rates under President Biden.  

People looking to convert money into a Roth may want to use extra cash on hand, such as from a bonus or tax refund, to pay the tax bill, so that their account balance doesn’t dwindle as much from being taxed in the short-term, Flurry said. 

Want more actionable tips for your retirement savings journey? Read MarketWatch’s “Retirement Hacks” column

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