How A Millionaires Got Away From Paying Taxes On His $500M Gains | Self-Made Millionaire Tips


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Washington Post’s Alan Sloan published a story about Ted Weschler, a relatively low-profile money manager based in Charlottesville whose retirement account has outperformed the S&P 500 by hundreds to 1.

How? Just like Peter Thiel, he used a RothIRA. Through that, he outperformed Vanguard’s low-cost S&P 500 index fund, a standard investment benchmark, by even wider margins.

His retirement account is now worth $264.4 million at year-end 2018, that’s more than 300,000 percent from 1989 to 2018.

This is the best part. He didn’t have to use any insider games that Thiel used. Weschler said he had put up his numbers by investing in only publicly available securities.

Weschler converted his regular IRA to a Roth IRA in 2012 but not before suffering a 52 percent loss in 1990.

What happened? In the early 90s, he had some gains but his fund’s holdings — Continental Health Affiliates stock and Intelogic Trace bonds — took hits of 67 and 55 percent, respectively, from what he paid for them.

Weschler converted what had become a nine-digit IRA into a Roth in 2012, even though that required him to pay $29 million of federal income tax.

As you know, the money going in is tax-deductible in a regular IRA, but withdrawals are taxable. And you have to start taking annual withdrawals when you turn 72. With a Roth, the money going in isn’t deductible, but the withdrawals aren’t taxable.

Weschler thought that he could save enough on future taxes to justify paying taxes today.

Converting to a Roth from a regular IRA cost Weschler serious money on his 2012 taxes — but he won’t have to pay the IRS anything when he takes money out of his Roth. This means that down the road, he’ll save lots more tax than he paid nine years ago.

Weschler maxed out his contributions to his 401(k) plan when he started working in 1983. By 1989, his account was up to $70,384.

By 2018, that $70,384 had grown to $221.6 million. That includes his contribution, employer matching contribution and capital gains.

Weschler eventually started his own hedge fund. He said that it produced more than 22 percent of after-fee compounded annual returns for investors. A terrific record.

In 2010, won the annual auction to have lunch with Buffett. He won twice. After the second lunch, Buffett offered him a job. He accepted it.

For Berkshire, he looks for investments that can absorb a minimum of $500 million without giving Berkshire a stake of 10 percent or more.

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