The ultra-rich have an unusual tax problem: when to sell?

Joan Crain’s job is to guide the wealthy through complicated financial decisions where mistakes can cost millions of dollars. That task is proving particularly tricky now thanks to Joe Biden’s proposed tax plan and the lack of clarity over what the Democrats will pass.

“We have to calm them down,” said Crain, global wealth strategist at BNY Mellon Wealth Management. “We don’t know what’s going to happen.”

Rich Americans and their advisers have known taxes could be going up at least since January, when Democrats won two Senate elections in Georgia that gave them effective control of both chambers of Congress.

The developing tax bill is making it hard to know when to part with assets.
The developing tax bill is making it hard to know when to part with assets.
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Now the lawmakers are pushing to raise taxes on Americans earning more than $400,000, with proposals that hike rates on corporations and capital gains. They’re also seeking to increase funding for the Internal Revenue Service and close a variety of loopholes that millionaires and billionaires have come to rely on.

What’s still up in the air though — and will remain uncertain until either President Biden signs a bill into law, or the whole effort collapses in Congress — is almost everything about the tax package, including which rates Democrats ultimately set and even when its various provisions go into effect. That’s making it particularly challenging for wealth advisers to figure out exactly how Democrats might force the rich to pay more.

“We have to look at every client to see where they’re going to be vulnerable tax-wise going forward,” said Crain.

Capital gains tax
In April, Biden and the White House laid out one plan, which alarmed the super wealthy with a proposal to almost double their tax rate on long-term capital gains — to the level that wage income pays — while requiring taxes on those gains be paid before assets are inherited.

Tax

The proposed law would ban all IRAs, regardless of size or owner’s income, from holding unconventional assets like stakes in private companies, real estate and startups.

September 28
Democrats would crack down on Roth retirement plans in ways that hit both ultra-wealthy earners and more modest savers.

Then, a House plan approved by the Ways and Means Committee this month scrapped that idea, merely proposing to raise the top capital gains rate to 25%, from 20%. But, after breathing a sigh of relief, advisers to the wealthy soon realized the bill contained language that would kill off some of the most popular ways the richest 0.1% legally circumvent taxes.

The proposal would block trusts and other techniques used to get around the estate and gift tax, which is a 40% levy on the transfer of large fortunes from generation to generation. It also would shrink a lucrative tax break primarily enjoyed by Silicon Valley, and tighten rules on wealthy Americans’ individual retirement accounts, or IRAs.

Tax

Two of the most generous tax loopholes are on the chopping block, the latest surprise in emerging tax increases.

September 15
Congress is moving quickly on proposed tax increases but also fighting about them.

Democrats are divided on how quickly they want to move this bill through Congress. Some progressive lawmakers are advocating for a vote in the House as soon as this week. Moderate Democrats, including Senator Joe Manchin of West Virginia, have said the negotiations should not be rushed and could extend into 2022. Many congressional experts expect the bill will pass just shortly before the Christmas holiday, a date that has historically served as a motivating deadline for lawmakers to reach a deal so that they can go home to celebrate with their families.

For advisers executing sophisticated tax-avoidance strategies, the details matter. So does exactly when changes get implemented. The White House’s plan said it would hike capital gains rates starting after the date it was announced — in late April — a retroactive increase that would have meant rich investors owe almost twice as much on transactions executed in May than in March.

Then the House proposal moved its more modest capital gains hike to start after Sept. 13. Other tax provisions in the bill had different effective dates, including the day they become law and the end of the year. There’s no guarantee any of those dates will remain in final legislation.
Clarity on the timing of tax hikes would make them easier to avoid. If investors know taxes are going up in the future, they can rush to sell now.

“It seems like they’re trying to create paralysis, so people don’t do anything,” said Jeremiah Barlow, head of family wealth services at Mercer Advisors. He thinks there’s a 50-50 chance that the effective date on the capital gains hike could slip to later in the year as negotiations over the package stretch onward.

Effective dates
The question of effective dates is especially important for people already in the midst of large transactions that would trigger capital gains. For clients about to sell a business, for example, the best advice may be to hurry up and hope your transaction falls under the lower tax rate, Barlow said. “Either the rate is going to go up, or you’re going to get the windfall of it being lower.”

The threat of higher taxes is pushing some rich Americans to make moves. Owners of multi-billion-dollar businesses have sped up plans to sell them off, advisers say, hoping the deals are completed in time to avoid the tax hikes. Other wealthy investors are exploring niche strategies, including one called private placement life insurance, that are designed to avoid taxes on future gains.

In some cases, haste could be a mistake. Both the White House and House legislation would hike the top ordinary rate back to the pre-2018 level of 39.6%, up from 37%, at the end of the year. The House bill would also add a 3% surcharge on incomes above $5 million next year. If those and other tax hikes take effect in 2022, it might be tempting to try to pay more to the IRS this year in ways that would lower future years’ tax bills.

Strategies for doing that include speeding up business income, deferring charitable contributions and other deductions to future years, or moving money from traditional IRAs to tax-free Roth accounts.

But all these moves could backfire. Taxes might not rise as much as expected — or might not happen at all. The House bill includes a $10-million cap on Roth IRAs, and Democrats have previously discussed limiting the total size of wealthy taxpayers’ deductions.

“I wouldn’t make any big moves in a client account until the final ink is dry,” said Dana D’Auria, co-chief investment officer at Envestnet. “We know the package probably gets cut back. You could have last-minute amendments that change the picture.”

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Tax Estate planning Retirement Roth IRAs Capital gains taxes
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