8 of the savviest loopholes wealthy investors use to reduce or avoid capital gains tax

In simple terms, there are only three places your money can go: to you and your family, to charitable organizations, and to the IRS. That’s the pep talk Nayan Lapsiwala, a director of wealth management and partner at Aspiriant, gives his ultra-high-net-worth clients.

The second part of his pep talk is to avoid letting tax avoidance undermine your financial future. It could be a bad idea to keep a stock solely to skip out on realizing capital gains.

“What if that stock falls 50% or more?” Lapsiwala said. “You are trying to save money on taxes, but your entire financial future can get wiped out with the market.”

This is why tax loopholes and deferral strategies exist, and why the wealthy seek out top advisors to help them navigate the complicated and intricate tax code. The right advice can buy time, reduce tax burdens, or even avoid them altogether without breaking any laws.

8 loopholes

Most investors know and have access to an exchange-traded fund (ETF). But what about an exchange fund?

For investors who have reaped high gains from a stock and want to shave some off to reduce concentration risk, Lapsiwala says choosing to pool their assets in an exchange or swap fund with other investors is the way to go. A manager then oversees this fund. Consider it a ‘you share your stocks, and I’ll share mine’-type scenario. It gives participating investors diversification without triggering a tax event. The catch is that the shares must be held in the fund for seven years to reap the benefits and defer the tax.

“The manager’s responsibility is to reduce capital gain taxes for everyone because now as you have a pool of assets, there might be some stocks that will go down in value, some might go up,” Lapsiwala said. “So, a tax-loss-harvesting type of trading will take place and then you are reducing your capital gains taxes.”

Another way to lock in profits on securities is by creating collars, which means buying a put option and selling a call option against the underlying asset. It hedges the share price because the put creates a floor, allowing the buyer to keep the stock but offload it if it falls below the agreed-upon price, which is the strike. But buying that put will cost a premium. Therefore, calls are sold to offset the cost, giving another buyer the right to purchase the stock if it rises. The downside is that it caps any upside potential above the strike.

“There are executives we work with, for whatever restriction, they cannot sell, or they have huge capital gains and they don’t want to take a big tax hit,” Lapsiwala said. This strategy helps them plan the timing of when they want to realize the gains.”

For those who need liquidity, once the stock is hedged, they can borrow up to 50% against its value on margin, Lapsiwala noted. This strategy could have a double tax benefit: One, the investor isn’t realizing a capital gain. Two, if the borrowed amount is used for another investment and there is investment income, the cost of borrowing is treated as investment interest. It can be used to reduce the overall taxable income.

Some investors will borrow against their stocks without hedging. This is common for short-term liquidity needs, like bridge financing to buy a property while waiting to sell another, Lapsiwala noted. The risk here is if the stock drops in value in the interim, you get a margin call and must come up with the capital to cover it.

As for investors who have philanthropic goals, charitable giving is tax deductible. Still, instead of giving cash that’s already taxed, some of Lapsiwala’s wealthy clients give their appreciated securities to a 501(c) charitable organization. This grants them a tax deduction while skipping out on capital gains tax.

Another way of giving to charity is by donating appreciated assets to a donor-advised fund (DAF). In turn, the investor get a tax deduction in the year it was gifted, but they don’t have to give the full amount to the charitable organization in that calendar year.

“This is a strategy when you have high taxable income, and you want to reduce your taxes but aren’t sure that you want to give charitable grants of a high amount in a year,” Lapsiwala said. “So what we typically do is, let’s say clients are giving $100,000 a year, we will say, ‘let’s fund that by a million dollars’ and they can get that million dollar deduction now, but over the next 10 years, give $100,000 annually from that account.”

Clients who want to give to charity while continuing to benefit from gains on their principal can opt for a charitable remainder trust (CRT). It allows them to transfer cash, property, or assets to an irrevocable trust that pays an income in the form of an annuity or a percent of the trust’s assets for a term or until their death, upon which it goes to the selected charities.

John Pantekidis, managing partner at TwinFocus, says CRTs are a win-win for the charity and donor. The latter gets a tax deduction up front and an annuity while helping a charity.

Pantekidis, whose average client is worth close to $200 million, says this setup is suggested for clients with highly appreciated assets who want an income from it but are also charitably inclined.

But perhaps the tax avoidance strategy that has been an absolute home run for high-net-worth clients, according to Pantekidis, is investing in qualified opportunity zones. These are economically distressed areas that require long-term investments in real estate and businesses.

If you have a million dollars of capital gains and if you invest it in a qualified opportunity zone, you get to defer that through 2026, Pantekidis noted. Any appreciation on that investment escapes tax permanently; that’s an avoidance, he said. Furthermore, an investor can depreciate the property for further tax deductions without depreciation recapture.

“So not only do you avoid tax on the gain, to the extent you get depreciation you can avoid tax on the initial gain. It’s become an absolute home run for ultra-high-net-worth clients who have capital gains. Even some of our hedge fund managers who get compensation through carried interests of capital gains can defer those capital gains and even avoid them.”

However, the investment must be held for five to seven years to defer a portion of those gains and at least 10 years for the new gains to be fully tax-free.

Finally, those with an appreciated property who can identify a similar property to swap it with can use 1031 Exchanges. It allows the client to defer the capital gains. If they die with the property, they can get a step-up in basis which permanently removes any tax originally deferred by the exchange, Pantekidis said.