These stocks have created enormous wealth for their shareholders.
But if you own one in a taxable account, that wealth can create a trap:
“I can’t sell. The tax bill would be too big.”
That is almost never the right way to think about it.
If you still believe in the company and the position is not too large for your portfolio then keep holding it.
You also do not have to make an all-or-nothing decision. If you accumulated shares at different prices, you may be able to sell only part of the position and choose which tax lots to sell.
But do not keep holding a stock solely because you are afraid of the taxes.
Taxes should influence an investment decision. They should not make the decision for you.
Under the new Opportunity Zone rules, an investor could sell appreciated stock now and reinvest the gain (not the entire sale proceeds) or a portion of the gain into a Qualified Opportunity Fund after January 1, 2027, within the applicable 180-day window.
Do that, hold the investment, and:
• The original gain is deferred for five years. For a qualifying investment made in early 2027, the tax would generally be paid with the 2032 return in April 2033.
• After five years, only 90% of the original gain is taxable.
• After ten years, the appreciation on the new Opportunity Zone investment can be excluded from federal capital-gains tax.
• If the fund invests in real estate, the investment may also produce depreciation-based passive losses, depending on the structure and the investor’s individual tax situation.
You still eventually pay most of the tax on the original stock gain.
But you get five more years to use the government’s money, receive a 10% reduction in the taxable gain and move capital from a highly appreciated stock into a real estate investment with its own tax-free growth runway.
The tax bill is not a reason to remain concentrated forever.
It may be the tool that allows you to diversify.