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Looking To Exit In 2027? Your Tax Structuring Window is NOW.

Written by Ryan Foley | Jul 31, 2026, 3:00:28 PM

When theOne Big Beautiful Bill Act passed last July, it handed business owners the most favorable exit environment in a generation. The estate tax exemption jumped to $15 million per person. Capital gains rates held steady. Bonus depreciation came back at 100 percent, permanently this time. And in the year since, every advisory firm in the country has landed on the same message: the window to exit your business at historically low tax cost is open.

They are right about the window. They are wrong about why it closes.

The window is not the law. The window is the calendar.

Here is what most of those articles will not tell you. Nothing in the current tax code expires next year. The $15 million estate exemption, the amount you can pass to your family free of estate tax, is permanent and grows with inflation. The 20 percent deduction that most business owners take on their company income is permanent too. The tax break for founders who sell qualifying company stock got bigger, not smaller. Congress did something unusual: it gave business owners certainty.

So why the urgency?

Because the strategies that will optimize your exit are not simple decisions or accounting choices. Think of them as construction projects. There are steps and they take time.

Take a GRAT, a trust designed to move the future growth of your business to your kids at a fraction of the normal tax cost. Done right, it takes 90 to 180 days to structure, fund, and put in place. Changing how your company is legally organized before a sale, which can determine whether your proceeds are taxed at 20 percent or 37 percent, runs on a similar clock, and some of those changes only take effect at the start of a tax year. The founder stock exclusion mentioned above requires you to hold the shares for five years before it pays off. A retirement plan built to shelter large amounts of income in your final years of ownership has funding deadlines.

Now run the math backward. A business that goes to market in early 2027 typically signs a letter of intent, four to eight months before the deal closes. The day that letter is signed, the buyer's team starts examining how your company is structured. Whatever structure you have at that moment is, for all practical purposes, the structure you sell with. Trying to reorganize after a buyer is at the table looks like a problem, and problems cost you leverage.

Which means the real deadline for a 2027 close is not December 2026. It is this fall.

What restructuring after the fact actually costs

When you sell a business, there are two basic ways to paper the deal: the buyer purchases your company's assets, or the buyer purchases the company itself. Which one you end up with, and how your company was organized going in, largely determines whether your proceeds get taxed at the 20 percent capital gains rate or at ordinary income rates that can reach 37 percent. On a $20 million transaction, that gap is measured in millions, and it is decided months before anyone signs anything.

The IRS does not reward good intentions. It rewards structures that were built, documented, and in place long enough that no one can argue they were created just for the deal. 

Permanent does not mean untouchable

For the record, "permanent", in tax law, means permanent until Congress changes its mind. The current provisions have no sunset date, but midterm elections are four months away, and the composition of the next Congress will shape what gets revisited. Nobody can tell you the exemption will still be $15 million in 2030. 

The sequence, if 2027 is your year

Between now and October, three things need to happen.

First, know your number. Not a guess or an estimate. Your number, from a defensible valuation, because every strategy in this article is priced off that figure. Getting it wrong in either direction costs you.

Second, pressure test your entity. The structure that was right for running your business is rarely the structure that is right for selling it. This analysis takes weeks, not days, and the fixes take months.

Third, decide what the exit is for. If wealth transfer to the next generation is part of the picture, the transfer strategies need to be in motion before the event, not after. Moving appreciated proceeds is expensive. Moving the asset before it appreciates through a sale is the entire game.

None of this is exotic. All of it is time bound.

The bottom line

The 2026 exit environment is the best business owners have seen in a generation, and for once, it is not because a deadline is forcing your hand. The law is stable. The rates are known. The exemptions are historic.

The only thing working against you is lead time. Strategies take 90 to 180 days to build. Buyers lock your structure at LOI. Tax years end whether you are ready or not.

If a 2027 exit is on your board, the structuring work starts now. Not because the sky is falling. Because the calendar is doing what calendars do.