Navigating Capital Gains and Deferred Sales Trusts

The last couple of weeks, we’ve been deep in the world of buying businesses. But what happens when it’s time to cash out? Maybe you’re ready to sell your business, that investment property you’ve managed for years, or another major asset you’ve poured your energy into.

If you’re like most people, the thrill of a big sale is quickly followed by a less-exciting thought: “Wait, how much am I going to owe in taxes?” It’s the classic one-two punch—first the celebration, then the sinking feeling as you picture Uncle Sam’s hand reaching for a chunk of your hard-earned gains.

But here’s the good news: you actually have options. Real, legal, IRS-approved options. And the right strategy can mean the difference between watching your profits shrink and putting your money to work for you—sometimes for years to come. Of course, things get a little trickier if you have a mortgage or other debt on the property, but don’t worry—we’ll break that down too.

Let’s start with one of the oldest tricks in the book: the 1031 Exchange. If you own investment real estate, you’ve probably heard about this one. The idea is simple: sell your property, buy another “like-kind” property, and—if you follow the rules—kick that tax bill down the road.

But here’s the twist: if you’ve got a mortgage, you’ll need to replace that debt with equal or greater debt on your next property, or pony up the difference in cash. Otherwise, the IRS will want a piece of the action right away. So yes, leverage matters!

Now, maybe you’re tired of being a landlord but still want those tax perks. Enter the Delaware Statutory Trust, or DST. This is essentially 1031 exchanging into a syndication that is designed for this type of thing. You sell your property and, instead of buying another one yourself, you buy a slice of a big, professionally managed property—like an apartment complex or shopping center. DSTs often come with their own loans, so you can match your old mortgage and keep the tax deferral going. The upside? No more midnight calls about leaky faucets. The downside? You’re trusting someone else to run the show and they need to be good at it (just like any syndication operator). And, there are some rules and restrictions that can affect your returns negatively.

But what if you’re selling a business? That’s where Employee Stock Ownership Plans, or ESOPs, come in. Imagine selling your company to the people who helped you build it—your employees—and deferring a big chunk of your capital gains tax in the process. It’s a win-win, but if your business has debt, things can get complicated fast. This is definitely a strategy where you’ll want a seasoned advisor in your corner.

Now, let’s talk about installment sales and structured sales. In this scenario, instead of getting paid all at once for your asset, you spread out the payments—and the taxes—over several years. Structured sales even bring in a third party to guarantee those payments, adding an extra layer of security. But—and this is a big but—if you have a mortgage, the IRS treats the amount the buyer pays off as if you got that money in cash on day one. So, you’ll pay taxes on that portion right away. For example, if you sell for $1 million but owe $600,000, you can only defer taxes on the $400,000 you actually receive over time. The more debt you have, the less you can defer.

And finally, we have the Deferred Sales Trust—the topic of this week’s Wealth Formula Episode. Think of this as the “supercharged” version of a structured sale. Instead of waiting on the buyer for payments, you transfer your asset to a trust, which sells it and invests the proceeds. You get to choose how and when you receive your money, and the trust can invest in all kinds of assets while your taxes stay deferred. It’s flexible, it’s powerful, and it gives you the chance to grow your money while you wait.

Which of these strategies is right for your situation depends on your goals, your assets, and whether you have debt on the property. The key is knowing your options and working with someone who can guide you through the maze.

That said, for assets that have no debt, I really do think the deferred sales trust is something that everyone should know about, and that’s what my guest on this week’s episode of Wealth Formula Podcast is an expert on.