Most business owners work too hard building their company just to hand a massive chunk of it to the IRS when they exit. But that’s exactly what happens when there’s no proactive tax strategy in place.

On a recent episode of the Scale Smart, Grow Fast Podcast, Brett Swarts, founder of Capital Gains Tax Solutions, broke down how entrepreneurs, real estate investors, and even crypto holders can legally defer 20–50% of capital gains taxes—and redirect that money into new investments or passive income.

Preferred listening on-the-go? Catch the full podcast episode on Spotify and Apple Podcasts.

Here’s a quick breakdown of what you need to know.

The Problem: Great Exit, Huge Tax Bill

Whether you’re selling a company, real estate portfolio, or large investment position, you could be handing over half your gains in taxes. And many founders don’t know this until it’s too late.

Most are only familiar with the 1031 Exchange, which:

• Only applies to real estate
• Has a tight 45/180-day timeline
• Requires reinvesting in another property (even if market timing is poor)
• Often forces buyers to overpay just to defer taxes

Brett calls this “a shotgun wedding for your money.” It may work sometimes, but rarely when flexibility matters most.

The Better Tool: Deferred Sales Trust (DST)

The Deferred Sales Trust offers a smarter way to defer taxes with more flexibility.

Works for real estate, business sales, crypto, stocks, etc.
No like-kind restrictions—you can move from real estate to stocks, Bitcoin, or private lending
No tight timeline—you can sit in cash until the right opportunity
Eliminates debt pressure and reduces risk
Creates passive income or funds your next big venture

Real-world example: One client sold a $17M digital billboard company and used the DST to diversify into Nvidia stock at the perfect time—avoiding capital gains taxes and unlocking exponential growth.

When Should You Plan for This?

The best time: now.
The worst time: after your buyer has removed contingencies.

Brett’s team can help business owners set up a plan in as little as five hours. If your deal is expected to have $1M+ in gain and net proceeds, it’s worth exploring this strategy early. Even better? You don’t need to fire your CPA. They partner with your advisor to handle the specialized work.

It’s Not Just Real Estate

DSTs work for:

• Business exits
• Bitcoin & crypto
• Public/private stock
• Land or asset-heavy portfolios
• Even luxury primary homes

If you’ve been scaling your company and want to eventually enjoy the freedom you’ve built—without being dragged down by capital gains taxes—this is a strategy to seriously consider.

Ready to keep more of what you’ve earned—and scale smarter?
Schedule a free discovery call to learn how our executive support team can help you implement high-impact strategies without adding complexity.

The post How Founders Can Keep More of Their Profits (and Stress Less About Taxes) first appeared on Workergenix.