What if you could sell your business, real estate, or other highly appreciated assets without losing 25%–50% of your profit to capital gains tax?
For many investors, this question feels like a dream scenario but for savvy real estate professionals and entrepreneurs, it’s a reality through a Deferred Sales Trust (DST).
In a recent episode of the Capital Gains Tax Solutions Podcast, host Brett Swarts sat down with Dave L., a seasoned multifamily investor and philanthropist, to explore how the DST is transforming the way investors think about building and giving back their wealth.
From Hawaii to Montana: Building Real Estate Wealth with Purpose
Dave’s journey began when he was just 15, investing in real estate alongside his father. Over the years, he developed commercial properties across Hawaii, including historic preservation projects and award-winning restaurants.
But Dave’s story isn’t just about wealth accumulation, it’s about using real estate as a vehicle to do good. As he shared, “Real estate provides stability for your family, but its true value is in helping the community.”
From funding public school classrooms to creating glamping experiences in Montana that teach corporate social responsibility, Dave embodies what it means to build impact-driven wealth.
Timing Is Everything: When to Buy, When to Wait
In real estate, most people obsess over location, location, location. Dave has a different mantra: “Timing, timing, timing.”
He explained that the key to success isn’t buying at the bottom or selling at the top it’s recognizing the right moment to act. During market downturns, he says, “Let the sharks feed.” In other words, allow the market to settle before jumping in.
This patient approach is where the Deferred Sales Trust shines. Instead of rushing into another deal to meet a strict timeline (as with a 1031 exchange), the DST allows investors to defer taxes, stay liquid, and re-enter the market when the timing is right.
Deferred Sales Trust vs. 1031 Exchange: Flexibility Over Pressure
For years, Dave used traditional 1031 exchanges to roll over his real estate profits. But as he approached retirement, he realized the downsides especially the pressure to reinvest within 45 days and take on equal or greater debt.
“The problem with a 1031 is that you’re forced to trade up,” Dave said. “Each time, the debt gets bigger, and the flexibility gets smaller.”
When he discovered the Deferred Sales Trust, everything changed. By using a DST, Dave could:
- Defer capital gains taxes indefinitely
- Pay off debt without replacing it
- Sit on the sidelines safely until a better investment opportunity appeared
- Reinvest into diversified assets from real estate to passive investments
When the pandemic hit and real estate markets turned uncertain, the DST gave him the freedom to pause, preserve his capital, and wait for the right opportunities.
Investing with Heart: Using Wealth to Give Back
Beyond profits, Dave believes wealth has a higher purpose creating change.
Over the years, he’s launched multiple social ventures, including:
- Adopt a Classroom / Stock Our Schools, connecting realtors to public schools in Hawaii and helping teachers fund classroom supplies.
- Hotels That Help, partnering hospitality businesses with homeless shelters and food banks.
- Camp Satori in Montana, a “glamping” resort that trains Millennial leaders to embrace corporate social responsibility.
As Dave shared, “It’s not about how much money you make it’s about what you do to help other people with your money.”
This mindset perfectly aligns with the mission behind Capital Gains Tax Solutions to help investors unlock their capital, create freedom, and make an impact in their communities.
The Bigger Lesson: Freedom Creates Impact
The Deferred Sales Trust isn’t just a tax strategy it’s a freedom strategy. It allows investors to:
- Exit highly appreciated assets without immediate tax consequences
- Reinvest in what matters most whether that’s new ventures, family time, or philanthropy
- Design a legacy plan that keeps wealth flowing toward meaningful causes
As Brett summarized on the podcast, “Using a proven tax deferral strategy like the DST is the best way to grow your wealth and your impact. It’s about freeing your time and energy to use your gifts to help others.”
Key Takeaways for Investors
- Timing beats location — Wait for the right market conditions instead of chasing hype.
- Avoid overleveraging — Debt can amplify returns, but it can also amplify risk.
- Flexibility equals freedom — The DST gives you breathing room 1031 exchanges can’t.
- Use wealth for good — True success is measured not by how much you make, but by how much you give back.
Final Thought
If you’re a business owner or real estate investor facing a major sale, it’s time to reimagine how your wealth can work for you and for others.
With the Deferred Sales Trust, you can keep your capital compounding, invest when it’s smart, and use your success to make a difference.
To learn more, visit CapitalGainsTaxSolutions.com and discover how you can build freedom, create impact, and reimagine your real estate wealth.