The Lifestyle Investor - Investing, Passive Income, Wealth

245: The Capital Gains Tax Strategy You’ve Never Heard Of (But Should Be Using) with Brett Swarts

Jul 3, 2025

Brett Swarts, Founder and CEO of Capital Gains Tax Solutions, shares his expertise in deferring taxes on appreciated assets. He reveals how the Deferred Sales Trust can enable investors to cash out without incurring capital gains taxes, unlocking financial freedom. The discussion highlights the limitations of 1031 exchanges and advocates for a flexible, strategic approach to tax mitigation. Brett empowers listeners with actionable insights to enhance wealth via effective tax strategies and investment planning.

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ANECDOTE

Brett's 2008 Financial Struggle

Brett Swarts shares his personal story of financial struggle during the 2008 crash while working at Marcus and Millichap.
He learned the importance of tax strategies firsthand and found his calling helping others avoid the same mistakes.

INSIGHT

Why DSTs Matter Most

Most investors want truly passive income that generates freedom and impact through compounding returns.
Deferred Sales Trusts (DST) are flexible, offering liquidity, diversification, and ability to reinvest in many asset types, unlike 1031 exchanges and Delaware statutory trusts.

INSIGHT

Comparing Tax Deferral Options

1031 exchanges only apply to investment real estate with strict like-kind rules.
Delaware statutory trusts offer passive investments but with lower returns, high fees, and lockup periods.
Deferred Sales Trusts allow investing in nearly any asset with more control and flexibility.

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What if you could cash out of any asset—without paying capital gains tax—and use the full value to create lasting financial freedom?

That’s exactly what Brett Swarts helps high-net-worth entrepreneurs and investors do every day—using the Deferred Sales Trust (which is what today’s episode is all about).

Brett is the Founder and CEO of Capital Gains Tax Solutions, a firm that’s closed over $500 million in Deferred Sales Trust and commercial real estate transactions. As a DST Trustee and expert in capital gains tax deferral, Brett equips clients and advisors with proven strategies to defer millions in taxes on the sale of highly appreciated assets.

While 1031 exchanges and Delaware Statutory Trusts serve a purpose, they often come with rigid rules, long lock-up periods, and limited flexibility. The Deferred Sales Trust, on the other hand, unlocks what most investors really want: tax deferral, liquidity, diversification, and the freedom to reinvest in nearly any asset.

Whether you're selling real estate, a business, crypto, or any other asset, this conversation could save you millions in taxes, so you won’t want to miss it.

In this episode, you’ll learn:

1.) How the Deferred Sales Trust works—and how it lets you legally defer capital gains, income, and estate taxes.

2.) The hidden downsides of 1031 exchanges and Delaware Trusts—and why many investors are moving to a more flexible strategy.

3.) How to reset your depreciation schedule after a sale to boost cash flow and reduce future taxes—without the pressure of like-kind rules.

Show Notes: LifestyleInvestor.com/245

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