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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