Podcast

Zen and the Art of Real Estate Investing with Jonathan Greene

288: Building a Capital Gains Tax Exit Plan with Brett Swarts

In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Brett Swarts, founder of Capital Gains Tax Solutions, to explore strategies for minimizing capital gains taxes when selling real estate or business assets.

Brett Swarts is the founder of Capital Gains Tax Solutions, specializing in advanced strategies to help investors defer or eliminate capital gains taxes. With extensive experience in structuring Deferred Sales Trusts and other exit strategies, Brett has guided numerous real estate and business owners in building tax-efficient, long-term wealth plans.

Brett explains how the Deferred Sales Trust (DST) offers a flexible alternative to traditional 1031 exchanges, providing investors with greater control over timing, liquidity, and investment choices while deferring taxes in a manner that is legally compliant under IRS guidelines. Brett outlines the mechanics of a DST, detailing how proceeds from a sale can be structured to defer capital gains taxes and reinvest in a variety of assets. You’ll get insight into the advantages of a DST over standard tax-deferral methods, including reduced pressure to time the market, expanded diversification opportunities, and the ability to preserve wealth across multiple investment vehicles.

Jonathan and Brett also discuss common misconceptions about tax-deferred strategies, emphasizing the importance of understanding legal structures and working with experienced professionals. The conversation highlights how these tools can fit into a broader estate and legacy planning framework, ensuring that wealth is transferred efficiently to future generations while maintaining flexibility for investors today.

Several real-world examples demonstrate how investors have effectively utilized DSTs to manage risk, maintain cash flow, and safeguard portfolio value in dynamic markets. Brett emphasizes that while a DST can benefit many investors, it is particularly effective for those with significant gains, complex portfolios, or long-term wealth preservation goals. The discussion concludes with actionable guidance on evaluating whether a DST aligns with an investor’s exit strategy and long-term financial objectives.

By the end of this episode, you’ll understand how to approach capital gains tax planning strategically, integrating DSTs into their broader real estate and business investment strategies. Jonathan and Brett provide a clear framework for deferring taxes, diversifying holdings, and protecting wealth, enabling investors to make informed decisions that align with both their financial and personal objectives.

In this episode, you will hear:

How the Deferred Sales Trust works as an alternative to 1031 exchanges
Ways to defer capital gains taxes while maintaining investment flexibility
Strategies for diversifying proceeds and protecting portfolio value
Common misconceptions about tax-deferred exit strategies
How estate and legacy planning can integrate with a DST

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