Structured Installment Sales Explained with John Dudek | Ep. 32 | My SBA Loan Pro

About this episode

In this episode, Ryan Smith and John Dudek discuss structured installment sales as a tax-mitigation strategy for sellers of appreciated assets.

Are you preparing to sell a highly appreciated business, investment property, or even your primary residence, but dreading the massive tax bill that comes with it? In this episode of the My SBA Loan Pro Podcast, host Ryan Smith sits down with financial strategist John Dudeck to unpack a powerful, underutilized tax-mitigation tool: Structured Installment Sales. Instead of taking a massive tax hit in a single year, John explains how sellers can leverage this strategy to safely defer capital gains, wipe out certain investment taxes, and create a predictable, guaranteed income stream for retirement. Key Takeaways in This Episode: The Double Whammy: Why traditional cash-out exits destroy your hard-earned equity through maximum Federal, State, and Net Investment taxes. Traditional vs. Structured: Learn how structured installment sales completely remove the buyer from the repayment equation, replacing them with a secure, A+ rated insurance annuity. The "Playing Field": A breakdown of the 4 key players needed to execute this strategy safely and legally. The Primary Residence Loophole: Why structured installment sales are a game-changer for homeowners downsizing or moving out of state…

People in this episode

Host: Ryan Smith

Guest: John Dudek

Topics covered

• tax mitigation
• structured installment sales
• capital gains
• retirement income
• real estate

Keywords

• structured installment sales
• tax bill
• capital gains
• investment property
• retirement income

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