#159 - How Deferred Sales Trusts Work with Trevor Kuresa
About this episode
The episode discusses the Deferred Sales Trust as a strategy for deferring capital gains with insights from tax attorney Trevor Kuresa.
Tait Duryea and Ryan Gibson sit down with Trevor Kuresa to unpack the Deferred Sales Trust, a lesser-known strategy for deferring capital gains after selling a business or highly appreciated asset. Trevor explains how the structure works, why it differs from a 1031 exchange or monetized installment sale, and when the costs, timing, and compliance rules make sense. For pilots, real estate investors, and business owners thinking about a future exit, this episode offers a practical look at tax planning before a major transaction. Trevor Kuresa is a corporate and tax attorney specializing in mergers and acquisitions, fractional general counsel, and advanced tax strategies for business owners and high-income professionals. With experience in tax structuring, legal transactions, and corporate counsel work, Trevor helps clients evaluate strategies for reducing or deferring capital gains and income tax. Show notes: (0:00) Chamonix race recap (2:14) Deferred Sales Trust intro (4:47) Trevor’s legal background (6:10) Tax strategy for pilots (9:37) Deferred sales trust explained (13:50) Rental property example (17:26) Best use cases (21:10) Tax deferral mechanics (25:15) IRS rules and risks…
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