#159 - How Deferred Sales Trusts Work with 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