Sean Whitehead is a structured settlement consultant and content contributor at StructuredSales.org. He writes about using structured installment sales under IRC §453 to defer capital gains tax on the sale of businesses, investment real estate, professional practices, and other appreciated assets.

His work focuses on translating the mechanics of the installment method — gross profit percentage, payment scheduling, assignment companies, and carrier-backed funding — into plain-English guidance that sellers and their CPAs, attorneys, and brokers can act on. Sean's articles aim to give a balanced view of both the benefits and the limitations of deferral strategies rather than a sales pitch.

Areas of focus

• Structured installment sales and the IRC §453 installment method
• Capital gains tax deferral on business and real estate sales
• Comparisons with 1031 exchanges and deferred sales trusts
• State-specific capital gains considerations
• Risk, carrier strength, and compliance for deferral structures

Recent articles

• What Is a Structured Installment Sale? A Complete Guide
• IRC §453 Explained: The Tax Law Behind Structured Installment Sales
• How Is a Structured Installment Sale Taxed? (With Examples)
• Structured Installment Sale vs. 1031 Exchange: Which Is Better?
• How to Minimize Capital Gains Tax When Selling a Business (2026)
• Browse all resources →

Articles by Sean Whitehead are for general education and do not constitute tax, legal, or financial advice. Always confirm current rules with your own CPA or tax attorney before structuring a transaction.