Selling a business or a portfolio can be the largest tax event an owner faces, and structure matters as much as price. These scenarios illustrate the questions that arise in four common exit situations, using hypothetical facts and simplified numbers.
All scenarios in this category are composite hypotheticals. None describes a real transaction, buyer, or owner. Figures are assumptions for teaching, not benchmarks. Tax rates, exclusions, and thresholds change, so every scenario points you to current rules and your advisor.
How to Use This Category
If you own an S corporation and are thinking about a sale, start with the asset versus stock scenario. If you are a founder of a corporation that may be eligible for special stock treatment, read the qualified small business stock scenario. If a buyer proposes to pay you over time, read the installment sale scenario. If you own rental properties and plan to exit, read the portfolio scenario for a comparison of a taxable sale and an exchange.
Exit planning benefits from time. Many of the decisions discussed in these scenarios must be made years before a sale, not after a letter of intent arrives.
Because sale terms are negotiated, the scenarios show how structure and allocation change the after-tax picture, not what any buyer will accept.
Guides in Exit Planning Scenarios
Want to Talk Through Your Own Situation?
These scenarios are illustrations only. Book a discovery call with AE Tax Advisors to discuss the facts of your own business or portfolio.
Book a Discovery CallEducational purposes only. This page is an illustrative educational scenario, not tax, legal, or accounting advice, and it does not describe a real client or a real result. Tax laws change and outcomes depend on individual facts, so consult a qualified professional before acting. No result is guaranteed.