Business Exit
The 18-month window: planning the business exit you actually want
Most owners start exit planning a year too late. Here's the 18-month window — and the tax decisions that get locked in early.
Scott Stevens · May 2026
Organized by practice track, not by publication date.
Most owners start exit planning a year too late. Here's the 18-month window — and the tax decisions that get locked in early.
Section 1202, charitable LLCs, and stacking strategies — what actually moves the needle on a $20M+ exit, and what just sounds good.
Different buyers, different deal structures, different post-close tax bills. A practical comparison from the seller's seat.
A short, sequenced list of decisions that should happen — and a longer list of the ones that absolutely shouldn't.
The election window is narrower than the SSA documents suggest. We walk through the breakeven math for three common scenarios.
Inheritance conversations go better with structure. A short framework we use with families navigating a major transition.
When concentrated company stock meets a real retirement date, the math changes. A framework for dual-income tech households at 55+.
What the rule does, what it doesn't, and the structure mistakes that cost meaningful tax dollars in year one.
Pre-IPO RSU acceleration on a change of control: the modeling, the tax surprise, and the cash management problem nobody mentions.