Preparing for a Clean Exit: Legal Lessons from Real-World Business Transitions

In this episode of Poised for Exit, we welcome James Olsen, Partner at Seiler Law PLCC, for a practical discussion on the legal realities business owners face when preparing for a sale or transition.

James shares insights from advising Main Street and lower middle-market business owners, highlighting common legal pitfalls that can delay or derail an exit. From handshake agreements and undocumented contracts to buyer due diligence, earn-outs, and post-closing obligations, this episode breaks down what sellers need to address before going to market.

Our conversation covers how to prepare foundational legal documents, evaluate buyer fit, navigate seller carry and earn-out structures, and think strategically about post-closing involvement. James also shares what he’s seeing in the current deal environment and how business owners can position themselves for a smoother transition heading into 2026.

If you’re advising clients or preparing your own business for a future exit, this episode offers grounded, experience-driven guidance to help you reduce risk, protect value, and move forward with confidence.

Connect with James Olsen here

Connect with Julie Keyes, Keyestrategies LLC
Founder, Consultant, Author, Pod-caster and Instructor