In this episode, we sit down with Brian Dukes, founder of Exitwise, to unpack the real mechanics of selling a business in the lower-middle market—before an investment banker ever gets involved. Brian works hands-on with founders to help them understand value, prepare for liquidity events, and avoid the costly mistakes that derail outcomes long before a deal is on the table.

We dive into how Exitwise helps owners think clearly about timing, readiness, and optionality; the most common blind spots founders have when approaching a sale or recap; and how today’s buyers are underwriting risk in a more selective M&A environment. Whether you’re years away from an exit or quietly evaluating your options now, this conversation offers practical insight into how smart preparation drives better outcomes—and better leverage—when it’s time to transact.