Put Your Chin Strap On: Interview with David Tobin

Elizabeth Shea chats with David Tobin, Managing Partner of TobinLeff LLC, about how founders can best prepare themselves and their businesses for a successful exit. Drawing on his experience as both a former agency owner and longtime M&A advisor, David explains what buyers are prioritizing in today’s market, including sustainable growth, strong margins, leadership continuity, recurring revenue, and reduced founder dependency. The discussion dives into the realities of adjusted EBITDA, client concentration risk, due diligence, and how AI readiness is increasingly becoming part of buyer evaluations. David also breaks down the differences between strategic and private equity buyers, including platform acquisitions, rollover equity, and earnout structures, while emphasizing why deal terms often matter just as much as valuation. Throughout the episode, he offers practical insight into creating competitive buyer dynamics, choosing the right advisor, and navigating the intensity of the M&A process.