Take the Leap: Interview with Bess Winston

In this episode of Branching Out, Elizabeth sits down with Bess Winston, the founder of The Winston agency. She talks about how one modest media relations project-turned-campaign laid the foundation for her to meticulously build a nationally respected boutique firm with a powerhouse team before ultimately selling her agency in 2022. Bess shares her journey with the humor and unfiltered honesty only an experienced founder can bring. She sheds light on the emotional jolt of parting with a company, the importance of protecting your people, navigating post-acquisition culture shifts, the advice she wishes she hadn’t ignored, and the moment she learned the hard truth: “When you sign your name, you’re done.” This episode is for anyone weighing a major inflection point — whether you’re debating when to slow down, when to scale up, or who really deserves a seat at your deal table.