When to Let Go: The Emotional Side of Selling Your Business
In this episode of The Exit: Host Steve McGarry sits down with Jonathan Bennett, advisor at Clearly Then and former founder of a successful B Corp consulting firm, to unpack the emotional journey of exiting a business—something rarely discussed, but profoundly impactful.
Jonathan shares his own story of selling his company through a gradual management buyout, and how the decision started with a casual walk in Dublin and a question from his wife. The episode dives into the often-overlooked inner challenges that founders face—identity loss, grief, and the fear of letting go. “The easy part is the legal and financial stuff,” Jonathan says. “The hard part is emotional.”
You’’ll learn:
Why selling at your peak (not in burnout) is critical
How to choose the right successor without hanging on too long
Why empty promises during a handover can backfire
What life after an exit looks like—and how to fill the void with purpose
Smart negotiation tips, including how to uncover the real motivations of a buyer
Whether you’re planning to exit soon or just building for the long game, Jonathan’s mix of practical wisdom and emotional intelligence will give you a fresh perspective on what it really means to walk away from something you built.
“Don’t wait until you’re depleted to sell—get off the stage while the crowd is still clapping.” – Jonathan Bennett
