When to Let Go: The Emotional Side of Selling Your Business – Lessons from Jonathan Bennett

The Exit - Presented By Flippa

Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- 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 -- Jonathan Bennett is an advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications. His coaching draws on 25 years of creativity and leadership success as a CEO, board member, and founder, and he is known for his deep-listening and his breakthrough solutions that create insights and new strategies. Jonathan on LinkedIn: https://www.linkedin.com/in/bennettjonathan/ Link to Private Podcast: https://clearlythen.com/listen Website: https://clearlythen.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/