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

The Exit - Presented By Flippa

Technology

5 • 2K Ratings

🗓️ 14 July 2025

⏱️ 29 minutes

🔗️ Recording | iTunes | RSS

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Summary

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/

Transcript

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0:00.0	Before we get into the exit today, I want to talk about the certified M&A advisors that are on Flippa.
0:06.1	If you are an operator right now running a business and you're thinking about exiting,
0:10.8	you are going to want to get a free online business valuation on the exit landing page.
0:16.7	Without a doubt, it is the smartest thing you can do to start a process and get yourself organized.
0:23.0	So you're going to go to the URL, flippa.com, slash exit, to check out more, and let's jump into
0:28.1	the interview.
0:29.3	Below and welcome to the exit presented by Flipup, the number one platform to buy and sell online
0:34.2	businesses.
0:35.2	Flipa manages over a billion in deal value annually and combines
0:39.4	expert buy and sell side advisory with its market leading valuation tool, deal room,
0:43.9	off market offering, market insights, an AI-based deal-by-deal matching engine. Now for the exit.
0:50.9	The exit is a 30-minute podcast featuring awesome entrepreneurs who have been there and they
0:54.8	have done it. The exit talks to operators who have bought and sold businesses of all different sizes.
1:00.3	You learn how they did it, why they did it, and get exposure to the world of exits. It's a world
1:05.1	occupied by a small few, but accessible to many. On this episode of the exit, I sit down with
1:10.4	Jonathan Bennett.
1:11.9	He is an advisor at Clearly Then and does an incredible job of breaking down the importance
1:16.6	of mentorship and really some of the tactics that he's learned from talking to hundreds
1:22.6	of different leaders all over the world about how they've gone through and exited their business.
1:28.7	One of my favorite parts of this conversation is the fact that he talks about his exit, where it's a
1:34.8	gradual selling to someone within his company that was in a leadership position. And it's a really
1:40.8	great story of a gradual, very smooth transition. And I think this is a good example of when the right time to sell is, who to sell to, and evaluating a potential buyer. And I think this was also a really good example on the emotional side of things. Jonathan talks about a lot of kind of ups and downs around emotions attached to selling a business,
	...

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