How to Sell Your Business Without Losing Yourself
What business owners should be thinking about long before they ever put their business on the market, and how to build a business – and a life – that you’re prepared to move beyond.
October 21, 2026
How to Sell Your Business Without Losing Yourself
Selling a business is one of the biggest financial decisions an owner can make, but the financial transaction is only part of the story. In this episode, Adam Cox sits down with Taylor Fish, partner and co-founder of Lakeside Partners, to explore what business owners should know before entering a sale process—and what they should be thinking about long before they ever put their business on the market. Adam and Taylor also discuss the emotional side of selling a business: identity, self-worth, family expectations, purpose, retirement, and the surprising sense of loss that can come after closing. They explore why some sellers feel fulfilled after a transaction while others struggle—and why the “last dollar” isn’t always the most important outcome.
For business owners thinking about an exit someday, this is a conversation about much more than maximizing a sale price. It’s about building a business—and a life—that you’re prepared to move beyond.
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