The One Phrase That Can Ruin a $10 Million Business Sale

“When I sell the company, then I’ll be happy.” Psychotherapist Jo Swann says that one phrase is the most reliable predictor of a miserable exit. She would know. She made her money in the 90s, retired to an oceanfront apartment in Borneo, and fell straight into an existential crisis. 

In this episode of Built to Sell Radio, part of our popular After the Deal series, Swann explains why the trap survives the wire transfer, and you discover how to: 

• Spot the “when I” trap, the language pattern that puts your happiness permanently in the future, even after the money lands 

• Recognize why the drop in mood after selling your company is chemical, not circumstantial 

• Tell the difference between genuine purpose and ego dressed up as giving back 

• Use boredom tolerance as a litmus test for how ready you are to exit 

• Identify the five biological drives your phone has hijacked, and why they make the good life feel unbearable 

• Avoid passing the achievement-equals-love wiring on to your kids 

• Apply Carl Jung’s two halves of life to figure out what comes after the business 

Show Notes & Links

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Definitions

Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.

Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.

Roll Over Investor: A rollover investor, in the context of selling a business, refers to an individual or entity that rolls some of their proceeds from the sale with the buyer. This strategy allows the seller to defer capital gains taxes and potentially leverage their expertise or resources in a new venture.

About Our Guest

Jo Swann

Jo Swann is a licensed strategic psychotherapist who specializes in helping entrepreneurs navigate the emotional and psychological challenges that often follow a successful business exit. After building wealth in the IT industry during the 1990s and retiring early, Jo experienced firsthand the unexpected loss of identity and purpose that can accompany financial freedom. Today, she works with founders, executives, and high performers around the world, helping them build lives that are as meaningful as the businesses they leave behind.