CHAPTER 10Four Exits Every Founder Needs to Make

How would you make business decisions now if you knew you were going to exit later?

“My husband wants to retire, but I don’t know if I can,” she said to me over Zoom with concern in her voice. While that might be an exciting proposition to some, it can invoke fear in entrepreneurs.

If I were new to understanding this paradox that entrepreneurs struggle with, or didn’t completely identify with what she was saying, I would have asked for more context. But this challenge is common for entrepreneurs, especially successful ones.

Erin built her firm from the ground up, turning it into a multi-million-dollar company with 50-plus employees and clients in every state. She has such depth, strength, and brilliance, and is completely down-to-earth and unaware of how she embodies each. She operates with so much ease and grace, it was almost as if she thought what she accomplished to this point was as common and unassuming as running daily errands.

The interesting thing about success is that it can bring an overwhelming sense of responsibility. Erin found herself buried in the day-to-day operations of the business, constantly juggling tasks, putting out fires, and wearing multiple hats to keep things running smoothly.

After years of pouring her heart and soul into building this company, she approached a certain point in her life where she and her husband began to entertain the idea of retirement. She knew that if she wanted her company to ...

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