Before You Exit: What I Wish Someone Had Told Me About Life After the Deal

By Anne-Wallis Droter, EO Staff Writer

Facing Post-Exit Challenges

As an entrepreneur, your business likely feels like an extension of yourself, since you poured your heart and soul into building it. So, when you receive an unexpected offer to buy your company —and it’s so significant that you can’t refuse it — you don’t necessarily have time to think and strategize about what your life might look like after your exit.

That’s exactly what happened to Steven Kapor, an EO Cincinnati chapter member who got an unsolicited offer from private equity (PE) to sell his company. He received the offer just after he launched a new game-changing software product that he was inspired to create after attending EO’s Jumpstart January program. (Read From Insight to Exit: How Jumpstart January Helped Me Sell for 50% More for details about Kapor’s inspirational journey.)

An Unexpected Exit

As background, Kapor’s business, Fundriver Inc., offered a software platform that helped universities and non-profits track donations from an accounting perspective. His idea, sparked by EO Jumpstart, was to create a new software platform focusing on the donor side of the equation, to help clients track exactly how funds from each major gift were used and who benefitted.

It was a game-changer: When Kapor’s clients showed major donors exactly how their funds were used, and even met students their generosity had impacted, donors were more likely to donate again.

The new donor-focused software attracted the PE firm that offered to buy Kapor’s company.

During sale negotiations, the PE firm insisted that they wanted to keep Kapor and his institutional knowledge as an active employee after the sale.

Post-Exit Challenges

Kapor experienced all of the post-exit challenges you can imagine, plus some:

• A few months after the sale, the PE firm’s promise to keep Kapor as a valued contributor fizzled. Kapor was laid off, along with several other long-time employees.
• Unexpectedly, Kapor’s marriage ended shortly after his business exit. He later learned that was not an uncommon occurrence. He had more time to spend with his young children, but  was not exactly experiencing his anticipated post-exit life reconnecting and travelling with his spouse.
• An added sorrow: His mother died that same year.

The Support of EO Forum

With so many negative outcomes to navigate, Kapor feels fortunate that he was a member of an EO Forum of other entrepreneurs who provided a sounding board and supported him as the hits kept coming.

“EO helped me get through it all. My Forum was instrumental in helping me process all of that stuff when I was just trying to keep the ship from sinking,” he recalled.

Now that a few years have passed, Kapor views that episode of his life as something that helped him grow even stronger.

“I grew, my kids grew, and now we are all in a much better place,” he shared. “That’s the real story of my exit: It was a rough road, but in some ways, it worked out for the best.”

What I Wish I Knew Before I Sold

Kapor had no prior knowledge that the period after selling a business can be one of the most difficult transitions of an entrepreneur’s life — especially for those who did not have time to properly strategize what post-exit life might look like.

Why is exiting such a difficult transition? Well, after working and sacrificing to build your business, an entrepreneur may feel like the company is an important aspect of their identity. That makes selling it extremely stressful.

In addition, the expectation to stay involved in the business doesn’t always turn out as hoped.

Finally, the speed of entrepreneurial life downshifts significantly after the sale, when founders go from days full of meetings and strategy to days with nothing more pressing to do than rearrange your desk.

How to Navigate Your Exit

John Rood, an EO Chicago elumni and author of Beyond the Exit, has interviewed more than 200 post-exit entrepreneurs, many of whom are EO members. Rood explained that it’s very common for entrepreneurs to experience an identity crisis after a business exit, especially if they haven’t formulated a comprehensive exit strategy.

Rood presented his findings in an EO virtual learning event, Beyond the Exit: Lessons From 70 Post-Exit Entrepreneurs, which you can watch on the EO Learning Platform.

Rood shared his exit insights several years after Kapor sold his business, but Kapor’s experience underscores the importance of making a plan for your business exit before engaging a sales broker.

“The happiest group of entrepreneurs I interviewed started thinking about what post-exit life would look like before the sale,” Rood explained.

“I wish I had known that!” Kapor said.

A New EO Executive Education Program: Navigating Your Exit

If you are an EO member who anticipates a business exit in the near future, EO recently introduced a new Executive Education program that could help you avoid a challenging exit: Navigating Your Exit, presented by EO with Harvard Business School.

Whether you plan to exit in two years or ten, this intensive, four-day program will help you understand how to build value, explore exit options, and prepare yourself and your business for a successful transition and legacy in order to make your next phase the best ever.

Registration is now open for the inaugural class of Navigating Your Exit, 2–5 September 2025 in Boston, Massachusetts. Just 80 spots are available; register today!