Most founders dream of the wire transfer. Sharon Gillenwater got hers — $25 million, all cash, no earn-out and spent the afternoon wandering in and out of furniture stores, talking to strangers, unsure what to do next. It was her birthday. It was also her last day.
Sharon built Boardroom Insiders over more than a decade, doing the kind of painstaking manual research on Fortune 500 executives that competitors simply did not want to do. Clients loved the product. Contracts expanded. People took it with them when they changed companies. But Sharon and her partner could not crack demand generation, and they could see a big tech crash on the horizon. They sold at the peak of the SaaS multiple market in 2022, and that crash came shortly after they closed.
In this episode, you’ll learn:
-
Why a PE firm dangling $48 million in a single phone call was the worst thing that could have happened to Sharon — and what her angel investor told her to do instead.
-
How Sharon pushed back on a $17–20M offer by writing a pointed email about strategic value and making her banker deliver it word for word.
-
Why all cash at close —even at a lower number — is almost always a better outcome than a higher price with earn-outs attached.
-
What it actually feels like to be walked out of the company you spent 13 years building, three weeks after closing, on your birthday.
-
How Sharon watched the acquirer run Boardroom Insiders into the ground, tried to buy it back, and then decided to rebuild from scratch.
Quote of the Week
We don’t know what our sales repeat button is. So that makes it very hard to scale sales.
