Convertible Notes and Cap Table Reality

When Sharon Gillenwater built Boardroom Insiders, she was doing something nobody else wanted to do: manually researching the personal work styles, business initiatives, and habits of Fortune 500 executives so that enterprise sales teams could finally get a meeting with the C-suite. It was hard, painstaking work — and that was exactly the point.

After more than a decade of bootstrapping, consulting on the side to fund payroll, and raising just $275,000 from three people she knew personally, Sharon sold Boardroom Insiders to London-based public company EuroMoney for $25 million — all cash at close, no earn-out. In this episode, you discover how to build and sell a business where customers love you so much they follow you from company to company.

You'll learn:

• Why a cold call from a PE firm offering $48 million was actually the worst thing that could have happened to Sharon — and what she did instead

• The one overheard side conversation that changed her negotiation posture entirely and helped her push from a $17–20M offer to $25M

• Why Sharon insisted on all cash at close — and why her angel investor told her a lower number in cash beats a higher number with strings attached

• What convertible notes look like after a decade — and why her investors converted their notes just six months before the sale

• Why Sharon cried on her birthday, the day she was quietly walked out of the company she had spent 13 years building

• How she watched the acquirer run Boardroom Insiders into the ground, tried to buy it back — and then decided to rebuild from scratch anyway

• The land-and-expand growth strategy that took Boardroom Insiders from zero to $5 million ARR without ever cracking the demand generation problem