Why This $5M Business Sold for $25M Cash

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 

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.

Re-Trading: This occurs when a buyer attempts to renegotiate the purchase price of a deal after initially agreeing to one. It is often seen unfavorably as it occurs after due diligence, seemingly exploiting newly discovered information.

TAM: “Total Addressable Market.” It’s a business term that represents the overall revenue opportunity available for a product or service in a specific market. To put it simply, TAM is the maximum amount of money a company could potentially make if they captured every single customer in a given market who might be interested in what they’re selling.

About Our Guest

Sharon Gillenwater

Sharon K. Gillenwater is a San Francisco-based tech entrepreneur, author, and speaker who bootstrapped her company Boardroom Insiders — an INC 5000 SaaS business intelligence platform — from a consulting practice to a $25 million exit when it was acquired by Euromoney LLC in 2022. She chronicles that journey in her debut book, Scaling With Soul: How I Built & Sold a $25 Million Tech Company Without Being an A**hole, which traces her path from working-class roots and waitress jobs to the top of the tech industry — all without venture capital and without compromising her values. Today Sharon advises and mentors early-stage founders, speaks at entrepreneurship events across the country, and is building her next company, ExecutiveIQ, with a mission to make entrepreneurial success more accessible to everyone.