Ep 537 Why this $5M Business Sold for $25M

Ep 537 Why this $5M Business Sold for $25M

Author: John Warrillow March 13, 2026 Duration: 1:06:38

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 


For any entrepreneur, the idea of selling the company they've built is both a daunting prospect and a potential pinnacle of success. Built to Sell Radio, hosted by John Warrillow, steps into that complex space with a clear, practical focus. This isn't about abstract theory; it's a weekly conversation grounded in real experience. Every episode features a different founder who has recently navigated the sale of their business. The discussion goes straight to the heart of the matter: understanding the personal and strategic reasons behind the decision to sell. Listeners get an honest breakdown of what worked, from preparation and valuation to negotiation, and perhaps more importantly, the unforeseen pitfalls and mistakes made along the way. It’s that candid post-mortem, the lessons learned in the trenches of a transaction, that provides unparalleled value. By compiling these firsthand accounts, the podcast builds a comprehensive library of exit strategies and cautionary tales. Tuning in feels like gaining access to a private mastermind, where seasoned entrepreneurs share the unvarnished truth about cashing in their life's work. If you're contemplating your own eventual exit, this series offers the nuanced, peer-to-peer insights you need to think like a buyer, protect your interests, and ultimately, build a business that is truly desirable. Built to Sell Radio serves as an essential guide, transforming the opaque process of selling a business into a clearer, more manageable journey.
Author: Language: English Episodes: 100

Built to Sell Radio
Podcast Episodes
Ep 542 The 15X Multiple That Let Him Walk Away in 12 Months [not-audio_url] [/not-audio_url]

Duration: 1:08:04
At some point every founder needs to ask a simple question: is it better to own a big slice of a small pie, or a smaller slice of a bigger pie? In this week's episode, we hear from someone who chose a smaller slice of a…
Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway [not-audio_url] [/not-audio_url]

Duration: 45:42
Jay Richards spent five months deep in an acquisition process. He had a letter of intent. He had mentally checked out. He was planning what came next. Then issues surfaced in diligence and the deal collapsed. This week o…
Ep 534 Why a "short list" of acquirers may be a trap [not-audio_url] [/not-audio_url]

Duration: 58:17
Andrew McConnell built a SaaS company that helped vacation rental managers price homes like airlines using dynamic pricing based on demand. He eventually successfully exited, but not before learning the hard way that bui…
Ep 533 Inside the Mind of an Acquirer: The Anatomy of a Failed Deal [not-audio_url] [/not-audio_url]

Duration: 1:00:08
This episode is part of our Inside the Mind of an Acquirer series, and it unpacks the ETA (Entrepreneurship Through Acquisition) wave now flooding the market. For business owners, ETA is a double-edged sword. On the upsi…