Built to Sell Radio

David Sinkinson and his brother Chris built AppArmor over eleven years without taking a single dollar from outside investors. They bootstrapped it by running side businesses, plowing the profits back in, and staying lean through long sales cycles and compliance-heavy buyers. By the time they were ready to sell, they had over 250 universities on the platform and roughly $6 million in annual recurring revenue — profitable, with no cap table to split with anyone. 

Then an acquirer asked them a simple question, and they answered it. That answer nearly cost them $20 million. 

Recorded live at the Value Builder Summit, this is David Sinkinson's second appearance on Built to Sell Radio. This time he goes beyond the mechanics of the deal — into the surprising struggles he faced after the sale, and a take on employee equity that is going to challenge what most founders believe.

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

Most founders approach a sale with one goal: get the highest price possible. But Mark Ferrer argues that focusing only on price can lead to the wrong deal, the wrong partner, and a painful transition after closing. 

In this episode of Built to Sell Radio, John Warrillow talks with Ferrer about what he has learned after moving from founder to buyer, and why every owner needs to know whether they are a transactional, transitional, or transformative seller before they go to market. In this episode, you discover how to identify your seller type before a buyer does it for you. 

You'll learn: 

Why a transactional founder who insists they just want the money often turns out to be something else entirely — and why getting that wrong poisons the deal 


What a buyer learns about you when they ask whether you would sell to your biggest competitor for the same price 


Why the multiple is just the starting point, and how cash at closing, seller financing, and rolled equity can swing the real outcome by more than most founders expect 


How Mark lost 8 to 14 percent of his own deal proceeds not because of bad faith, but because he did not ask the right questions about his rolled equity 


Why pushing for agreement after a sale closes is the fastest way to destroy a partnership — and what to focus on instead 


What working capital and normalized earnings actually mean, and why founders who gloss over both almost always regret it 


How to clarify the role you want after closing before it becomes the source of tension no one saw coming

Most business owners assume their buyer will be a private equity group or a strategic acquirer. But if you run a smaller business in a niche category, the person most likely to buy you is an individual — someone who likes what you've built, can see a path to improve it, and is willing to put their own name on the line to finance the deal. 

This week on Built to Sell Radio, Joe Soelberg joins the Inside the Mind of an Acquirer series to pull back the curtain on what that kind of buyer actually looks like — and what it means for you as a seller. Listen and you discover how to: 

spot the tells of a real buyer versus "capital partners" theater 


pressure-test proof of funds without turning it adversarial 


use a seller note as a credibility filter, not just a concession 


understand why individual buyers consistently misread the cash down, seller note, bank structure and how to use that to your advantage 


ask questions that surface risk early, before lawyers get involved

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 building a company and selling one require two entirely different skill sets. 

In this episode of Built to Sell Radio, Andrew walks through the pivot that saved his business, why his VC backers stayed on board, and the exact moment he realized that a "short buyer list" is a dangerous trap for founders. 

Listen in to discover how to: 

Spot the "hidden ceiling" in a business that looks like it's doubling—right up until it isn't. 


Move a cap table from a failed bet into a new one without lighting your professional relationships on fire. 


Understand liquidation preference in plain English (and why it can erase a founder's take-home pay at exit). 


See why a banker's real value isn't just managing the process—it's forcing pressure and widening the field of potential acquirers 


Avoid the "I can sell this myself" mindset that often results in a year of free research for buyers and zero leverage for you.