Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M
Release Date: 03/20/2026
Ep 541 Mastering the Deal: 7-Figure Negotiation Mistakes Founders Make When Selling Their Business with MIT's John Richardson, Author of Never Settle
Built to Sell Radio
Most founders think they're not great negotiators. John Richardson thinks they're wrong. Richardson has spent decades teaching negotiation at MIT's Sloan School of Management and before that at Harvard Law, where he was an associate at the Harvard Negotiation Project and co-authored foundational texts with Roger Fisher and Howard Raiffa. His new book is called Never Settle. In this episode, you discover how to use a "best guess" about a buyer's motivations to get them talking, even when they're deliberately keeping their cards...
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Ep 540 From $40K to 8 Figures -- How Murray Kent Sold His Electrical Conduit Business for 6.2x EBITDA
Built to Sell Radio
Murray Kent had no background in electrical conduit fittings when he paid $40,000 for a four-person business that, as he put it, looked like a bit of a crack den. What he did have was Value Builder's 8 drivers -- pinned to the wall next to his desk as a literal road map for every decision he made. In this episode of Built to Sell Radio, you discover how to negotiate a clean exit with no earn-out complications and no equity rollover. You'll learn: Why posting the eight drivers next to your desk changes the decisions you make every day How Murray...
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Ep 539 Deal Collapsed at LOI, Sold for 6x EBITDA Anyway
Built to Sell Radio
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 on Built to Sell Radio, Jay walks John Warrillow through the full story of selling Imagen Insights, a qualitative research platform with clients like Visa, Google, and Amazon, and how you discover how to navigate two very different acquisition conversations and come out the other side with a deal you are genuinely happy with. ...
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Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M
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...
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Ep 537 Why this $5M Business Sold for $25M
Built to Sell Radio
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...
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Ep 536 Mastering the Deal: 3 Types of Sellers, 3 Very Different Deals — Which One Are You?
Built to Sell Radio
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...
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Ep 535 Inside the Mind of an Acquirer: When Your Buyer Is Risking Their House
Built to Sell Radio
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...
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Ep 534 Why a “short list” of acquirers may be a trap
Built to Sell Radio
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: ...
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Ep 533 Inside the Mind of an Acquirer: The Anatomy of a Failed Deal
Built to Sell Radio
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 upside, more buyers courting you means more choice, more urgency, and more liquidity. On the downside, many ETA buyers are first-timers who lean on heavy leverage and seller financing. If they misread your business or hit a snag they can’t handle, the part of the deal you financed can quickly become the part you never collect.
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Ep 532 Is Your Business Worth More Dead or Alive?
Built to Sell Radio
We often think of a "successful exit" as handing over the keys to a perfectly oiled machine—a business that is growing, profitable, and operationally sound. But what happens when the machine starts to sputter? What if the margins are too thin, the operations are exhausting, and you are simply burned out? It is easy to assume that a broken business model means a worthless company. But as this week’s guest on Built to Sell Radio proves, sometimes the individual parts are worth more than the whole. Meet Jason Patel. Jason...
info_outlineDavid 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.