Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M

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.

You can listen to Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M online on Radio and Podcast. Open the player on this page to stream the available audio.

Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M is an episode from Built to Sell Radio by Hosted by John Warrillow, the creator of The Value Builder System™..

This episode is 01:11:36 long.

This episode was published on Mar 20, 2026.

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