Episode
Ep 538 How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M
- Podcast
- Built to Sell Radio
- Published
- Mar 20, 2026
- Duration seconds
- 4296
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Summary
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.