How 2 Brothers Bootstrapped AppArmor to a $40M Exit — The Answer That Almost Cost Them $20M
March 20, 2026 |
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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.
In this episode, you discover how to protect yourself when a buyer asks a question you weren’t expecting.
You’ll learn:
- Why one offhand answer to an acquirer nearly cost the Sinkinson brothers $20 million
- How turning down a $20 million offer led to a $40 million all-cash deal a year later — with no earn-out
- The unexpected struggles David faced after the exit — and what nobody tells you about life after a big sale
- Why David thinks giving employees equity is a mistake — and what he believes works better
- The co-founder dynamic that made the Sinkinson brothers work — and what most founding partnerships get wrong
Show Notes & Links
Connect with David on LinkedIn
Definitions
Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.
Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.
Letter of Intent (LOI): This document outlines the basic terms and conditions of a deal before a formal agreement is drawn up. It serves as a mutual commitment between the buyer and the seller to move forward with the transaction on the agreed-upon terms.
About Our Guest
David Sinkinson
David Sinkinson is the co-founder of AppArmor, a company developing custom-branded safety apps and emergency notification systems. Founded in 2011, AppArmor was acquired by Rave Mobile Safety this year. David’s journey began while working at his alma mater, Queen’s University, where he identified gaps in campus safety and pitched the idea of a custom-branded safety app. This initiative led to the creation of AppArmor, which now helps keep millions of people safe during crises. Before AppArmor, David worked at a major telecommunications firm in Canada, launching customer-facing marketing retention projects.
