Canadian Co-founder Brothers Bootstrapped to a $40 Million Exit

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I always love?Bootstrapping to Exit?stories. AppArmor Co-founder Chris Sinkinson and his brother bootstrapped a wonderful startup and sold it for $40M. Read on for the nuances.

Sramana Mitra:?All right, Chris, let’s start at the very beginning of your journey. Where are you from? Where were you born, raised? What kind of backgrounds?

Chris Sinkinson:?I’m from a small town called Kingston in Canada located about halfway between Toronto and Montreal. Our parents had three boys. I was the oldest. I have a brother who’s three years younger than me, who’s a very successful researcher. He’s currently working for the Kellogg School of Management in Chicago. My youngest brother, David, is the one that I ended up starting my company with.

Here’s an interesting story. There’s a ten year gap between me and David. I was very much into technology. I did an undergrad in Computer Science. You must remember the dot-com bubble. I was in my second or third year when IBM was on campus and told us Computer Science students, “Just quit now. We’ll move you to the big city. We’ll get you an apartment. We don’t even need your degree. We’ll just hire you right now.”

Me being very wise, I said to myself, “Well, no way! I’m going to get my degree, and then they’re really going to have to pay me a lot more when I graduate.” In the meantime, the dot-com bubble kind of burst.?I graduated in 2002, which was a little bit after the peak of tech. There weren’t a lot of jobs. I don’t know if you remember Nortel.

Sramana Mitra:?Were you still in Canada?

Chris Sinkinson:?Yes, I was still in Canada when I did my undergrad.

Sramana Mitra:?The optical networking boom was also starting to burst.?

Chris Sinkinson:?Exactly. So all of a sudden freshly minted Computer Science Chris was up competing with very experienced people that had been let go from Nortel and other big firms like that. So it was a little bit tricky finding a job at that point. So I did what any good person would do and I started the business instead. It was essentially just me for the first ten years.

Sramana Mitra:?Were you were doing services work?

Chris Sinkinson:?I was doing software development. I had built a document management product. I built some e-commerce things. I’d written a lot of code, but I had a very difficult time capturing actual value from it. I probably was too much of a developer and not enough of a marketer. I didn’t do a good job of selling it.?I always felt that my products that I was building were excellent and could compete with the best in the world, but I just never got the value out of it because I didn’t have a salesforce. I didn’t have an effective way that I could consistently go to market and sell those products.

So fast forward to about 2010 when I decided to go back to school and get my MBA because I needed to figure out why am I not getting more out of all these great products I’m building. I completed my MBA the same time as David was finishing his undergrad degree. He was at the same school that I went to for my MBA. We would have lunch every day, and I’d be telling about all these great things that I was learning about in the MBA program.?

He was a student, but he was the business manager for the campus newspaper and was implementing some of the things that I was telling him about from business school. So he got the business bug and we started working together. We actually built a mobile app for newspapers.

It wasn’t a great market. It was definitely one of those markets that was headed in the wrong direction. But we started incubating some ideas together and a year later David ended up taking the same MBA program that I had just completed. He’d actually taken a job after he finished his MBA with a large telecom and did that for about eight months and decided it wasn’t for him.

This was about 2013. We decided to work on our side hustle business ideas. We both moved to Toronto. Toronto’s a big city, obviously closest to us, and a bit of a tech hub. We took all our worldly possessions with us and got an office space and a small incubator there. We kept working on these products. Our public safety product AppArmor, which was actually one of the ideas that we incubated at the MBA school ended up being the winner.

It started to gain more traction than the others,?so we decided to shed some of the other product lines. We sold some of them for a very small amount of money. We just shut down a couple of them and focused all of our efforts on the AppArmor product. It worked extremely well.

Our conversation continues here.

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