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You know that we believe in the Bootstrapping Using Services methodology quite firmly. Here is Square Root Founder Chris Taylor’s story from 2016 – a great example of how and why bootstrapping using services works. In 2021, CDK Global acquired Square Root for $25 million.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Chris Taylor: I grew up in rural West Virginia. You won’t meet a lot of entrepreneurs out of West Virginia. When I was four, my father passed away, so my brother and I were raised by our mother. She did a fantastic job. My brother is also another entrepreneur. In college, I went to Carnegie-Mellon and studied Computer Science, Psychology, and Mathematics.

Sramana Mitra: When did you come out of Carnegie-Mellon?

Chris Taylor: I graduated in 1995 and that’s when I moved down to Austin, Texas, to work for a startup called Trilogy.

Sramana Mitra: How long did you stay at Trilogy?

Chris Taylor: I was there for 10 years. When I joined Trilogy, I came down as the kid who joined their two-person automotive team. They had a Sales and Business Development person. I joined to be the technical kid. Over the next 10 years, that team grew to be the largest vertical in Trilogy. It had more than 100 employees. I had that journey from a single contributor technical person to where Trilogy did a lot of startup spinouts.

Sramana Mitra: By the time you left, Trilogy had already exited?

Chris Taylor: They actually never exited. Trilogy was always privately-held. Eventually, the founder bought all the stocks back and still runs it today.

Sramana Mitra: I didn’t know that actually. What prompted you to leave? What were you looking for after 10 years?

Chris Taylor: It was the time to start my own thing. I always knew that I wanted to do entrepreneurship. I had some money in the bank. I had some flexibility. I had skills and relationship both on the potential client side as well as the team. The interesting part of that story was I didn’t have the big idea. I was the entrepreneur without an idea trying to figure out what’s next.

Sramana Mitra: What was next?

Chris Taylor: I went back via some of the relationships I had, primarily in the automotive and the startup industry. I went to a bunch of the folks who were fantastic at Trilogy and said, “If I can get Elizabeth, would you hire us to solve this problem?” Then I went to Elizabeth and said, “I just got hired by Nissan. I want you to come work with me.” That’s how it started. We had a couple of different product ideas those first couple of years.

Sramana Mitra: Who’s Elizabeth?

Chris Taylor: Now, she’s our COO.

Sramana Mitra: She was your colleague at Trilogy?

Chris Taylor: Yes. She knew a lot of the folks who I knew.

Sramana Mitra: You and Elizabeth paired up to start this company?

Chris Taylor: Kind of. I was the Founder and CEO. I had a bunch of hired talents that I was paying as consultants to come in. I was the only employee for the first three years.

Our conversation continues here.