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Bootstrapping Using Services to $12 Million: Square Root CEO Chris Taylor (Part 1)

Posted on Thursday, Aug 4th 2016

You know that we believe in the Bootstrapping Using Services methodology quite firmly. Here’s yet another story of how and why it works.

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.

This segment is part 1 in the series : Bootstrapping Using Services to $12 Million: Square Root CEO Chris Taylor
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