Chris Taylor, CEO and founder of Square Root

Publisher and Reporter with Silicon Hills News

As a kid growing up in rural West Virginia, Chris Taylor launched his first entrepreneurial venture, ranching turtles.

In the summertime, he would capture turtles from the woods and create a “Turtle Ranch” that people would pay $1 to visit. At the end of the summer, he would let the turtles go. And do it all again the next year.

Today, Taylor is one of Austin’s most successful bootstrapped entrepreneurs. He founded Square Root, which ranked number two on Fortune Magazine’s list from Great Places to Work of the 25 Best Small Workplaces in the country.

Before launching Square Root in 2006, Chris held operational and strategic roles in several Internet and software companies, including TrueCar, US Digital Gaming, Pricelock, CarOrder, Wayfare Interactive, Brighthouse and Trilogy Software. He graduated Phi Beta Kappa from Carnegie Mellon University with degrees in Computer Science, Mathematics and Psychology.

“I started Square Root in 2006 and at that time I was an entrepreneur looking for an idea,” Taylor said.

He was 10 years into his career and he had some money in the bank. He had a lot of experience. But he didn’t have that big idea.

Initially, Taylor went to Nissan and they agreed to hire him to solve a problem for them in order management.

“The first idea ended up not to be a very good idea,” Taylor said.

But it did provide cash flow to build his team. And in 2009, the company started working on solving a problem for the electric car market, Taylor said.

But in 2010, four years after he started the company, Taylor hit on the big idea: Square Root makes store relationship management software for Nissan and other customers. Its software helps automotive sales managers run their dealerships. And the company has recently entered other markets in the retail industry.

Square Root not only pivoted a few times on its way to find the right product with the big idea, but it also changed its name from Oceanus to Square Root around 2009.

“Everyone thought we were an oceanography company,” Taylor said.

Square Root emotes math, data science and all the right things, Taylor said.

Today, Square Root has 55 employees and $12 million in revenue.

To date, Square Root has not needed outside capital, it’s been completely bootstrapped, Taylor said. Now it’s exploring options around raising growth equity money to really increase the size of the company, he said.

Austin is known for its scrappy, bootstrapped culture.

Taylor gives a talk on the three terrors of bootstrapping. The first one is coming up with the idea, Taylor said. The second is learning how to spend money to hire great talent and making the right investments, he said. And focus is the most important one.
Focus is one of the hardest things for a young entrepreneur to figure out, Taylor said.

It’s something he has struggled with too, Taylor said. Square Root had a product aimed at the electric vehicle industry, which is a personal passion of Taylor’s. When the new line of business, store relationship management software, started to take off, he made the decision to shut down that line of business. He fired 80 customers. He had to shift the company’s full attention to its flagship product. That’s when he first began to feel like a real CEO, he said.

At Square Root, Taylor has also focused on building a great company culture which has gotten the company national recognition.

One of Square Root’s five Craftsman-style bungalows that serve as its corporate headquarters in Austin.

Square Root’s campus is unique. It consists of five 1920s Craftsman-style houses, about a mile from downtown Austin. It’s dog friendly and the workplace has a “home away from home work” and family environment, Taylor said.

Maintaining its great company culture as it grows is extremely important, Taylor said. The big way to do that is to communicate regularly with everyone and empower the team to take over the culture and participate in it, he said. Square Root also writes down its values and its mission statement.
He also recommends entrepreneurs read Scaling Up and Traction. Those books are about how to get everything written down about mission and goals and how to put a framework in place to manage that, he said.

And Taylor is president of the Entrepreneurs Organization of Austin. As a sole founder, the organization has helped him to network and learn from other CEOs and founders in Austin.

“Surround yourself with people you can talk to,” Taylor said.

For more about how Taylor built Square Root into a profitable bootstrapped company in Austin, listen to the podcast.