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by Chris Taylor

I have a passion for entrepreneurship. It’s not only been my job for the last twelve years, but it’s also my hobby—I enjoy spending time mentoring and working to develop young entrepreneurs, bright with ideas and scared of the unknown. I would love for our daughters Zoe (3rd grade) and Shelby (2nd grade) to know the highs and lows of entrepreneurship that both my wife Teri and I have enjoyed (and endured!). And we often talk about how we as parents can raise them with the right skills to thrive as entrepreneurs, should they decide to take that route with their lives. I’m thankful for this opportunity to share some of my thoughts on how the curriculum at The Magellan International School is helping our children learn the key entrepreneurial trait of risk-taking, and opening a world full of problems to solve.

Learning to Embrace Risk 

Entrepreneurship is only possible through risk-taking and celebration of failure. Many of the International Baccalaureate (IB) attributes—communicating, inquiring, thinking—are hallmarks of great entrepreneurs, but the one foundational trait I our hope daughters can master is risk-taking. Fundamental to risk-taking is confidence, self-acceptance, curiosity and a large dose of vulnerability. And risk taking has always been hard for me…

I got off to a great start. As a kid growing up in rural West Virginia I launched my first entrepreneurial venture at 9 years old: the Taylor Turtle Ranch. Finding box turtles in the woods was the neighborhood’s summer pastime, and it was an enormous unmet need to keep those turtles somewhere safe. And so the Taylor Turtle Ranch was born. I cataloged each turtle brought to the ranch with a little red painted number so that we could track its name, where it was found, and the owner. Then, for only a dollar a month, each turtle-turned-pet had luxurious room and board in a hand-crafted pen in the woods behind my house with unlimited visitation. And the repeat business! We would find the turtles the next year with their numbers still intact — Dale’s pet “Speedy” had returned (that’s $1 a month, Dale). I was smitten! The spark of entrepreneurship was planted. But I realized I had much to learn, as it ends up a turtle eats more than a dollar’s worth of tomatoes and lettuce a month. Doomed to financial failure, the Taylor Turtle Ranch only made it two summers.

That’s when risk aversion took over.

3rd graders learning Agile methodology

It took me 25 years to start my next venture. Safely rooted in my college, I pursued a “safe” degree in Computer Science and Math—all the while the excitement of the Taylor Turtle Ranch burning quietly in my memory. Hired by Trilogy directly out of college, I slowly gained experience in business and sales, watching and learning from those around me. It was the mid-90’s in Austin and the city was rife with people taking risks, forming new tech companies and turning Austin into the tech city that it is today. But I stayed safely tucked into my job, watching and learning from the outside, taking small risks with clients, but working within the confines of someone else’s company. But memories of the Turtle Ranch began to glow brightly. And slowly I allowed myself to open to the idea of taking the leap, taking the risk, to starting my own company. And in 2006, I finally took the leap and formed Square Root.

In the early days, I was very conservative and safe in many of the decisions I made at Square Root. And because of that we had a much slower start than was necessary. I was petrified to fail and scared to invest. Looking back now twelve years later, I realize I’d learned the value of risk taking and failure the hard way. Had I the guts to take the hard risks twelve years ago that I take now, I truly believe the company would be in a much different place.

And it’s not just me. Risk-taking is such a hard thing for most of the Square Root team. We dedicate a huge amount of energy weaving risk-taking into the fabric of the company. For example, every month we have a “Fail. Learn. Cake.” event where we kick off a happy hour with the best example of something that didn’t work, but was a great learning event (and then we celebrate with cake!). Even with all this focus, it is hard to teach risk-taking to our team. I firmly believe if we can give our children the room to try and fail and try again when they are young, we will prepare them for all the challenges of life, including becoming entrepreneurs. I’m thankful that Magellan gives our kids that space and encouragement to take risk so they take a much more direct path to success and happiness than I did.

Conscious Entrepreneurship on a Global Scale

I didn’t know much about the IB curriculum when Teri and I first decided to send our daughters to Magellan. However, I have always had a deep belief that a global perspective and ability to communicate were going to define the leaders of their generation. We were very drawn to the Magellan focus on language, diversity, and inclusion.

I recently met Raj Sisodia, founder of Conscious Capitalism and talked with him about how the world is changing faster than businesses are adapting. The average age is increasing, people are smarter and better educated than ever before, and the level of connectivity and access to information has skyrocketed. However, trust of big business has plummeted over that same time. Entrepreneurship and capitalism are going to need to adapt if we are going to tackle the world’s biggest problems.

After talking with Raj, I thought about how different the business challenges are going to be for the next generation of entrepreneurs, and just how great an opportunity for impact they will have. The opportunity to help lift the world out of poverty. The opportunity to build companies on a new economy of caring and thoughtfulness. These aren’t only amazing opportunities, but also amazing responsibilities for our children’s generation.

Rising to these challenges, opportunities and responsibilities of this century is going to take a special type of leader. A leader that understands global perspectives. A leader that can communicate and connect. A leader that cares. And a leader that’s not afraid of risk. That’s all I can hope for Shelby and Zoe, and why Teri and I are so supportive of the education and perspective they are getting at Magellan.

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About the author: Chris Taylor is the Founder and CEO of Square Root, a Store Relationship Management Software firm in Austin, TX. Square Root was recognized by Inc. magazine as one of the fastest growing software companies in the US and by Fortune magazine as one of the top small-to-medium size companies to work for in the US.  He and his wife Teri – entrepreneur and founder of Row on Austin – are active members of the Austin philanthropic community, supporting organizations such as The Magellan International School and Girlstart and proud parents of Shelby and Zoe.


Also published on Medium.