Courtney Wiley Caldwell ’97

Courtney Wiley Caldwell ’97 is one of the youngest-known members of TMI’s 1893 Society for alumni and others who remember the school in their estate planning. A former director of digital marketing and innovation at Oracle, she is cofounder of ShearShare, a mobile app that connects salon owners and stylists to fill their empty stations and suites by the day, for which she was named to the 2019 Inc. Female Founders 100 list. Courtney is a member of the TMI Board of Trustees and of the Southern Methodist University Alumni Board. Recently, she shared her reasons for membership in the 1893 Society:

I had my first will drafted during the 2011-2012 school year, when I was in my early 30s. TMI and SMU are both named as beneficiaries because they are not just schools but ministries.

TMI was a big part of what has made me the leader I am today. It was the best place to learn how to lead from the back because you are allowed to fail: If we didn’t succeed as a unit or make the best choice for the group, we were given the opportunity to try again. Every administrator, every teacher, every coach at TMI inspired us to be our best selves.

While I was in my senior year at TMI, (as a staff officer in the Corps of Cadets), Sgt. Maj. (Turner) McGarity pushed me to think outside the box and reminded me that I could be and do whatever I wanted. In English, Mr. (Bob) Bell encouraged me to hone my communication skills; the mental stamina required in his class constantly challenged me. Mr. (Mario) Rivela pulled the best out of all of us, including remembering how to have fun. And Mrs. (Jill) MacDougal, the college counselor, was pivotal in helping me to select the best university for me. As many 18-year-olds do, I had planned to spread my wings and leave Texas, but she recommended going to SMU for its College Experience program the summer before my senior year. That did it for me; after taking two courses and spending 2 months on campus, it was SMU or bust.

If given the chance to relive that part of my life—whether high school or undergrad—I would do it all again, the same way, at the same schools. TMI was so rich in exposure – Fiesta, Military Ball, competitive sports, pep rallies, community service events – there’s a spirit I still feel when I’m back on campus, that says, “This is home.”

In my short time on earth, I’ve learned that the world has a lot of followers and not a lot of leaders. All you have to do is stand up and lead. The values that make up the DNA of TMI – integrity, honor, genuine care for yourself and the person standing next to you– prepared me to lead a successful startup. For so many people, school is just a jumping-off place; for me, it was the start of the rest of my life.

To discuss leaving a legacy gift, please contact the Advancement Office, (210) 564-6241.
MISSION: TMI provides an exceptional education with values based on the teachings of Jesus Christ that challenge motivated students to develop their full potential in service and leadership.
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TMI Episcopal
20955 W. Tejas Trail
San Antonio TX 78257
phone (210) 698-7171
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