Flying High and Mentoring Innovators

Matt Reedy’s life story is one of constant movement—an embodiment of the entrepreneurial spirit that has shaped not just his own career, but the lives of many young innovators he has mentored.

Born in Monterey, California, Reedy ’79 had moved 11 times by age 17 before his father retired from the Marine Corps and was hired by USAA in San Antonio. Looking back, he believes all of the relocations helped him grow as a person.

“It was challenging having to lose friends and trying to get plugged into a new community, but it was probably the best thing for me. I was a natural introvert, but the moves pushed me into becoming more of an extrovert,” he explains.

On top of learning how to adapt and be flexible, skills that would serve him well in his professional life, these formative years ignited Reedy’s passion for technology, especially when he began dabbling in computer programming in high school.

“It was just the coolest thing to be able to create something out of nothing,” he says.

As he completed his senior year at Churchill High School, he committed to Trinity University for its computer science program and small class sizes. Reedy jumped headfirst into experiential learning opportunities and secured part-time jobs off campus so he could learn the ropes of software development in the business world.

After graduating from Trinity a semester early in December 1979, Reedy went on to receive his MBA from St. Mary’s University. During that time, a small software company recruited Reedy. He was involved in all aspects of the company, watching it grow from three employees to about 50, and he had a sort of epiphany.

“In a way, this company was like creating something out of nothing in programming. It was incredible to be part of its growth, and I realized that’s what I wanted to do—to build something up and make it valuable,” Reedy says.

Reedy connected with two of his colleagues from the company and took the plunge into entrepreneurship with the idea to create a piece of software that ran on the IBM PC. They put together a business plan, but nobody was investing.

“It was very frustrating,” Reedy admits. “However, my dad was very insightful and believed we had a window of opportunity. He funded the development of the software because he thought someone else would create it if we didn’t jump on it. Everything took off, and we literally doubled in size—employees, customers, and revenue—every year after 1986. We were in the right place at the right time.”

In 1992, Reedy and his co-founders took the company public. Eventually, they had seven foreign language versions of their software and had 900 software companies around the world reselling their product. As the company expanded internationally with offices in England, France, and Germany, Reedy began to feel the weight of its size.

“It had become the biggest company I had ever worked for. I wanted to go back to something small,” Reedy says.

After a couple of setbacks with his new companies related to Y2K, the dot-com bubble burst, and the Great Recession, Reedy joined USAA’s innovation department, which functioned like a mini incubator where he worked on ideas for new products and services for customers.

“I always felt like Trinity equipped me with enough of a knowledge base and skill set that if a startup didn’t work out, I could always get a job somewhere else. I’ve never been afraid to try something different,” Reedy says.

Reedy worked in the innovation department for about seven years before moving to another department to work on analytics and reporting. After approximately 11 years at USAA, one of Reedy’s old coworkers reached out with an idea for a software product. Intrigued, Reedy came aboard and helped develop a mobile app called WingMan For Recovery, a conversational mobile app designed to support individuals experiencing substance use disorders.

Once WingMan for Recovery was on the market, Reedy felt the urge to continue his journey and learn something new.

“I’ll do something as long as I’m learning something. My curiosity and drive to be a lifelong learner always push me to the next thing,” Reedy reflects. “As we know, life is short. It’s too short to be doing something you’re not enjoying.”

Having obtained his pilot’s license in 1992, Reedy clearly enjoys being around airplanes. He has owned eight of them through the years and currently has a four-seat single-engine propeller plane. He wanted to be able to work on his own airplane, so he signed up for a 16-month full-time program at St. Philip’s College and became a fully FAA-certified aircraft mechanic in December 2024.

Reedy continues to fly through life, literally and figuratively. He finds joy in giving back through Angel Flight, a nonprofit charitable organization that provides free air transportation for people in need of health care who are financially distressed or who are in a time-critical, non-emergency situation due to their medical condition.

“I love flying, and I love helping people, so it’s a win-win,” Reedy says. “I think I get more out of it than the people I’m serving because they inspire me with the sense of optimism they have. They tell me about the struggles they’ve gone through, what they’ve overcome, and the victories they’ve had.”

For one of his missions, Reedy flew a baby under a year old to San Antonio to be treated for craniosynostosis, a condition where a baby’s skull bones fuse before the brain fully develops. As it turns out, Reedy was diagnosed with craniosynostosis and had to have the same procedure when he was a baby, so he was able to share his story with the baby’s parents and reassure them that everything would be alright.

Another way Reedy enjoys giving back is through mentorship. As he was searching for aircraft maintenance jobs, he came across a LinkedIn post from Carmen Aramanda, director of Trinity’s Center of Innovation and Entrepreneurship, for the entrepreneur in residence position.

“I love helping young entrepreneurs,” Reedy says. “There’s so much you don’t know when you get into a startup. I think having a mentor makes the entrepreneur aware of the speed bumps, the pitfalls, the roadblocks—the things that somebody who has been through the school of hard knocks can relate to and prepare them for.”

Reedy is on campus from Monday through Thursday, sharing his experiences with students and talking through their ideas. One of the programs he is involved in is Trinity Venture Mentoring Service (VMS). A sister program of the MIT VMS, Trinity VMS helps entrepreneurs from the Trinity community overcome challenges by connecting them with high-level mentors, providing more in-depth insight than traditional 1:1 relationships.

“I like the mechanics of building a business from the ground up, but it’s very hard to be an entrepreneur by yourself,” Reedy says. “You almost always need a co-founder or two. Sometimes the downside is it’s like a marriage. This person is like your spouse. You better really like them and have the same values, because if you don’t, that’s going to cause problems later on. Trinity VMS can provide advice and guidance on topics like that from mentors who have lived through that experience.”

In addition to working with students, Reedy has shared his expertise with Trinity alumni. During Alumni Weekend 2024, for instance, he offered a workshop titled “Starting Your Own Business—Where to Begin?” in which he guided alumni through a series of business idea brainstorming techniques, baseline market considerations, and lean business plan creations.

“What impressed me is the quality of the questions they asked,” Reedy remembers. “Even though they’re new to entrepreneurship and new to startups, their Trinity background gave them this ability to ask really insightful and probing questions.”

This summer, Reedy will be working with alumni again as he facilitates connections with students in the Trinity Accelerator, part of the Louis H. Stumberg Venture Competition. This phase of the competition feeds into the skill-building, discovery, and development of the Stumberg finalists.

“We’ll have events in Austin and San Antonio where the teams can connect with former Stumberg finalists, business and community partners, and Trinity alumni. My message to those participating? Approach networking and approach life with the perspective that there’s something I can learn from everybody,” Reedy advises.

As Reedy looks ahead to the 2025-26 academic year, he wants to find ways to emphasize the innovation ecosystem of the Center for Innovation and Entrepreneurship’s mission.

“The term entrepreneurship can be a little intimidating to people. I would like to think about the innovation aspect of the Center for Innovation and Entrepreneurship,” Reedy shares. “An innovator is somebody who can look at things from a different perspective than everybody else and maybe see something that other people are missing.”

From a childhood of constant change to a career defined by innovation, Reedy has mastered the art of embracing uncertainty and turning it into opportunity. Now, as Trinity’s entrepreneur in residence, he continues to pass on the lessons he’s learned, helping the next generation of Tigers find their own path to success.