Hindsight

Hindsight Series: Matt Reedy, USAA Executive Director of Innovation

September 12, 2017

Matt Reedy is the USAA Executive Director of Innovation and an experienced entrepreneur, having successfully co-founded and developed multiple technology startups. His enduring passion for technology and entrepreneurship led him to earn his computer science degree at Trinity and MBA at St. Mary’s. Now, those same passions have culminated in his current success, mentor status, and desire to grow San Antonio’s technology ecosystem.

What was your biggest failure? How do you cope with setbacks?

The biggest failure was my second startup, a consulting service company. It was a failure in the sense that I wound up not being able to pivot to a successful BM and stuck too long with the original BM. Ultimately, we ran out of business. Lack of ability to find new ops so that could continue one. I learned there is a fine line between being persistent and beating your head against the wall. Learning from my failure helped me cope. The ability to differentiate between the two has helped me in other ventures.

Learning from failure requires a combination of self-reflection and discussion. Talking with business mentors helped me to understand it my failure as a learning experience. I started with reflection, however mentors helped reverberate back to me the lessons I needed to learn.

 

How do you define a strong mentorship relationship?

For me, it is about finding someone that can understand what my goal is and then apply their wisdom to what I’m trying to do. My best mentors have been able to connect where I am going to where they have been, applying business challenges they have encountered and rules of thumb to my present situation.

 

What keeps you up at night?

Finding the product market fit. While it might be fun for a big company like USAA, in R&D we often chase shiny objects vs. finding real problems that need to be solved. Even in bed, I’m constantly wracked with questions. What customer problem are we solving? How can we do a better job?


What is the advice you would give to the pre-career version of yourself?

The things I have learned since then revolve around the importance of networking and relationships. That version of myself was a bit of an introvert, had to get out of the shell, and go out to meet people. I would advise them to realize who you know is more important than what you know, from both an entrepreneur and career standpoint that. Start networking sooner.

 

What advice to you give to the next generation of business leaders?

Become really good at bridging the gap between business and tech. Nowadays, we use business technologists at USAA. Although I’m reviewing debts and credits with CFO, I’m also looking for bits and bites with the programmer.  Become an expert on the intersection between technology and business.

 

 

Books, podcasts, or resources you recommend?

Entrep standpoint: HBR Ideacast

 

Other resources: Follow Jim Rohn he was entrepreneur and he has an organization that was set up before he died

Success Magazine

Darin Hardy used to be the publisher of Success Magazine, a daily email and video cast. A good inspiration and slap to the face when needed.

 

Other bits

When talking to kids about going into their own business:

 

Find a business that you are so passionate about that you would do it without getting paid.  

 

The reason is that it’s extremely hard work and you will be tempted to give up unless you have the deep passion for it. Don’t just do it for money or hobby. Above all, it must be a passion.

 

Great work: having an impact on people or society. DO something that makes people’s lives better, something that you have a strong desire for and would do without pay.

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