Five Questions For … Geekdom Fund Co-Founder Michael Girdley

San Antonio—Michael Girdley grew up as a self-described “techie kid,” who whiled away the hours trying to take apart his Apple II computer.

“I was always attracted to tech,” he says. That interest led him to pursue a computer science degree at Lafayette College and, eventually, land in ground zero of the Internet age in the 1990s.

Girdley says he rode the wave of the tech boom in Silicon Valley working for companies such as BEA Systems. But, eventually, Girdley says he decided to listen to a feeling that suggested climbing the corporate ladder wasn’t for him.

With proceeds from stock sales sold before the dotcom crash, Girdley and his wife traveled, and then settled in his hometown of San Antonio, where he ran his family’s fireworks company.

“Then, in terms of being true to myself, I knew I wanted to be back in the tech industry again,” he says. So, Girdley began getting involved in startup organizations, co-founding the San Antonio Angel Network and CodeUp, a San Antonio coding school. He co-founded the Geekdom Fund in 2013.

“This is still a game around possibilities,” he says. “In poker, you can be the best player in the world, and still go lose 1,000 times in a row. You can be the worst and win 1,000 times. All we can do is increase the odds the best we can.”

In this week’s “Five Questions For,” we speak to Girdley, who talks about heeding that inner voice, thinking differently, and the KPIs of joy. Here is a lightly edited transcript of our conversation.

Xconomy: What’s your blind spot?

Michael Girdley: Man there’s a lot. I think it’s really easy to solve for problems that you have and investing in companies along that path. It’s why you see so many companies get VC funding in the Bay Area that happen to have a “1-percenters really want this product”-type [mission]. Who needs a $500 juicing machine? There still is a big challenge with our industry in that there is a lot of homogeneity, not just of cultural and racial backgrounds, but also of thought as well. The VCs happen to all go to the same schools and belong to the same clubs. That’s a real challenge to be mindful of. You should think about what your background is in terms of biases and drill down to the root cause of that stuff.

I think that’s one of my strengths. I’ve taken a weird path to get into this industry. I know for sure that I’m the only tech VC that was CEO of a fireworks company.

X: What’s the worst business decision you’ve ever made, and what did you learn from it?

MG: Every time I look back on a bad decision, it’s [that] I knew the right answer and I didn’t take action fast enough.

I wasn’t a big company person—I love change, it’s one of my core values—but I got suckered into a lot of the unhealthy ideas that come along with being at a big company, to chase title and status, and you end up being untrue to who you really are. The decision to stay as long as I did in big company-America [was a mistake]. I learned a lot but at the same time, I say, why didn’t I do the thing that I knew was right? Why didn’t I have the courage? We all fight that courage challenge all the time. That decision to stay in for longer than I should have … I wish I could go back and tell me, “Hey, be true to who you are.”

Some lessons take longer to learn than others. After the 30th time you feel a little regret for not acting sooner. Also, getting older just helps. It’s easier to have perspective on things when you’ve in been in business 20 years rather than five.

X: What leadership lessons did you get from your parents?

MG: I think my parents really impacted upon me that harmony is super important. I think I invest a lot of effort in having great relationships with people, sometimes to an extreme, because I saw how hard they worked both in business and their personal lives to make that happen. I hate drama. I make it a priority on doing a little bit extra to make sure people are happy and feeling fulfilled in what they’re doing.

I have a very 21st century career. I don’t have a specific office. I have multiple titles and I can work where my laptop is. I deal with people as a partner, customer, mentor, mentee, those are all relationships where that philosophy extends. In practice you spend a lot of time trying to be a great listener, not to what they say but what they don’t say. Ask direct questions, “How are you feeling? How can I make things better for you?” Just trying to be a giving type person rather than a taking type person.

X: Where do you think your drive comes from?

MG: I don’t know! I think I’m highly motivated to accomplish things. I haven’t really sat down and asked myself, “Why am I motivated to do this stuff?” I’ve just accepted me for who I am, and I feel like going to do things. It’s never been something I’ve thought about. Why did I feel compelled to do that? I got up early to go the gym. Did it feel good to do it? Yes. I got to see my friends, hang out, and worked out—it makes me happy. I’m not going to worry about why. I worry about things that don’t work and the things that make me feel bad. Accomplishing things makes me feel good, so I keep doing it.

X: How do you define success?

MG: I see my life’s mission as maximizing my personal joy and other people’s joy. Are there KPIs for that? Not really. But in your gut you know if you’re leaving the world a better place than you started with it, if you’re helping other people achieve their goals, if you see people smiling more than they’re frowning because they’re near you, that’s important.

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