From Student to Mentor and Back

Some of the best advice I ever received was to always have a mentor throughout life. If you don’t have a mentor, then how intentional or accountable are you about seeking self-improvement and growth? I found my first business mentor at 17 working as a handyman for a successful entrepreneur, Mike. He had built his wealth over time through hard work and persistence. He had slowly worked his way up to 20 or so rental properties, and his full-time business was simply maintenance and improvement of his properties. He wasn’t content to sit on his ass and collect a check like most landlords. He believed that we can only grow if we continue to invest in ourselves. Mike taught me so much about who I wanted to be as an entrepreneur and helped me realize that I could achieve anything if I had the fortitude.

As I launched into adulthood, I knew that I wanted to do something intersecting between graphic design—which I had studied in high school and college—and technology or computers. The mentors I would seek over the years represented the personal development and growth I was seeking at various points in my career. Dennis Ritchie, John Resig, Matt Mullenwag, Brad Feld, Jim Deters, and the list goes on to include some pretty humbling and noteworthy names. The point isn’t to name-drop them, I’m anonymous after all, but to point out something that I don’t see many of my peers do: seeking mentorship intentionally. It seems like the average person resorts to trial and error or absorbing wisdom through others without purpose or intent. While I’m not dismissing the value of passive mentorship, I don’t think I would have been successful in life without purposefully seeking mentors with clear goals of what I wanted to learn with their guidance.

Dennis Ritchie taught me the value of open contribution and contributing to a non-profit that you believed in. As a budding software engineer, I volunteered as much time as I could to Mozilla, WordPress, and the Linux Foundation. I was quick to jump into any project to get my foot in the door and privilege to work alongside the “grey beards” as I liked to call seasoned developers.

John Resig showed me how someone my own age could challenge the status quo and that not everything had to have a price tag. He led me to value myself and if only one other person said “thank you” for freely publishing something, that was worth something, if only a smile. This led to a future adage I would learn about providing value first in business and technology.

Matt Mullenwag proved the value of open source at scale, with WordPress being one of the biggest successes in the history of free software. But on a more personal level, he challenged me to think beyond the dollar. I realized that money will come and go, but if you stay consistent with pursuing something that you believe in, you will ultimately find a way to pay the bills and keep the lights on. You just have to rise above the fear of the unknown.

Jim Deters was a very close mentor for a few years. The fact that I told him “no” to a job offer when we first met kicked off a relationship of mutual respect and collaborative ventures. He was still my mentor far more than the other way around, I was just a smart tech guy to have at his side. Jim showed me the ropes of enterprise business and how to play the capitalist game. One of my favorite lines from him:

You keep saying how ‘anti-capitalist’ you are, but to me that’s like if we were playing poker and you kept saying how the rules are ‘no fair.’ All I see is a bad poker player and how I’ll get one step closer to taking the pot and you’ll be the first one I take out. These are the rules and that’s just the way it is. Either learn the game and how to play your cards right, or just keep bitching and watch your chips roll away. Either way, you are in the game because you choose to be here.

– Jim Deters, circa 2010

Brad Feld showed me that you can be really successful without caring what people think too much. How to be yourself and not compromise on who you want to be regardless of material wealth. Working alongside Tech Stars I was able to start mentoring budding entrepreneurs. I was able to give back in a way that felt even bigger than open-source software. This would inevitably lead me to a career in agency and consulting. All from the simple idea of being exactly who I want to be and that someone would value me. He also led to an expansion of my definition of value-first business and that giving away my time for free wasn’t always a poor investment.

There are many more I would love to name and share. Ultimately, I just wanted to share my gratitude today in an open-sourced environment. I love the mission of No Cap and the goal to freely give away information. I think we could all benefit from a little more wisdom in our lives. I know I certainly have!