“The startup CEO's job is so glamorous!” Anne Dwane, jokingly said, as I chatted with her recently. Anne is an accomplished, smart, helpful and wonderful person who I was lucky enough to work for at Military.com. Anne founded Military.com, and from her I learned so much about how to be data-driven and an effective leader. No. No. It's not glamorous, we both actually agreed. Being CEO of a startup is hard work, is having to do everything, and feeling immensely responsible for our customers, our employees, and our investors. However - there's never been a day where I wasn't happy that this is my job.


When I biked cross country solo, self-supported from Bellingham, Washington to Washington, DC, it was an incredibly hard job. To ride 3,300 miles, every day I had to figure out my route, where I was going to eat, get sufficient fluids, and where I was going to sleep. Add on top of that the sheer physical labor of propelling myself. And oh by the way, I was solo self-supported, so I was carrying everything I needed myself. If anything on my bike broke (and it did), I was chief engineer to fix the tire, gear, shaft, or whatever was keeping me from moving forward. If I didn't fix it, I wasn't going forward - there was no uber to summon to "take me 500 miles to the next bike shop". Roads would have a narrow shoulder with worse traffic than I thought, no shoulder at all due to construction, or be closed completely. A cafe I had counted on for food wouldn't be open on Tuesday (when I was there), or shut at 2 pm, or have been shut for years. The weather was a constant wild card with wind, rain, heat, hail, cold, all impeding my progress.

Every single day however, I was happy I was riding my bike. Whether it was the joy of waving to the Empire Builder train speeding by once a day, seeing an antelope bounding through the farm fields, rainbows over North Dakota badlands and the smell of fresh rain, the tart taste of Michigan cherries, miles of wildflowers bending in the breeze, cresting 5477 foot Washington Pass between snowbanks - there was always a moment of pure joy that made all the effort and agony worthwhile. I named my cycling journal “Never a bad day to ride” as even on a day when I had near complete physical and mental meltdowns from hunger, exhaustion, stress, thirst, weather, and whatever else the world threw at me, I was glad I was on my journey.

Startup life is similar - we have a goal and a destination, but every day is somewhat unknown, with wildcard challenges and issues. However, the payoff is immense in improving the life of our customers. Last week I started to give a demo to the CEO of an interested company. After two minutes, he stopped me. “Please stop - this is what my CTO needs to see too - he'll want to use it!” Moments where our customers understand how we'll make software development faster, it makes all the hard, glamorous work not just endurable, but enjoyable.