Moral of the story: if you see the potential in someone, be persistent. They just might be your next COO.
In 2013, we had just finished going through an incubator (one I found by googling “Nashville Startups”), where I learned for the first time about venture capital. Prior to this incubator, I had no idea what venture capital was, or that there were people out there who were willing to invest money in our ideas and our website.
Coming out of the incubator, we were generating a few thousand dollars in sales per month and I had no interest in raising more money. We wanted to focus on growing the business, and I knew we needed more employees to do that–because there was so much work to be done.
I met Tyler Newkirk through the incubator, where he was working as an intern. Something struck me about him–maybe it was the fact that we both liked working out, and as a former D1 athlete, he was actually good at it (unlike me). It’s an obvious trope, but there is something to be said about the fact that folks who are great athletes are also great executors. The tenacity and focus it takes to achieve greatness in sports is unparalleled. Based on his attitude and doggedness, I knew we wanted him on the team. The problem was that we barely had enough cash to spare to cover the founding team’s living expenses, let alone pay someone else the wages they rightly deserved.
So, Tyler ended up taking a job at Home Depot while we tried to get our company scaling. In addition, I also convinced a friend of mine, Matt Bodnar, who is a very successful real estate investor, to hire Tyler on with his company. We went into the agreement with the expectation that Gun.io would hire him away eventually, and in exchange Matt got some advisory shares in our company. This turned out to be a great investment for both him and for us.
I can’t recall the exact timeline, but within a few months, we were able to pay Tyler some nominal amount of money every month. Sometimes it was via a cash app, sometimes it was just an envelope full of cash. What started as managing some odds and ends of the business eventually evolved into a hybrid sales-and-customer-service (which was a literal godsend to me, because I had spent the last three years on the phone, fielding every. single. call.).
In 2016, we set up payroll at Gun.io and gave him his first full-time salary. I know his wife was very pleased with this turn of events, and we were stoked to officially bring Tyler on board. Six years on, Tyler now runs Operations for all of Gun.io and is integral to the company’s success. He was the first hire we made, and has been a critical part of the company’s growth for nearly a decade.
I often sit with people who say they can’t afford to make a hire that they need to make. To me, this is nonsense. You can always find a way if there’s trust and alignment. And the way to do that is to start small, start narrow, start with a project or two, and go from there. 10 years later, you might have yourself a COO.