Nearly a decade ago I was two years into starting a new company, one that was growing quickly, but at the same time struggling with all the classic problems of a startup. We needed to raise more capital, we needed to hire more of the right people, and we needed to retain and motivate the people we already had brought onboard.
But more than anything, I was personally struggling with whether I could keep up the pace. This was my fourth startup, and I’d been at if for nearly 20 years. At that point in my career, I had serious questions about whether it was worth the time and energy, given that the pay was low (gotta keep burn down) and the hours were insane. I had three young children, all in expensive schools, and a mortgage to worry about. I wasn’t making enough to cover our monthly nut, and I wasn’t certain that the upside of any startup – even one I believed in with all my heart – was worth potentially failing my obligations to my family. After all, I was reasonably established, and I could always go get a higher-paying, more stable job.
So one morning at my kitchen table, I poured out my concerns and dreams to a close friend, Chris Albinson, who just happened to be a venture capitalist. I explained my dilemma – my responsibilities as a father and husband were in direct conflict with my career as a startup founder. I remember Chris asking what I’d need to keep my focus on my startup. At that moment, the reality was, I needed cash. I needed to be able to look my wife in the eye and say “Don’t worry, if this doesn’t work out, we’ll have enough to cover living expenses while I look for another job.”
Read More