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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.”