Startup Status: It’s Complicated

Aug 5, 2015 · 2 min read

One of my favorite bits of startup mythology is the prototypical entrepreneur: This person so overcome with zeal, so overflowing with passion that they’re willing to sacrifice sleep, relationships, years of their life, and a respectable credit score for the sake of their “Idea.”

This maniacal, singular devotion compels them to stick it out through years of torment, eating copious amounts of glass, until — finally — vindication. The Idea is made a reality, and the entrepreneur is made a billionaire.

Suffice it to say, I have not found this to be the case. I’ve been an entrepreneur my entire career, and if I had a nickel for every time my zeal wavered, my passion found a bottom or my conviction was, let’s say, hypomanic, I’d be committing 90% of my net worth to charity along with Zuckerberg and Buffett.

The truth is, most entrepreneurs would probably tell you their relationship with their company is often complicated. Even when things are going well, they’re constantly in motion. People come and go, roles and responsibilities change and new challenges appear out of thin air.

It’s possible to wake up one day and find that you’ve fallen out of love with your company. The thing that kept you coming to work everyday, that helped you emerge from periods of darkness, is gone.

As in marriage, we’re left with three choices:

  • Get divorced - leave your company or wind it down
  • Stay together for the kids - grind it out for those you’re indebted to, even though you’re unhappy
  • Fall in love again - find something else that gets you out of bed every morning

I think the ability to fall in love with your company again and again — not a maniacal, unwavering conviction — is the real trait that keeps entrepreneurs going through thick and thin. The things I love about my company today are very different than the things I loved about my company a few years ago. What those things are isn’t that important, what is important is the confidence I have in knowing that, when the time comes, I’ll find a way to keep the flame going.

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