Those were the ten words that ended my Zendesk career and my almost fifteen-year journey in Startupland. I was talking to two of the private equity partners who’d led the Zendesk acquisition. The transaction had just closed and we were having a beer (which was so unusual, but we tried to make it super caj and not awkward at all). It was sobering hearing the words out loud. Had I even given it any real thought until now? Probably. Did it matter? Probably not. And it was true. People like me didn’t like working for people like them. They knew it. And before I got back into my car, I knew it too. We said goodbye, and as I pulled out, I came to peace knowing this was the end.
Soon after, we told the team. Made it official. And that day I completely logged out. Deleted all my social profiles. Got off all our systems. Stopped taking calls. Ignored my emails. And within a few days it was as if Startupland had never happened. That long and all-encompassing journey that I had been on since founding Zendesk with Morten and Alex, taking it public and building an organization with more than $1 billion in revenues and thousands of employees, was over. What had been the entirety of my life for so many years.
My days easily filled up. Three dogs. Five kids. Laura, my partner and soon-to-be wife. Bicoastal households. A small foundation. A family office. My health and sanity. Art. Cocktails. A big world to explore outside of conference rooms. Plenty of areas to invest my time and money. I wore a lot of denim and started playing tennis like an old fart.