Jerry Colonna is a Trojan horse of the best kind. Back when I became CEO of Etsy in 2011, I was introduced to Jerry as the best CEO coach around. He had been Fred Wilson’s venture partner. He knew business. I thought of him as an advisor who was going to help me build my management team, raise money, crush it as a CEO. And that’s the Trojan horse aspect — who knew that inside this container of business excellence that some kind of spiritual transformation was in the offing? I certainly didn’t. But in the six years I worked with Jerry as a CEO, I learned how to live a better life, love more fully, and be the man I had been trying to be — so much more than being a chief executive.
Jerry’s book, Reboot: Leadership and the Art of Growing Up, comes out today and I couldn’t be more thrilled for my friend. The book is also very personal to me. Chapter 2, “The Crucible and the Warrior,” leads off with the story of Jerry and me sitting on the rooftop at Etsy after I knew I had been fired** but hadn’t yet told the company. Lots of things got written about me and Etsy through that period — some true, some shaped to better fit the corporate narrative that was needed at the moment — but what Jerry writes in Chapter 2 of his book is the most real and true thing ever written about me. It’s because Jerry was there for me and he listened and he witnessed. He previewed the chapter with me and I didn’t ask him to change anything. Jerry is a truth-teller.
A story of a private moment between Jerry and me that isn’t in the book tells you a bit more about how Jerry thinks and what working with him meant to me. In one of our sessions, I was a little worked up because I had taken a personality test and the results had shown that my personality type was a strong fit for the occupations of “poet” or “priest.” I couldn’t reconcile this with being a CEO. Jerry smiled and said, “Why can’t you be a poet and a CEO?” Good question. I was reminded of my studies and how Wallace Stevens, one of our greatest American poets, won the Pulitzer Prize for poetry in 1955 while serving as a vice president at the Hartford Accident and Indemnity Company, where he spent this days evaluating surety insurance claims. Jerry has a way of reminding you of these things.
And that is really the point. The proportions are different for everyone, but we all have a little poet and priest in us because we are human. To live a full life, you have to embrace all parts of yourself. Selectively suppressing parts can have a high cost. (Jerry also told me I should read Parker Palmer’s book Let Your Life Speak: Listening for the Voice of Vocation, which I did read and highly recommend).
Leaving Etsy started a very difficult time for me but also a new beginning, and the beginnings of that beginning are captured beautifully in Chapter 2 of the book. Today I’m working on a project that very few people know about that has absolutely nothing to do with tech. I text Jerry about it regularly and he sends back words of encouragement. I think it’s fair to say that this project calls equally on the poet, priest, and CEO within me. I’m not sure exactly where it will go, but it’s important to me regardless of the outcome.
The book is important because it captures Jerry as truth-teller so perfectly. When I read the book, I hear Jerry’s voice in my head and it sounds exactly like the hundreds of hours of conversations we had. It is a gift to the world and I believe will touch many lives in the way I’ve been touched. I’m glad to see it out in the world.
Thank you for helping keep the poet and priest alive in me, Jerry.
**the fact that I publicly said I had gotten fired versus some “decided to pursue other opportunities” corporate bullshit is largely due to the sense of truth I gained from working with Jerry. Life is full of pain — lean into it. If you got fired, speak the truth. It always catches up to you anyway.
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