Jerry Colonna on Co-Founder Resentment

This post was written by Jerry Colonna and Andy Sparks.

Ask Jerry is a new limited series produced by Andy Sparks and the team at Everything, featuring Jerry Colonna, author of Reboot: Leadership and the Art of Growing Up, and CEO of executive coaching and leadership development firm Reboot.

Since founding Reboot in 2014, Jerry has developed a reputation for helping leaders grow through what he calls “radical self-inquiry,” and he is one of the most sought after coaches in the world of startups. In this series, we discuss questions about psychological habits, behavioral patterns, and the inner demons that can lead people to succeed—yet can be detrimental to their relationships and well-being. Submit your question here.

Andy Sparks: When Nathan Baschez pitched me on this column, I had to try and play it cool.

Nathan already knew I’d be leaving my role as CEO of Holloway, a digital publisher, to study co-founders’ different relationships—my hope being to help leaders deal better with each other, their companies, and society. Only days before speaking with Nathan, I’d enrolled at The Hudson Institute’s coach certification program on the recommendation from Reboot co-founder Khalid Halim.

Both Jerry and Khalid parlayed their experience building and investing in companies into establishing one of the world’s most famous coaching programs. Jerry’s ideas around radical self inquiry and bringing our whole selves to work have transformed leadership best practices, and are a constant through-line in the conversations I have with other founders.

I’d had the pleasure of crossing paths with Jerry in the summer of 2015 when Danielle and Kevin Morrill, my co-founders at Mattermark, went on a week-long co-founder “bootcamp,” joined by several other groups of co-founders for what was essentially couples (or thruples) therapy. I marveled at how Jerry and his team at Reboot—the coaching business he started in 2014—were able to get people to see how complicated our relationships are.

Listening to each group share truths and tears in our circle of couches in the mountains of Colorado, I developed a deep reverence for the struggles co-founders go through with each other when building companies. I can easily trace the roots of the new path I’m on to that one week with Jerry. Getting a chance to work with him felt like that Paolo Coehlo line from The Alchemist: “And, when you want something, all the universe conspires in helping you to achieve it.”

Lo these many years later, I sat down with Jerry again (virtually) to begin a series of conversations that we’ll split into questions and answers which we’ll publish here and in the Everything bundle.

In this inaugural edition, we chose a question from the community (send us yours here!) about resentment between co-founders, a familiar challenge to those who sign up to work together. Jerry shares his thoughts on what's at the root of resentment between co-founders and how to address it.