Jerry Colonna On Leadership and the Art of Growing Up

Jerry Colonna felt suicidal at the age of 38. He had risen from humble beginnings in Brooklyn to being worth millions as a venture investor during the 1990s internet boom, yet he wanted something more. Despite the success, he didn’t feel happy – so he turned inwards, got help, and figured out what he needed to do for himself. Talking with peers he realized the core of his experience wasn’t completely unique, and in 2007 he began to work formally as a business coach. In 2014 Colonna founded to help companies and their leaders focus on improving the experience of this thing we call “work.” Any professional interested in improving how they help others can benefit from Colonna’s perspectives.


Here’s one of many insights: Colonna says our job as a parent, co-founder, investor, manager, advisor, etc., is not to stand in front and clear the way, nor is it to stand behind and push. Our job is to stand shoulder to shoulder saying, “It’s a hard road. Watch out – there are potholes over there.” That job is really, really hard. It takes tremendous discipline and self-awareness to do well. 


In order to gain satisfaction from work itself, we often have to find the mid-point between having everything done for us and carrying the entire world on our shoulders. We have to look inward to understand what we’re outwardly trying to accomplish. Colonna uses the act of work to help people and organizations find this mid-point out for themselves. When we understand why we’re doing what we’re doing, we start to put meaning to our methods. We like work that is purposeful. We don’t like work that feels pointless.   


Likewise, our best client relationships are those where we join them on their journey. If we are anywhere but shoulder to shoulder, we aren’t building the strongest type of consultative relationship we can build. If we’re constantly clearing the way of all obstacles or pushing them into traffic, sooner or later they’ll figure out that we’ve put them on our journey instead of the other way around. Part of giving work meaning is helping others to own their progress while feeling our presence and support.


Pursuing success and the struggles that come with it can feel lonely. Colonna embodies the professional support we all want to know we have in our corner. If interested in learning more, check out his book, Reboot: Leadership and the Art of Growing Up, find him doing the podcast rounds with Jason Calacanis and Tim Ferriss, or read his former business partner Fred Wilson’s book review here.