Reboot: Leadership and the Art of Growing Up
How I’ve grown up through my relationship with Jerry
(In celebration of my friend, colleague, mentor, wedding officiant, teacher, and partner, Jerry, releasing his amazing, incredible, book Reboot: Leadership and the Art of Growing Up last week, I wrote an introduction to our special podcast recalling the story of how I met Jerry. I’ve shared it below. If you haven’t already, go buy the book now. It’s amazing!)
“Well, I want to learn how to become a better entrepreneur,” I told him, sitting on his plush couch. A trickle of water flowing from a zen fountain soothed the room. My eyes scanned the wall behind him which was filled with the many glowing articles about his career success. The clippings celebrated one of the finest investors of all time, the former “Prince of New York.” ere was the man himself in front of me. I could feel a nervousness rise up inside me, but it eased when I saw his face. He smiled, leaned back in his chair and said: “tell me more about your parents.”
I didn’t go to NYC looking for a coach, a therapist, or a fix. I went because I needed a change, a challenge, a new place to find myself., I needed to connect with people who challenged me. But I told people I really went because I wanted the big time; I wanted to be “successful.” I had experienced the thrill of entrepreneurship in my time in Ohio, so I wanted to do it bigger in NY, as I imagine a lot of people dream of doing. But deep down I was lost. Very lost. My mom had just died after a battle with breast cancer, and despite moments of tremendous grief, I had convinced myself I was more or less “over it.” I wasn’t. Looking back I can see the ways in which I was hoping going back to the life of entrepreneurship and finding success would fill the holes I felt inside — both in missing my mom and in my greater fears about my own worth. I “needed” to build a successful business not only to work through my deep sadness of losing one of the most important people to me, my mom, but also to once and for all prove I was “enough.” If only I could build a successful company, then I would be happy. I was barking up the wrong tree — and Jerry saw right through it, thankfully.
I connected with Jerry in early 2007. When I first moved to NYC, I was ant overactive networker. I attended just about any event I could find and would meet with anyone. The event bouncing ultimately led me to a panel about angel investing, and Jerry was on that panel. I’m not exactly sure what struck me about him, although I do remember him mentioning that he was doing a lot less investing and more teaching, mentoring and coaching. I felt like I had to speak to him. Unfortunately, after the event, he was mobbed by people and I didn’t get to connect with him. Upon returning home I did a Google blog search for “coach board member Jerry Colonna.” I found someone who had written about their experience both of having Jerry on their board and being coached by Jerry (Thanks Scott! I don’t know if you realize how much your willingness to forward an email impacted my life). I emailed him, he forwarded to Jerry, and Jerry emailed me a quick note with the subject line: Boo! I remember the excitement and the terror. Somehow I knew it was an important connection. We set a meeting.
As I sit here today, nearly 12 years later, I can without a doubt say that was one of the most important moments of my life. With Jerry’s coaching, support, guidance, and teaching, I can say with certainty that I’m truly a better man, a better partner, a better husband, a better father because of the time I spent with Jerry.
When I was learning to ride a bike, I remember being so angry with my mom. “Why can’t you just tell me how to balance,” I would shout at her. I can only imagine how hard it was for her to reflect the reality back to me..no matter how bad she wanted to, she would never be able to tell me how to balance. I had to fall. Get back up. Fall. Get back up. Rinse and repeat until I felt it for myself. That’s how my coaching experience was with Jerry. He never told me what to do, he was just there alongside the bike supporting me when I was trying, and making sure I was ok after a fall. He made sure that I understood that falling was not just another proof point of my brokenness, it was a proof point of my aliveness. He showed me that compassion for myself didn’t need to be earned through some external event — it was something I was entitled to as part of my humanity. He showed me that even the more challenging moments in our work, our lives, our relationships, are moments where we can truly grow. He shared his stories of falling and his stories of success. He never told me how to balance, but I did learn through him that the key to balancing is not to obsess over avoiding the falls but to know you can get always back up from them.
I think back to that first meeting with Jerry often and find myself filled with gratitude and a sense of indebtedness. What if I Jerry had been too busy to email me back? What if he was too full to take me on as a client? What would my life look like now? That indebtedness and gratitude have driven me to where I am today, to support the “scaling Jerry” experiment that is now part of Reboot. My secret and somewhat selfish wish is that, hopefully, the next 24-year-old Dan and anyone lost and in pain can find the support they need so badly, whether that be with Jerry or not. I’m thrilled many more people get to connect with the wisdom, the love, the compassion, and the brilliance that is Jerry through our company, Reboot, and now through his book, Reboot.
The funny thing I can see now as I think back to that first meeting with Jerry and my journey since: He did actually make me a better entrepreneur, but I’m even more grateful that he helped me become a better man. A father. An adult.
It’s truly my privilege to introduce to you all to a man who means so much to me, a man who has impacted my life and my kids’ lives more than he even might ever realize despite how often I tell him. A man you already know as Jerry the coach and teacher, Jerry the podcaster, I now proudly present to you today as a published author: Jerry Colonna.
