How I met Jerry & Why I do this work

“I want to learn how to become a better entrepreneur,” I told him, sitting on the plush couch in his office. My mind wandered over and found momentary stillness in the soothing sound of the trickling water from a Zen fountain near his chair. My eyes couldn’t help but fixate on his record of career success, depicted in glossy magazine articles and prominently displayed on the wall. He smiled and looked at me with curious, supportive eyes. He then leaned back in his chair and said: “Tell me more about your parents.”

I didn’t come to NYC looking for a coach, or a therapist or a fix. I came here because I needed a change, a new place to find myself, to push my limits and to connect with people who would challenge me. I told people the real reason I came here was because I wanted to play the big game. I wanted to be “successful.”

I had experienced the thrill of entrepreneurship in Columbus, Ohio where I had attended school and had (and still do today) a very strong belief in my ability to at least generate an income. So I wanted to do it in a bigger way in NYC, 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 recurring bouts of tremendous grief, I had somehow managed to convince myself that I was more or less “over it.” I wasn’t. I’m sure everyone but me could tell just how lost I was, especially a guy like Jerry.

I connected with Jerry in early 2007. When I first moved to NYC, I attended just about any event I could find that was related to tech, entrepreneurship, web (even web 2.0 which now sounds so archaic). Bouncing from one event to the next, I found myself at a NextNY Panel on Angel Investing. Jerry was one of the panelists. I’m not exactly sure what about him stuck out for me, although I do remember that him mentioning he was doing less investing and more teaching, mentoring and coaching. I felt a compelling sense of urgency to speak with him. Unfortunately, after the event was over, he was mobbed by people, and I didn’t get a chance to connect with him.

Upon returning home I googled “coach board member Jerry Colonna.” I found a business owner who had written about his experience of having Jerry both as a board member and as a coach. I emailed him, he forwarded my email to Jerry, and Jerry got in touch with me. We set up a meeting.

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 watch me fall, repeatedly, and try as she might, be unable to just tell me what to do. Because balance isn’t a trick you learn by watching or listening. It’s a skill you acquire by feeling.

I had to fall. Get back up. Fall. Get back up. Lather, rinse, repeat – until I felt it for myself.

That’s how my coaching experience has been with Jerry. He never told me what to do. He was just there, alongside me on that unicycle of life, supporting me while I was pedaling hard . He also made sure I was OK after a fall. He shared his stories of falling and his stories of success. He gave me permission to cry. And sometimes, he cried with me. He never told me how to balance in life, but he told me how I could get up after a particularly big fall. He also taught me how to make amends with the falls, how to connect and find support in others and how to open myself up to life.

As I sit here today, over seven years later, I can without a doubt say that meeting Jerry was one of the most important moments of my life. Thanks to Jerry’s guidance and my work, I am a better man. More importantly, I now have the tools and perspective for continual improvement.

I found more balance and meaning in my life. I’m more energized and less burnt out. I have a loving, open, supportive relationship and partnership with my wife. I find joy and beauty in the ordinary moments. I can find richness and beauty in the falls, the pain. I still miss my mom, and now I’m aware of the pain instead of hiding from it.

Most importantly, I have the desire and ability to extend that help to others. If I can help just a few people experience the growth and richness I find now in my life due to my work with Jerry, then my work will be an enormous success. I want to support the 25 year old, lost, Dan.

In a sense, that’s what we’re aiming to do at Reboot: to reconnect people to the magic of their lives.  I’m so grateful to be part of this work.

PS. Somewhere along the way, Jerry managed to make me a better entrepreneur, too.