Serial entrepreneurship can be a lonely gig. There’s no comfort in working your way up to a leadership position when you’re building a company from the top down. I started my first company straight out of grad school, and nearly twenty-five years later, I can’t see myself doing anything else. A commitment to this life path requires ample support, especially from peers who are growing their companies in tandem and from business leaders who are further along on their journeys. I was lucky enough to find such support early on. It came in the form of Young Presidents’ Organization.
I joined YPO in 2000, four years after founding FatWire Software in my parents’ guest room. The software we developed was one of the earliest web enterprise content management systems on the market. Between 1996 and 2000, FatWire had seen immense growth—more than I could’ve expected, but not enough to trip us up. We tripled our workforce and took on some big names as clients. FatWire tapped into a high-tech market at just the right time, and the attention was in equal parts overwhelming and invigorating. I found myself craving support from others in the same boat, but I didn’t know where to look.
After years of wooing investors and clients, a chance to be wooed finally fell into my lap—and at a most unexpected time. I was in the hospital when I got the recruitment call. My wife, Marisa, was in labor with our first daughter. With her blessing, of course, I answered the phone call from a prominent local businessman who was looking to initiate me into YPO. I didn’t take much convincing. After some introductory research on the organization, I recognized it immediately as a perfect fit for me and for what I hoped to be my growth trajectory as a CEO. I was immediately drawn to its values of lifelong learning and meaningful connection. And I loved how it was inclusive of spouses and kids, because it recognized that a successful business career requires a ton of family support.
I quickly found myself taking on leadership positions within YPO. While part of the Long Island chapter, I served as Education Chair and Chapter Chair, highly rewarding positions that were well worth the effort invested. I found great satisfaction in organizing events for the YPO community, and I appreciated the opportunity to interact with some serious industry titans. My wife and I had a chance to exercise our creativity by planning a chapter retreat to Chicago with our chosen theme “The Art of Storytelling in Everyday Life.” It included a trip to a Second City improv class; talks by a screenwriter, sports writer, and novelist; and a surprise nude figure drawing class (getting people out of their comfort zones is another YPO value).
I met some of my best and most trusted friends through YPO. Through my YPO forum, a smaller group of members that meets monthly for confidential discussion, I’ve found strength and wisdom when facing some of my greatest challenges. The mutual exchange and support is invaluable to me, as life as a CEO throws its many curveballs my way. Now, with a couple decades of membership under my belt, I am a proud member and the Membership Chair of the Big Apple Gold chapter, having graduated from YPO upon turning fifty. No more kids’ table for me. What I get out of YPO is what I put into it: a willingness to organize, share, and grow as a business leader is rewarded with priceless experiences.