In many ways, I didn’t have a typical upbringing. About a week before my seventh birthday, my father passed away suddenly after a stroke. It happened within seconds. I was watching as he took his final breath.
He had no life insurance and his small savings account didn’t go very far in supporting five children. My grandmother lived with us as well since her memory was failing and she couldn’t live on her own. For several months we lived without hot water and for many years my mother struggled to put food on our table.
I’ve often reflected on what my life would have been like had my father lived, how different it would have been for me, my siblings and my mother who sacrificed much to be sure we did not go without. While I certainly was sad my father was not around, in some ways I felt my life was easier because I didn’t have two parents to pit my desires against: I had only one — and she was fabulous.
I was always acutely aware of how my mom stepped in, taking on the role of two parents and somehow having the instinct and energy to excel at all of it. There were other people, coaches and mentors, who also took an interest in my well-being and served as father figures to me.
Every Father’s Day, I remember my dad, and on this one I wish to honor the various father figures in my life who taught me about being fair, coaching and helping others, management skills that have served me so well in business. The lessons I abide by the most aren’t from management books or school: They are what these individuals taught me along the way.
Always have a game plan. Charlie Rowe was a lawyer in my town and my Little League coach. “Show up, be present, try hard no matter what you do,” he said. And he led by example.
While most coaches canceled practice in the rain, Charlie moved us inside and took an academic approach to baseball. He would set up scenarios for us to think through like this one: “OK, there is one out and a runner on second base. The ball is hit hard to you at third base. What do you do?”
(The correct answer: Look the runner back to second base and then throw out the runner at first.)
“If it’s a slow roller what do you do?” (Answer: Charge the ball and get the out at first.)
He would then grill the shortstop and other players about their secondary roles. Charlie taught us to always think about all the variables before something happened. It helped us become better prepared for any scenario. It was an important lesson and, because of Charlie, I have spent my career thinking out in advance each play happening at the moment.
Charlie drove me home from practice and always told me how much potential I had. He gave me guidance off the field as well. A decade after my Little League stint he helped me land my first job at IBM. I was conflicted about whether to accept it as I was in school studying criminal justice and planning to attend law school. He told me that although I was hoping to be a lawyer, he knew (from his own work) that being a lawyer hadn’t been everything he had expected it to be. He encouraged me to explore other options and this made a huge difference.
Be professional. At IBM I worked for John Martone, who became another important mentor. He suggested that I start to dress more professionally and helped me do so by giving me some of his old suits. He also stressed that everything I did — how I communicated and conducted myself — was a statement to the world. He taught me to walk with purpose — like I knew where I was going (even when I didn’t). And he demonstrated the importance of always giving things my best effort. He helped me crisp up my writing so I could present my ideas in a more professional and engaging way.
Aim high. I’m grateful that my brother, Tony, spent an inordinate amount of time with me, even though I was four and a half years younger. Although I periodically his punching bag, he invested a lot of time helping me improve myself. He was always willing to coach me. He taught me how to pitch, for example. He escorted me to the library so I could take out books about Sandy Koufax and encouraged me to aim high, saying I could be like the legendary left handed pitcher.
Tony expected me to be tough and we were very competitive. I had to learn to lose because he always beat me. In that respect, he also taught me how to lose with grace. I hated it, but l learned how to get over focusing on how I played and be more inspired by how the team played. It wasn’t all about me!
That tenet has inspired my management style and influenced everything I do now, including the investment network I created (Webb Investment Network) to help entrepreneurs grow their companies and my new company, Everwise, which mentors people in their careers. Tony taught me the value in seeing more in everyone — one of the most important lessons in career and life.
Stay humble. After my father passed away, my mother went back to teaching. She was incredibly industrious, always driven to improve herself and to take any opportunity available. She believed that people were capable of more than they thought. She always said “We have high expectations for you.” That inspired me to dream big. As a kid, that meant a career as a Major League Baseball player.
I was pretty good at sports, and after I was awarded MVP in Little League, my mom thought I was getting too big for my britches. She and my brother, Tony, started calling me “the Hero,” instead of Maynard. The next year I made the Babe Ruth All Star team. But during one of the key games en route to the state championship, I struck out and became angry. I strode out to third base and threw the ball as hard as I could to first base.
“Too bad you can’t hit as hard as you throw, Webb,” someone screamed from the stands.
The shortstop came over and said, “Why don’t you tell that lady to shut up?”
“I can’t,” I said. “That’s my mother.”
My mom passed away 29 years ago. Not a day goes by that I don’t think about her and miss her. She left a mark on everything I’ve done and do. So did my father as well as the others who stepped in to make sure I had what I needed along life’s journey.
As the author James Baldwin once said, “Children have never been very good at listening to their elders, but they have never failed to imitate them.”