I got into coaching basketball when I was 33 years old, volunteering at the Mercy Home for Boys in Chicago. Mentoring inner-city youth had always been an interest of mine, and working with the foster kids there reinforced for me the power of coaching as a platform for teaching positive values and life skills, all while being involved in a game I love. A few years later, I began volunteer coaching the Illinois Warriors Basketball Club. We had many talented young players, mostly from the South and West sides of Chicago. It was part coaching, part social work—there were discipline and academic issues, gangs, guns, and homelessness. Over the five years I coached the program, 25 of our players went on to earn college basketball scholarships, including two who made it to the NBA. On the flip side, several players also went to jail.

That experience in Chicago was hugely challenging but incredibly worthwhile—nothing compares to the feeling that you are making a difference in a young life. As my 40th birthday approached, I realized two things: I wanted to transition from my work in real estate investment to make coaching a full-time commitment; and I wanted to do it in my hometown of San Francisco, simply because I wanted to be closer to my parents and my brother and sister. Now I serve as the full-time head coach for boys’ basketball at University High, a private school, and as a volunteer coach for the Bay Area Warriors, a nonprofit I cofounded that draws inner-city players like those I had in Chicago. Many of the challenges are the same too: In 2010, one of our players was shot and killed on a street corner.

Losses like that—real losses—are difficult, but I try to remember that coaches can have a tremendous impact. Basketball can be preparation for life: You learn how to work hard, how to deal with adversity, and how to be on a team. My more granular philosophy as a coach is driven by what I liked as a player, which is why we play up-tempo, fast-paced basketball that gives our players freedom to read and react on the court. I trust them, and if they make the wrong decision, I correct it and let them go again. If things don’t go well, you’ve got to transition. One of my favorite sayings is, “The most important play of the game is the next play.”

It’s an approach that has parallels in business. In both cases you’re finding good people, training for the requisite skills, and trusting them to make the right moves. It’s about motivating and empowering people, even if sometimes you have to reel them in. Players win games, not coaches. And underlying it all is a shared understanding of values. One of our core beliefs, for example, is that on our team, we care about each other. When things don’t go well, you can reflect on those values and find the answers that will help get you through some tough moments—whether they happen on the basketball court, in the boardroom, or any place in between.

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Since joining University High in 2005, Coach Randy has led the Red Devils to a 320–105 record, 10 league championships, 3 trips to the State Final Four, and a NorCal Championship in 2015. The Bay Area Warriors have helped more than 100 players go on to play college basketball.

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