I know a little about sports. In that context, anyone who’s worked with me can attest to the fact that I love using sports metaphors to help explain how startups can frame unique opportunities and challenges. Why are sports metaphors so ingrained in how I speak with my teammates at work? Well, the simple answer is that my formative years were spent playing baseball (that’s what happens when your dad’s the varsity baseball coach at your local high school) and consuming as much sports content as I could get my hands on.
Baseball became such a big part of my youth that I basically chose my initial college path based on my desire to play college ball. In fact, one of my lasting memories from baseball is pitching in college — or as my teammates would describe it — throwing batting practice for the opposing team. Yet despite an otherwise unspectacular Division III college career, I reflect on my time pitching and think how in many ways it was great training for life as a startup CEO. The parallels are striking.
It’s lonely on the mound. You, standing by yourself toeing a rubber slab, initiate action with each pitch and then watch as events unfold, pitch by pitch. Your teammates do so much to determine your success (more on this later). It’s equally lonely as a startup CEO. The same dynamic unfolds, just without you having to stand on a dirt hill. Instead, you initiate action not by propelling a white ball with red stitches, but by propelling audacious objectives onto a whiteboard or Google slide. Then, day by day, you encourage and challenge your teammates to perform amazing plays in order to reach your team’s lofty goals.
As a hurler, so much rests with the team behind you. Once you release the ball, you’re at the mercy of a shortstop’s ability to field ground-balls or a centerfielder’s ability to chase down a sinking liners. You coach your defenders to move to the left, to the right, to move up, to move back, to be ready, and to plan a couple plays ahead. You pat them on the back if they make an error and sometimes you have to yell at them to get their head in the game — all in a spirit to help them grow into great players. So it goes for startup CEOs. You rely on your team members, every single one of them. Can they make their plays, can they work together and support each other on the “field”? Like a pitcher, the startup CEO can do a lot to help players grow, yet at the same time, as pitchers and CEOs, our success rests so heavily on how well our teammates perform on their own along side us.
Pitching is one of those things that doesn’t look too physically demanding from afar, but it’s utterly exhausting. Strenuous bursts of energy that place undue stress on the body ultimately depletes you in every outing. Oftentimes you’ll glance over at the dugout and hear advice, encouragement, or even a dose of admonishment. The coaches and managers watching closely (or not?) from the sidelines bring different perspectives either from having watched a lot of games and, if you’re lucky, from having actually been a pitcher themselves.
For the startup CEO, the dugout of experts is your board. You do well to listen to them, take their advice, and like everything you process, fold it into the decisions you make around what “pitch” to throw next as a CEO. You’re lucky to have these people in your dugout, and the good ones know how hard your job is and that ultimately you’re the one on the mound dealing with everything. Ultimately they let you throw the pitch you think best at that moment in the game.
Every pitcher who has logged enough innings knows what it feels like when you have great stuff and pitch a great game. By the same token everyone of us who takes the mound has gotten smacked around by the opposing team. Success and failure go together in baseball — just as they do in startup companies. What matters most is how you as a pitcher respond to a rough inning or outing. Do you give up — letting a bad game crush your resiliency? Or do you bounce back and look immediately ahead to the next batter? It’s the same in a startup. Every great day or win is usually followed by a body blow of some kind. The CEOs who have been through highs and lows, and who know how to pattern match experiences (good or bad) to future prospects in an even keel manner are the ones who give their teammates the confidence to play forward.
Ultimately a pitcher needs to call their own game. Yes you rely on your catcher, (who in the startup world might rotate from day-to-day between your heads of product, sales, marketing, engineering, success, or finance), to offer up pitches you might throw. In fact, the best flow for a pitcher is when you can rely on your catcher to call a good game, you can rely on helpful advice from coaches in the dugout (they’ve seen lots of games and can bring some experience that’s potentially helpful), and you can rely on your teammates to make the plays around you pitch after pitch.
But whether you’re a pitcher or a startup CEO, you have to be willing to shake off your catcher and ignore the dugout every once in awhile. You have to have the guts — and heart — to throw the pitch you feel is the right one to throw, knowing that even if it gets hit, your team will make the play. And you have to be resilient in the face of failure. Always remember, each outing is a learning experience and so long as you love the challenge of pitching and being a startup CEO, the next batter you face is always digging into the batters box ready to take a swing at your next pitch.
Originally published on Medium on September 2, 2018. This Substack version is maintained as the canonical archive.