My brain is definitely in baseball mode right now. My high school coaching is heading into the final few games of what has been a challenging yet very rewarding season. And I write this post from Santa Barbara where I’ve come for the weekend to watch the UCSB Gauchos play their long-time rivals the CSU Fullerton Titans in a three-game series.
Spring is a time I find myself observing how so many elements of baseball translate to “real life”, and how true this is no matter the competition level. While the speed and polish improve from level to level, so many of the truisms remain consistent from how the game evolves from youth to high school to college and to ultimately the professional level.
Every sport provides learnings that apply to one’s worklife, but there’s something about the game of baseball that I find particularly relevant to what it takes to navigate the ambiguity and challenges of working in a company, especially an early stage company. Specifically, there are four characteristics inherent in baseball that I see embedded in what also matters for people working in a startup organization either as the CEO, a people manager, or an individual contributor.
Failure and Resilience
There’s a lot of failure in baseball. The best hitters succeed well below 40% of the time and the best pitchers can all recite countless outings over their career in which they got “lit up” by opposing hitters. Likewise, there’s a lot of failure in startups. Most of these companies fail, and the failure rate of startups is even lower than the batting average of the weakest MLB hitters.
If you can’t handle failing and aren’t willing (or able) to learn how to be resilient, then don’t play baseball or start/join a startup. In baseball, the line is “flush it”, a refrain used to remind the hitter to forget taking that called third strike so they can immediately refocus their attention on playing great defense and can restart preparing mentally for their next at-bat.
The same applies to what you do in a startup. Forget that customer product feature that bombed or that sales pitch that resulted in a “no thanks”. Flush it. Figure out what you’re building and shipping next, or shift your focus to how you’ll tweak that next sales presentation.
Repetition and Iteration
Baseball is a game of repetitions or “reps”. You can’t master the game just because you can run fast, jump high, or have amazing strength – just ask Michael Jordan. It’s a game that requires hitters take thousands of swings at thousands of pitches that move and dart in different directions and varying speeds. It’s a game that requires pitchers to throw thousands of pitches that they are endlessly trying to command moving in multiple directions and speeds.
Startup companies are also built on “reps”. Ask any startup founder or CEO how many times they have to iterate on their fundraising pitch. Most of these CEOs will tell you stories of the thousands of versions of their presentation they had to create over the course of their fundraising efforts, and the hundreds of meetings in which they presented those pitches to investors.
With each rep those CEOs got a little better; they told their company’s story a little more clearly and with increasing conviction and confidence. But they never stopped getting reps, they never stopped iterating, and neither does anyone in a startup no matter what your role or level might be. Like baseball, you’re constantly trying to perfect the imperfectable and, just when you think you’ve got it all figured out, you get smacked down. The pitch falls flat, the marketing channel doesn’t react as hoped, or the hiring strategy yields lackluster results. At that moment you know it’s time to tap into your resilience and get in some more reps.
Playing Every Out
Baseball has no clock (well, the pitch clock doesn’t really count). Both teams get the same number of outs and you learn pretty quickly that no matter the score or situation, neither team can hold the ball and run out the clock.
This is exactly why maintaining resilience and getting in your reps are so crucial. As Yogi Berra said so well: “It ain’t over until it’s over.”
This ethos applies so beautifully to life in a startup. While venture capitalists like to ask “what’s your burn, how much runway do you have?”, this doesn’t ever mean as a startup CEO you are on a defined clock. With any amount of capital raised, as a startup CEO you and your team have a certain number of outs you can play. You need to play every one of them because it may be the bottom of the ninth when you get the breakthrough you need, like figuring out product market fit or getting that first customer closed.
Unlike a baseball game that eventually ends once the losing team has used up their 27 outs, a startup has levers to create more outs it can play. Whether that’s raising more capital, slowing down the pace of investment, or both, your company can continually adjust the length of the game so long as you stay mindful that there’s no clock defining when the game’s over and that every “out” matters.
Individual and Team
Being resilient, focusing on getting reps, and playing every out are all elements deeply inherent in both baseball and startups, but my favorite dynamic by far is how both experiences combine the individual and team.
In so many ways baseball is the most individualistic team sport out there. The pitcher on the mound, the hitter in the batter’s box, and the fielder on the diamond are all alone, individual in their respective pursuit of getting the hitter out, getting on base, or successfully fielding the ball hit to them. At the same time, there are ten players (nine position players and a designated hitter) in the lineup at any time and it takes their collective team effort to score as many runs as possible when at bat while concurrently yielding as few runs as possible when pitching and playing defense.
The startup company is no different. Everyone plays a position in the field and hits in the lineup. The metaphor can be extended however you want. Maybe the CEO is the pitcher, maybe she’s the manager, or maybe the catcher, shortstop, and centerfielder represent the head of product, go-to-market and finance respectively. However you slice it, the theme is the same. Every functional role is critical in the company, and every individual has to make plays on defense and do their best job possible when it’s their turn to hit.
And yet, the team doesn’t succeed because of a single player’s performance, nor does it fail because of a single player’s error or strikeout. A team can – and often does – lose because the commitment to win isn’t held by every player, the individual effort isn’t contributed by every player, and the culture of “picking a teammate up” doesn’t exist within the team.
It’s this last point that brings it all together. Because the experience of playing baseball and working in a startup company are so challenging and full of failure on the individual level, the team ethos of supporting every player when they struggle can play an outsized role in how a baseball team or company navigates tough times. It’s the combination of CEOs that lead in this way, managers who manage in this way, and individual contributors who step beyond their individual efforts in this way that powerfully transforms a game of individual contributions into the result we all remember most – team success.


