Scoring Crazy Little League Games vs. Running a Startup…

Steve Wiesner
5 min readJun 25, 2017

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It’s All-Star season for youth baseball leagues across Southern California. Youth baseball in SoCal is just as crazy as hockey was when I was a kid growing up in Canada — maybe even more so (and that’s really saying something). I was speaking with Corey Barak, a good friend of mine, this morning about the challenges we face as scorekeepers of our kids’ baseball games. Corey is the COO of a successful software business and I’m running a startup so, inevitably, my mind started to draw comparisons between scorekeeping and my day job. There’s actually a shocking number of similarities between scoring and startup life…

  1. We work our asses off and don’t get paid… As many of you know, scoring youth baseball is a ton of work — especially during tournaments. Rather than kicking back in the stands with the smart parents, you’ve got work to do. You’ve often got a matter of minutes to find a score book and make sense of poorly written and incorrect lineup cards. You’ve got to stay on top of pitch counts. Sometimes you have to drive a scoreboard. You’ve got coaches and umpires looking to you for count confirmation. I can go on and on. I’d have to check my bank statements to confirm but, as best as I can remember, I don’t think I’ve ever received a paycheck for doing this over the past ten years… Reminds me a lot of my startup CEO gig. I dream of those long-lost days when my paycheck made me smile. One of the first things to go out the window when you start a company is a fat W2. All work and low (or no) pay is something you need to get comfortable with.
  2. Everyone’s an expert and they will second guess your decisions. “What?!?” “How did you score that an error?!?” “Are you kidding me!?!” “There’s no way junior made an error on that play! Look at the video on my phone!” Parents are incredibly defensive (and aggressive) towards scorekeepers. Reference point #1, WE DON’T GET PAID TO SCORE THESE GAMES! The scoring of that play won’t impact your boy’s ability to make All Stars. The scoring of that play will not reduce his/her chances of making varsity when they go to high school IN SIX YEARS. The scoring of that play will not prevent him/her from that D-1 scholarship. If your kid is as good as you think, just relax and enjoy your seat in the stands. And either way, WE DON’T GET PAID TO DO THIS. This is also something you need to get used to if you’re running a startup (or any business). Rare will be the day when you make a decision that others don’t question. You need to look past it, trust your gut, and don’t second guess yourself despite the noise. Your primary obligation is to always do what you believe to be in the best interests of the business, not a specific individual.
  3. Details matter. You can’t be sloppy scoring a baseball game. “Ooops, I missed that run” simply won’t cut it. Every error in a pitch count is one more pitch on an over-stressed 9 year old arm. The same applies to leading a startup. As hard as it may be at times, you need to pay incredible attention to the details and make sure you get them right. Let’s face it — you will make mistakes — we all do. But when that happens, own it, make it right, and then move on. You never have time to dwell when you’re scoring a game — you just get on with the next inning.
  4. Empowering people to make great decisions. One of the many things I love about scoring baseball games is that you have a real impact but you’re rarely in the spotlight. It’s a welcome relief from work, where you’re often front and center. A good scorekeeper provides the league with critical information. He/she provides the managers and coaches with the data and insights they need to make the best decisions possible about the lineup and defensive positioning. That’s so critical for a startup CEO as well. In my opinion, one of my most critical roles is to empower people to make great decisions: give them data, give them context, and give them the confidence and responsibility to make the right call. If I can build a team of excellent decision makers, I’ve done my job.
  5. Do the job that no one else wants to do. Most people HATE scorekeeping. I get it — it’s a hard and thankless job. At the parents’ meeting to kick off each season, most people sheepishly look at their shoelaces when the manager asks for volunteers. Then, one person raises their hand. That person has the mindset of a successful startup CEO. If it’s a critical task and no one wants to do it, someone has to own it, and that someone will be me. Running an early stage company is a freaking grind. Hollywood and the media may have made it look glamorous but, trust me when I say this, it’s not. When something needs to get done and no one is putting up their hand, the best answer is often to step in and do it myself. No job is below me at this stage — I’ll do everything in my power to make this team successful.
  6. Get comfortable making sense of chaos with extreme time constraints. Scoring an MLB game is a cakewalk. It’s so clean and easy. Scoring a 9U rec league game can make your head explode. A wild pitch and four errors on that play. Junior threw home instead of tagging the runner who was a foot away and now three runs score on another. Little kids make big mistakes and that makes for a messy scorebook. You need to decipher and memorialize the insanity that just happened and you’ve got sixty seconds to do it before the next pitch gets thrown. The parallel is so spot on to a day in the life at a startup. You never know what challenges a new day will present. All you know is that, as crazy as they may be and as messy as the day may become, you need to deal with it and get on with the tasks at hand.
  7. You need to focus. It’s 3,000 degrees in the shade. Someone has spilled Mountain Dew on the scorers’ bench. Parents are sniping that the scoreboard is wrong (often when it’s actually right). You’ve got an umpire with laryngitis who’s strike zone changes with every pitch. You’ve got a tiger Dad standing over your shoulder in the scorers’ box yelling at Bobby not to step out on the next pitch. It is so incredibly difficult to stay focused on getting those counts right with all of the distraction. And yet people will cut you absolutely zero slack if you get something wrong. I’m sure this sounds familiar to all of you running startups…
  8. Both can ruin your weekend! Scoring youth baseball games turns Saturdays and Sundays into work days. Startup life does exactly the same. The best way to keep a smile on your face is to step up and embrace the challenge because, in the end, it’s amazing, fun, interesting and rewarding work to do and I’m blessed to be able to do it. I wouldn’t have it any differently.

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Steve Wiesner

CEO of pelotonRPM, recovering finance-type, thrilled to be living this life.