This article was originally posted, in a somewhat different form, on David Squires’s LinkedIn account. Follow David on LinkedIn.
We’re big believers in the idea of bringing humor to your business. A few years back, INSTORE’s Chris Burslem wrote an award-winning lead feature on the subject. Definitely read it if you have 10 minutes.
Anyway, today’s lesson comes from baseball — my favorite sport — and, specifically, from Scott Boras, without a doubt the most famous agent in the game.
Now I don’t want to be mean to Boras. Actually, that’s not true. I do want to be mean to him because of all the heartache he’s inflicted on my favorite team (the New York Yankees) over the years.
So here’s the thing: Boras is NOT a funny guy. He typically exhibits all the charm and charisma of a cease-and-desist letter. He looks like a man who dreams in Excel spreadsheets and wakes up screaming if the columns don’t align. It wouldn’t be a shock to learn that he proposed to his wife with a slide deck instead of an engagement ring.
And yet every year, Boras stands before the assembled baseball media and, with a straight face, delivers spectacularly groan-worthy puns about his clients who are looking to sign free-agent contracts.
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A sampling*:
- “There’s been a lot of talk about this being a Bear market for first basemen, but for Pete’s sake it’s the Polar opposite.” (Pete Alonso)
- “There’s no doubt the Snelling salts created a lot of whiffs.” (Blake Snell)
- “Man, I, uh, need a left-handed pitcher like that.” (Sean Manaea)
- “He’s provided the Astros with that infusion of championship blood. Everything about him is AB positive.” (Alex Bregman)
- “It’s simply una-Boyd-able that I need a guy like that.” (Matthew Boyd)
* Granted, many Boras-isms won’t make much sense if you don’t follow baseball.
But these are objectively terrible puns. And there are dozens of additional examples.
And yet, Boras’s clankingly awful jokes never cause clients to walk away or alienate anyone. In fact, during the 2025 signing season, he closed $1.7 billion in deals and earned $85 million in commissions. $85 million. That’s about as successful as you can get as a salesperson.
My point? Boras proves that it’s not the quality of your jokes that makes you memorable or successful. It’s simply the fact that you tried. That’s because even a cringe-worthy sense of humor is 100 times better than none at all.
People don’t remember whether your joke landed. They remember you were human enough to make an attempt.
So go ahead. Tell your customer your pearl collection is “absolutely clam-tastic!” Ask them if they’ve heard about your new payment plan — “it’s interest-ing! Get it? Interest-ing?” Tell them your locket holds two photos — “which makes it perfect for your partner and your backup partner!”
You don’t need to be funny. You just need to be willing to try. Take it from Scott Boras.
