From Coaching Reps to Building a Company

Going from coaching one hitter at a time to building a company for thousands of them is a strange leap. Some of what I learned in the cage transferred perfectly. Some of it didn't transfer at all. And the single most important lesson turned out to have nothing to do with baseball or software.

What carried over

More than I expected. Teaching a swing is really just breaking something hard into simple, doable steps — which turns out to be exactly what building a good product is. Trust transferred too: earning a family's confidence one lesson at a time is the same muscle as earning a cage owner's confidence one listing at a time. And my time at that ad agency became my unfair advantage — because I'd learned SEO and web development, I could actually build and grow CageList myself instead of waiting on someone else to do it.

What didn't transfer was the pace. Coaching is instant and one-on-one; you watch a kid get better in real time. Building a marketplace is slow, indirect, and humbling. For years it was fragmented and quiet, with none of that immediate "click" to tell you it's working.

The lesson that actually matters

If I had to boil down everything I've learned, it's this: caring more than the other guy is a real competitive advantage. When you care that much, you don't give up — and not giving up is most of the game. I stopped framing the slow years as some sacrifice of the one-on-one impact I loved. Coaching was always about changing the world one hour at a time, because baseball is a portal for creating your own greatness. CageList is the same mission, just at a scale I could never reach one lesson at a time.

What I want it to do for everyone else

I'm a baseball guy, so I catch myself saying "baseball" when I mean the whole game — softball is 100% part of this too. The vision is simple: let the people who pour into this game earn from it, and make access normal everywhere. Coaches shouldn't be at the mercy of a facility's schedule. Owners should be able to turn a great cage into income. And I want to help build the next generation of cages, too — connecting owners with the space and builders to make more of them so the setups out there keep getting better for years.

One piece I'm especially fired up about is little leagues. Take a league like West LA — they've got a handful of awesome cages families would gladly pay to use, but right now that time mostly gets hoarded by whoever's on the board, because it isn't safe to just let anyone walk in. Put those cages on CageList with a real standard around them and the whole league can book time, every rental sends money back into the league, and everybody wins. We don't have an insurance solution yet — I hope we get there — but the model is right.

Why I didn't quit

Honestly? I love baseball — it's what I do. I love business. And I love puzzles. CageList has been one long, hard, genuinely fun puzzle, and I'm so glad I didn't give up on it, because after years of grinding we're about to take off. If you want to be part of it, come find a place to hit — or put your own cage to work. Either way, we're just getting started, and honestly the best part of this puzzle is still ahead of us.

— Isaac Hess, Founder of CageList