Why my wiffle ball tournament has a payments platform

Every summer I run a wiffle ball tournament called the Schott Classic. It's a family-and-friends tradition with real teams, real brackets, and increasingly real logistics. For years, that meant the usual duct tape: group texts, a spreadsheet, cash in envelopes, and me chasing captains for rosters the night before.

Last year I did what any reasonable person with a strategy job and a building habit would do: I built it a platform. This year it committed to git 1,778 times.

What it actually does#

SchottClassic.com now handles:

• Team registration with live capacity - captains sign up, the site knows how many slots are left, and I stop being the bottleneck.
• Square payments - entry fees are paid at registration, reconciled by webhook. No envelopes. No "I'll get you next week."
• Waivers - signed digitally at registration, chased automatically when they're not.
• Brackets and live scoring - pool play to bracket, scores entered from a phone at the field.
• Umpire scheduling - yes, we have umpires. Yes, they get assigned through the platform.
• Sponsors - local sponsors get real placement, tracked in the same system as everything else.

Stack, for those who care: Next.js and PostgreSQL, hosted on Replit, Square for payments. Built mostly at night, heavily with AI tools.

The honest reason#

I could pretend this was about efficiency. Some of it was - the week before the tournament used to be miserable, and now it mostly runs itself.

But the real reason is that the tournament is a thing my family and friends genuinely love, and building software is a thing I genuinely love, and pointing the second at the first makes both better. My kids check the registration count like a stock ticker. Captains who ghosted my texts for years now register in February because the site makes it feel official. It IS official. There's a confirmation email.

The transferable lesson#

Small, personal projects are the best AI-era training ground I know. Nobody's career depends on my bracket generator, so I can try tools and patterns there before they touch anything at work. Half of what I've brought to my day job - agent workflows, payment webhooks, feedback pipelines - got proven out on a wiffle ball tournament first.

Find your wiffle ball tournament. Build it unreasonable software.