An AI-powered sports marketplace, from zero to $250K in 90 days.

Discovery is the athlete side's core promise — and the hardest thing to deliver on a young marketplace. A plain search box over early-stage inventory returns empty results, and empty results teach athletes to never come back.

The fashionable option was an AI chat assistant bolted on top of the app — great in a demo, hollow in daily use. The conservative option was classic filter-and-browse taxonomy, which works only when inventory is deep. The third option was quieter: put AI inside the surfaces athletes already understand.

We built intelligent search into the existing surfaces — search, profiles, dashboards — instead of shipping a chatbot. The cost: it demos less flashily and took longer than wrapping an off-the-shelf chat UI. The win: AI that personalizes results athletes were already asking for, invisible as a feature, useful as a behavior.

Intelligent search across events and organizations, plus map-based court and venue discovery — the physical places of the sport as a first-class surface. I also built a court map generator, so venues that exist nowhere online can exist on Midseason.

Anchoring discovery to the map was the cold-start counterpunch: courts and venues are real even before marketplace inventory is deep, so the app is useful on day one in a brand-new region.

Club sport money moves through e-transfers, cheques and spreadsheets. For organizations it's unpaid admin work; for parents and athletes it's friction and zero visibility. And for a marketplace, payments aren't a feature — they're the proof the model works.

The standard startup play is to launch free, build an audience, and add payments "later" — it's less build, less compliance, and less risk for an early-stage founder. The alternative was to make payments part of v1 and carry the full weight of marketplace payments compliance from day one.

Payments shipped in v1, built on Stripe. The cost was real: the heaviest engineering lift in the product, compliance obligations, and Stripe's constraints baked into my flows. But a sports platform without payments is a directory — and a marketplace thesis you can't test. Revenue is the only validation that doesn't lie.

End-to-end marketplace payments: registration checkout designed for the athlete-and-parent side, payment visibility for the organization side, sponsorship integrations, and the investor-facing financial model behind the pricing. Both sides of every transaction got a designed experience, not just a processor bolt-on.

$250K+ in transactions processed within 90 days of launch. That number is the payments UX doing its job: organizations trusted the rails enough to move their registration revenue onto a brand-new platform, run by clubs, paid by parents, in three regions.

Club operators are coaches, parents and volunteers — not analysts. A platform that quietly accumulates registration, league and payment data gives them nothing unless it can answer their actual questions: how is my league doing, who's coming back, where's the money.

The default is the everything-dashboard: charts and tables for every metric, configurable by nobody who'll ever configure it. The bet I preferred: fewer, opinionated views — AI turning platform data into personalized insights per organization, at the risk of hiding raw data a power user might want.

Opinionated insights won. An operator running a league between a day job and a family doesn't want a BI tool; they want to be told what matters and what to do about it. The tradeoff is real — some flexibility sacrificed — but the design principle held: serve the operator you have, not the analyst you imagine.

Organization analytics dashboards and league analytics that turn platform data into personalized insight — registration, engagement and revenue readable at a glance by a non-technical operator, on the same design system as the athlete side.

A sports community needs messaging and visible athlete profiles — and a youth-sport user base makes both a safeguarding problem before they're a growth feature. This is the design decision most social products get to ignore and a youth-sport platform absolutely cannot.

Open DMs are the growth-friendly default — every social loop gets faster when anyone can message anyone. The safeguarding alternative deliberately adds friction: structured, purpose-bound communication designed around the most vulnerable user rather than the median one.

Safeguarding won, and it wasn't close. Messaging is designed with guardrails as deliberate product decisions — communication scoped to the sport contexts it belongs in, not an open social graph. The cost is slower viral growth; the return is a platform parents can trust, which in youth sport is the growth strategy.

Scouting-oriented athlete profiles — built to get players seen for the right reasons, by the right audience — alongside messaging with safeguarding designed in from the first wireframe. Trust here is what lets the other three deep dives exist at all: nobody moves their club, their kids and their money onto a platform they don't trust.