FifthYear
Registration, payments, teams, brackets, results, and discovery for adult recreational athletes and the volunteers who run their competitions.
FifthYear is a two-sided platform for adults who enjoy competing and the people who organize those competitions: league commissioners, race directors, run club organizers, gym owners running a local tournament. One athlete profile spans every sport. One set of organizer tools replaces the spreadsheet, the Venmo requests, and the group chat.
Setting the scene
FifthYear was built in partnership with my brother Ryan. The concept formed around our own needs. We both enjoy running, yoga, and sports. We were well aware of Chicago’s thriving rec leagues. However, if I want to sign up for a 5k, join a rec soccer league, and find a run club to train for both I am forced to hunt down each registration in fragmented experiences across multiple platforms. It’s too easy for events to come and go, and have no idea they are happening until they are over.
The experience is frustrating. More and more we see our friends want to participate in a veriety of activities, not be locked into one hobby. Content for hybrid athletes is taking off. Pickleball swept the nation. People are looking to build community and socialize in real life. The signals are there, so we built the product we want to exist.
Athletes discover events, register (or enter a lottery), form teams, recruit free agents, and follow their results and standings over time. Organizers run the whole lifecycle of an event: registration & fees, waitlists, brackets and schedules, broadcast announcements to partcipants, and manage staffing.
See FifthYear in action
Discover
Scores and standings
Architecture
Challenges of growing a marketplace
Two sided marketplaces are notoriously difficult to get started because they require both supply and demand. On FifthYear, leagues, events, and clubs are the supply. Athletes/participants are the demand. Without athletes organizers don’t have an incentive to join and vis versa.
We have decided to make a bet: target run club organizers. These are the lowest friction organizations and often operate more informally than something like a half marathon that needs a course and paid registration. Run clubs are often free and community focused. Our hypothesis is that with these clubs we can build a passionate user base. These initial events may be low revenue, but help will seed demand on the marketplace and encourage more supply to join.
What we will measure
- Club profiles created
- Club event registrations
- Club announcements and message volume (is it being used to communicate)
What the heck? Where’s the AI?
The goal is to get people out into the world to be active and build community. Our AI strategy is to make the events, leagues, and clubs easily discoverable by AI agents. That way someone chatting with Claude or ChatGPT about how they want to join a volleyball league or find a walking group in their city can find exactly what they are looking for and get signed up.
There will be opportunities to provide organizers AI tooling to help with things like creating league and staffing schedules or answering questions from inquiring participants. For now our focus is on building the demand side of the equation.
Closing thoughts
Building for experiences that continue off screen is truly a whole lot of fun. Which is ultimately what FifthYear is all about: creating more opportunities to have fun and stay in the game long after the NIL checks stop rolling in.
P.S. If we have an chance to talk about this project ask me about the internal app we built to allow us to support the platform with a lean two person team!