For more than a decade, my 3-on-3 pickup hockey game has been a fixture in my life. It’s not a formal league, just a dedicated group of about 15 regulars who split the cost of ice and a ref for a full season. It’s the best kind of hockey: fast, friendly, and competitive.
I’m the organizer. And for most of those 10 years, that title felt like a penalty.
I loved the game, but I was slowly drowning in the “admin” it took to make it happen. My passion project had turned into an unpaid, part-time job, and the tool at the center of my misery was a massive, clunky spreadsheet.
If you organize any kind of pickup sport, this probably sounds familiar.
The “Before” Picture: My Descent into Admin Hell
Every single week, I was a slave to a manual process that was fragile, time-consuming, and deeply frustrating. My job as “organizer” involved:
- The Weekly Headcount: Sending out a mass email or text (“Who’s in for this week?”), then meticulously tracking the “yes,” “no,” and “maybe” replies in my spreadsheet.
- The Spare Scramble: We need 20 players to run. If we only got 17 “yes” replies from regulars, I’d have to dive into my other spreadsheet—a long list of spare players—and start the “waterfall.” I’d text the first 5 spares. Wait. Get one reply. Text 5 more. Scramble. Beg. It was a stressful, anxiety-inducing puzzle every time.
- The Money Chase: At the start of each season, I had to collect fees from 15+ guys. My spreadsheet had columns for “Paid,” “Owes,” and “Payment Method.” I had to cross-reference Venmo, cash-in-hand, and e-Transfers, all while gently nagging my own friends to pay me.
- The Team-Making Headache: Once I finally had a full roster, I’d stare at the list of names and try to do the mental gymnastics of building two fair teams. I had to balance skill levels while also trying to keep things fresh, so guys weren’t playing with the same linemates all season. It was impossible to get right, and I’d inevitably hear complaints about lopsided games.
- The Final Email: After all that, I’d have to manually type up the teams and the game details into another email and send it out to the group.
This 5-step-dance took hours every week. I was spending more time in spreadsheets than on the ice. The “admin” was killing my love for the game.
The “Aha!” Moment: The Market Gap
I knew there had to be a better way. I searched for an app to help me.
I found dozens. But they were all built for “real” leagues. They were designed for formal teams in a 12-team soccer association, with fixed rosters, parent-coordinators, and static schedules.
They couldn’t solve my problems. They didn’t have a way to automatically invite spares when regulars dropped out. They didn’t have a “make fair teams” button for a new group of 20 players each week. They were bloated, complex, and built for a totally different purpose.
I realized what I needed didn’t exist. The world didn’t have an app for organized pickup.
So, I decided to build it.
The “After” Picture: Building My Sanity
I created HappyRoster to be the app I desperately wished I had. I built it, feature by feature, to kill off every single one of my manual tasks.
- Instead of chasing RSVPs, HappyRoster sends invites and tracks availability on a simple dashboard.
- Instead of the “spare scramble,” the app automates it. When a regular drops out, it automatically invites the next person on my spare list until the spot is filled.
- Instead of a payment spreadsheet, I have a simple tracker that shows me who’s paid and who owes, all in one place.
- Instead of team-making anxiety, a one-click algorithm uses win/loss stats to generate fair and fresh teams every single week.
- Instead of a manual email, the app automatically sends the team announcement to everyone.
What used to take me hours of stress and spreadsheets now takes me about three minutes.
I didn’t just build an app. I built a way to eliminate the headache, save time, and make sports fun again—especially for the organizers. I finally got to hang up my administrator hat and just go back to being a player.