In 2014, James Gibbons was building BlackBerry apps while living with a friend who had couch space in New York City. In his free time, the University of Waterloo computer science grad would try to organize pickup basketball games in the city but found it difficult. He didn't know his neighbors, and everyone had crazy schedules. Biking around Manhattan one day, Gibbons asked some basketball players about using an app to organize games. Good idea, they said. His market research done, Gibbons started writing the code. "The nature of pickup," he says, "made it easy for people to join without a long-term commitment or having to worry about costs."

In 2016, OpenSports was launched (thanks to $60,000 that Gibbons won in a hackathon) to help organize pickup games in soccer, basketball, hockey, and even quirkier pursuits, like quidditch and dragon-boat racing. The Toronto-based startup's first customer was that city's department of recreation and culture. But the bureaucracy resisted digitizing its offerings and providing real-time updates, so OpenSports pulled a reversal and opened the platform up to the public. Open­Sports does the scheduling and check-ins, collects payments, executes waiver forms, and keeps win-loss records; users can choose among dozens of customizations.

The three-person startup, which takes 5 percent of the organizer's revenue (from player fees and event sponsors), works with nonprofits like Philadelphia Volleyball and corporations like WeWork, which created a pickup soccer league for its co-working spaces in Toronto so members could compete each week. "We cater to a diverse group of players, from the side hustlers working multiple jobs to recent immigrants wanting to play their favorite sport," says Gibbons. "Even visiting Hollywood actors want to get in a game of footy, just like everyone else."