The YouTube of crossword puzzles? How a North Vancouverite is gaming it out

Felim Donnelly founded Crossplay Digital to bring puzzles to the masses

The first thing you see on a Zoom call with Felim Donnelly is a skinny dude in his mid-30s who, you figure, has dressed up as Waldo for Halloween at least one in his life. The second thing you see is a massive stack of board games that takes up about a third of the screen. Either it’s posturing for the interview or the guy who started an online crossword platform is obsessed with board games.

In any case, during the pandemic, Donnelly was working with the District of North Vancouver as a senior strategic advisor, putting his master’s degree in public policy from SFU to good work.

An entrepreneur at heart—a previous venture attempted to help governments adopt technology more efficiently—Donnelly was playing all sorts of board games during the pandemic and started thinking about creating a platform for crossword builders and players alike.

“It turns out that there’s this vibrant scene of people who love to make crosswords as a pastime,” he says. “There’s a Discord server with thousands of people that love to talk about the creativity and creation around crosswords, which I hadn’t explored before.”

The typical problem with creating crosswords, explains Donnelly, is that there are gatekeepers—usually newspaper editors—that control what gets to the public. “If you don’t go that route, it’s very hard to get an audience,” he says. “That struck me as a disconnect. You have all this creativity, and yet the industry was working the way it always had, through this one-size-fits-all mentality. If you run a big publication, you have to make a puzzle that’s going to be as fun for as many people as possible.”

Donnelly founded Crossplay Digital in 2022 and launched its first product, online crossword platform Crosswordr, in summer 2023. The idea, he says, is to bring constructors (the technical term for crossword creators) and solvers together. “YouTube did this for video content—instead of having one site where people would pick what the best videos are, you give people the tools to create their own and build their audience,” says Donnelly.

Along the way, Donnelly picked up veteran Silicon Valley exec Andrew Anker to be the company’s board chair and raised both a $150,000 pre-seed round and a US$440,000 seed round. The company currently has six employees and sees about 450 users a day on its platform.

“Our focus from the beginning has been on building a community and creating that two-sided marketplace,” Donnelly says. “It’s very difficult to get that going initially, but it’s extremely powerful once you’re successful with it. Instead of trying to maximize users from day one, we’ve tried to build the foundation, with a lot of good construction tools and a puzzle directory so that people can sign up for the type of puzzles they like.”

The marketplace seems to be there for the taking. “There are a million crossword searches a month in Google,” says Donnelly. “There are 2.7 million people on the New York Times games app, and that’s a paid subscription. Literally tens of millions of people solve crosswords every day.”

One of the lightbulb moments for Donnelly when he first started the venture two years ago was a custom crossword puzzle that showed the vast potential a platform like Crosswordr could have in an open marketplace.

“It was entirely Taylor Swift lyrics, I had never seen one like that before,” says Donnelly. “People often say, I’m bad at crosswords, it’s too hard to understand the clues. But this doesn’t feel like a crossword if you’re a Taylor Swift fan, it’s just doing a fun puzzle about something you love. Eventually, Crosswordr will have puzzles about all sorts of things, whether it’s Taylor Swift, Beyoncé, Star Wars, the Vancouver Canucks. Instead of having one puzzle for 10 million people, we’ll have a million puzzles for 10,000 people each. It’ll make it more enjoyable for people who love crosswords and will grow the market of people who love to play them.”