Aaron Brown is a lifelong Jeopardy fan who has divided his time between entrepreneurial ventures, side hustles and hospitality work. In June of 2022, he quit his full-time job at a Toronto pizzeria to pursue a career as a trivia master.
Brown’s enthusiasm for trivia goes back to his youth, when he was a self-proclaimed “know-it-all kid” who watched Jeopardy at his grandma’s house and would yell the answers at the TV. In his early twenties, he began an annual tradition of applying to be on the show.
In many years of tryouts, Brown has had one glimpse at the second round, and refuses to give up his dream of being on the show. In fact, his aptly-named Almost Jeopardy Trivia events are a commemoration of that step towards his ultimate life goal.
What started as a side hustle hosting one weekly trivia night at Collective Arts Brewery in June of 2022, has since grown into a city-wide business. At the time, Brown held a full-time job at Get Well pizza on Dundas West.
When the Collective Arts event ran its course, Brown sought other bars to host his trivia, and was happily surprised to find that there was a sudden surge in demand.
In a short time, Brown secured a regular trivia night at The Drake Hotel and other popular venues. “It really just blew up from there,” he says. Soon enough, he was too busy to continue working at the pizzeria and left his job to focus on trivia full-time.
“I’ve started a lot of businesses, little fun projects, and side hustles over the years and this is the one that has actually turned into something viable,” he reflects with amusement.
In the year since quitting his job, Brown has hosted regular trivia events at Pennies, Junction Craft Brewing, Bar Hop, Praise Wine Bar and The Drake Hotel, to name a few. The full schedule of trivia games can be found online at Toronto Trivia.
To expand his trivia business even further, Brown began accepting private bookings. “We go to people’s offices, we’ve been to Ubisoft, we’ve done a bunch of private events at the Drake, high-profile law firms,” he lists. He’s even hosting his first wedding trivia soon. “I’ll do any gig,” he laughs.
He’s helped by a group of “trivia minions,” including his brother Keith Brown, who acts as his assistant and even stands in as a game host when needed. As a professional magician of twenty years, his brother’s insight into professional entertainment has been crucial to the success of Almost Jeopardy Trivia.
Bar trivia is not new to Toronto, but Brown uses his love of Jeopardy to put a particularly wacky, fun-focused spin on his games that keeps attendees coming back.
Before each trivia game, Brown playfully warns participants that the trivia god a.k.a. the late Jeopardy game show host Alex Trebek, is watching from above and will know if they look up answers in the bathroom.
Significant role models in the ever-important trivia universe include Jeopardy hosts Ken Jennings and Mayim Bialik, as well as Mattea Roach, Canada’s greatest Jeopardy player (and, Brown hopes, his future best friend).
That makes Brown the humble priest of trivia, tasked with the responsibility of creating questions for Toronto trivia players. “This is how I stay ready for the day that I get that call to L.A.,” says Brown.
Really, the purpose is to make the game fun. “Trivia can be intimidating for people,” he explains, “[because] they might think they don’t know anything, or they’ll get a question wrong.” Instead, he says, the point of the game is rather to bring people together to collaborate as a team.
Not everyone in the bar is there to play, Brown points out, “but if I think you might want to play at all, I’ll just find out what it is holding you back and try to make you feel better about it,” he says. In the end, you might even win yourself some beer or a gift certificate.
When Brown isn’t hosting trivia, he’s at home writing questions, researching at the library, watching weird Youtube videos for inspiration, or doing a crossword in the corner of a local bar– “anything I can do to keep the hopper full of new questions,” he says.
“I can’t believe my job,” says Brown, “But I’m like the happiest guy in the world. And I’m just gonna ride this until the wheels fall off and it’s not fun anymore, which is hard to imagine.”