Jeopardy! has been the background noise of my life ever since I was a child. My whole family would watch it together at grandma’s house. Austin Rogers, a bartender from New York, was my favourite contestant. He was so quirky and fun to watch, and I saw myself in him. Over the years, I started shouting my own answers at the TV, and eventually I realized I was getting a lot of them right.
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So, when I was 22, I started applying to be on the show. The first step is an online test that you can attempt once a year. You have a limited time to answer 50 questions, and then they follow up with people who score really well. It’s mysterious, though, because you don’t get to see the answers or your score—you just have to wait. For a long time, I didn’t hear back, but I’d always set a reminder in my calendar to apply again the next year.
Then, in 2021, when I was 35, I was pulling into an IKEA parking lot when my phone pinged. It was from Jeopardy!, and it wasn’t just a mailing list—it was an actual person from the show saying I’d gone on to the next round. I went crazy, smashing the steering wheel in excitement. The next step was to take a similar test while being observed on a Zoom call. After I completed it, no one ever got back to me, but the experience lit a fire under me anyway. It felt like there was a real possibility that I’d get on the show one day.
At the time, I was working at Get Well pizza on Dundas Street West. I’d hosted trivia nights a couple of times before, but in 2022, I decided to get more serious about it. I started reaching out to different bars, eventually securing a weekly trivia night at Collective Arts Brewing. Those first trivia nights were a lot of fun for me. It was a comedy of errors as I retooled the show and learned on the fly, but I was committed to being an amazing host. One night, my microphone died, so I made a fake one out of a rolled up piece of cardboard. The show must go on!
Eventually, I started hosting regular trivia nights at the Drake Hotel, Pennies and Junction Brewing. It really blew up from there. The crowds started to grow, and I had regulars who would play every week or follow me from bar to bar. I didn’t get into any of this hoping to make it a business, but by the fall of 2022, it was taking up too much of my time to be anything else. So I left Get Well to focus on trivia full time. It was a risk, but I had an opportunity to do something I was really passionate about. That was more valuable to me than money.
I named the business Toronto Trivia, but all of my trivia events are under the name Almost Jeopardy, a nod to my love of the game. For me, coming up with the questions is the most time-consuming part. I spend a lot of time at the library, doing crosswords, listening to podcasts, watching weird YouTube videos and documentaries—anything I can do to keep the hopper full of new questions. When I’m hosting, though, it’s all about being as kooky and hammy as possible. Trivia can be intimidating, but it’s meant to bring people together. I try to bring some humour and levity to the game.
By January of 2023, I had so many trivia gigs that I needed help. I hired a second host and someone to do our marketing. We started getting requests to do private events—baby showers, weddings, bachelor and bachelorette parties, birthdays. Eventually, we were hosting upward of 10 shows a week. I actually started losing my voice from doing so much public speaking. To keep up, I expanded the team even more, and now there are a full 12 of us.
Of course, I was still doing my annual Jeopardy! test. In August of 2023, I decided to go to a Game Show Boot Camp in Las Vegas run by Jeopardy! legend James Holzhauer. It was a full day of seminars and workshops for people who want to get onto game shows. I got to meet heroes of mine like former contestants Mattea Roach, Amy Schneider, Sam Kavanaugh and many more. After that, I bought a ticket to a trivia convention in Washington, DC, where they were hosting in-person Jeopardy! auditions. I really wanted to be the perfect contestant, so on the day, I tried to be funny and personable. I didn’t hear back for several months, but I had a strong feeling I was getting closer and closer.
Then, this August, I was sitting at the Drake when I got a text. It was someone from Jeopardy! saying they wanted to discuss the details of my application in a phone call. It was the contestant producer at the show, and I knew his job was to invite people on. I could barely keep my emotions together, so I immediately paid my bill and left. The call was the next day, and I had a friend film it for me. They invited me to compete in LA. It was the best phone call I’ve ever received. At the end, I said, “Thanks for picking me. Thanks for putting me on. Let’s make some great TV.”
After that, I entered into full-blown training mode. For about 28 days, I watched six old episodes of Jeopardy! a day and answered north of 10,000 trivia questions that I compiled from old episodes and online trivia games. When it came time to fly down for the taping, my whole family joined me—my mom, dad, two brothers, sister-in-law and girlfriend. It was amazing to have a six-person cheering section. It felt like the Olympics.
On the day, I was mostly focused on staying as calm as possible. I knew I had done everything I could to prepare. I’d even practised breathing exercises to manage my nerves. They tape five episodes each day and don’t tell you when you’re going to go up—instead, contestants are randomly drawn before each new episode. If you win, you change outfits after your episode and walk back out with two fresh opponents.
It’s incredibly nerve-wracking to be sitting in the green room after each episode ends, waiting to hear if you’ll be next. I’d been anticipating that moment because I knew it was going to feel shocking and I didn’t want to let it destabilize me. When they called my name, I got a big surge of adrenalin, but I used my breathing to focus and try to direct it. I had so much energy that I bounced up and down like a boxer. I was ready for a trivia showdown.
When it was time to walk onto the stage, I took a breath and said one last thing to myself: Dare to be great. From the stage, the crowd was loud and the lights were bright. It felt like being at Madison Square Garden. Ken Jennings was right there looking at me. It was one of the highlights of my life.
I’m a pretty open book, so it’s been hard not to discuss the results—you have to keep everything very secret until after your episode airs. But it’s been amazing to see how many people are cheering me on. I’m really excited for everyone who’s been supporting me in my trivia journey to see the episode, which comes out on October 17. Toronto Trivia is hosting watch parties at bars all over the city, including Bellwoods Brewery, Steadfast Brewing, Bickford Brewing and Danforth Sidebar.
It’s a surreal feeling to have finally achieved my dream. It may seem like an ending, but I think it’s actually the beginning of an incredible new chapter in my life. I’m going to need a new challenge and somewhere else to direct my passion and energy. I still love trivia, but I’ll looking forward to finding a new dream to chase.
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