There’s a game within a game that Ryan Wickens, founder of Quizmaster Trivia, likes to play when he hosts trivia night at The Landing at Hoyt Park in Wauwatosa.
It’s called the “Spot Prize.” Wickens asks one ridiculous question, usually involving a number that’s almost impossible to guess: “What is the world record for most golf tees in a beard?” or “Most blueberries eaten in three minutes?”
The teams with the lowest and highest guesses are lovingly mocked before Wickens reveals the actual answer. The team that comes closest wins candy from his native England, often a Dairy Milk, Wispa, or Flake. It’s a little taste of the UK, handed across a table in Wauwatosa.
Twenty years ago, Wickens brought something else over from England: the pub quiz itself. And what started as one British import has since grown into something much bigger.
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This December marks two decades of Quizmaster, the popular pub trivia company that began at the BritInn in Shorewood in 2006. What started as a weekly quiz at a British pub in a Milwaukee suburb grew into a business that now brings trivia to venues across the Midwest; survived a pandemic that brought the hospitality industry to a standstill; expanded into themed trivia, Feudmaster and Tunemaster; and is now venturing into a new arena with a physical trivia card game.
Spot Prize Question: How many trivia questions has Wickens written in 20 years?
The answer is more than 100,000.
But somewhere along the way, Quizmaster became about more than the questions. It became about the people answering them: the weekly rituals, the table rivalries, the strangers who end up sitting together by round two, the couples who met over a trivia sheet, even a wedding Wickens was asked to officiate for two people whose relationship began at one of his venues.
To understand how Quizmaster became all of that, you have to go back to the beginning, to a British soccer player who arrived in Milwaukee in 2003 with no idea he was about to build a trivia empire.
Round 1: History
At 18, Wickens came to Milwaukee after receiving an offer to play soccer, or “football,” as he calls it, for Cardinal Stritch University.
“It was somewhat a shot in the dark because I didn’t really know much about the place,” Wickens says. “In 2003, the internet wasn’t really what it is now. You didn’t have as good an idea as maybe you would if you were doing this kind of thing today.”
Cardinal Stritch’s soccer program had recruited heavily in England, so Wickens quickly found himself surrounded by other players from home. “It made me fit in quickly,” he says.
He met his future wife just as fast. Naomi, a Wisconsin native running cross country at Cardinal Stritch, was introduced to him through mutual friends the Sunday night before his first week of classes, and they started dating soon after.
Between classes, Wickens worked odd jobs around campus, in landscaping and even babysitting. He wasn’t dreaming up a future company. “I was just kind of living one day at a time, to be honest with you,” he says.
By happenstance, two of his English soccer teammates noticed a new British pub opening on Oakland Avenue and got hired as bartenders. “It was very authentic, because you got these English guys actually from England who actually know British culture and all the kind of slang,” Wickens says.
Naomi, by then dating him, started working there, too, as a server. Because British pubs have a long tradition of pub quizzes, it wasn’t long before the BritInn had one, too. “It’s something we’ve been doing in the UK for decades, and it really wasn’t a thing in the States yet,” Wickens says.
In December 2006, Wickens ran the first quiz with no grand plan. “I was not intending at that time to turn it into a business,” he says. But the pub, which held about 60 people, was packed to capacity almost every week.
Wickens still remembers the regulars: Clan McLeod, a team of sharp older guys, one of them Scottish; and the Hot Grad Students, Marquette students who drove all the way to Shorewood because there weren’t many other quizzes to play. The two traded first place back and forth, but Wickens realized there was more to a good trivia night than simply being the team with the most correct answers. He wanted to give everyone a chance to win something, even if they weren’t the smartest team in the room. That idea eventually became a Quizmaster staple: the prize for best team name.
“We’ve got to give these people that are here every week a chance to win something, even if it is a minor prize,” he says.
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The operation itself was decidedly low-tech. “I remember going to the BritInn on a Wednesday and 30 minutes before the quiz I was still writing the questions,” Wickens says, laughing. But he remembers the atmosphere, too. “Everyone was so engaged. Everyone in there was playing. It was just a lot of fun.”
The quiz didn’t stay in one place for long. Regulars connected him with the Carlton Grange, another British pub in St. Francis, and he added Tuesday nights alongside his Wednesdays.
Then came the Milwaukee Ale House downtown, the real game-changer, drawing 120 or 140 people some Monday nights and putting Quizmaster on the map. More venues started calling, and Wickens, who by then was working a day job in public relations, kept saying yes until nights began to overlap.
“I was like, okay, I’m going to have to hire some people,” he says.
Round 2: General Knowledge
The basic Quizmaster formula hasn’t changed much in 20 years. Six rounds. Five questions per round. A lightning round with 10 answers to one question in two minutes. Pen and paper. A person behind a microphone reading the questions aloud. The only time phones come out is for the picture round.
“I found a winning formula immediately and then I just kind of stuck with it,” Wickens says.
It’s a formula summed up in the company’s motto: “Drink While You Think.” The point has never been simply to see who knows the most. It’s to give people a reason to gather at a bar, order a drink, argue over an answer, and spend a couple of hours together.
Along the way, Wickens has modified the format, adding wager rounds, the lightning round, and the latest, Master Majority, a subjective either-or round he’s now trialing. (One recent question: Would you rather be one foot tall or 20 feet tall?) But he’s resisted one major evolution: putting the game on a phone.
“I think that it kind of takes some of the charm away from what a pub quiz is supposed to be,” he says. “There is something to be said about the quizmaster speaking. We’re all going to listen for a second, and then we can all talk amongst ourselves.”
The format has also let Wickens hold onto something rare as the business has grown: one person writing the content. “I do not have a team. There is no team for content. I am the team.”
His database now holds more than 100,000 questions, organized by category. When writer’s block hits, he steps away. “I’ll take a break, do something else, play with my kids, go exercise,” he says. “I am responsible for like 99% of the content. All of the general knowledge quizzes that you play, like on weeknights, 100% coming from my brain.”
Round 3: Wager Round
Every growing business makes a few bets along the way. For Wickens and Naomi, the first one came quietly, years before the biggest.
Wickens was still working his day job at a PR agency and expanding the business when he and Naomi married in 2009. She’d been by his side throughout college and had a front-row seat to Quizmaster’s growing success. From her point of view as a participant, she recognized the value.
“It’s just so nice to get together with a group of friends and just hang out and do something fun,” she says. “For years, that was my life with trivia. I was on I don’t know how many teams, but it was like three days a week.”
So when Wickens eventually approached her about making Quizmaster his full-time job, she encouraged him to go all in. Naomi eventually became more than a spectator to that growth. She was working full-time at Cardinal Stritch when she decided to join him, betting her own steady job on the business, too.
Her role has largely been behind the scenes: invoices, spreadsheets, and the tasks that keep a growing company running. Her graphic design background has also given her a natural hand in the visual and marketing side. “Ryan always has so many ideas, so it’s nice to have someone to bounce those off of,” she says. “I guess that’s me.”
The decision gave the couple something that became increasingly valuable as their family grew. They now have two children, and Quizmaster’s flexibility has allowed them to build the business around family life in a way a traditional 9-to-5 job might not have.
“The greatest thing about being self-employed is like the freedom to make choices,” Wickens says. “Not being told what to do, where to be.”
Their biggest wager, though, was still ahead of them. The Wickenses had just had their second child and moved into a new house when COVID-19 shut down the hospitality industry, much like everything else. “My income basically went to zero overnight, literally,” Wickens says.
Within days, he was looking for a way forward: a bet that trivia could survive without a bar. They launched virtual trivia on March 19, 2020, hoping for 30 or 40 teams. Some nights, they had 500. “It wasn’t as fruitful as my pub trivia business, but it certainly helped us kind of get through that rough patch,” Wickens says.
For Naomi, it was a familiar kind of gamble. “Ryan immediately started coming up with ideas: What can we do, how can we pivot, how can we make this work?” she says. “He’s always been so confident about just, let’s try it.”
The wager paid off beyond survival. The virtual game reached participants far outside Wisconsin, with some later showing up at Quizmaster nights in person and telling Wickens they recognized his voice from their screens.
Round 4: Geography
Over the years, Quizmaster has run quizzes as far away as California and Nevada, and for a time, the company was technically international. Wickens’ younger brother, Sam, who had attended college in Wisconsin before moving back to London, eventually started running Quizmaster nights there while working as a radio producer for the BBC.
“He started talking to some bars and pubs in London and got like three or four venues to do Quizmaster,” Wickens says. “I just transplanted the format and the brand directly to him. We actually had our logo on the walls in pubs in London at one point, which was kind of nuts.”
Eventually, Sam relocated to Australia, where he now runs his own trivia company, The Trivia Tap, a Quizmaster offshoot. The experience taught Wickens something about the limitations of expanding a trivia business. “Trivia is such a localized business that you kind of need someone on the ground,” he says. “Bar owners want to see you. They want to know that if they call you, you can stop in the next day or the next week.”
Today, the company has about 65 to 70 hosts running roughly 70 to 100 events a week, including Quizmaster, Feudmaster, and Tunemaster games, themed nights and private and corporate events. More than 100,000 people played Quizmaster events last year alone; its busiest week drew 3,727 participants. The company has also taken its games beyond the bar, hosting events for corporate clients that have included MillerCoors, Northwestern Mutual, the Milwaukee Brewers, the Green Bay Packers, and Harley-Davidson.
Wickens still takes the mic himself most weeks, including Wednesdays at The Landing at Hoyt Park in Wauwatosa, one of the company’s most popular venues. In summer, the outdoor beer garden can draw upwards of 70 teams.
Round 5: Wild Card
Quizmaster’s biggest growth hasn’t necessarily been geographic. It’s also been in what Wickens has built around the original game.
The first major expansion came with themed trivia. The first was Breaking Bad. Wickens remembers the date exactly: September 29, 2013, the night of the series finale. He timed the quiz to end about 20 minutes before the last episode, and most of the players stayed at the bar to watch the show. Naomi made blue rock candy inspired by the show and handed it out to players.
Then came Harry Potter.
“It was insane how many people came to it,” Wickens says. “We were overflowing with people.”
That convinced him themed trivia could be its own draw. Today, Quizmaster runs roughly two themed events a month, with topics ranging from Disney and Harry Potter to Taylor Swift and New Girl.
The company also expanded beyond traditional trivia. Feudmaster was developed as a more subjective, Family Feud-style game. TuneMaster came later, after a venue gave Wickens an ultimatum: develop music bingo or they would find someone else to provide it.
“That kind of prompted me to get my butt in gear and come up with the goods to produce music bingo,” Wickens says. Now TuneMaster is played at more venues than Feudmaster.
Round 6: Connections
For all of Quizmaster’s growth, its greatest entertainment value may have little to do with the questions. Ask people what makes the experience different, and they talk about what happens between rounds. The relationships that emerge from a Quizmaster night can be just as durable as the business itself.
Sally McVey started hosting around 2016, initially drawn to it for the public-speaking practice. She hosted through 2022 and, along the way, met her husband, Mike. Mike and his friends were regulars at the venue where McVey hosted.
“They were not very good at the trivia portion of it,” she recalls. They were, however, very good at team names, and their repeated wins eventually earned them enough free brewery-tour tickets to invite McVey along. “I just kind of became friends with the whole group, and it sprung from there,” she says.
Asked when she realized there might be something more, she doesn’t hesitate. “Probably when we went on the tour.” They dated for six years and got married last summer.
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Trivia has sparked a few proposals, too. During the run of virtual trivia, one regular asked Wickens to help him pop the question. They built it into question 61, one beyond the usual 60: a photo of the couple filling the screen, “Danielle, will you marry me?” The multiple-choice answers were all some version of yes.
Asked whether he thinks of himself as being in the trivia business or the entertainment and community-building business, Wickens pauses. “I think it’s both,” he says. “Obviously it’s a trivia business in the sense that that is the content. That’s what I do. But certainly what’s allowed us to last this long is that people come and they engage with their friends and their community over trivia.”
Now, 20 years after the BritInn quiz that started it all, Ryan and Naomi are working together on Quizmaster’s newest venture: a physical trivia card game to celebrate the company’s anniversary. Wickens wrote the questions; Naomi designed the cards and packaging. They’d tried something similar once before, a Wisconsin-themed bingo game that never quite found its footing.
The new game, Quiz Me Gently, is built around gameplay rather than simply a box of questions. Players answer cards categorized as “gentle,” “sassy,” and “savage,” with harder questions worth more points. The first player to reach 10 wins.
Wickens hopes to launch it later this year, potentially in conjunction with other anniversary events. Naomi has also returned to a more active role in the business as their children have gotten older. Their daughter, now 8, has started coming to themed trivia nights and helping hand out pens.
“She’s like, ‘I could do this,’” Naomi says. Maybe someday she will.
Lightning Round
Twenty years. More than 100,000 questions, nearly all written by one person. A pandemic that forced the business temporarily online. A brother’s spinoff trivia company on the other side of the world. An 8-year-old daughter who is already eyeing the family business. Looking back, Wickens says he always believed he could make the business work. What he didn’t know was whether it would still be going 20 years later.
“I don’t want to sound cocky, but I don’t know if I would be too surprised, because I was always confident in my ability,” he says.
What makes him proud is not simply that Quizmaster succeeded, but that it endured. “The thing that would surprise me, or I would be happy with, is just the fact that we were able to make it 20 years and keep going.”
Naomi agrees. “I think I’m just most proud of the fact that he’s really built such a great community.”
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Maybe a better Spot Prize question is not how many questions Wickens has written, but rather how many friendships have started over them? How many relationships have grown out of them? How many people have spent a weeknight laughing with friends, arguing over an answer or meeting someone who would eventually become a friend, a spouse or simply someone they’d know for years to come?
Those numbers are impossible to guesstimate. But on Wednesdays, Wickens is still the one up at the mic at Hoyt Park, handing out candy from a country he left more than 20 years ago and asking questions that bring people back, week after week.
Two decades later, the questions keep coming. So do the people.
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