Whaddayaknow? is Bringing Chicago's Trivia Spirit to Bars Across the Country, One Night at a Time

On any given weekday in Chicago, when most bars would be fighting for foot traffic, there are groups huddled around tables with pens and paper in hand, debating answers to trivia questions that are as clever as they are unpredictable. That scene is the signature of Whaddayaknow? Free Pub Trivia, the entertainment company founded by Daniel Burns, has grown from a small idea into one of the city's largest communities.

For many bars, it has become the secret weapon for filling seats, building regulars, and infusing a little Chicago-style grit and humor into otherwise quiet nights.

Burns began hosting trivia in his home city of Boston, almost on a whim, nearly two decades ago. His passion for the game brought him to Chicago, where his vision expanded into a full-fledged entertainment company that today runs live team trivia, music bingo, and numerous other fun bar games that fill seats across the city every night.

"I think what makes it work is that it's live, it's fun. People can get together with their friends every week and know they're going to have a great time," Burns says. "We're giving them a few hours a week where they put their phones down and just connect. It sounds simple, but it's rare now, and it builds real community in these bars."

For bar owners, the appeal is immediate. The Whaddayaknow? model is straightforward. They don't implement contracts or stringent commitments, just a flat fee that includes a host, materials, and promotion. "Bars don't appreciate being roped into 10-week deals," Burns explains. "We let our product do the work. If the venue likes what we bring in, they'll keep us. Our track record speaks for itself."

Trivia nights regularly draw in groups of friends forming teams, who not only fill seats midweek but often become regular patrons on weekends as well.

It's this balance of entertainment and business impact that has allowed Whaddayaknow? to thrive organically. "Chicago's bar scene is tight-knit. The owners and managers all know each other," Burns says. "Most of our new venues come through word of mouth."

Their process involves a simple inquiry on their website, which gets the ball rolling, and from there, the team coordinates logistics like timing, AV setup, and promoting. Within weeks, a bar can transform a slow Tuesday into one of its busiest nights.

The energy, however, is uniquely Chicago. As Director of Operations, Gordon Schrenk puts it, "We bring that rough-around-the-edges vibe, but we're also loyal and funny. Everyone can connect with that and have a great time."

The Whaddayaknow? content emphasizes invigorating conversation and collaboration. Rather than leaning on straightforward "know it or you don't" trivia, the questions are designed to spark discussion, with layers of clues and cultural references that keep players engaged.

Their flagship trivia nights are only the beginning. Twice a year, the company runs its Tournament of Champions, a citywide event that has grown into a major draw. After 10 weeks of qualifying rounds across multiple bars, the top teams earn their place in a grand, all-day trivia showdown.

"We just wrapped our 26th tournament, which drew nearly 200 teams," Burns says. "It's an absolute blast — just a huge celebration of everything we've built together!"

That sense of belonging has fueled the Whaddayaknow? expansion, with connections in other cities and plans to franchise the model. The company is also open to prospective hosts who want to pitch trivia at their favorite neighborhood bar. "Sometimes we'll get an inquiry from someone who says, 'I'd love to host,'" Schrenk says. "We tell them, if there's a bar you had in mind, talk to us. We'll provide everything you need."

While the live, in-bar experience remains the core product, Whaddayaknow? also built out a virtual model during the pandemic, and now streams games every Tuesday and Thursday via their website. The virtual component has kept long-distance teams and loyal participants connected, underscoring the adaptability of the brand.

At its heart, Whaddayaknow?is an entertainment engine for bars, one that turns otherwise slow nights into something electric. "It's about community," Burns says. "People come back because it feels good to be there. They get to know the staff, they make friends, they laugh a lot, and for those two hours, they're part of something bigger than just a night out. That's what keeps this growing."