Lyssa-Noel Frater
Daniel Burns – Founder of Whaddayaknow? Free Pub Trivia
Somewhere in the lively pubs of Chicago, crowds of people gather to escape the routines of daily life, and Daniel Burns, founder of Whaddayaknow? Free Pub Trivia, has been the quiet pied piper transforming ordinary weeknights into celebrated spectacles of wit, camaraderie, and collective joy.
Burns turned his love of pub quizzes into a thriving entertainment company. But this love began unexpectedly, during a night out at an Irish pub in Boston, which sparked an idea that would define his career.
At the time, trivia was something he did with his friends, a midweek ritual. But the host at the pub recognized Burns’ knack for engaging people, eventually asking him if he wanted to run the game for a few nights. Burns agreed, and what began as a side gig for fun became something more. For almost a year, he hosted weekly trivia in South Boston, discovering not just the joy of testing knowledge but the energy that comes from a room full of people connecting through laughter, debate, and friendly competition.
In his mid-20s, Burns found himself at a crossroads. He had grown up in Needham, Massachusetts, studied psychology and music at college, and was pursuing sound engineering on the side. But he wanted a new chapter. “I’d been in Boston my whole life,” he recalls. “I wanted to switch it up. Chicago just appealed to me. I’d never even been there, but something told me to go.”
With little savings, no job lined up, and only a rental apartment waiting, he and a friend packed up his car and drove west.
At the time, Burns found that trivia wasn’t nearly as popular in Chicago as it had become in Boston or Atlanta. What the city did have was an endless array of neighborhood bars, fertile ground for a new idea, which fueled Burns’ vision. He walked through neighborhoods, walked into bars cold, pitching the concept of a trivia night.
“I literally just said, give me two weeks, pay me with a beer. If people show up, great. If not, no harm done,” he says. Two venues took him up on the offer. Within weeks, their quiet Tuesday and Wednesday nights were packed. Within a year, Burns was hosting six nights a week, and Whaddayaknow? was born.
Whaddayaknow? Free Pub Trivia
It was an unlikely start for someone with no business background. But the results spoke for themselves. In Chicago’s competitive nightlife scene, word spread quickly. Managers told their friends, owners with multiple venues booked him for more nights, and soon Burns couldn’t keep up alone. That’s when he began bringing in other hosts, including Gordon Schrenk, who started as one of the earliest emcees and is now the Whaddayaknow? Director of Operations.
“Gordon and I go way back; we even played in a band together,” Burns says. “He was one of those people who could walk into a room and make it fun. That’s been the spirit of Whaddayaknow? ever since. We’re about energy, humor, and connection. Our large roster of hosts reflects a wide range of personalities, and all of them bring these elements to their bars.”
For over a decade, Whaddayaknow? has grown steadily into one of Chicago’s largest entertainment companies, expanding its formats to include trivia, music bingo, karaoke, and other games. Twice a year, it stages the Tournament of Champions, a biannual citywide showdown where hundreds of teams represent their local bars. “It’s essentially just a massive party celebrating the community we’ve built,” Burns says.
Then came 2020. Practically overnight, Chicago’s bars went dark. For Whaddayaknow?, which was built entirely on in-person gatherings, it could have been the end. Instead, Burns and Schrenk improvised. “As soon as the shutdowns hit, we just started winging it on social media, live sessions,” Burns says. “Our teams missed the connection, and they showed up.”
With the help of a friend who understood streaming, Whaddayaknow? moved to a global video game live-streaming service, refined the format, and eventually built a custom virtual platform that allowed players to submit answers online.
What began as a lifeline during lockdown has since become a permanent part of the company. Today, Whaddayaknow? runs two subscription-based virtual games a week, streamed live from their office with interactive features and polished production. For $25 a month, teams across the country, or even across continents, can log in, reconnect with friends, and play.
“It’s amazing to see groups who used to play together in Chicago but now live in different cities still doing it every week,” Schrenk says. “It’s kept that sense of community alive.”
The dual model, live in bars and virtual online, has given Whaddayaknow? staying power beyond what Burns imagined when he first walked into those Chicago taverns 18 years ago. What has remained constant is the mission: to give people a reason to gather, unplug, and belong.
“For a couple of hours, people put their phones down, laugh, argue, and cheer together,” Burns says. “That’s what trivia is really about. It’s not just questions and answers, it’s a community. That’s why it works.”
Whaddayaknow? has proven that a simple idea can grow into something lasting when it’s rooted in joy and shared experience. And in true Chicago fashion, it’s built with grit, humor, and just enough competition to keep people coming back.