WILLIAMSBURG — He’s known around town as the “Trivia Guy,” but Matt Chambers is a man of all trades.
Since starting Squared Away Entertainment three years ago, Chambers’ Hampton Roads-based business has grown into a service with multiple operations.
During the week, locals will see him hosting SpeedQuizzing trivia nights at restaurants or bars like Virginia Beer Company or Precarious Beer Project.
But he mainly provides DJ services to weddings or events, as well as photo booth operations for a variety of events.
Originally from Buckingham County, a small town south of Charlottesville, Chambers moved to Williamsburg in 2012 with a love for DJing.
“I wanted to DJ, and I was trying to get into different bars around here but it wasn’t really working out,” he said. “So I focused mainly on doing some small events and weddings, and I found out that I loved doing weddings.”
He performed his first wedding in 2015, and it was the success that followed that led him to starting his own company.
Chambers had a love for music since he was a child.
“Every person I connected with as a youngster put me on to different music types,” he said “My mom listened to R&B, my dad listened to blues music, and my sister listened to hip-hop. In high school my friends taught me about classic rock and all different types of music.”
But he first found his love for DJing while he was deployed in Iraq back in 2007 and 2008.
Chambers, who has served 18 years in the Army National Guard, had a friend who was DJing at the time and taught him the ropes.
Chambers soon found himself going from a bedroom DJ to being booked every weekend for weddings and other events.
It was military vernacular that gave Chambers the name for his business, Squared Away Entertainment.
“Squared away” is a military saying that refers to a person who knows what they are doing and has it completely covered.
And that’s how Chambers wants the community to view him.
“I’m not just a DJ,” he said. “I can host trivia, I can do photo booths, so everything is kind of all under one umbrella.”
June 28 marked Chambers’ fourth year hosting trivia night at Virginia Beer Company, where he tried out his SpeedQuizzing trivia game.
Chambers’ games are much faster and more competitive than the average game of pencil-to-paper trivia.
Along with Virginia Beer Company, Chambers has hosted trivia nights at Precarious Beer Project, Brass Tap, Green Leaf Cafe and other local spots.
“It kind of ballooned from this cool little idea to something that’s pretty much been a lifesaver during the pandemic,” Chambers said.
Many businesses in the wedding and DJ industry struggled during the pandemic, including Chambers, who went from being booked all year to having no weddings or events.
But he found that he could still host virtual trivia nights during the pandemic.
“People told me all the time that this was the highlight of their week, because they were in quarantine with nothing to do, and they were able to play trivia with their friends and family via Zoom,” he said.
As bars slowly began opening back up this year, Chambers has made a return to hosting trivia nights in person and seeing familiar faces.
“Some places I go to I’m just known as the “Trivia Guy,” he said. “It’s really cool to think that if I didn’t focus on anything besides DJing, some people might not even know me because when I DJ weddings and corporate events, you might not see me at all.”
However, with a wife and children as well as a business to run solely by himself, Chambers sometimes finds it challenging to balance his family life with his work.
“I’m always working,” he said.
Even with his already busy schedule, he is still finding new ventures to take on.
“For 2021, I wanted to do more things for the community,” he said.
Since January, Chambers has been hosting virtual trivia fundraisers once a month for various charities and organizations in the Williamsburg area, including Heritage Humane Society, Weighted Angels, Avalon Center and the Warhill High School band.
With a goal to reach $5,000 for the year, Chambers has already hit around $3,400.
“I have people playing from all over,” he said. “There’s a family that lives in Greece because they have a family member living in the U.S., so they play with them online.”
Chambers hopes to host more of them in-person too and is still looking for any charities or organizations to work with.
Those who frequent Virginia Beer Company will soon see more of Chambers, as he is returning every Thursday starting July 1.
Unlike the trivia leagues he used to host there, these will be normal trivia nights with different themes.
His trivia theme nights include TV shows, movies, and of course, his favorite theme – music.
For more information about Chambers and Squared Away Entertainment, visit his website.
