
WILLIAMSBURG — Squared Away Entertainment, a local company providing DJ/MC services, interactive SpeedQuizzing trivia and modern photo booth rentals, is ready to move to the next level, with owner Matt Chambers looking to increase its involvement with the community.
Chambers launched the company seven years ago with a focus on providing DJ services for weddings and events, as well as photo booth operations and trivia nights at loacl venues. In total, he said he’s hosted over 1,400 trivia nights around the area.
After retiring from the military last summer and spending his time as a stay-at-home dad, Chambers wants to grow Squared Away Entertainment into a full-time operation focused on the community.
Having experienced recent success hosting trivia nights as fundraisers for nonprofits and other organizations, he developed an interest in working with other nonprofits in the area to help them raise money. This includes virtual trivia, something he has been hosting since 2020.
He aims to continue holding trivia nights at locations around town, as well.
“I want to keep doing that, because I can do that for the rest of my life, just wholesome trivia,” Chambers said. “It’s so fun, and I can’t think of a better job calling for me.”
Chambers works closely with Matt Mullins, who also hosts trivia events, and shares the credit for creating the area’s SpeedQuizzing community. Mullins owns his own DJ company, Mullins Entertainment.
Squared Away Entertainment will celebrate eight years in operation tonight at Virginia Bee Company.
The current weekly trivia schedule:
- Sunday at Williamsburg Winery at 2 p.m.
- Monday at Green Leafe Cafe and Pub at 7:30 p.m.
- Tuesday at Alewerks at 7 p.m.
- Tuesday at Duke’s Aloha Eats at 6:30 p.m. (Hosted by Matt Mullins)
- Wednesday at Precarious at 6:30 p.m.
- Thursday at Virginia Beer Company at 6:30 p.m.
- Friday at Billsburg 7 p.m.
- First Fridays at Eagles at Kingsmill at 7 p.m. (Hosted by Matt Mullins)
Squared Away Entertainment’s website is currently under construction, but the company can be reached via its Facebook page.

