About

Matt Chambers is a retired Army National Guard Staff Sergeant, husband, dad, and small business owner from Williamsburg, Virginia. He served for 20 years in the military, including three deployments to Iraq, and that experience helped shape the way he leads, works, and shows up for others.

Today, Matt is the owner of Squared Away Entertainment and Speedquizzing VA, where he helps create fun, organized, and memorable events throughout the community. From trivia nights and weddings to fundraisers, school events, corporate events, and private parties, Matt enjoys bringing people together and creating experiences that feel easy, welcoming, and full of energy.

At home, Matt is a family man first. He is married with kids and understands the balance of building a business, serving the community, and being present for the people who matter most. His life has been shaped by service, hard work, humor, and the belief that doing the right thing matters—even when no one is watching.

Whether he is behind a microphone, helping plan an event, supporting a local cause, or spending time with his family, Matt brings a steady, approachable, and genuine presence to everything he does.