YOUR EVENT,

SQUARED AWAY

From weddings to trivia nights and corporate events, Squared Away Entertainment brings personality, professionalism, and a stress-free vibe to your event — all powered by Matt Chambers.

What I Offer

At Squared Away Entertainment, I make it easy to book high-quality entertainment tailored to your event, your crowd—serving Williamsburg, Richmond, Virginia Beach, and surrounding areas.

A bride and groom dancing at a wedding reception, with guests dancing in the background.

Weddings & Private Events

I’ll provide the perfect soundtrack for your wedding or private event, from the aisle walk to the dance floor. Planning is easy with the VIBO app, and on the day, I’ll make sure the music and energy never miss a beat.

Three women sitting at a wooden table, smiling and laughing together in a casual indoor setting, with drinks and personal items on the table, and a colorful graffiti mural in the background.

Speedquizzing Trivia

Keep your crowd hooked with fast-paced, app-driven trivia that’s interactive and unforgettable. Perfect for bars, fundraisers, company events, and private parties that want more than the same old trivia night.

Outdoor photo of a booth with signs, leis, and decorations, set up for an event or celebration. The booth has a black tablecloth with white text, and signs with playful messages like "Good Vibes Only" and "Let Me Take a Selfie". There are also colorful flower leis hanging on the front of the table. Behind the booth is a large blue flag with yellow and black logos, and a sign acknowledging sponsors. The setting appears to be on a brick-paved area outside a building.

Photo Booth Rentals

Add extra fun with sleek open-air iPad booths, customizable backdrops, and props that guests love. Every booth delivers instant, shareable snapshots that make your event even more memorable.

Indoor event in a large hall with audience seated at tables, two people speaking on stage, multiple screens and stage lighting.

Corporate Events & AV Rentals

From music to mic work, I’ll set the tone and keep your event on schedule. Need gear only? AV rentals are available for meetings, galas, or corporate parties of any size.

Whether you’re throwing a fun corporate party, planning your dream wedding, or hosting weekly trivia at your venue, I’ve got the gear and experience to make it unforgettable.

Not Sure Where to Start?

Send me a few details, and I’ll take it from there.

What to Expect

Simple. Smooth. Stress-Free.

    1. Get Started – Fill out the contact form, and I’ll send you a personalized link with everything in one place: your brochure, pricing, contract, and invoice information.

    2. VIBO App Access – I’ll invite you to the VIBO app so you can build your event timeline and playlists with ease

    3. Discovery Call – We’ll jump on a quick call to walk through the vision and make sure nothing’s missed.

    4. Touchpoints – I’ll check in every few weeks to make sure you’re feeling good about the flow.

    5. Event Day – You focus on enjoying the event. I’ll keep things running smoothly.

    6. Wrap-Up – After the event, I’ll send a thank-you message and a quick link to leave a review.

    Sound like the experience you’re looking for? Reserve your date today.

DJ mixing music on a professional DJ controller with colorful LED lights in a nightclub setting.
A newlywed couple is celebrating their wedding with guests as they walk through a shower of white flower petals. The bride is in a white wedding dress and holding a bouquet, smiling and raising her arm. The groom is in a black suit, smiling, and holding hands with the bride. Guests on both sides are clapping and taking pictures inside a decorated venue.
Group of smiling people holding up a trivia Speedquizzing championship belt at a celebration in a restaurant or bar.
Group of women dancing at a wedding smiling and having fun.
Matt Chambers, owner of Squared Away Entertainment, with curly hair, glasses, and a headband sitting on a wooden stool with one leg up, showing the sole of his sneaker, smiling at the camera, wearing a light blue denim shirt and beige pants.

Your DJ, MC & Trivia Host

— All in One

Hey, I’m Matt, a retired military veteran and the man behind Squared Away Entertainment. Years in the service taught me precision, preparation, and how to keep things running smoothly no matter what. Now, I bring that same level of discipline and attention to detail to every event I host.

I started DJing back in 2012, spinning tracks in bars and clubs just for the fun of it. But over time, I found my sweet spot in more meaningful events like weddings, corporate gatherings, fundraisers, and private parties where the experience actually matters.

In 2018, I officially launched Squared Away Entertainment to take on more than just the music. I wanted to manage the full flow of the night from announcements to timelines to making sure the energy stays just right.

I’ve been told I have a strong mic presence and natural hosting skills. But, honestly? What I really value most is creating an environment where people can feel at ease, celebrate, and enjoy the event.

Matt Chambers, owner of Squared Away Entertainment, sitting on a wooden chair, holding a microphone, wearing a light blue denim shirt, tan pants, white and blue sneakers, and glasses, with a thoughtful expression.

Why Work With Me?

DJ wearing headphones playing music at a party with colorful purple and pink lighting, and people dancing in the background.

Over a Decade of Experience

I’ve done it all: bars, weddings, school dances, corporate events — you name it.

A woman laughing and clapping at a social gathering of trivia, with other people in the background, seated at a table with drinks.

Local & Trusted

Based in Williamsburg, VA — proudly serving Richmond, Virginia Beach, and surrounding areas.

People dancing and enjoying themselves at a lively party or celebration.

Naturally Engaging Host 

I don’t just press play — I keep the energy up, the timing right, and the vibe strong.

People dancing and having fun at a lively celebration or party, with one man in a suit singing or shouting, surrounded by women and other men, some with glasses and bow ties.

Modern Tools for Easy Planning

Every booking comes with access to the VIBO planning app.

Matt Chambers in a white shirt and glasses smiling and enjoying himself while DJing at a wedding, with his arm raised in celebration.

No Middlemen, No Confusion  

No handoffs or middlemen. Just me, Matt, from first message to final song.

When experience, energy, and ease matter — I’ve got you. Let’s talk about your event.

Client Love

“Highly recommend for your wedding! Matt DJ’d our wedding in Sandbridge, VA. Our venue was located in a large beach house rental and we needed sound in multiple locations. On the beach, outside of the house and inside for the dinner. There were a lot of moving parts and Matt handled it like an absolute pro! He also facilitated the different events throughout the night effectively and was highly organized. Not to mention he killed it with music selection and handled requests very well, and definitely knew how to keep the party going. We couldn’t have pulled this wedding off without him! Squared Away Entertainment is a very suitable name because Matt is truly squared away. Thank you for everything Matt!!”

Chris B.

Group of people celebrating at a party or wedding reception, smiling and holding drinks, with a wooden ceiling and chandeliers in the background.
Four people sitting at a restaurant table with drinks and plates of food, two of them are talking animatedly, and one woman is pointing or gesturing with her hand. There is a blackboard sign in the background with green and white text about drink specials.

”Matt is always so entertaining to have trivia with. Lots of category variety, great music and interaction between rounds, and just a fun atmosphere wherever he pops up!”

Jessi N.

Where I Travel

I’m based in Williamsburg, VA and regularly travel to Richmond, Virginia Beach, and surrounding areas within about 50 miles.

Need me a bit farther out? Let’s chat!

Matt Chambers in a white shirt and glasses is DJing at a party, smiling with his eyes closed, with one arm raised in celebration.

Let’s Make It Happen

From weddings and trivia nights to fundraisers, galas, and private parties, Squared Away Entertainment makes every event seamless, lively, and stress-free.