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Bio
🎶 DJ • 🏆 Trivia Host • 📸 Photo Booth ✨ Your Event, Squared Away 📍 Williamsburg, VA + Beyond ✌🏾 Run by @omgmattchambers
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squaredawayent.com-
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Recent posts
A year ago today, I bet on myself, left my day job to chase my passion full-time — hosting trivia nights, DJing, and running photo booth events. That and my family truly make me happy. So, I walked away with one goal: build Squared Away Entertainment into what it was truly meant to be.
It’s been a journey, but I’m proud to say the official relaunch of Squared Away Entertainment is finally here!
To everyone who’s supported me — the friends who’ve tagged me in posts, the venues that took a chance, the regulars who show up every week, and everyone who’s helped spread the word — thank you. Every referral, every share, every “you should call Matt” means more than you know.
This next chapter is about doing what I love, full-time, and doing it squared away.
✌🏾❤️
sqaredawayent.com
15 Oct 2025
Rain on your wedding day? We make the best of it!
Sometimes that means waiting for the rain to stop before heading outside for portraits. Sometimes it means finding beautiful indoor spaces with gorgeous natural light. And sometimes it means hiking up your wedding dress, trudging across wet grass, and hopping into a golf cart to get to the perfect photo spot!
And sometimes, like Megan and Jonathan’s wedding at Ford’s Colony, it means ALL of the above!
Despite the rain, these two had such a beautiful day celebrating with their family and friends, and I loved how they embraced every part of it!
Here’s a little sneak peek from their Ford’s Colony wedding! Congratulations, Megan and Jonathan!
#FordsColonyWedding #WilliamsburgWeddingPhotographer #VirginiaWeddingPhotographer #RainyWeddingDay #WilliamsburgWeddings @fordscolonycountryclub @squaredawayent
19 Oct 2026
BIG shoutout to our friends at @squaredawayent for providing the photobooth for Cannon Country Fest at the @williamsburgwinery - we love seeing that everyone had an absolute blast! 📸🍷🤠
13 Aug 2026
Congratulations to Charles + Samantha! All set up for their wedding at St. Bede’s in Williamsburg, VA!
‘Your Event, Squared Away’
Venue: St. Bede’s Catholic Church @kaplan_parish_hall
DJ: @squaredawayent
Photographer: @bluerosetori
Catering: @salsbyvictor
09 Aug 2026
Ilsa & Matt 🤍 A day filled with love, emotions, and memories to last a lifetime.
Photography: @luvidastudio
Venue: @sevenspringsva
Dj: @squaredawayent
Florist: @poppyflowersco #WeddingPhotography #lovestory #WeddingDay #luvidastudio #ᴡᴇᴅᴅɪɴɢᴍᴏᴍᴇɴᴛs
26 Jul 2026
Celebrating 9 years of @speedquizzingva at @virginiabeerco! 🎉
Thank you to VBC for giving me my first opportunity to try out this crazy idea I had. I genuinely appreciate all the support the staff and all of the players have shown me since Day 1.
Seriously… thank you. Love you. Mean it.
✌🏾❤️
16 Jul 2026
Reminder: no trivia tonight at @greenleafepub BUT we are having another SpeedQuizzing Live game held this Saturday by @omgmattchambers at 7pm 📣‼️
With SpeedQuizzing Live, you can join us for trivia in real time from any location! Buy tickets NOW for entry to play and try to make it to first place for a $50 Amazon gift card! Every ticket includes the zoom link and PIN to play 🛜
A link to purchase tickets will be in our stories, and is also on our Facebook page. We can’t wait to see everyone from the trivia community Saturday night! 💙
06 Jul 2026
Our feed has been full of wedding content lately, and we love it! 🦢
As we’re deep into wedding season and looking forward to all the beautiful celebrations still to come, we’re also thinking of special moments we’ve already been lucky enough to share in. This week marks one year since Catherine and Ian said “I do” and celebrated their big day with us!
Happy Anniversary, Catherine and Ian!
✨ Planner: Maggie, Wedding Co. of VA
✨ Caterer: Mosaic Catering
✨ Ceremony Venue: Bruton Parish Church
✨ Florist: Williamsburg Floral
✨ DJ: Matt Chambers
✨ Cake & Desserts: Twisted Sisters
16 Jun 2026
Congratulations Chris + Alexa! I was looking forward to DJing for you and your guests for months! Thank you for entrusting me to DJ your wedding Sunday night!
Your Event, Squared Away.
@thechristopherw
@alexadoiron
@millatfinecreek
@squaredawayent
29 May 2026
Squared Away Entertainment
@squaredawayent
Contact me for DJ, trivia, and photobooth services. Williamsburg and Hampton Roads
Your Event, Squared Away!
757.603.2371
13 May 2026
Highlights from @heritagehumane’s Black Ties & Tails Gala from Saturday! Thank you all for stopping by my photobooth!
Tag your friends if you see them!
23 Apr 2026
W&M Barrister’s Ball 2026 at Williamsburg Lodge.
Packed dance floor. Smooth from start to finish. Your event, squared away.
@squaredawayent
@wmlawschool
@william_and_mary
11 Apr 2026
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