Level99 Founder & CEO
The category leader in out-of-home Social, Challenge-based Entertainment
- Social, active, life-sized, mental & physical mini-games for adults
- Designed to be approachable & infinitely replayable, with updating content
- Set in an energetic, artistic enviroment to explore & discover
- With award-winning, chef-driven, scratch-made food & beverage
5 Wits Founder & CEO
The world's first escape room style entertainment business
- Many millions of guests served for over 20 years
- Walk-Through Adventures: Tomb, Espionage, Drago's Castle, Deep Space
- Theme park quality immersive sets
- Fully-automated, self-resetting puzzles
- The Original: developed in 2002, incorporated in 2003, opened in 2004 in Boston
Box Fort Founder & CEO
Design / build of custom interactives, effects, and environments
- Creative design & engineering for theme parks, museums, theaters, and corporations
- Clients ranged widely: Walt Disney Imagineering, Blue Man Group, The Smithsonian, Hasbro, The International Spy Museum, Raytheon, dozens more
- Now a part of LEVEL99, Box Fort served entertainment and educational clients for 17 years
Fun Stuff
In addition to my companies, I've been fortunate to work with quality people and organizations.
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MIT: Product Design
For 18 years, I've been on the MIT Faculty, as part of the teaching team for 2.009: The Product Design Process at the Massachuetts Institute of Technology (MIT), my alma mater. This is the capstone class of the mechanical engineering major, as students work in teams to conceptualize a consumer product and build a fully-functional alpha prototype in 3 short months.
I've also helped teach 2.007, the famous robot competition class. Fun.
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Act III
Building LEVEL99, I've had the great pleasure to work with Ron Shaich, founder and former CEO and Chair of Panera Bread and current Chairman and lead investor of Cava, Tatte Bakery, Life Alive Organic Cafe, and Honest Greens.
Ron's firm Act III Holdings is a $1 billion+ investment vehicle that partners with consumer facing brands to build tomorrow’s market-leading restaurant and entertainment companies.
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Awards
My teams have received three THEA Awards (the Oscars of themed entertainment) for work on Disney's Animal Kingdom Lodge, the International Spy Museum, and Level99.
My attractions have earned dozens of local "best of" and "things to do" awards. I'm also pretty proud of Level99 winning "Best Pizza in Boston" from Boston Magazine!
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Patents
I've been awarded several US patents relating to the configuration of digital avatars, game rooms that situationally adapt, methods for games to detect state and "self-reset", and multiple specific game designs.
Our teams are always working on something new, so there are others pending, stay tuned.
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Talks
If you'd like to hear about some of our team's projects and design philosophy, here are a couple presentations of interest:
TEDx Boston, "Go Analogue," way back in 2013
SATE: Storytelling, Architecture, Technology, Experience. 2015, with Cory Rouse
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Podcasts
A few recent conversations I've been a part of:
Future of Storytelling, "Building a Business out of Play," April 2026, hosted by Charlie Melcher
Where We Buy, "Inside Level99," July 2025, hosted by James Cook
Reality Escape Pod, "Optimizing Throughput," July 2023, hosted by David Spira
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Other Ventures
There's been some hare-brained stuff over the years, too.
I helped turn around an interactive/exhibit/video production company as COO for a year, owned a mirror maze in a mall (great business actually), and even owned a frozen yogurt shop (ouch, not recommended).
DuPlessie Creative LLC, my personal consultancy, has helped develop a few amazing experiences for private companies.
Since 2003 in total, I've started 13 separate entities and raised over $125M committed capital from investors, banks, and landlords.
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Family
And at the top of the important list: my wife Beth and our three wonderful kids.
Year after year, enjoying adventures together, active in service and worship in our church and relationship with God, part of the community in Foxboro MA, and homeschooling the whole way K-12 (Beth is a hero).
It goes by very fast — put your focus on what is actually important.
Here's a recent Family Christmas Photo.
Recent Press
Matt and his businesses have been covered in the New York Times, Wall Street Journal, Boston Globe, Wired, Fortune, Axios, and NPR. Here is some recent coverage.
June 17 2026, Florida Today
Level99 Disney Springs Opening Date, Ticket Prices Announced
"A massive new player is entering the Central Florida entertainment scene. Level99..."
June 16 2026, Orlando Businesss Journal
Level99 Reveals Disney Springs Opening Date, New Details for its Largest Gaming Venue Yet
"The new gaming venue at Disney Springs will span two floors and nearly 47,000 square feet, making it the largest location yet for the adult-focused entertainment concept."
June 16 2026, Orlando Magazine
Opening Date Set for Level99 Orlando Location at Disney Springs
"The highly anticipated attraction transforms the former DisneyQuest site into a 46,800-square-foot playground packed with more than 60 interactive physical and mental challenges... Instead of sitting behind a screen, guests will step into real-world games that require teamwork, strategy, agility and problem-solving."
June 16 2026, Attractions Magazine
Level99 Disney Springs: Opening Date, Games, Dining, and Ticket Details
"The building that once housed NBA Experience and DisneyQuest is preparing for its next chapter."
June 16 2026, Disney Tourist Blog
Level99 at Disney World Announces Opening Date, Ticket Sales Start...
"Games are active, social and re-playable... And the game continues beyond one visit."
June 10 2026, BISNOW
Fun Is The New Foot Traffic... Challenge Rooms Plot Huge Expansion
"Level99, a chain that caters to teens and adults with elevated dining, has started to expand to Class-A malls..."
June 10 2026, Axios Raleigh
Crabtree Valley Mall adding new entertainment venue
Announcement of Level99 coming to North Carolina
May 20 2026, CoStar
As Americans pinch pennies, affordable fun reshapes retail real estate
"One of the up-and-comers in the escape-and-challenge room category is Level99..."
April 30 2026, Future of Storytelling
Building a Business Out of Play
A half hour conversation on Level99, Matt's Background and History, and the use of IP in location-based-entertainment.
March 16 2026, Business Wire
LEVEL99 to Open at Westfield Garden State Plaza in 2027
Announcement of Level99 coming to New Jersey.
January 15 2026, Parade Magazine
Disney Springs Is Getting a Huge New Space That Feels Like Living Inside a Game
"Think hands-on challenges, puzzles and physical games—all under one roof."
October 23 2025, CBS News
Level99 expands into the Philadelphia market with the King of Prussia Location
Announcement of Level99 coming to the greater Philadelphia market.
September 9 2025, Axios Pro Rata
Announcement of Level99 raising $50M in growth equity from ACT III Holdings.
September 2 2025, Blooloop
Don't Hate the Player, Rethink the Game
An interesting analysis of competitive socializing venues, featuring Level99 and quoting Matt, who the author humorously describes as "a guy who can MacGuyer an escape room out of a stapler, a roll of duck tape, and a dare..."
July 18 2025, Where We Buy Podcast, with James Cook
Inside Level99 with Founder & CEO Matt DuPlessie
A 48-minute podcast interview delving into the origins and design philosophy behind Level99.
May 19 2025, The Worcester Business Journal
Matt named to the 100 most influential professionals in Central Massachusetts for 2025.
More historical press coverage is available in the Media Archive
A Few Project Photos
On a phone, rotate to landscape or long press, to enlarge.
Get In Touch
I'm always looking for new adventures and collaborators. Drop me an email, and make sure to spend a moment to fully explain who you are, I'm interested.