Natick, Massachusetts just threw down a move that feels less like another entertainment startup and more like a statement. Level99 isn’t a bar with distractions or an arcade dressed up for Instagram. It’s an engineered collision of brains, bodies, and craft cocktails designed by someone who knows how to build experiences that stick. That someone is Matthew DuPlessie, Founder, President, and CEO, who pairs an MIT mechanical engineering degree with a Harvard Business School pedigree. After building 5 Wits and Box Fort, then merging the lessons from both, DuPlessie doubled down on a concept that took five years to refine and now looks poised to define a category.
The product is deceptively simple. Fifty-plus interactive challenge rooms, each running two to four minutes, built around physical, mental, skill, and communication puzzles. Groups of two to six enter, compete, and track their progress on Veloband, a proprietary wristband platform that unlocks rooms, saves player data, and manages digital rewards. Venues average 30,000 to 45,000 square feet, with Natick stretching to 48,000, Providence at 40,000, and Tysons, Virginia launching this summer with more than 40,000. Disney Springs in Orlando is under construction, loaded with over 60 challenge rooms and the ability to host 1,000 players simultaneously. West Hartford opens in early 2026, with more than 15 additional states under negotiation.
The company isn’t playing small. Level99 just closed a $50 million growth equity round led by Act III Holdings, the $1 billion-plus evergreen fund run by Ron Shaich, the founder of Panera and current CAVA Chair. Act III Holdings has been the sole equity partner since the beginning, backing DuPlessie with an eight-figure launch before anyone else believed in “challenge-based entertainment.” Shaich also chairs the board, a signal that this isn’t a side investment. Natick drew 400,000 visitors in 2023, and the first two venues doubled projections. That’s traction, not hype.
The team is stacked with operational firepower. Chief Development Officer Doug Schnell spent more than a decade shaping Panera’s real estate growth before stepping into Level99’s expansion strategy. The roadmap calls for opening four new venues a year after Orlando, targeting the top 20 to 25 U.S. markets. Each location isn’t just built for weekends; it’s designed as a regional hub, with exterior visibility, strong daytime populations, and food and beverage programs that stand on their own.
The takeaway here isn’t just about raising capital. It’s about what happens when a founder with patents on interactive environments partners with investors who know how to scale consumer brands nationally. The entertainment market is shifting because the 21-to-39 demographic doesn’t want to watch; it wants to play. Level99 is showing how you meet that demand at scale, with challenge, with craft, and with confidence.
