Matt DuPlessie

Matt DuPlessie is founder and CEO of Level99 Entertainment and 5 Wits, a social gaming playground for adults and the original escape room-style attraction respectively. Level 99 combines dozens of short, highly replayable physical and mental challenges with technology, original artworks, social competition, and food and beverage, creating a distinctive new form of real-world gaming.

Under DuPlessie’s leadership, the concept has expanded from Massachusetts into multiple markets. In 2026, Level99 opened its most ambitious venue yet at Disney Springs at Walt Disney World in Florida.

“Matt DuPlessie has helped move immersive entertainment away from passive consumption and toward active, social participation. Through decades of experimentation and the continued growth of Level99, he is influencing not only what immersive experiences look like, but creating a whole new category,” said one person who nominated DuPlessie.

DuPlessie says: “I've been fortunate to spend my professional life conceptualizing new location-based entertainment categories and building winning business models around them.

“From developing and opening the first escape-room style concept in the world over 20 years ago, to designing and building some of your favorite attractions and exhibits at your most-loved theme parks and museums, to serving dozens of clients and many millions of guests, [and] now leading the way in the emerging challenge room entertainment space.”