Matt DuPlessie
Backstory: This Is Fun
Matt DuPlessie
The tale of a career developing and operating new location-based entertainment concepts.
WARNING: Long Read, this is for the seriously interested.
I started the first escape room style concept in the world, founded in 2003, open to the public in Boston in 2004. Then spun off Box Fort, a company providing specialty creative, design, engineering, and fabrication services for museums, theaters, and theme parks for 17 years. Then founded Level99 – the category defining Challenge Room concept.
I’ve been into games since I was young (witness: embarrassing 8th grade science fair picture… First place, and I don’t want to hear any cracks about the pastel flower tie, it was the 80's.)
Now I’m pushing 50. Really? Time has gone fast.
If you are interested in the full story, how my professional life came to be, warts and all, … here it is: a career developing new entertainment concepts.
A Crummy Internship
It’s 1998, and this internship is not a winner. It was the summer between my junior and senior year. I was studying Mechanical Engineering at MIT, and I was so pleased to have gotten a position at a “real” engineering firm for the first time. After washing the pots for a couple years in the kitchen at Sturdy Memorial Hospital, spending a summer as a door-to-door knife salesman, and even working in an underground lab at MIT (that gave me a cough for a decade), it was time to try a real corporate product design job.
This company in Warwick, Rhode Island will remain nameless, to protect the guilty. My job required sitting in a cubicle 40+ hours a week, rarely talking to another human, designing detailed mechanical parts in 3D. Back in 1998 the computers were so slow that we had two workstations in our cubes. You would round-over a curve in your 3D model on one computer and then, while the machine struggled for a few minutes to render that change, you’d roll your chair four feet away, to the other side of your sad little box, where a separate computer would let you do email while you waited for the software to catch up. Then back you’d roll…
I was 20 years old and designing the protective boots that guard a portable printer from a fall on concrete. Maybe you've picked up a rental car at an airport and a person printed a receipt for you right out in the parking garage? That printer clipped to their belt is covered with a protective shell so it can take a drop. Well… that glorious piece of rubber, that could have been me. Rough summer. I decided this is not what I want to be doing for the rest of my life. There must be something more fun and engaging I can do with my education.
IAAPA Show 1998
It’s senior year, I am fencing 2-3 hours a day, working hard for NCAA nationals (and bonus: I met my wife Beth on the MIT fencing team). In the background is this vague idea of a “career”... or at least a “job.” A roommate in my fraternity house at MIT and I started looking at options and industries that were off the beaten path, avoiding the sad cubicle experience. Perhaps every mechanical engineering student at one point has thought about rollercoasters, and so he stumbled upon IAAPA – the International Association of Amusement Parks and Attractions.
IAAPA has a monster trade show each November, generally in Orlando (though in 1998 it was in Dallas, where my roommate was from – free room & board!) This tradeshow is the industry gathering place for anyone buying or selling to the attraction industry. Everyone from the plush you’d win at your county fair to the cotton candy machines to the consultants and designers who create the world’s largest and most exciting location-based entertainment (LBE) projects. There are rollercoasters and rides set up on the show floor, and themed environments everywhere, over 1,000 companies make an appearance.
Back in ‘98 there was no concept of student admissions (or the current “Next Gen” program) so the organizers didn’t really know how to classify two 21-year old students. When we got our name badges to enter the show floor, they just said “BUYER” in bold letters. That worked out well. We could walk up to any of the booths, flash that “buyer” nameplate, and ask to talk to the highest ranking person there. When that person came over, I’d whip out a resume with a big M-I-T on the top, and ended up having a couple dozen mini-interviews in the span of a few days on the IAAPA show floor.
Both my roommate and I eventually scored job offers from that show floor walk. One of the easiest tactical pieces of advice I offer when college students ask for wisdom on finding their first job: if you know an industry you are interested in, go to their tradeshow. Just about every niche field has an annual gathering – if you want to work in cars, go to the car show; if you want to work in product design, or jewelry making, or musical theater… find their most closely related trade gathering. There is one for nearly every industry. You can make connections, land interviews, and importantly begin to really understand the big players and how your target industry really works. You might discover it’s not for you… or land your dream job. Either way, you learn a lot in a couple of days that a college class has a hard time teaching.
Starting a career in Living Color
I landed an interview with a young, scrappy, fast-growing company called Living Color Enterprises, in Fort Lauderdale, FL. They flew me down for an interview in January 1999. The company was working out of a collection of garage bays – this was a somewhat-disorganized startup, with expertise building custom aquariums (including the most realistic coral reef sculptures) and they were trying to get into large-scale themed environment fabrication. When it comes to themeparks, I love the environments, the immersion, the details, even more than the rides themselves – so this was pretty exciting.
I sat for an interview with their head of engineering… who was not an engineer. During our conversation, the head of the Living Color paint department burst in. She had to order paint for a giant sphere, a big ball on a Mardi Gras float they were building, and had no idea how much paint to buy – how could anyone know the surface area of a big ball? (This was early days for the internet). “It’s 4*pi*r^2” I blurted out. They both looked at me. “How large is the ball?” I continued. “It’s about 8 feet in diameter.” I did some quick mental math: “You should be buying enough paint for about 200 square feet.” My interviewer looked at me and said “You knew that formula off the top of your head? I think you might have a job.”
I moved to Florida that June, after graduation. The toughest part was Beth. We’d had our first date on Valentine’s Day 1999, during our last semester as undergrads. I had already accepted the job at Living Color, and she was staying at MIT another year to get her masters in environment engineering. I didn’t know it at the time, but we were going to stay together, long distance, for over two years, on that foundation of 3 months together, before I would move back and we’d get married. But that’s later in our story.
Disney’s Animal Kingdom Lodge
I moved into an apartment in Fort Lauderdale (soon to move to Pompano Beach) in June of 1999, and started work at Living Color. I got a big sunburn in a square on my back my first week there, playing volleyball on the beach and not knowing anyone in the state to put suntan lotion on my back… so you could see exactly where I couldn’t reach for a month afterward. Spray sunscreen is a great innovation. Initially, I worked on aquarium projects, doing drawings and developing an automated tool for calculating the required thickness of these massive slabs of acrylic the shop was bonding together to hold the pressure of these very large custom tanks. I got to design and build a few interactives for a travelling museum exhibit called Extreme Deep, about deep sea exploration (an exhibit that is still in service today), establishing a relationship with Evergreen Exhibitions, who many years later would be a repeat client for my design/build firm. It really pays to exceed expectations — projects are not one-off, the relationships are still paying off over 20 years later. But the project I was most excited about was one that Living Color had just signed: the theming scope for Disney’s Animal Kingdom Lodge (DAKL), a 1,300 room premier hotel in Orlando.
I was given the role of Project Engineer on DAKL — essentially the grunt on the project, resolving design details, helping the PMs, and greasing the wheels of bureaucracy. The Project Manager and Assistant Project Manager, above me, were leading the project and had a compensation structure in which they would receive bonuses based on the gross profit on the project. Except that… there wasn’t going to be any gross profit on this project. Shortly after I joined the team they realized: they had missed scope and severely underbid the project. The company was going to lose money, and for the PMs: no bonuses. And so, the Project Manager quit. A few days later, the Assistant PM quit. This was my first lesson in the perversities of poor incentive design.
The CEO walked into my office and essentially said (I paraphrase, but this is what it felt like): “You’re a snotty-nosed kid who doesn’t know anything yet, but you know more about this project than anyone else. So I need you to get to Orlando tomorrow morning, buy steel-toed boots on your way there, and try not to make a fool of us.” When I walked into that construction trailer the next morning, surrounded by ~20 grizzled superintendents of various trades, the first fellow I met told me how he wanted his coffee… and I had to say “I’m not here to make your coffee, I’m here to run this meeting, let's get started.”
For the next two years, I got beat up. I was over my head… which means you learn to swim fast. The team did an amazing job on that hotel, I still remember to the inch the dimensions of the lobby, and the design details of every column in the building. I hired 120 people (tripling the size of our team), got in the trenches, and through some efficient design, hands-on site management, and thoughtful change-orders we were able to produce an amazing hotel, which won the THEA award, my first, for thematic design.
And importantly for Living Color, we made up ground on the budget and were able to break-even on the project. As no one thought that was possible, the company owner/CEO gave me some of the credit for “saving the company.” So when the day came that I told him I was giving six month’s notice before I went to business school, he asked “what can we do to keep you?” I told him it wasn’t about money, I was going to school and the girl I wanted to marry was in Boston. He told me “OK, I can accept that, but when the time comes and you want to do your own thing, I want to be the first person you call…” He ended up being the second.
”I Love It When a Plan Comes Together”
-Hannibal Smith of the A-Team
I moved back to Massachusetts and started my MBA at Harvard Business School in September 2001. I stayed in a dorm (shoutout Hamilton), as Beth and I weren’t married yet, but it was so great to be back in the same city with her — there is little loneliness like a long-distance relationship.
The first day of class was memorable for tragic reasons – September 11, 2001 – my first professor came hurrying into the classroom and said “Class is cancelled. We’ve been attacked.” We all rushed to the student center and watched the live feed. A terrible day.
But the semester went on. The rigor at HBS was at a different level than MIT (lower), but I learned a lot and grew in confidence. It was a place that forces you to take a position and defend it, to make the case. I saw that no one knew everything, even if some people did an excellent job of sounding like they do. And I learned again that you sometimes have to go out on a limb to create something new. If you wait for complete knowledge or a sure thing, by the time it’s that clear, someone would already be there ahead of you. Once you know 80% and can see a path to that potential future... Go, full speed ahead.
So each day I began working on a business plan. First question: What’s the business?
While it would have been great to open my own version of Disney World, no one was handing $4+ billion dollars out to 20-something kids. So I determined to think of a way to shrink down a theme park style experience into a single retail storefront — something I could actually design myself, with a small team… and raise money for. What if we could transport people into their favorite movie or video game, to actually live it? 
To be the hero of their own story, have their own adventures, solve the puzzles themselves, rather than watching it from a padded chair looking at a glowing rectangle on the wall. This type of language sounds too familiar now, as everything from VR/AR to digital games to escape rooms and other location-based concepts all promise to transport you “into the game” or “into the story.” But in 2004, my conceptualization of this idea was new and felt strange. What would that even look like? To get started, I had to pick one theme, a story that was public domain (no licenses, no IP) and had a lot of shared points of reference I could build on. I settled on an archeological dig site discovering an ancient Egyptian Pharoah’s burial chamber.
OK, so we’re going with a Tomb, and my time at Living Color gave me some understanding of how to design and fabricate a realistic set. But if it was a walk-through exhibit, folks would be done in 10 minutes… how would the economics work? No one is going to pay enough for a 10 minute experience to make the business make sense. We have to make a longer experience with higher engagement (people generally associate duration with value, as just one variable among many, when it comes to entertainment). What would make a four-room experience last, say, 45-60 minutes? And how could we keep the cycle time short enough that we could run multiple 45 minute experiences at once, to get the throughput up? The theme parks used rides (and lines), I didn’t have the space or budget for that, so what would pass the time, while engaging and engrossing guests for the better part of an hour?
I settled on puzzles. A few mental and physical games or challenges in each room, coupled with some theatrical special effects moments, which Pharoah could present as part of “proving our worthiness.” The group of 2-15 people would work to solve collaboratively, players against the game, not each other. The narrative would unfold, as they progressed room to room, serving as the protagonists in their own story, their own adventure, rather than passively watching a show on a screen. Toward the end of the hour, the group would either escape from the Tomb in honor, or “die,” seeing a separate failure ending to the experience, like dying in a video game. I didn’t know what to call this idea, the term “escape room” wouldn’t be coined for several years, so the working title for a year was “The Puzzle Room.” In the final semester of business school, I did some "research" with a focus group of friends and family, and decided to name the business "5 Wits," which would not pin us down quite as strongly as the very stark name "The Puzzle Room."
Each night I would write the section of the plan that was based on what I had learned in class — if I had marketing class, I would work on the marketing section, if I had finance class, I would work on the pro forma profit & loss statements.
At HBS, professors largely teach by the case method. Instead of lectures, most classes revolve around a situation a company finds itself in — there is a decision to be made. The “case” is 20-30 pages of background reading, stats, financial data, etc — each student needs to analyze the material and decide what to do, as if you were in charge. When the class meets, one unfortunate student gets the “cold call” — randomly selected by the professor to provide their strategy and open the class discussion. And if you do very well in a particular class session, you might get a handwritten letter from the prof in your mailbox, thanking you for your contribution to the class. I got two letters at HBS, and one was from my Entrepreneurial Management professor. And so, when it came time in our second year for me to enter “The Puzzle Room” in the annual business plan competition, I asked him to be my faculty sponsor.
Financing the First Escape Room
The competition did not go well — I was eliminated in the first round. I just remember being asked, “In what year will your business hit one billion in revenue?”... Suffice it to say, the venture capitalist judges looking for the next tech unicorn in 2003 did not see the merits in building an ancient Egyptian pharaoh’s tomb in downtown Boston.
But sitting in that professor’s office after the failed competition, he asked if I was serious about this idea. So I decided to show my commitment: I picked up the phone and cancelled my remaining interviews with the major consulting companies and decided to take the entrepreneurial plunge. I think my classmates, going to McKinsey, Bain, Goldman, or some new hedge fund, probably thought I was crazy. But that professor was willing to put in $50k of the $650k I had estimated it would take to get a high-quality Tomb attraction open. So, with a “Harvard Business Professor” on the team, I flew down to talk to the owner of Living Color, my old boss, and give him my powerpoint presentation on this strange idea.
I will never forget how he responded. After an hour, showing sketches and explaining the concept, giving it my all, I asked, “What do you think?” And he replied “I’ll be honest, I don’t get this at all. I have no idea whether enough people will pay to solve puzzles in a stage set of an ancient Egyptian tomb… or not. If this business succeeds, that’s you, and if it fails, that’s because of you too. I’ll invest, but I want you to know I’m not investing in the concept, I’m investing in the person. This is on you.”
Yikes, talk about a sobering conversation. It’d be easier if he fell in love with the concept! Years later, I’ve used a talk like that several times myself – it’s pretty effective motivation.
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At the end of the conversation, he was willing to put in $500k, big money for me, and also to introduce me to a friend who was looking for investment opportunities. He set up a call to this third angel investor and said “I’ve sent along my copy of your business plan. Just answer his questions on the phone, and if it feels like it goes well, then at the end of the conversation ask him for money.”
I was thinking, “Ask a guy that I’ve never really met for money, this is wild,” but I took the call and the conversation went well. It’s actually quite a blur to me. Thinking back, the only question I remember clearly, because it was strange, was “So, if you are calling the business 5 Wits, what does that mean?” I explained the Five Wits from Shakespeare’s Much Ado About Nothing.
And the follow-up “So, that name starts with a number – will that come at the beginning or the end in alphabetical listings?” I answered that numbers are generally listed first. “Oh, that’s good, that’s good. How much money are you short?” I said I needed another $100,000... “The check’s in the mail.”
No paperwork, no nothing, that came later. It was several years later, when I was more in a position to advise and invest in other startup concepts that I fully grasped: this final bit of investment had little to do with me, it was about the confidence of his friend and trusted associate investing that made it easy to jump in and go along. The guy who did know me well, the owner of Living Color, was taking all the evaluation risk out for his friend and telling him, “get in on this.” All I had to do was not screw it up.
I was the fourth and final investor myself – I put in essentially my whole life savings at that point.
$1,000.
Beth and I got married over Christmas of 2002, my second year of B-school with one semester to go. We lived in a *tiny* third floor walk-up apartment by Fresh Pond in Cambridge MA. Like tiny. It was in a converted attic with the ceiling sloping along the roofline on both sides, I hit my head every morning trying to brush my teeth. Much of the business plan for 5 Wits was written in that apartment, on my “desk,” which was a pine plank laid across a file cabinet on the right and a stack of my HBS cases (two and a half feet of solid paper) on the left. That summer, Beth remembers being shocked the day she came home and her typically frugal husband had gone out and spontaneously bought a window A/C unit. I explained that this third-floor apartment got so hot, I was dripping so much sweat onto my keyboard while I typed that I was afraid I would short out my laptop. The whole apartment ran on one circuit, when we’d run the microwave and A/C at the same time, we had to shlep to the basement to reset the breaker. Humble beginnings.
After much thought and prayer, Beth and I talked it through, and decided I had two years. She would work (as a licensed professional engineer, specializing in water resources) and support us both as I tried to get this new business off the ground, since I wouldn’t be taking any salary until it was open and profitable. After a couple years, either I would be able to replicate the salary she was making as an engineer and support us, and she would get to stay home to start a family… or else I would have to pack it up and get a real job, because we were going to start a family either way!We made it in 17 months. And Beth has been with our three kids, including homeschooling them the whole way K-12, since our oldest was born in 2006. Coley recently graduated homeschool and is now a student at MIT, living in the same dorm Beth did 30 years ago, at the school where we met. Again, life comes full circle. She calls it the best investment she could have made, but I think I’m the winner to have her and this family.
5 Wits Boston
With the $650,000 investment committed, I continued to tune the business plan, and started writing scripts and designing floorplans and individual games and special effects, one by one. It was really stumbling along at the beginning, particularly learning electronics and control systems, a little bit from the fast growing internet, some from vendor materials, and even from paper books (remember those?).
I rented a tiny storefront in Rhode Island as a shop, and hired my cousin, Nathan, a mechanical engineering student, as an intern, as we prototyped games and designed show elements together. The original waterscreen effect and cartouche kiosk, the tests of sight and sound... all my first games were prototyped in that ridiculously small shop.
I began to write the experience: Professor Cavendish (a name I got off a package of frozen hashbrowns one morning, when I was writing the script over breakfast) would meet us in a dig site tent, and a group of 2-15 people would find our way into the Tomb every 15 minutes, with the show control system I was programming managing the throughput and keeping groups separated. Every room would have 2-3 puzzles and neato effects like a dropping ceiling, a water projection screen, and in the grand finale the pharaoh's mummy would magically float down from the ceiling (electromagnets). I won’t go into all the details on design and effects, that’s for another article, but it was a lot of work, and a lot of fun. We made MANY mistakes (now it was a “we” instead of an “I,” a fun transition moment in starting a business), and my team holds on to some of those learnings to this day.
You can still play versions of that original TOMB in the northeast USA. We ended up building seven different Tombs over the years.
With the investment money committed, I contracted my old company Living Color to build that first Tomb set, according to my designs. Shoutout Lori and Adrian. It was a huge advantage to essentially be buying services from my own team, people I had worked with for a few years, and knew their strengths. And I think it was a good deal for the investor — he was giving me $500k, most of which I just turned around and paid back to his company for the first Tomb set. He kept his team busy in a slow season, and essentially traded their extra bandwidth for equity in my company. (I took a lesson from this, and did the same years later, helping out Boda Borg Boston in exchange for an equity stake.)
One of the hardest parts of launching a new business model, with no precedents, is finding the real estate. It might come as a surprise: landlords of valuable Boston real-estate aren’t psyched about 26-year-olds trying to lease their property to build an Egyptian Tomb. You plan to pay the rent… how? The hunt took many months. I worked with my good friend Marti who was in my section at business school — she was working to launch a new karaoke concept in Boston at the same time. Two hare-brained entertainment concepts? Might as well work together. We did our research, made a thousand calls, even spent time methodically walking certain key neighborhoods to identify empty buildings and unlisted spaces.
In the end, I settled on a 6,000 square foot storefront in the Fenway, a neighborhood which was accessible but not as nice in 2004 as it is today, and that was particularly true of 186 Brookline Ave! I was able to convince the Landlord to take a chance on our concept, we moved from our RI shop to the Fenway hole-in-the-wall space, in a single U-Haul trip on Martin Luther King Day, 2004. What helped get the deal done: the building was under option to be knocked down, and I was willing to accept a one-year notice to vacate the premises in the lease. In actuality, it took 6 years for that option to be exercised, and I was able to operate the Tomb at low rent through 2010 before leaving. I got the space for $12 / sf, gross all-in. In retrospect, that’s crazy – rental rates on that block now are 10-times the amount I was paying in 2004. A good deal really helps launch a business, and a key learning: everything in real estate tends to take longer than people think. Anyone who tells you “this will happen next year”... it’s probably three.
With the help of a couple great guys in Boston who I hired (Mike, Tim, Jorge, who still works with me decades later), we put the set together and started building the custom games in the back at 186 Brookline Ave, a couple blocks from Fenway Park in Boston. I was posting for engineers who wanted to help on Craigslist, and integrating custom games and special effects into the set as we went. We were scrappy: I bought many of the electronics, controls, and pneumatics used off Ebay. My desk was a folding table (upgraded from my pine board), and my desk chair I pulled out of the neighboring sandwhich shop's dumpster (it didn't look bad, lasted me for several years!) This earned me the slightly insulting, but I like to think love-motivated, nickname "Frugal D" from my staff, in those early days. We got a major score when the Boston Museum of Science hosted a temporary exhibit on Egypt. When the exibit was closing, I reached out, and they were going to throw their entire retail setup, all custom built shelving and displays, in the trash when the exhibit closed. I bought it all for a few thousands dollars. A couple more U-Haul trips, and we got our gift shop setup.
In September 2004, just before opening, 5 Wits got a break — we were the cover story of the Living Arts section in the Boston Globe (at left). I got home late enough to buy the next day’s paper, and crept into our *tiny* third floor apartment in Cambridge MA. I woke my wife Beth up, shaking, and showed her the article. It came a bit too soon, as the article said we were opening the next week, but it actually took us three more weeks to get our permits. No fun standing at the front door turning people away when we weren’t able to open yet. Another lesson learned. Yet I consider this one of many acts of God that have set my course over the years. We were nothing yet, but that article got just enough attention to pay the rent when we finally opened on Columbus Day, 2004.
Tomb built traffic slowly. We had no budget for marketing, so it was word of mouth, and we were struggling. This concept was a hard thing to describe to people back in 2004. I remember a Friday in November. I paid payroll to our small team, and paid all our bills. Quickbooks showed about $400 left in the bank. This was it, either it would go or it wouldn’t, and I was going to find out pretty quick.
5 Wits Productions, later Box Fort
Not long after Tomb opened, 5 Wits began to receive inquiries: “That was great, could you design and fabricate things for us?” I decided to spin off a separate design/build company to serve third party clients, with the goal of building exciting projects, and learning more and more on the budgets of larger institutions, while isolating liability from the 5 Wits entertainment venue mothership. We called this new entity 5 Wits Productions, and some years later changed the name to Box Fort Inc, to minimize confusion between the design/build company and the public entertainment venues. And yes, that is me in silhouette in the photo... a few pounds lighter. What the photo doesn't show is that the entire front of my body is covered in clothes pins, as the photographer kept adding one after another to shape my clothing the way he wanted the silhouette to look. We got a lot of mileage out of that photo.
The first two big clients were the Strong Museum of Play in Rochester NY (shoutout, JP) and the International Spy Museum. In 2007, we opened Operation Spy, an hour-long, 9-room walk-through covert mission, following the throughput model of a 5 Wits.
Part of the deal with the Spy Museum allowed us to use the ideas and designs we developed for Operation Spy for our own attractions, and so we developed our own spy experience: Espionage, which opened at Patriot Place in Foxboro MA in 2010. The following year, we added 20,000 Leagues, a Captain Nemo undersea adventure. To finish this project, doubling the size of our business from one walk-through adventure to two, I sold the original Tomb to a businessman in Pigeon Forge, TN. We moved the Tomb set down to Tennessee, where it continued to operate for another decade.
5 Wits expands, MIT recruits, Box Fort builds
5 Wits continued to grow, organically — no big capital raises, just gradually accumulating profit until we could invest in the next project. Doubling from two adventures at Patriot Place to four in Syracuse NY. Opening new venues every few years, many of which are still open. To date, there have been ten locations with 5 Wits' content, with the core five adventures (Tomb, Espionage, 20,000 Leagues, Drago's Castle, and Deep Space), each produced in variants for a total of 22 separate stage sets. Here’s the full list, in chronological order:
These walk-through adventures have operated since 2004, in five states and enjoyed by many millions of guests. As the first of its kind, opening before the term “escape room” existed, and breaking new ground in location-based entertainment, I’m proud that 5 Wits is even now a gold standard for immersive sets, special effects, computer automation, self-resetting puzzles, and a throughput / economic model that most escape rooms still haven’t caught up to, 20 years later.
In addition to designing and building the sites and walk-through adventures for those locations, Box Fort was also busy with project work for third parties — museums, themeparks, theaters, trade shows, entertainment concepts, corporate projects. A partial list of Box Fort clients includes:
And there’s been other endeavors, some successful, some less so, making life quite full.
In 2006, I got recruited to join the teaching team in the mechanical engineering department at MIT for the senior capstone Product Design Class, 2.009. I had taken this class, under amazing professor David Wallace, when I was a senior at MIT, and coming back to help teach it was a thrill. I was responsible for two lab sections, helping the students ideate, prototype, fabricate, and complete a fully functional alpha-prototype of a novel product between September and December each year. I taught over 30 teams, hundreds of students, over 18 years helping with 2.009. 
It is extremely rewarding, and seeing the energy and innovative capability of those students keeps my own mind fresh with ideas. Now, my own son, Coley, is a student at MIT — we’ll see if he takes 2.009 himself in the years ahead!
I also taught sections of 2.007 a few times — MIT’s famous robot design competition for sophomores. What a great time, and so formative in young engineer’s careers.
I bought and operated a mirror maze in a mall in Syracuse, before selling it again (great business, actually). And I bought and sold a frozen yogurt shop (run, don’t walk, away from businesses like this).
I served as the COO for a video / interactive / exhibit production company to help a friend for a year. This was a turnaround situation, where I got the call the day before they weren’t going to make payroll, and I had to parachute in to help pull it back from the brink. We lost some people in the struggle, and found some other great ones, kept the projects running and the clients happy. Now, many years later, the slimmed down version of Boston Productions continues to produce great work, wonderful videography and interactives.
As I worked on all these projects, from Box Fort’s clients, to these smaller businesses, to 5 Wits’ own ups and downs, I started to see patterns: what worked in location-based entertainment and what failed to gain momentum. What was successful for a couple of years, and then tapered off, versus the concepts that drove repeat attendance year after year and had real staying power. So on my nights and weekends, I started to design a new concept. Code named: Open World after the open world style of video games.
The beginning of LEVEL99
It was the summer of 2016 when the idea started to take shape; by October, I was sketching. (Though the sketches shown here are all by others, some fantastic creative folks I have had on my team over the years like Adrian, Kat, Chris, and Kyle.) That winter I dove into the presentation materials — what was this? Why would anyone come, why was thi better than existing entertainment options? Why would anyone invest?
Imagine an “open world” where the guest could choose where to go and what to do. Dozens of short, punchy, challenging experiences in a wide variety of themed and artistic environments. Collaborative rooms and competitive PvP games. All surrounded in a wild artistic space, rather than gray hallways. I could go on for pages on the design criteria, but we’ll save that for another article.
This would be much more expensive to do correctly, so I started talking to the landlords that I had relationships with... “If you’ll contribute this many million, we’ll open Level99 in your centers first and pay it back in rent.” The response: “Sounds great, we’re interested… after you get the first one open, call us.” Well great, if I already had the funding to get the first one open…
In November 2017, I was introduced to Ron Shaich. Ron had recently sold Panera Bread, which he founded and served as CEO, growing to a public company with 2,600+ successful stores in the US that dramatically outperformed competing restaurant concepts. He took some of his Panera success after the sale and founded Act III Holdings, “a $1 billion+ investment vehicle that partners with consumer facing brands to help them build a dominant position in the categories of the future.” Ron was talking to my good friends at Boda Borg Boston, who Box Fort had helped open, and came to see 5 Wits in Foxboro, MA.
Ron probably thought he was going to get a sales-story to invest in 5 Wits, but instead I pulled out the powerpoint I’d be using to pitch landlords and told him I had something else to show. We had lunch every few weeks thereafter, as we both got comfortable, getting to know each other as people, neither asking the other for anything. We talked business, philosophy, religion, family; months went by, and several lunches, until one day he just said “So, are we going to do something or not?” The negotiation began and we shook hands on a deal on March 28, 2018 for Act III to invest $10,000,000 to get a new concept called Open World Entertainment off the ground… Some months later, after market research, we would give the new company a “doing business as” name of Level99 to go to market. We signed all the paperwork and made it official July 3, 2018.
Now this was a paying gig for Box Fort, I was my own client, so we could get to work. What followed was two years of concept design and the real estate hunt to find location #1. (Once again, real estate is hard for a new idea, with no track record to point to.) We signed the lease for the Natick Mall, taking an old Sears department store spot, on 1/2/20… a couple months before COVID hit, decimating out-of-home entertainment for over a year.
Could a location-based entertainment startup get up to speed in a world where people were afraid to go out of the house? We pushed off the opening, slowing things down and letting the virus burn off, finally opening June 14, 2021 with our first 53 challenges. Well, we didn’t open with all of them online; in fact it took over a year to get every challenge dialed in and open. But we got the doors open, and were fortunate in how our concept resonated in the post-COVID world. Number one: people were anxious to get out and live again, and Number two: our model was a small-group experience, where you are in a room with just your 2-5 friends that you came with. Not sitting next to someone coughing on you in a theater, or with the forced social interaction with strangers inherent in so many large-format entertainment experiences.
And so, it started to work. Traffic built slowly, because once again, it’s not really clear what to call this. What is the name of Level99’s niche? Even as I write this in 2025, it doesn’t have a clear name yet. This business is hard to describe — try to explain Level99 in one soundbite. And if you can do it, email me, I’ve got a job for you.
But it was working. The “investment case,” the numbers I had presented to Act III as our targets, on which they invested — we doubled what we'd projected. The team was excited, this thing was going to fly.
Having started several different entertainment concepts, even genres, over the years, there is always this “oh, my” moment, early on, usually a few weeks before opening day, where you see it coming together, out of your head now real, when any sane person has to ask themself “Am I crazy? Did we just waste millions of dollars building this? Or is this going to be the next fun thing to do?” Well, Level99 was a hit.
Growing LEVEL99
We followed up with leases in Providence RI (opened January 2024), and Tysons Corner VA (opened August 2025).
Level99 acquired Box Fort in the last week of 2021 to become our in-house team, entirely focused on design and fabrication of our own unique challenges, no more work for third party clients (hooray). It was a strange experience to acquire my own company… bringing back in-house an entity that was deliberately spun out of 5 Wits back in 2006. Life can come full circle.
Interesting trivia: Box Fort’s very last client was the same as our first, the Strong Museum of Play in Rochester NY. Great relationships there and many wonderful exhibits our team got to help create from 2006 to 2022.
More recently, the Level99 team has grown, with 400+ employees as of September 2025, including over 80 in our corporate Support Center, far more than any company with three locations has any business having. But we are intentionally getting ahead of it, building a world-class team, investing in the future.
On September 9, 2025, we announced "Level99 Raises $50 Million in Growth Equity”" from Act III to continue supporting Level99’s growth.
Next up? The Corbin Collection, West Hartford CT and a big one… Disney Springs in Orlando FL.
With 50+ real-world mental & physical games, amazing artistic environments, and farm-to-table, chef-driven food & beverage, Level99 is a sprawling world of life-sized, active, social challenges that are approachable, endlessly replayable, and best enjoyed with others… This is an amazing platform for location-based entertainment, and the team is having a blast building something that will last. I’m seeing guest engagement and repeat play rates higher than the dozens of entertainment projects I’ve worked on in my several decades in this industry. And we've been so blessed to work with Ron Shaich, and the good people at his investment firm Act III Holdings, that has provided wisdom and countless resources, dollars, talent, and ideas. Perhaps most importantly, we've been able to build a truly world-class leadership and design team. We are so careful to only hire A+ people, and our culture of honesty, humility, productivity, and creativty is a joy to work in — I really love the people I get to work with every day.
My encouragement to you, if you’ve read this far: make something new. If you're in entertainment, don’t just add lights and digital scoring to a bar game. Don’t copy the nearby escape room, or even the soon-to-be-nearby Level99. To make your mark, to own your niche, to build something people love… think it through — what is the world missing, what are people craving, asking for, wishing existed — and solve for the way in which you can you structure an economic / ROI / throughput model to make that a sustainable business, not just a short-term hobby or labor-of-love. And if you're still learning, still on the way up, I washed pots too — work at a place that is doing these things, actually cares about the people, and cares about building something great, not making a quick buck.
Story Still in Progress
Level99 is growing fast, accelerating to a pace of four new venues a year. I’m still the majority shareholder at 5 Wits. And there’s always another idea percolating somewhere in the darkest spaces of my mind in the middle of the night...
I am incredibly blessed to work with great people every day, designing and producing experiences that bring joy to real people.
Stay tuned for the next chapter.
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Many are the plans in a person’s heart, but it is the Lord’s purpose that prevails. -Proverbs 19:21