Celebrating Five Years of Imagination

February, 28th, 2025


Five years ago on February 10th, my dream began. Whereas I would usually take the time to thank all the people who’ve made the last few years possible, I already did in December, so I’ll take the floor for now.

Since I had been up to my eyes in the branding of pop culture and entertainment giants as a kid, I’ve always wanted to be a brand; not in the capitalistic, materialistic sense, but to be a part of the tapestry of pop culture and design; to put my stamp on the world. However, it’s become more than that; I want to tell stories, both human and fantastic, to bring fantasy into mundane reality and give people something to remember. I’ve gotten to visit two of the most popular theme park resorts in the world four times, and right after the fourth trip, realized how much of a privilege it is to have a day where nothing matters but magic, fantasy and exploration. I knew there had to be a way to bring smaller glimpses of it to people that can’t make it over their paywalls. The journey has just begun, but we get closer to the goal with every day, every month and every year.

Within a few weeks of our founding, we hit our first hurdle- in the midst of planning our debut press conference, rumblings about the first case of COVID-19 brought into our hometown of Northampton, Massachusetts became more serious. A few weeks later and those rumors became reality; cases spread as our city and region shut down in quarantine, crushing our hopes of a proper introduction to the public. Attempts at virtual events were not fruitful.

As regulations relaxed and people once again ventured out into their communities, we introduced Pepperoni in his walkaround form in 2021 to great success at A2Z Science and Learning Toy Store on the first day of the first ever Pepperoni’s Craftsy Colorween. Unbeknownst to us and the store’s owners, a preschool class had come to see him, nearly mobbing him on the lower level of the store. I don’t think he’s ever given that number of high fives since. 2021 also marked our first appearance in the Florence Holiday Parade, a local tradition since 1989.

The next two years were filled with numerous Pepperoni appearances and months of planning for our biggest event yet: our Dark of Fright Halloween Party, our first solo-hosted event. A public Dark of Fright (or DOF for short) had been a dream of mine since testing out the third annual prototype in my backyard, but, again, the 2020 pandemic dashed my hopes. 2024 was my chance to really pull this thing together, and with the help of an amazing team of family and friends, pull it together we did. Dark of Fright used the largest venue we’d ever booked, was the first of our events to use radio advertising and the second MDE event to offer food.

How do you measure success? I suppose for an event-based company, in attendance numbers and profits… However, I’d say as a fledgling company I’d have to measure success in how many people you make happy regardless of expected turnout, how many special moments you create and how many people recognize Pepperoni a year later. We can never lose sight of the importance of making sure our guests have a wonderful time and an experience unlike any other in their area of the country. From my vantage point, the next five years look to be very exciting, and I hope that all of you will be along for the journey.

Warmest regards,

Matt Dibrindisi signature

Matt Dibrindisi
Principal Creative at Matt Dibrindisi Entertainment

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