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Exploring Life & Business with Derrick Cowit of TrulyNewYork

Today we’d like to introduce you to Derrick Cowit.

Hi Derrick, so excited to have you with us today. What can you tell us about your story?
I’ve always been excited about bringing people together. Long before I thought of it as a career, I loved the idea of creating an environment where strangers could share an experience and leave with memories shaped by the people, the place, and the host who brought it all together.

I started in the event business producing everything from private birthday celebrations and graduation parties in high school to large-scale events and concerts in college. At 18, I was bringing musicians to perform in my fraternity house parking lot. I was fortunate to produce events for the late Avicii and Mac Miller early in all of our careers, eventually drawing crowds of as many as 11,000 people right outside my college residence.

As my career grew, so did the scale of the experiences I was fortunate enough to work on. Over time, my focus shifted from my personal taste in music to experiences with a more timeless, universal appeal. I began focusing on some of New York City’s most iconic traditions—the same moments I was fortunate to grow up looking forward to with my own family.

That evolution ultimately led to TrulyNewYork.com, a platform dedicated to providing premium access to New York City’s most treasured traditions and unforgettable moments.

I started Uplyft in 2011 through my work around New Year’s Eve. I was brought on to support Icon Marketing with its events for Tao Group, beginning with the debut New Year’s Eve celebration at the newly opened Dream Downtown Hotel. Those early years helped define what premium hospitality and customer service still means to me today. I had the opportunity to watch Tao Group emerge as the defining force in New York nightlife and to learn from Jonathan Schwartz and Matt Strauss, by way of nightlife veteran David Schulman. Those experiences had a lasting influence on how I approach hospitality and ultimately helped shape what Uplyft would become.

That foundation in premium hospitality, combined with the New York traditions I grew up experiencing with my own family, ultimately became the foundation for Uplyft and TrulyNewYork.com.

Today, we build experiences around some of New York City’s most treasured traditions—from the Thanksgiving Day Parade and New Year’s Eve Ball Drop in Times Square to the Rockefeller Center Christmas Tree and other major celebrations. Our goal is to combine access with thoughtful hospitality, giving families, friends, and visitors from around the world a way to experience these iconic New York moments together.

Looking back, the venues, events and scale have changed tremendously, but the reason I love what I do really hasn’t. Whether it was one of my earliest events or an experience for thousands of guests in the heart of New York City, it has always been about bringing people together and creating memories around moments that matter.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
I’ve learned that growth brings a responsibility to work even harder. As we’ve been fortunate enough to welcome more guests each year, the challenge has been making sure that growth never comes at the expense of the individual experience. I try to approach every event with humility and the understanding that each guest has chosen to spend an important moment of their life with us. That’s something I never want to take for granted.

My goal has always been simple: treat every guest with the same care and attention I would want given to a member of my own family. We’re never going to be perfect, but we can always listen, work harder and find ways to improve. As the business grows, I want to make sure that mindset grows with it.

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Uplyft is our event production and hospitality company I started in 2011. Over the years, we’ve been fortunate to produce experiences across the country surrounding major celebrations, destinations, and cultural moments. Our work brings together event production, customer service, food and beverage, entertainment, and hospitality, with a focus on creating an experience that feels thoughtful from the moment a guest arrives.

In New York, that work has grown into TrulyNewYork.com, which brings together our experiences surrounding some of the city’s most treasured traditions, including the Thanksgiving Day Parade, the Rockefeller Center Christmas Tree, Broadway, and New Year’s Eve in Times Square.

What I’m most proud of is the hospitality behind what we do. Many of our guests have been looking forward to these moments for years, and we try not to lose sight of that. As we’ve grown, I’ve always tried to approach each experience by asking how I would want my own family to be welcomed and cared for.

TrulyNewYork.com is a reflection of that philosophy and of my own connection to these traditions growing up in New York. I’m proud to now have one place where we can share these experiences with families, friends, and visitors from around the world and hopefully help make their time in New York even more memorable.

Are there any books, apps, podcasts or blogs that help you do your best?
More than any app, book, or podcast, my greatest resource has always been the family, friends, and colleagues who answer the phone when I call with a crazy idea, an ambitious goal, or something I’m trying to work through. I’ve been incredibly lucky to grow up in a creative, entrepreneurial-minded family that has always entertained some of my wildest ideas while giving me the constructive feedback needed to help shape them into what they are today.

My little sister—although she’s now married, a very successful entrepreneur in her own right, and hates when I still call her that—has always been one of my biggest supporters and sources of creative fuel. She was there for nearly every early ideation session and probably 99% of our events in their first iteration. Life doesn’t give us quite as much time for those sessions anymore, but I’ll always credit her with providing some of the encouragement and push it took to get many of these concepts off the ground.

The same is true of my wife, so many friends, colleagues, and mentors I’ve been fortunate to have around me. They may never fully realize how much I value those conversations or how much their perspectives have influenced the way I think. Having people willing to listen, challenge an idea, offer advice, or simply be a sounding board has been invaluable. I’m incredibly grateful for their influence and for the role they’ve played in shaping both the person and entrepreneur I am today.

Contact Info:

People dancing in a dimly lit venue with tables, screens, and cityscape images in the background.

Two performers in feathered costumes pose with a large reflective sphere at an event, surrounded by guests in formal attire.

Three people smiling outdoors at night with city lights in background.

People looking at a large Pokémon-themed float in a city street, with buildings and a parade in the background.

Assorted baked goods on a table in a busy cafe with people sitting and walking outside through large windows.

People watching a large inflatable character outside a glass building, with reflections of a crowd inside.

People gather inside a large modern building with glass walls and a stage with lighting equipment, some seated and others standing.

People watching a colorful light display on a window, some taking photos, in a dimly lit room.

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