meet stephen

Hey Stephen! 

I feel like I’ve watched Raise A Toast grow from an idea into something real and rolling. How does it feel seeing your vision fully in motion?

It’s been truly the most rewarding feeling watching my dream become reality

You’ve spent over a decade in the hospitality industry, all while balancing a full-time career outside of it. At what point did you decide to turn years behind the bar into something that was fully your own?

All the years working through school and day jobs that would help me have a stable income with benefits, it never really sparked my soul. I had to follow rules, do things the way others wanted, basically, be told what to do daily, and that becomes mundane and soul crushing after a while. I was bouncing around jobs and careers, trying to find my purpose or where I would fit in. The one thing that I always fell back on was bartending. It never felt like a job to me, even though at times it can be overwhelming in the moment, when the shift was over, it always felt worth it to me. I love people, I love making people laugh and catering to people while also being in a positive environment in a party setting. That’s what led to me taking a leap of faith on myself to start Raise A Toast.

Raise A Toast isn’t just bartending — it’s an experience. Where did the concept of the mobile trailer come from?

Initially, I wanted to do a food trailer. I started doing research on trailers, permits and certifications I would need, even worked on a business plan to try to present to a bank for a business loan. I was still a bit hesitant just because I had never ventured into cooking and preparing food and the self-doubt would set in every once in a while. I had gone to a backyard family party and when I walked into the backyard the first thing I saw was a bar trailer with bartenders serving guests at the party. In that moment it all made sense to me that this was the path I should take. I mentioned it to my wife’s aunt, who is also a small business owner and she was the one that really drilled it into my head that this could be a reality if I wanted it. I didn’t just want to start a mobile bartending business, I wanted to create an experience that would be custom to the clients’ wants and needs. I wanted to bring the party to the clients while making it as stress-free as possible. Not just custom drinks, custom décor, delicate presentation matched with notable flavor, but I want our bartenders to be part of the party, not just a body serving drinks.

For those reading, Stephen is the Founder & CEO of Raise A Toast Mobile Bar, servicing events across Long Island — from backyard birthdays to full-scale weddings. What does it take logistically to pull off events at that scale?

First it takes getting to know the client, I want all our events to be as personal as possible. Learning about my clients, I try to put myself in their shoes, and getting to know them and what they envision for their party, I feel is so important to making the best experience possible. The rest is just numbers.

There’s been a noticeable move toward sober-curious lifestyles, mocktails, and wellness-focused events. Has that shift impacted your business model at all?

I know for myself, I’ve shifted more towards self-care in my daily life, so it’s been an easy transition for the business. There are still folks that enjoy classic cocktails, myself included, but when it comes to mixers and non-alcoholic options, I made a point to provide fresh fruit juice rather than processed, mass-produced brand names. Along with providing sugar-free soda. For guests that prefer sober options, mocktails have become a permanent option for every event, and opens the door to more creative ways to enhance the client experience.

When you own the trailer, multiple side bars, and the inventory behind it all, there’s real operational pressure. What’s been the biggest challenge of scaling a mobile bar business?

Storage and logistics are the biggest challenges but that just requires some planning ahead of each event. I am lucky to have the connections I do that help me tremendously to make everything work. As the business grows, its something I will have to constantly keep in mind and work through.

Running events — especially weddings — means high expectations and emotional stakes. How do you handle that pressure in real time?

Believe it or not, I feel more stress leading up to events, especially weddings. I had years of experience working for catering halls that hosted weddings weekly, some as large as 400 guests. For events such as weddings, I make sure to put my best staff on those to assure everything goes smoothly.

When people book Raise A Toast, what do you hope they walk away remembering most? 

That the clients and their guests enjoy every second of the party and that our service provided a stress-free experience.

Thank you for being part of this segment. Watching someone turn a craft into a brand — and adapt with the times — is something special.