Alright – so today we’ve got the honor of introducing you to Caroline Mazzarella. We think you’ll enjoy our conversation, we’ve shared it below.

Caroline, appreciate you joining us today. Can you talk to us about a risk you’ve taken – walk us through the story?

May 3rd, 2023….the day I made my first social media post advertising the establishment of my small business baby, Rye Street Events!
This is when taking risks became just another normal daily task in the life of Caroline Mazzarella. Ever since designing and executing my own wedding as well as frequently taking on the role of being “the hostess with the mostest”, the passion for starting my own event and wedding planning business began to itch at my subconscious harder and harder. With still holding onto another full-time job, I wanted to step into this creative space on a deeper level -Giving myself the opportunity to truly create something special and unique from the ground up. The risks to come along with that?…very much unknown at the start, but I was so willing to take the leap.
With still maintaining a commitment to a full-time work from home job, I launched Rye Street Events, out of the desire to fill spaces (big and small) with collective groups of friends and family, all together in one place to celebrate some of life’s most meaningful events and milestones.
By the end of 2023, I was preparing for a steady first season in 2024, and by the end of 2024, I was already looking at a 2025 calendar with double the amount of contracts on my docket.
All of my life, I have been seen and considered as the ultimate planner between by friends, family and acquaintances, however, I can truthfully say, that never in a million years, could I have planned for the growth and unwavering support that has come from taking the initial risk of starting my own business.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your background and context?

Hi Friends! Caroline Mazzarella here – the owner and lead planner of Rye Street Events. Founded in 2023, my small business baby was born from a deeply personal place: the joy that I discovered while planning and executing the wedding day of my dreams with my wonderful husband, Eric.

Born and raised in a small town in Western Massachusetts, I now reside outside of Hartford, Connecticut where my husband and I take care of our dream home property and our three fur babies; Louie, Neah, and Mylo.

Inspired by the joy and creativity found in bringing our own special day to life, I launched RSE with a mission: to turn each client’s unique vision into an unforgettable reality. Although weddings are serviced by me and my dedicated seasonal team a majority of the time, RSE also offers planning and coordination for showers, dinner parties, milestone celebrations and more.

With a strong unwavering commitment to excellence, Rye Street Events specializes in crafting one-of-a-kind experiences that leave lasting impressions and relationships for years to come. What began as a solo endeavor has quickly blossomed into a high-quality event planning company, thanks to the support of our passionate, talented team, and strong industry partnerships built over these past 3+ years.

I make it clear to our clients and couples that no two people are alike, and your event should be uniquely theirs. Therefore, we tailor our services to curate those unforgettable experiences that truly feel like YOU! Offering a variety of services from hourly event coordination, month-of wedding management and up to partial planning, there are flexible offerings available for each of our prospect clients. From behind the scene design and budget calls to run of show day-of logistics, our team supports and guides our clients throughout the duration of their planning experiences from the first hello to the final goodbye!

Any advice for growing your clientele? What’s been most effective for you?

Honestly, the most effective strategy for growing my clientele has been word of mouth. There’s something incredibly powerful and moving about a personal recommendation—when someone trusts you with such an important event and then shares that experience with others, it speaks volumes.
I focus heavily on creating seamless, thoughtful, and genuinely positive experiences for every client, knowing that those relationships often lead to referrals.
Over time, that trust has built a strong network of past clients, vendor partners, and supporters who continue to recommend my services, and that’s been the foundation of my growth.

There was a moment last year during a wedding that stopped me in my tracks. As I stood with the bridal party before the ceremony, I realized my current bride was standing next to a past bride—and right beside her was a future bride of ours. Seeing those connections come together so naturally was incredibly moving. It’s one of those moments that perfectly captures the power of trust, relationships, and word-of-mouth in this industry.

How do you keep your team’s morale high?

Running a business as both the owner and lead planner, it’s very easy to fall into the mindset of ‘I can do it all myself.’ In the early years especially, that approach led me straight toward burnout—and if I’m being honest, that feeling still creeps in from time to time.

What’s made the biggest difference is learning to trust and build a team around me. As the business has grown, so has my confidence in bringing on incredible seasonal assistants who truly help bring each event to life. I still manage the behind-the-scenes planning, but in the weeks leading up to an event—and especially on the event day itself—I fully lean on my team.

For me, maintaining high morale comes down to creating an environment built on trust, respect, and collaboration. Being open-minded, empowering my team to take ownership of their roles, and letting go of the need to control every detail has not only strengthened our events, but also created a more positive and supportive experience for everyone involved.

Contact Info:

• Website: https://ryestreetevents.com/
• Instagram: @ryestreet_events

Image Credits

Photo credits to:
Shannon Bialy
Kari Bjorn
Mermaids Reel
Allison B Photo