Meet Jennifer Rose

 

We’re excited to introduce you to the always interesting and insightful Jennifer Rose. We hope you’ll enjoy our conversation with Jennifer below.

Jennifer , we’re so excited for our community to get to know you and learn from your journey and the wisdom you’ve acquired over time. Let’s kick things off with a discussion on self-confidence and self-esteem. How did you develop yours?

I spent a lot of years feeling like a little kid at the adults table, unsure of myself in fear of not being taken seriously. It took a long time to get past this sense of insecurity and find confidence in my abilities. Surrounding myself with good and positive people as well as finding a spiritual practice has been pivotal to my build up.

Thanks, so before we move on maybe you can share a bit more about yourself?

Gypsy Social is an events company that offers planning services, live entertainment, and custom event decor in NY and across the US.

I was always drawn to the hospitality industry. I owe my interest in event planning to my family who treated every get together like a major celebration. I learned the basics of portioning food, proper party etiquette, and even crowd control at my Grandma Janet’s house. Get togethers were fun and frequent and growing up this way made community gatherings the basis of my life.

From elaborate themed parties in my 20’s to a city-wide scavenger hunt and once I even recreated high school prom – I’ve always strayed from planning anything basic or redundant. Creating events is an art form and creative outlet for me and I was excited to jump into the workforce. After almost a decade of working in this industry in various roles, I found myself bored and uninspired by the work I was doing. Most events were essentially the same – the same decor, food and cocktail menu, itinerary – nothing was original. The job became more mechanical and less heartfelt. I knew I wanted to create more profound and unique events and to do so with freedom.

I didn’t exactly know what I meant by that or how it would happen and what started out as a party planning company has developed with the collaborative efforts of my partner, Anthony. Anthony is an incredibly talented artist and craftsman who shared similar goals of getting into events. When we met, the vision of Gypsy Social became clearer and the elements of our business began to take shape.

When Anthony and I decided to join forces and blend his skillset with mine, beautiful things started happening.
We created an event called The Live Art Experience, an exhibition where artists are given a surprise prompt and have 1 hour to freestyle paint, that became popular at breweries, galleries, and event spaces in NY. The Live Art Experience allowed us the chance to work together, meet other creatives and network with community. The more events we had under our belt, the more we grew and evolved our ideas. From there, we called on some of the participating artists to work more with them in new capacity by booking them as live painters for events. One of Anthonys passions is building with a range of materials and when he created the backdrop for The Live Art Experience, we were led down yet another pathway of what we could do. We now offer unique backdrops and other items for rent or commissioned for purchase. Anthony has also developed a framework that could change the game for balloon artists and others in the backdrop community.

Allowing our passions to lead the way and develop organically allowed Gypsy Social Events to diversify our offerings and has been crucial to our success. I now only take on events that move me and we’re currently working towards purchasing property to live and use as event space.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

Being an entrepreneur is NOT for the faint of heart and for total transparency, we struggled and still do at times in all of these areas.

When Anthony and I made the decision to make Gypsy Social Events happen, we understood that with life’s responsibilities that there would need to be an important time of transition before going all in on our business.The strategic balance of time and energy is so majorly important. Gypsy Social sat on a shelf for a long time while I devoted insane hours in the events industry. There was always that part of me that wanted to go all in, but was too involved in other work. When I switched from full time work to freelance event planning, I was still able to hone my skills, build contacts and have time to apply my learnings to Gypsy Social. Anthony, who is a brilliant tattoo artist, made the decision to take on less appointments to make time for learning a new industry and designing and building decor for our events. This transition is important because you don’t want to go for broke, but you don’t want to loose momentum either.

It’s easy to feel motivated by a new idea, but just as easy to feel defeated when things don’t go as expected. Managing expectations is crucial, both in business and for maintaining mental health, it helps prevent discouragement and fosters a more balanced perspective when challenges arise. And challenges will 100% arise! Finding the balance between staying optimistic and preparing for things to take longer is key.

Another valuable resource is having a group of people in your world to consult with or a “mastermind group”. These are friends, colleagues, and mentors who offer their diverse perspectives and advice. Anthony and I spend a lot of time brainstorming and we often come up with great ideas, but by surrounding ourselves with people who have different skills, experiences, and viewpoints, we often gain insights that lead us to make better decisions and push us through challenges.

For those early in their journey, my advice is that you don’t need to have everything figured out right away—often, the most powerful business ideas are shaped by the lessons you learn along the way and the people you surround yourself with. Patience, experience, and the right community can offer opportunities you never even considered.

Okay, so before we go we always love to ask if you are looking for folks to partner or collaborate with?

Working with people who share the same hunger and passion for their craft is a true gift. That’s how it feels collaborating with the incredibly talented souls who have entered our lives. We couldn’t do what we do without their support and expertise. Some we’ve worked with in previous jobs, others came recommended to us, and some we met by pure serendipity. We are grateful for each one and are always seeking to connect with more like-minded individuals and venues—artists, DJs, event vendors, fellow event planners—who can help elevate our shared vision. If you’re interested in talking more, it doesn’t matter if you’re in NY or not, we plan on traveling and living out our true Gypsy life email us at thegypsysocial@gmail.com.

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