Embracing Their Rebel Soul: How a Family-Owned Lifestyle Brand Is Elevating Experiences with Wine, Excursions and Design

Published on May 10, 2024 | Webster Bank

When three cousins connected, they blended their shared passion for travel, wine and elevated design to build Rebel Soul Lifestyle Brands.

For Executive Director Theresa O’Neal Redd, the start of Rebel Soul Lifestyle Brands allowed her to feed her own “rebel soul.” The term, coined by her cousin and business partner Tenisha Ramsay, captures the essence of the burning desire to see and experience the world—to travel, drink wine, and have fun beyond the confines of the regular day to day.

Redd brings 30-plus years of experience in marketing, public relations, branding, communications and development. She has been involved in entrepreneurial opportunities for social and cause marketing and building nonprofit events and fundraising, all skills that jump started the foundation and growth of Rebel Soul Life. Her recent work as managing director of REALEMN Productions left a positive impact on the world of live theater.

“I came from working with Broadway marketing with up to 15 shows at a time, developing audiences for Tony award-winning and nominated productions. I am always looking for the right opportunity that will feed my passion and make me excited,” Redd says. “‘Rebel soul’ is that burning desire when you’re in the working world and need to get out, drink wine, see the world and have fun.”

Within Rebel Soul Lifestyle Brands, Redd is focused on development, branding and strategy for the lifestyle and excursion company. She focuses on corporate partnerships and identifying client experiences across the globe. Ramsay has been working in corporate marketing in Fortune 500 companies for 20-plus years. From her family history and upbringing, she has always been driven to travel. That passion for seeing the world has taken her to all but one continent— and Antarctica is in her plans for the future, too. Inspired by her lifetime of travel experiences and love of wine, Ramsay sought to learn more about and sell wines. As a brand ambassador for the Boisset Collection, Ramsay hosts tastings and represents more than 100 wines and 30 vineyards and wineries in California and France.

After Ramsay and Redd hosted a wine tasting with Tenisha at the helm, the cousins considered how they could blend their shared passions—wine, seeing the world, and concierge group travel experiences—into a family business. Ramsay’s wine relationships helped fuel the beginnings of excursions for Rebel Soul that connect guests with top wines and memorable experiences no matter the destination. Redd and Ramsay also recruited their cousin Antoine Jones Jr., an award-winning creative director, production artist and graphic designer with depth of experience in advertising and marketing to further develop the company.

Rebel Soul Was Born

in 2023, Rebel Soul moved through intensive research and design stages before building out wine tastings and sales, international excursions, domestic experiences and lifestyle products. “We’re a one-stop shop for guests looking to buy a wine, schedule experiences locally or excursions abroad, and buy leisure lifestyle travel accessories to complete the picture,” Redd says. “Research is a strength for all three of us— we have a lot of experience figuring out how to reach our audiences.” As cousins, Rebel Soul’s leaders appreciate their shared passion for travel and experiencing the world.

“It’s special for us to have these partnerships and dialogue and drive to achieve the same goal,” Ramsay says. “It’s so much sweeter when you’re sharing it with someone else.”

Knowing Their Audience

While the family business is a team of three, Redd, Ramsay and Jones rely on liaisons and their experience in excursions, project management, special events, and the Broadway world to support Rebel Soul’s regional excursions and international travel. The team crafts experiences around the world, with eight upcoming trips, including one to Turkey, Egypt and Morocco.

“I’m the product of a family who travels, and it’s a passion that’s grown in me. Travel has always been part of my life and I feel like I’m fulfilling my destiny continuing that tradition.” – TENISHA RAMSAY

As a Minority and Women Owned Business Enterprise (MWBE), Redd wants to reach audiences who are underrepresented in the marketplace, including BIPOC (Black, Indigenous, People of Color), women and the LGBTQ+ communities. They want to reach people eager to experience something different they’ve never done before. “[Serving that audience] reflects who we are,” Redd says. “I’m Jamaican born and my cousins are of Jamaican descent. As a woman, and as a traveler, it’s not necessarily comfortable to travel alone. Am I going to be well received based on my background and the community I represent? A lot of people feel more comfortable traveling in groups where they see themselves and having a concierge experience.”

Designing Memorable Experiences for Guests

As travelers themselves, Redd and Ramsay know the ins and outs of their excursions and events, and their goal is to create exclusive group packages curated with local flavors, top wines, and hometown favorites. They strive to include hidden gem experiences, whether it’s visiting the hippest designers in Paris, an art gallery you wouldn’t expect or the latest influencer chef everyone is talking about. They want to make trips and local excursions memorable—and a little different.

Beyond experiences and excursions, the family trio is in the process of creating their own Rebel Soul wine, bottled out of Portugal, and they’re connecting with distribution and raising capital to bring it to market.

“It’s our goal to create these exciting moments for our guests through travel, paired with wine and the chance to even see where it was made,” Redd says. “In our initial research among peers, we knew we wanted to be able to schedule weekend trips so our guests can travel and still have a workweek. We want to create cool excursions, with great reception, live music, local art or a sporting event that creates a sweet, memorable experience.”

Redd says it was important to create a lifestyle brand that considers all aspects of life—travel, wine and design—not just because of their passions but because it made good business sense to diversify their bottom line. “Our north star is doing what we love and making sure we’re doing things that our guests will love as well,” Ramsay adds. “We’re focused on our communities and what they’re passionate about. We’re thinking about experiences people haven’t thought about doing or that they didn’t want to do alone.” Within Rebel Soul’s wine shop, Redd is developing cause-related shopping so guests can purchase wine from a woman-owned winery, or black or minority owned business.

Growing Relationships and Their Network

As Redd conducted market research in the initial planning stages, she knew it was vital to establish a network of strong relationships. Through Webster Bank, Rebel Soul’s partners received support from a bank and relationship manager who understand small businesses and can connect them to valuable resources.

“Webster has been a strong supporter of our team and business, and not only have they helped us, but we’ve been able to help them build connections in the state and region. We have a two-way partnership. We’ve supported Webster during certain Business Resource Group engagements and moments,” Redd says. “They connected us with the Black Business Alliance, where Tenisha is based, and helped us grow our relationships and find resources that support our business, such as legal counsel and accounting.”

Redd says big hurdles for starting Rebel Soul were refining relationships and sharing their business with the right communities. “It’s important to let people see where you’re headed, to help them envision the result and bring passion along with it,” Redd says. “I’m confident in the way we’re approaching business because of the information and guidance we received from Webster.”

Using Personal Experience to Guide Design

Rebel Soul’s founders say their business certification opened doors to resources and access to the Black Business Alliance in the marketplace that helped them grow the business.

“As part of Webster Bank’s diversity initiatives, we’re able to further build out relationships and have conversations in regards to supplier diversity and what that means—it added another outlet that we wouldn’t have had the opportunity to pitch,” Redd says. “As an MWBE, we are part of our core audience—minority individuals and women—and we’re able to bring our personal experience to how we create our excursions, trips, wine and our design. We’re fortunate that we’re able to bring our whole selves to the design process and business.”

Given their background in corporate industries, Redd says their experience enables them to move in a different way and understand the needs of a larger organization when securing sponsorships. She and Ramsay can see how Rebel Soul can align with a company’s overall strategy and goals.

Supported By Their Webster Relationship

Rebel Soul’s partners started their relationship with Webster Bank in 2023, and they met over wine. Ramsay and Redd were pouring wine and speaking on a panel for a women’s empowerment brunch sponsored by Webster Bank and felt an immediate connection with the organization.

Beyond their banking relationship, Rebel Soul has supported Webster’s Business Resource Group events and Webster employee celebrations with custom-designed wine gifts. “Personally, it’s the first time I’ve had a real relationship with my bank. They’ve truly supported us,” Redd says. “The onboarding was seamless, and Barrett Stokes, our relationship manager, was amazing in walking us through the process and ensuring we have all the tools we need for our small business.”

Both Redd and Ramsay appreciate that they can make a call or email to Webster and always get a response. “We’re truly a small business, and we know we’ll scale quickly,” Redd says. “It’s nice to have bank representatives who are patient and work with us whatever the scenario. They know what tools are available to small businesses. Having a bank representative stand behind you means a lot in the business world.

Credentialing for Success

What started as a wine ambassadorship has grown to a robust and thriving travel and lifestyle business—bringing together wine, experiences and excursions around the world. Along the way, Rebel Soul’s partners have taken methodical steps to solidify the business and brand, from formulating an LLC, building out the company’s structure, and finding the right support to avoid pitfalls. Redd and Ramsay also maintain American Society of Travel Advisors (ASTA) and Cruise Lines International Association (CLIA) memberships and are seeking Airlines Reporting Corporation (ARC) accreditation.

“Travel opens and expands your horizons. As we plan excursions, we consider destinations we find exciting so guests can see and experience the world.” – THERESA O’NEAL REDD

“As we built our business, we knew we had to stand behind our work and give guests and shoppers peace of mind—the proper insurance and appropriate credentials for in-person wine tastings and travel-related special events,” Redd says. “We wanted to ensure we’re doing good business, which extends to the lengths we go to ensure our trips are seamless for guests.”

Through all workings of Rebel Soul, the partners strive to deliver great wine, travel and lifestyle experiences for guests. With the support of Webster Bank, Redd says she feels confident to grow the business and reach new heights.

“I encourage other small business owners to go for it—and to make sure you’re getting what you need from your bank,” Redd says. “Now is the time to jump in and get going—and really feed your rebel soul!”

Webster Bank is committed to helping small businesses— particularly Minority- and Women-owned Business Enterprises (MWBEs)—grow and thrive through personalized relationship management and comprehensive business banking services tailored to their unique needs. To learn more about how we can help, click here.

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