Wedding and event specialist Bailey Brooks Mashburn curates experiences that linger long after the last toast.
By Jenny Starr Perez.
Wedding and event specialist Bailey Brooks Mashburn curates experiences that linger long after the last toast.
Being a bride comes with a staggering amount of pressure—the dress, the guest list, the endless details that somehow all need to align for one perfect, fleeting day. And if she chooses to hire a planner, she’s placing her trust in a relative stranger to orchestrate the biggest event of her life. The solution? Find someone who is both a consummate professional and the kind of confidante who just gets it—a best friend with unshakable precision, boundless creativity, and the uncanny ability to bring even the most extravagant dreams to life.
As the founder of How 2 Wed, a premier event planning company, Bailey Brooks Mashburn has mastered the art of turning dreams into meticulously orchestrated realities. From luxury weddings in Los Cabos to high-profile events for celebrity clients, Bailey’s expertise lies in creating spaces that feel effortless yet unforgettable.
“An event isn’t simply what people see—it’s what they feel,” Bailey says. “When I design, I consider every sense—sight, sound, taste, touch, and scent—because the best events aren’t just attended, they’re remembered.”
Her journey into event planning was anything but conventional.
What started as a favor for a friend turned into an internationally recognized business. “I didn’t even realize wedding planning was a profession,” she admits. “I was doing it for free because I loved it. Then one day, I thought—why not make this a business?” Within a month, she had a website, marketing materials, and 13 booked clients. Fast-forward to today, and she’s one of the most sought-after event designers in the industry.
Born in Winnipeg, Canada, Bailey was raised in a multicultural household—Trinidadian on her mother’s side and German on her father’s. That diversity, coupled with a sharp entrepreneurial spirit, shaped her into a businesswoman with an instinct for storytelling through design.
“Culture plays a huge role in weddings,” she says. “The overall experience often reflects the couple’s identity, their heritage, and their journey.”
Her approach is both artistic and tactical.
Take, for example, her now-famous “walking on water” wedding concept. During a wedding at Nobu Los Cabos, Bailey envisioned a plexiglass aisle submerged in water, giving the illusion that the couple was gliding across the surface. “I just blurted it out—what if they walked on water?” she recalls. “The hotel had never done it before, but we got engineering approval, CAD drawings, and the whole thing was executed flawlessly. Now every bride wants it.”
But behind the jaw-dropping moments is a keen understanding of logistics and problem-solving. She’s fielded requests for elephants at an Indian wedding, sky-high floral installations, and multi-day affairs that involve flying in chefs, designers, and entertainment from around the world.
“I love when clients dream big,” she says. “But I also love figuring out how to make it happen—whether that means securing permits for an elephant or suggesting a more elegant, practical alternative.”
While weddings remain her passion, Bailey has expanded her focus to philanthropy, venue ownership, and the art world. She is a board member of the NSU Art Museum Fort Lauderdale and the Volunteer Executive Director of the Kennedy Kids Foundation, a mental health awareness organization.
“When I joined the NSU Art Museum board, I knew nothing about art,” she admits. “Now, I’m collecting, curating, and planning major fundraising galas. Art is storytelling, just like event design—it captures a moment in time that will never exist again.”
In addition to curating one-of-a-kind experiences for clients, she now owns and operates an event venue, the 20,000-square-foot HANGAR 1815 in Fort Lauderdale. “I still love planning weddings, but now I’m thinking bigger. How do I create environments that serve as the backdrop for hundreds of extraordinary moments?”
Bailey’s ability to balance high-stakes event production, philanthropy, and business ventures is matched by her personal life—she is married to Jamal Mashburn, the former NBA star turned business mogul.
“We’re both constantly moving, constantly building,” she says. “Jamal is involved in so many industries—real estate, automotive, restaurants—and during COVID, I officially took on the role of Chief of Staff for his businesses.” That position means managing projects ranging from real estate development to international ventures, all while running How 2 Wed and raising a blended family of five children.
“I always knew I wanted to be part of something bigger than myself,” she says. “Whether it’s planning a wedding, opening a venue, or building something from scratch—there’s no better feeling than bringing a vision to life.”
Bailey Smith Events
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