Two Directors, 20 Years: A Conversation About Legacy, Dreams, and Charleston’s Culinary Heart

Episode 34 of Never Stop Dreaming Biggie brought me full circle in the most beautiful way. I sat down with Alyssa Smith, the Executive Director of the Charleston Wine and Food Festival—the event I founded 20 years ago—and we had one of those conversations that reminded me exactly why I started this podcast in the first place.

Because here’s the truth: dreams don’t just happen once. They ripple forward, touching lives you never expected, creating opportunities you couldn’t have imagined, and coming back to you in the most unexpected ways.

THE POWER OF WRITING IT DOWN (AND THEN DOING SOMETHING ABOUT IT)

Alyssa’s story is one for the vision board believers out there. She was running her own successful PR and communications company, working with multiple clients, and doing well. But she started asking herself the questions that every entrepreneur eventually faces: Who do I really want to work with? What values do I want my business to reflect? What legacy do I want to build?

So she did something simple but powerful: she wrote “Charleston Wine and Food” on her vision board.

But here’s what made the difference—she didn’t just write it down and wait for magic to happen. She took action. She reached out to Laura Kate Whitney (who was the marketing communications director at the time and is now running her own business like the total boss she is). She asked for a coffee meeting. She made her case: “You need me. You need a local perspective. You need someone who understands this community.”

And it worked.

That’s the lesson right there. Vision boards are powerful, but they’re not magic spells. They’re commitments. They’re declarations of intent that require follow-through. Alyssa manifested her dream job because she combined belief with bold action.

FROM MY HOUSE TO A LEGACY

When I started the Charleston Wine and Food Festival in 2005, I was running it from my house. Literally. We had volunteers everywhere, boxes stacked in rooms, and a whole lot of faith that this crazy idea would work. We believed Charleston’s culinary story deserved to be told, celebrated, and shared with the world.

Twenty years later, sitting in Charleston Wine and Food’s beautiful office with Alyssa, looking through my box of original festival artifacts—the first tickets, the early agendas, the handwritten notes—I was overwhelmed with gratitude. Not just because the festival survived, but because it’s thriving in the hands of someone who truly gets it.

Alyssa understands that this festival isn’t just about five days of incredible food and wine. It’s about community. It’s about giving back. It’s about creating opportunities for the next generation.

THE RIPPLE EFFECT: 1,200 STUDENTS AND COUNTING

Here’s what most people don’t know about Charleston Wine and Food: the real work happens year-round, not just during festival week.

The organization now has an education outreach administrator whose entire job is focused on internships, mentorships, and working with youth to showcase the culinary and hospitality industry as a viable career path. They’re in 10 high schools across Charleston County and Dorchester County School District Two, serving over 1,200 students.

Let that sink in. 1,200 young people who might never have considered a career in culinary arts, hospitality, events, or food service are now learning from James Beard award-winning chefs in their own classrooms. They’re participating in externships during the festival, working alongside industry professionals, and seeing firsthand all the career possibilities this industry offers.

And when these students complete the program? They’re awarded scholarships to continue their education at the Culinary Institute of Charleston.

This is what legacy looks like. This is what happens when you build something with intention, with heart, and with a commitment to giving back to the community that supports you.

WHAT MAKES CHARLESTON WINE AND FOOD DIFFERENT

Alyssa and I talked about what sets Charleston Wine and Food apart from other food festivals around the country. And it really comes down to this: authentic community connection.

This isn’t a festival that parachutes in for a weekend, makes some money, and disappears. It’s deeply rooted in Charleston’s culture, history, and people. It celebrates local chefs, local restaurants, local ingredients, and local stories. It supports scholarships, disaster relief, and community programs throughout the entire year.

The festival showcases not just what Charleston tastes like, but what Charleston feels like—that spirit of hospitality, collaboration, and caring for your neighbors that makes this city so special.

As someone born and raised here (my son goes to James Island High School, just like Alyssa did!), this local authenticity matters deeply to me. Charleston has grown and evolved, but at its heart, it’s still about the people and the stories and the connections that make this place home.

THE 20TH ANNIVERSARY: TICKETS LAUNCH THIS THURSDAY!

If you’ve been following along, you know that tickets for the 2026 Charleston Wine and Food Festival launch THIS THURSDAY, October 23rd at 11 AM. And trust me when I say: you want to be online right at 11.

Why? Because things sell out. Fast.

Especially the seated restaurant experiences—some venues only have 12 tickets available because that’s literally how many seats are in the restaurant. So if you’re trying to snag one of those intimate dining experiences, you need to be ready.

Here are Alyssa’s insider tips:

• Use the new “favoriting” feature on charlestonwineandfood.com to browse the schedule now and heart the events you want
• When Thursday comes, check out will be much faster because you’ve already marked your favorites
• Don’t miss Opening Night—it sets the tone for the entire festival
• The Finale is going to be incredible this year, programmed with next-wave talent and the people pushing Charleston’s culinary scene forward
• Keep an eye out for special 20th anniversary events and tributes throughout the weekend

And here’s a little tease: The Holmestead Bar and Retreat will be making a special appearance at the festival! We’re planning something fun to announce our Caribbean island location and give people a taste of what we’re building. I can’t wait to share more as we get closer to March!

WAYS TO SUPPORT (BEYOND BUYING TICKETS)

One thing Alyssa emphasized that I want to echo: there are so many ways to support Charleston Wine and Food’s mission.

Volunteer: They need hundreds of volunteers throughout the festival weekend. It’s an amazing way to be part of the action, meet incredible people, and support the cause.

Sponsor: If you have a business or brand that aligns with the festival’s values, sponsorship opportunities are still available. Alyssa and her team do such a thoughtful job of connecting sponsors with the right audiences and creating meaningful partnerships.

Donate: Every dollar supports year-round programming—scholarships, education initiatives, disaster relief, and community support.

Attend: Simply showing up and buying tickets funds all of this incredible work. You’re not just getting an amazing culinary experience; you’re investing in the future of Charleston’s food industry and the next generation of culinary professionals.

THE “B” IN BIGGIE: BELIEVE

The “B” in BIGGIE stands for Believe—in your vision, even when others don’t see it yet.

Twenty years ago, when I was running the Charleston Wine and Food Festival from my house with a team of passionate volunteers, we believed Charleston’s culinary scene deserved national recognition. We believed in celebrating local chefs and restaurants. We believed in giving back to the community. We believed that food brings people together in powerful ways.

Today, Alyssa is carrying that belief forward and elevating it in ways I couldn’t have imagined. She’s expanding educational opportunities. She’s creating pathways for young people to build careers in this industry. She’s ensuring that the festival stays true to its roots while embracing Charleston’s evolution.

That’s what believing looks like in action. That’s what happens when you combine vision with values, dreams with determination, and passion with purpose.

FULL CIRCLE MOMENTS

Sitting with Alyssa and talking about the festival’s journey felt like one of those rare, precious full-circle moments. To see something you started—something you poured your heart and soul into during those early, uncertain years—not just surviving but thriving in capable, caring hands? That’s a gift.

It reminded me why I’m so passionate about creating spaces for women to build meaningful connections and support each other’s dreams. Whether it’s through this podcast, The Brighter Side Society online community, or Like Minded Charleston’s in-person gatherings, I believe we rise by lifting each other.

Alyssa’s success is my success. Her leadership elevates the entire Charleston culinary community. Her vision for the festival’s future honors its past while creating new opportunities for the next generation.

That’s the ripple effect of dreaming big and staying committed to your values.

YOUR TAKEAWAY: MANIFEST WITH ACTION

If there’s one thing I want you to take from this episode and this blog post, it’s this: write down your dream, then do something about it.

Alyssa didn’t just hope she’d end up working for Charleston Wine and Food someday. She wrote it down. She reached out. She made her case. She showed up with intention and took bold action.

What’s the dream client or dream job you’ve been thinking about? What’s the organization or brand you’d love to work with? What’s the vision living in your heart that you haven’t fully pursued yet?

Write it down. Then ask yourself: what’s one bold action I can take this week to move toward that dream?

Maybe it’s reaching out to someone for a coffee meeting. Maybe it’s applying for that position. Maybe it’s starting the business or launching the project or making the pivot you’ve been considering.

Whatever it is, take the action. Because dreams combined with action? That’s when magic really happens.

LISTEN TO THE FULL EPISODE

This blog post only scratches the surface of our conversation. In the full episode, Alyssa and I dive deeper into:

• Her journey from PR entrepreneur to nonprofit leader
• The challenges and rewards of values-driven leadership
• Behind-the-scenes festival stories and planning insights
• The future of Charleston’s culinary scene
• How the festival creates economic impact year-round
• What it’s like to step into a leadership role for an established brand

Listen to Episode 34 wherever you get your podcasts, and don’t forget to subscribe so you never miss an episode of Never Stop Dreaming Biggie!

Get Your Charleston Wine and Food Festival Tickets:
Head to charlestonwineandfood.com this Thursday, October 23rd at 11 AM sharp. Browse the schedule now and use the favoriting feature to mark the events you don’t want to miss!

Until next week, keep dreaming big and taking bold action.

With love and gratitude,
Angel

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CONNECT WITH ME:
🎙 Podcast: Never Stop Dreaming Biggie
📱 Instagram: @neverstopdreamingbiggie and @angelpholmes
🌐 Website: sipindipity.com
📧 Email: angel@neverstopdreamingbiggie.com
🌴 The Holmestead Bar & Retreat
👩‍💼 The Brighter Side Society

CONNECT WITH CHARLESTON WINE AND FOOD:
🍷 Website: charlestonwineandfood.com
📱 Instagram: @charlestonfoodandwine
🎟️ Tickets: Launch Thursday, October 23, 2025 at 11 AM