Summary

In this incredibly special Episode 34, Angel Holmes sits down with Alyssa Smith, Executive Director of the Charleston Wine and Food Festival, for a full-circle conversation celebrating 20 years of Charleston's premier culinary event. This episode is a masterclass in manifestation, values-driven leadership, and community impact as the festival's founder and current director share their unique perspectives on building a legacy brand. Alyssa reveals how she manifested her dream job by writing "Charleston Wine and Food" on a vision board, then boldly reaching out for a coffee meeting with the marketing director—proving that vision boards work when combined with action. Angel shares vulnerable stories from the festival's early days running operations from her house with a team of volunteers, while Alyssa discusses how she's expanded the festival's mission to serve 1,200 high school students across Charleston and Dorchester counties with culinary education, mentorships, and externships alongside James Beard award-winning chefs. They discuss what makes Charleston Wine and Food different from other festivals: year-round community impact, authentic local storytelling, and a commitment to giving back that extends far beyond the five-day event. With tickets launching this week and the 20th anniversary celebration approaching in March 2026, this episode offers insider tips for festival-goers, inspiration for aspiring entrepreneurs, and proof that dreams really do become reality when you stay true to your values and your community.

The "B" in Biggie stands for Believe—and this episode is all about believing in your vision even when it seems impossible, then taking bold action to make it happen.

Key Takeaways:

• Write your dream job or dream client on a vision board, then take bold action to pursue it
• Don't be afraid to reach out to people you admire—coffee meetings change lives and careers
• Values-driven leadership attracts aligned opportunities and creates authentic connections
• Charleston Wine and Food now impacts 1,200 students through culinary education programs in 10 schools
• High school students learn from James Beard award-winning chefs and participate in festival externships
• Community-focused businesses create ripple effects far beyond their core mission
• Most events don't give back year-round—Charleston Wine and Food supports scholarships, mentorships, and disaster relief
• Festival tickets (especially seated restaurant experiences) sell out quickly—be online at 11 AM launch time
• Use the new "favoriting" feature on charlestonwineandfood.com to plan your perfect festival weekend
• Opening Night and the Finale (featuring next-wave Charleston talent) are must-attend 20th anniversary events
• Local roots and authentic storytelling are what make Charleston's culinary scene nationally recognized
• The festival is a microcosm of career opportunities: culinary, events, marketing, hospitality, design, and operations
• Supporting through tickets, volunteering, or donations funds year-round educational initiatives
• 20 years of success proves that community-focused dreams become reality with persistence and heart

Connect with Us:

🎙 @neverstopdreamingbiggie

📱 @angelpholmes

🌐 sipindipity.com

📧 [email protected]

https://sipindipity.com/neverstopdreamingbiggiemaster

Learn More:

🍷 Charleston Wine and Food Festival: charlestonwineandfood.com (Tickets launch Thursday, October 23 at 11 AM!) and follow on https://www.instagram.com/chswineandfood/

🌴 The Holmestead Bar & Retreat (Special appearance at Charleston Wine and Food 2026!)

👩‍💼 The Brighter Side Society