Summary

In this special travel episode "Live from the Caribbean: Island Hopping Adventure," Angel and Brian Holmes take you on their real-time research journey through Grenada, Bequia, and Barbados as they scout locations for The Holmestead Bar & Retreat. From navigating treacherous mountain roads in Grenada to falling in love with the sailing culture of Bequia, and experiencing the party atmosphere of Barbados, they share unfiltered insights about each island's potential. The couple discusses the realities of seasonal tourism, infrastructure challenges, and what it really takes to build an international business. Angel reveals her vision for each location while Brian provides his practical "Director of No Fun" perspective on the logistics and financials. They share honest pros and cons, from Grenada's amazing people and stunning scenery to Bequia's perfect sailing community and Barbados's party scene. Their adventure includes everything from rum punches at 8 AM to hiring local drivers as tour guides, showcasing both the excitement and exhaustion of location scouting. This episode proves that turning dreams into reality requires boots-on-the-ground research, cultural sensitivity, and the flexibility to adapt when plans don't go as expected.

FOLLOW US:

Instagram: @neverstopdreamingbiggie and @angelpholmes

Learn more at https://neverstopdreamingbiggie.com/spirits

Follow us at https://www.instagram.com/neverstopdreamingbiggie/

Learn more about The Holmestead Bar at https://neverstopdreamingbiggie.com/the-holmestead-bar-retreat

Places we loved during our stay:

True Blue Bay Resort: https://www.truebluebay.com/

Bequia Plantation Hotel: https://bequiaplantationhotel.com/

The Cocktail Lab Bequia: https://www.instagram.com/thecocktaillabbequia/?hl=en

Frangipani: https://frangipanibequia.com/

Sweetfield Manor: https://sweetfieldmanor.com/

Takeaways

• Research seasonal tourism patterns before committing to international business locations
• Build genuine relationships with locals when scouting new markets - they provide invaluable insights
• Consider transportation logistics for both operations and customer accessibility
• Grenada offers amazing people and scenery but challenging roads and short season
• Bequia provides perfect sailing culture and community but limited year-round tourism
• Barbados has great infrastructure and energy but doesn't match their intimate bar vision
• Factor infrastructure challenges like narrow roads into business planning and vehicle choices
• Document your journey for both content creation and future business planning
• Trust your instincts while remaining open to unexpected discoveries and opportunities
• Plan for multiple transportation scenarios when international travel is involved
• Prioritize becoming an asset to the community rather than just extracting value
• Off-season visits reveal the true local culture and business sustainability challenges

Chapters

00:00 Welcome from Grenada...

Summary

In this deeply personal episode "BIGGIE Dreams, Bigger Legacy," Angel Holmes sits down with her dad, Ernie Passailaigue, the entrepreneur and public servant who transformed Charleston into the thriving destination we know today. When Angel mentions her dad's name and people respond "who?" it breaks her heart—because this is the man who has a connector named after him, helped build the Cooper River Bridge, created the Charleston RiverDogs (originally the Rainbows!), and launched the South Carolina State Lottery from absolute scratch.

From his days as a CPA to owning Charleston's baseball team to serving in the State Senate for over a decade, Ernie shares the untold stories behind Charleston's biggest transformations. This father-daughter conversation reveals what real public service looks like, how to start major ventures with nothing but vision, and why his greatest accomplishment isn't any bridge or business—it's his family of seven kids and 14 grandchildren. Their story demonstrates how dreaming BIGGIE while staying grounded in service creates lasting legacies that impact generations.

FOLLOW US:

Instagram: @neverstopdreamingbiggie and @angelpholmes

Learn more at https://neverstopdreamingbiggie.com

The Brighter Side Society: https://sipindipity.com/brighter-side

The Holmestead Bar + Retreat: @theholmesteadbar

Takeaways

• True public service means representing everyone in your community, regardless of party affiliation
• Starting major ventures from zero requires vision, persistence, and strategic relationship building
• Fighting for your community's fair share of resources takes patience and calculated persistence
• Family relationships should be prioritized as your ultimate measure of entrepreneurial success
• Documenting your journey helps future generations understand how foundations were built
• Creating memorable community experiences builds lasting traditions and connections
• Building coalitions across political lines requires focusing on shared values and common goals
• Honoring those who came before while building for those who come after creates true legacy
• Waking up each day with gratitude transforms how you approach business and life challenges
• The fragility of life reminds us to appreciate every opportunity to make meaningful impact
• Real leadership involves listening to constituents and taking detailed notes on their actual needs

Chapters

00:00 Introduction - Why This Episode Matters Most

02:53 Meet Big Ern - Charleston's Unsung Hero

05:11 From Porter Military Academy to USC and The Citadel

07:01 CPA Days and Building a Practice in Charlotte and Charleston

08:03 Charleston Royals/Rainbows Baseball Team Ownership Story

15:19 Running for State Senate - The Political Journey and Philosophy

20:04 Major Accomplishments - Bridges, Lottery, and Legislative Wins

25:14 The South Carolina State Lottery Launch from Scratch

29:05 Biggest Dreams Come True - Family as Greatest Legacy

31:34 Role Models and Life Influences That Shaped His Journey

35:53 Future Dreams, Daily Gratitude, and Final Thoughts

Have ideas, questions, or comments? Email us at angel@neverstopdreamingbiggie.com.