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.

Summary

In Episode 16 of Never Stop Dreaming BIGGIE, I'm tackling the biggest struggle facing multi-passionate women entrepreneurs—feeling scattered and overwhelmed by traditional productivity advice that just doesn't work for creative minds like ours. If you're tired of having 27 browser tabs open, waking up with 15 business ideas before 9 AM, and feeling like you're the only one who can't "just focus on one thing," this episode is your validation and solution.

I'm sharing the organization secrets that helped me manage 20,000+ person festivals while running multiple businesses, revealing why energy-based planning beats time management and how to create systems that work WITH your multi-passionate brain, not against it. Plus, I'm joined by the incredible Jen El-Haddad from Jennifer Mary Photography, who shares her inspiring journey from corporate layoffs to building a thriving branding and wedding photography business in Charleston.

Jen opens up about her "come-to-Jesus moment" at a church conference that changed everything, her approach to authentic community building through events like Stretch and Mingle, and why professional photography should be your second business investment. This is the "G" in BIGGIE—Grow—through challenges by creating systems that honor how your brain works and building community that supports your biggest dreams.

Instagram

@neverstopdreamingbiggie and @angelpholmes

Learn More

🌴 The Holmestead Bar & Retreat

👩‍💼 The Brighter Side Society

📧 Email: angel@neverstopdreamingbiggie.com

🌐 Website: sipindipity.com

Takeaways

• Understand why you're not broken—you're just a multi-passionate women entrepreneur
• Learn energy-based planning strategies that work for ambitious women
• Discover business organization systems for managing multiple projects
• Master the profit priority matrix concept for focusing on what matters most
• Explore Jen's inspiring corporate to photography entrepreneur journey
• Recognize the importance of professional branding photography for business success
• Build authentic community networks that grow your business organically
• Apply collaboration over competition principles in women's entrepreneurship
• Create accountability partnerships that keep multi-passionate women on track
• Transform scattered energy into laser-focused business action through proven systems

Chapters

00:00 Introduction - The 27 Browser Tab Reality

02:30 The "G" in BIGGIE: Growing Through Challenges

04:45 Why Multi-Passionate Women Feel Scattered

10:15 Festival Organization Secrets for Business Systems

15:30 Energy-Based Planning vs Time Management

20:25 Guest Introduction: Jennifer Mary Photography

22:10 Jen's Corporate to Photography Journey

28:15 The Power of Authentic Community Building

34:45 Professional Photography for Business Branding

40:30 Collaboration Over Competition Philosophy

45:15 The Brighter Side Society and Accountability

Summary

In Episode 15 of Never Stop Dreaming BIGGIE, the Holmes boys finally take the mic! Join me for this special live recording with my husband Brian (the famous "Director of No Fun") and son Chase as we answer real questions from The Brighter Side Society community. This unfiltered family Q&A gives you exclusive access to our Caribbean bar planning process, business strategies, and authentic entrepreneurial journey.

You'll get the inside scoop on our upcoming island-hopping trip to scout locations for The Homestead Bar & Retreat in Bequia, Barbados, or Grenada. Brian shares why we're leaving the hurricane zone, what we're looking for in the perfect sailing community, and our timeline for spending 6-9 months per year running our disaster relief bar. Plus, Chase undergoes his hilarious "job interview" for entertainment director (complete with toilet cleaning duties) while we break down The Brighter Side Society membership benefits and upcoming price changes.

Whether you're curious about international business ventures, struggling with imposter syndrome as a female entrepreneur, or wondering how family support systems fuel big dreams, this episode delivers both entertainment and practical insights. This is the "B" in BIGGIE—Believe—that your wildest dreams are meant for you, especially when you have the right people cheering you on.

Instagram

@neverstopdreamingbiggie and @angelpholmes

Learn More

🌴 The Holmestead Bar & Retreat

👩‍💼 The Brighter Side Society

📧 Email: angel@neverstopdreamingbiggie.com

🌐 Website: sipindipity.com

Takeaways

• Discover the three Caribbean islands being considered for The Homestead Bar & Retreat
• Learn complete details about The Brighter Side Society membership ($75/month)
• Master strategies for overcoming imposter syndrome through community support
• Understand how family business dynamics strengthen entrepreneurial ventures
• Explore the disaster relief mission driving The Homestead Bar concept
• Navigate international business planning and island selection criteria
• Recognize the importance of sailing communities for bar location success
• Apply manifestation techniques through faith and consistent visualization
• Build supportive partnerships that fuel rather than limit your dreams
• Create authentic family business content that connects with audiences

Chapters

00:00 Live Setup & Caribbean Bar Introduction

02:30 Meet Brian & Chase: The Holmes Boys

05:45 Island Hopping Plans: Bequia, Barbados, Grenada

08:20 Chase's Entertainment Director Job Interview

12:15 The Brighter Side Society Membership Breakdown

18:30 Homestead Bar Timeline & Investment Details

22:10 Overcoming Imposter Syndrome as Female Entrepreneurs

28:45 Family Business Dynamics & Partner Support

32:20 Community Building & Women Supporting Women

35:50 Caribbean Trip Planning & Attorney Guidance

38:15 Closing Thoughts & Community Appreciation

Summary

In Episode 14 of Never Stop Dreaming BIGGIE, I'm getting vulnerable about my entrepreneurial journey from founding the Charleston Wine & Food Festival to making the difficult decision to close Like Minded Charleston and focus on building The Brighter Side Society globally. This solo episode explores business pivot strategies, community building secrets, and how faith-based decision making led to creating multiple successful ventures from scratch.

You'll hear the real story behind building events with billion-dollar economic impacts, losing everything during COVID, and why sometimes you have to shut successful doors to open bigger dreams. I share my "superpowers" of community building and organization, how prayer guided my pivot decisions, and the vision for taking The Brighter Side Society worldwide while building The Holmestead Bar & Retreat in the Caribbean.

Whether you're a female entrepreneur feeling pulled in multiple directions, considering a major business pivot, or ready to turn overwhelming dreams into organized action, this episode offers both vulnerable storytelling and practical business strategies. This is the "B" in BIGGIE—Believe—in your bigger vision even when it means closing chapters you love.

Instagram

@thebrightersidesociety and @angelpholmes

Learn More

👩‍💼 The Brighter Side Society

📧 Email: angel@neverstopdreamingbiggie.com

🌐 Website: sipindipity.com

Takeaways

• Discover how to identify your core business superpowers and lean into them
• Learn when to close profitable ventures to pursue your bigger purpose
• Master community building by focusing on connection before monetization
• Create systems and organization to turn overwhelming dreams into action
• Navigate major business pivots with faith and strategic planning
• Transform COVID setbacks into comeback stories through purpose-driven decisions
• Scale from local impact to global reach through authentic storytelling
• Balance entrepreneurial creativity with practical implementation
• Recognize when you're spreading yourself too thin across multiple ventures
• Use prayer and reflection to guide life-changing business decisions

Chapters

00:00 Welcome & Life Changes Announcement

02:15 Angel's Career Background & Journalism Roots

05:30 World Cup Internship That Changed Everything

08:45 The Birth of Charleston Wine & Food Festival

15:20 Building a 6-Figure PR Business Empire

22:10 COVID Setbacks & Rock Bottom Moments

28:35 Reading "Purpose Driven Life" & Finding Direction

35:40 Creating Like Minded Charleston Community

42:15 The Brighter Side Society Vision Goes Global

48:30 Making the Difficult Decision to Close Like Minded

52:20 Future Plans: The Holmestead & Caribbean Dreams

56:45 How to Join The Brighter Side Society

59:30 Faith, Purpose & Next Steps

In Episode 13 of Never Stop Dreaming BIGGIE, I’m joined by two powerhouse mentors in the world of Christian entrepreneurship and kingdom leadership—Tim and Rebecca Lindsay, founders of the Unstoppable Growth program. Together, we explore how faith can fuel your business, how spiritual gifts reveal your true calling, and how sharing your story creates breakthrough.

You’ll hear how church planting led to coaching over 500 entrepreneurs, how their bar church in Zurich transformed a city’s club culture, and how their influence helped inspire The Brighter Side Society and my upcoming vision for The Holmestead Bar & Retreat in the Caribbean.

Whether you’re launching a purpose-driven business, craving spiritual growth, or seeking clarity on your calling, this episode is packed with practical wisdom and divine inspiration. This is the "I" in BIGGIE—Impact—in full motion.

@neverstopdreamingbiggie and @angelpholmes

🌴 The Holmestead Bar & Retreat

👩‍💼 The Brighter Side Society

📖 Unstoppable Growth Program

📸 Follow on Instagram

📬 Email: angel@neverstopdreamingbiggie.com

• Discover how Christian entrepreneurs turn vision into purpose-driven reality
• Learn the key elements of the Unstoppable Growth framework
• Understand the importance of spiritual gifts in leadership and business
• Hear the power of vulnerability and storytelling in faith-based transformation
• Explore the intersection of faith, business, and community building
• See how church planting and kingdom business strategies align
• Be inspired to build your own God-led business or movement
• Understand how to navigate closed doors and discern divine direction
• Get practical tools for Christian leadership and impact
• See why your most powerful decades may still be ahead

00:00 Introduction to Christian Entrepreneurship

02:15 Meet Tim & Rebecca Lindsay

05:00 What is Unstoppable Growth?

08:10 Why Sharing Your Story is a Spiritual Breakthrough

12:30 Planting Churches with a Business Mindset

16:45 How a Bar Became a Church in Zurich

21:00 The Vision Behind The Holmestead Bar & Retreat

26:30 Faith-Led Leadership Tools for Impact

30:00 Helping Young Leaders and College Students

32:00 Big Impact in Your 60s and 70s

34:30 Closing Prayer & Final Thoughts

Summary

In Episode 11 of Never Stop Dreaming BIGGIE, I'm diving deep into the transformative power of manifestation and how it connects with faith. I share my personal journey of visualizing The Holmestead Bar & Retreat before it exists, and the incredible Brandon Lake manifestation story that proved the power of belief! Whether you're skeptical about manifestation techniques or looking to strengthen your practice, this episode offers practical tools for training your mind to overcome negative self-talk and create your dream life. Learn how to use breathwork, visualization, and faith-based practices to manifest your BIGGIE dreams into reality. The B in BIGGIE stands for Believe - and this episode shows you exactly how to believe bigger!

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

Learn more about Taylor Kornegay at https://taylorkornegay.com/

To get with Rebekah Hogan, visit https://rebekahhogan.com/ and https://cart.rebekahhogan.com/kit

Takeaways

• Discover how manifestation connects with faith and spiritual practice
• Learn practical visualization techniques to make your dreams tangible
• Understand how to overcome negative self-talk that limits your potential
• See how breathing exercises enhance your manifestation practice
• Hear Angel's real-life manifestation success stories
• Learn the importance of releasing expectations about how manifestation works
• Discover why Jamie Kern Lima's book "Worthy" is a must-read for manifestation
• Understand how setbacks can be protection for something better
• Learn why making your dreams public accelerates manifestation
• Get introduced to powerful manifestation tools from Rebekah Hogan

Chapters

00:00 Introduction to Manifestation & Faith

03:25 The Power of Controlling Your Mind

08:40 Visualizing The Holmestead Bar & Retreat

12:15 The Brandon Lake Manifestation Story

16:30 Resources for Your Manifestation Journey

18:40 Preview of Next Week's Episode

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