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Summary
In this special birthday episode "Turning 52 and Still Dreaming BIGGIE: Birthday Cocktails with the Director of No Fun," Angel Holmes celebrates turning 52 with her husband Brian behind the bar at The Holmestead, testing cocktail recipes for their upcoming bar venture. This unfiltered, authentic episode captures the real entrepreneurial journey as they mix "The George Bush" (Irish whiskey and ginger ale) and "The Harry and Maude" martini while sharing stories about their advisory team and Charleston connections. From Angel's multiple wardrobe changes featuring her Pig Slayer shirt and tribute to Julian Smith, to Brian's technical bartending skills and concerns about sound quality, this episode showcases the messy, fun reality of building dreams with your spouse. The couple reveals their custom bar setup, discusses their BevCon history, and introduces their growing team of advisors including Jayce McConnell, High Wire Distilling's Ann and Scott, Gary Crunkleton, Chris Finley, and Roy Milner. Angel reflects on authenticity, aging gracefully, and honoring the people who inspire your journey, while proving that entrepreneurial dreams get messier—and more meaningful—when you're building them with the people you love.
FOLLOW US:
Instagram: @neverstopdreamingbiggie and @angelpholmes
Learn more at https://neverstopdreamingbiggie.com
Follow The Holmestead Bar: @theholmesteadbar
The Brighter Side Society: https://sipindipity.com/brighter-side
Takeaways
Chapters
00:00 Birthday Introduction and Technical Challenges
01:45 Welcome to Never Stop Dreaming BIGGIE - Birthday Edition
05:30 The Homestead Bar History and Setup
08:45 Brian Makes "The George Bush" Cocktail
15:20 Angel's Wardrobe Changes and Stories
18:30 Advisory Team Introductions
22:15 Angel's "Harry and Maude" Martini
28:00 Julian Smith Tribute and Co-Pilot Spirit
31:30 Bar Vision and Menu Planning
33:18 Tour of The Holmestead Bar Setup
35:45 Birthday Celebration and Closing
Have ideas, questions, or comments? Email us at [email protected].
Episode Description for Podcast Platforms:
In Episode 21 of Never Stop Dreaming Biggie, Angel Holmes sits down with Gary Crunkleton, the heart-driven entrepreneur behind the legendary Crunkleton bars in Chapel Hill, Charlotte, and Raleigh. This inspiring conversation reveals how leading with authenticity and vulnerability creates both meaningful connections and sustainable business success.
Gary shares his incredible journey from Navy service to becoming one of North Carolina's most beloved bar owners, building his empire not through traditional profit-first thinking, but by treating employees like family and creating spaces where everyone feels welcome. He opens up about choosing to pay above-market wages and provide health insurance long before it became trendy—and how this "backwards" approach actually led to greater profitability.
From losing his father and sharing that vulnerability with a stranger to creating the "two-drink business model" that built his Chapel Hill empire, Gary demonstrates how authentic connections drive real business results. He reveals why creating the right atmosphere brings out the best in people and shares insights from his upcoming book "Authenticity in the Bar."
The "H" in Biggie stands for Heart—and Gary's story perfectly embodies leading with heart in everything you do.
Key Takeaways:
Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected]
Learn More:
🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
🍸 The Crunkleton - Chapel Hill, Charlotte & Raleigh
Summary
In this solo episode "From Boring to Biggie: How to Live a More Interesting Life," Angel Holmes tackles the universal struggle of feeling stuck in routine and reveals her proven strategies for breaking out of your comfort zone to create a more fulfilling, interesting life. Sporting her new Vegas co-op hat (despite never having been to Vegas!), Angel shares personal stories about pushing through the "I don't want to go" feeling and how showing up anyway has transformed her life and business. From taking different routes to work to saying yes to the right events while learning to say no to energy-draining commitments, Angel provides practical steps for diversifying your experiences and building meaningful community connections. She opens up about everything from her Jim Gaffigan comedy show insights to the importance of being around people who "get it" in your entrepreneurial journey. Angel reveals why travel, new experiences, and getting out of your bubble are essential for personal growth, and how community building through organizations like The Brighter Side Society and Like Minded Charleston has been game-changing for ambitious women. This episode is perfect for anyone feeling isolated in their entrepreneurial journey, stuck in the same routines, or ready to start living their BIGGIE life with more purpose, connection, and joy.
FOLLOW US:
Instagram: @neverstopdreamingbiggie @thebrightersidesociety and @angelpholmes
Learn more at https://neverstopdreamingbiggie.com
Follow us at https://www.instagram.com/neverstopdreamingbiggie/
Join The Brighter Side Society at https://sipindipity.com/brighter-side
Learn more about The Holmestead Bar at https://neverstopdreamingbiggie.com/the-holmestead-bar-retreat
Follow Becky Connelly at Non Disclosure Apparel at https://www.instagram.com/nondisclosureapparel/ and shop at https://ndapparel.com/
Follow Co-Op at https://www.instagram.com/coopsullivansuncensored/
Takeaways
Chapters
00:00 Introduction and Vegas Hat Story
02:30 The Vegas Co-op and Never Being There
05:15 Birthday Month and What Makes Someone Interesting
08:45 Adam and Eve Community Story
12:20 Breaking Out of Routines and Comfort Zones
18:30 The Jim Gaffigan "I Don't Want to Go" Insight
23:10 Pushing Through and Showing Up Anyway
28:45 Saying Yes to the Right Things
32:00 Community Building and The Brighter Side Society
36:15 Travel and New Experiences
40:30 Closing Thoughts on Living Your BIGGIE Life
Have ideas, questions, or comments? Email us at [email protected].
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
Chapters
00:00 Welcome from Grenada - First Impressions
02:30 Grenada Pros and Cons Discussion
07:39 Traveling to Bequia via Multiple Transportation Methods
09:15 Bequia Beauty and Sailing Culture
12:45 Finding Potential Locations and Meeting Locals
15:15 Barbados Reality Check from the Hotel Room
17:30 Why Barbados Isn't Their Scene
19:45 Overall Trip Reflections and Next Steps
Have ideas, questions, or comments? Email us at [email protected].
Summary
In Episode 18 of Never Stop Dreaming BIGGIE, I'm diving deep into the one thing that determines everything in your business and relationships—your energy. If you've ever wondered why some people naturally attract opportunities while others struggle to connect, or how to maintain positive momentum even during challenging times, this solo episode reveals the game-changing mindset shift that transforms everything.
I'm sharing my personal journey from being someone who craved attention to learning the art of putting the spotlight on others, plus the daily practices that keep my energy aligned with my biggest dreams. I open up about navigating difficult seasons, the morning routine that sets me up for success, and why stepping outside yourself to observe your own energy might be the most important skill you never learned.
This episode is perfect for ambitious women who feel isolated in their entrepreneurial journey, struggle with energy drains from negative people, or want to build the kind of magnetic presence that attracts the right opportunities and relationships. This is the "E" in BIGGIE—Elevate—raise your standards for yourself and create the energy that naturally draws success to you.
@neverstopdreamingbiggie and @angelpholmes
Learn More
🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
📧 Email: [email protected]
🌐 Website: sipindipity.com
Takeaways
Chapters
00:00 Introduction - Birthday Month & Caribbean Energy
02:15 The Energy You Give Off Determines Everything
05:30 The Exercise: Step Outside Yourself and Observe
08:45 Angel's Morning Energy Routine for Success
12:20 The Spotlight Principle: Making It About Others
15:30 When Your Energy Struggles: Navigating Hard Times
18:15 Hot Yoga & Community Energy at The Works
22:00 Dealing with Energy Drains and Negative People
25:45 Why Doing What You Love Boosts Natural Energy
28:30 Breaking Free from Self-Absorption Culture
32:15 Building Two-Way Relationships vs One-Sided Conversations
35:00 Angel's Inner Circle: The Power of Authentic Friendship
38:45 The WAIT Technique: Transform Your Conversations
41:30 Action Steps for Better Energy Management
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
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 [email protected].
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.
@neverstopdreamingbiggie and @angelpholmes
Learn More
🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
📧 Email: [email protected]
🌐 Website: sipindipity.com
Takeaways
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.
@neverstopdreamingbiggie and @angelpholmes
Learn More
🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
📧 Email: [email protected]
🌐 Website: sipindipity.com
Takeaways
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.
@thebrightersidesociety and @angelpholmes
Learn More
👩💼 The Brighter Side Society
📧 Email: [email protected]
🌐 Website: sipindipity.com
Takeaways
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.
Instagram@neverstopdreamingbiggie and @angelpholmes
Learn More🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
📖 Unstoppable Growth Program
📸 Follow on Instagram
📬 Email: [email protected]
Takeaways00:00 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
From the publisher's feed