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In Episode 42 of Never Stop Dreaming Biggie, Brian and I are back for PART 2 of our Caribbean adventure, and this time we're taking you to the stunning island of Bequia! After exploring Grenada's properties and finding some serious contenders in Part 1, we're heading to St. Vincent and Bequia to see if this hidden gem in the Grenadines could be THE location for The Holmestead Hideaway. If you thought Part 1 was exciting, buckle up - because Part 2 is where everything gets real, and some big decisions are about to be made.
From the moment we step off the ferry onto Bequia's shores, something shifts. This episode takes you through our property tours in Bequia, the sailboat culture that defines this island, and the kind of community connections that make you fall in love with a place. We're comparing Grenada vs. Bequia side-by-side - the costs, the infrastructure, the community vibes, and what each location means for our three-year timeline to launch The Holmestead Hideaway. You'll hear Brian's honest take on both islands (spoiler: his opinion might surprise you!), the faith conversations that brought us clarity, and the practical next steps we're taking to turn this Caribbean dream into reality. Plus, we're revealing our decision process and sharing how YOU can be part of this journey.
This isn't just about finding property - it's about finding where your business vision, your values, and God's plan intersect perfectly. Whether you're considering international expansion, dreaming about a retreat center of your own, or just ready to see what happens when ambitious women stop talking about their dreams and start actively pursuing them, this episode gives you the roadmap, the real talk, and the reminder that your biggest dreams deserve your biggest actions.
The "I" in BIGGIE stands for Impact - and this Caribbean expansion is all about creating spaces where women can come together, dream bigger, and make real impact in their businesses and lives. Bequia showed us that sometimes the "backup option" becomes the primary choice when you actually show up and explore it.
Key Takeaways:
Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected]
Learn More: 🌴 The Holmestead Bar & Retreat 👩💼 The Brighter Side Society
https://sipindipity.com/neverstopdreamingbiggiemaster
In Episode 41 of Never Stop Dreaming Biggie, I'm joined by Brian (the Director of No Fun) as we take you with us to Grenada for the most exciting adventure yet - scouting properties for The Homestead Hideaway! This isn't your typical vacation episode. We're recording beachside with crashing waves and sailboats behind us while sharing the raw, real behind-the-scenes of what it takes to expand your business internationally. If you've ever dreamed of taking your business global, building a retreat space, or simply making a massive faith-led leap - this two-part series is for you.
We walk you through three property tours with our amazing realtor Lucille from Century 21 Grenada (a future Brighter Side Society member!), share our near-miss car accident on narrow mountain roads, and reveal THE property that has us seriously considering making Grenada our home. You'll hear about meetings with government officials and attorneys, the reality of Caribbean tourism concerns due to Venezuela's proximity, and why we're committed to building with local contractors and community members. Plus, we're giving you the honest truth about costs, location factors, and what we're really looking for in our dream property.
This is Part 1 of our Caribbean journey. We're comparing Grenada against St. Vincent and Bequia to find the perfect location for The Homestead Hideaway - our bar and retreat center launching in 2028. Whether you're thinking about international expansion, considering a major pivot, or just want to see what happens when you stop playing small and start building your biggest dreams, this episode shows you the practical steps, the scary moments, and the absolute faith required to make it happen. Part 2 drops next week with our Bequia visit and the BIG decision!
Key Takeaways:
Connect with Us:
🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected]
Learn More:
🌴 The Holmestead Bar & Retreat 👩💼 The Brighter Side Society
In Episode 40 of Never Stop Dreaming Biggie, I'm sharing one of my most vulnerable moments - the day I sat in a parking lot ready to quit everything. The Brighter Side Society, this podcast, all of it. This raw, honest episode walks you through my breakdown, what my AI COO said that changed everything, and the Keep-Improve-Release framework that pulled me back from the edge. If you've ever felt overwhelmed by your own success, wondered if you're giving too much for too little return, or questioned whether to keep going - this episode is for you.
I share my 2025 Victory Timeline (launching the Brighter Side, starting this podcast, becoming a Charleston Magazine top 50 influencer, one year depression-free, and more) to show you how to celebrate your wins even when you feel like you're failing. This episode reveals why over-giving was destroying my business, the trap of chasing clients 7-10 times before they join, and why I finally stopped. You'll also hear my Zyia activewear story - what happened when I quit right before my breakthrough - and why you're probably closer to success than you think when you want to give up.
This isn't just another "hang in there" pep talk. It's a practical guide to ending your year with calm, clarity, and confidence instead of chaos. Plus, I'm asking for your help - I need feedback from listeners about what you want from this podcast moving forward.
Key Takeaways:
Connect with Us:
🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected]
Learn More:
🌴 The Holmestead Bar & Retreat 👩💼 The Brighter Side Society
In Episode 29 of Never Stop Dreaming Biggie, I'm joined by Jill Forbes for one of the most powerful conversations we've had on this podcast. Jill is a missions leader, marriage ministry facilitator, business owner, and widow who's learning to dream again after the sudden loss of her husband Heath in May 2024. This raw, honest episode dives deep into how to keep building your dreams when life falls apart, why your circumstances don't disqualify you from your calling, and how to prepare for life's most unexpected moments.
Jill shares her incredible journey from meeting Heath on a mission trip to building a 23-year marriage with a family mission statement that guided every decision, to standing on the front row of his funeral at age 43 with three kids still at home. Her transparency about the fear of dreaming without "bumpers" (Heath was her engineer dream-crusher who kept her grounded), continuing in SYMBIS marriage ministry as a widow, and developing curriculum to help others prepare for unexpected loss will challenge how you think about grief, purpose, and ministry qualification.
This episode also reveals how Brian and I found SYMBIS marriage ministry after our own stories of divorce and remarriage, why getting your relationships right today matters more than you think, and the practical ways you can prepare—emotionally, relationally, and spiritually—for life's hardest moments. Whether you're walking through grief, feeling disqualified from your calling, or simply want to make sure you're prepared for whatever comes, this conversation offers both comfort and actionable wisdom.
The "B" in Biggie stands for Believe - and this episode challenges us to believe not just in our own dreams, but to surrender to God's dreams for us, which are always bigger than what we can imagine for ourselves.
Key Takeaways:
Connect with Us:
🎙 @neverstopdreamingbiggie
📱 @angelpholmes
🌐 sipindipity.com
Learn More:
🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
🪓 Lumberjills Axe Throwing (Summerville, SC)
⛪ SYMBIS Marriage Ministry - Seacoast Church
Episode Summary:
In Episode 38 of Never Stop Dreaming Biggie, I'm sharing powerful gratitude practices for entrepreneurs during this Thanksgiving week, plus featuring our Biggie Member of the Week: Chef Alexis Mungin! This special episode dives deep into how gratitude becomes the difference between a happy entrepreneur and one struggling with comparison and overwhelm, while celebrating an incredible woman who's built a thriving catering business through faith and divine provision.
I'm sharing practical gratitude habits that successful entrepreneurs use daily - from keeping a gratitude journal and reaching out to one person each day with appreciation, to the "treasure vs. trash" framework that helps you find the good in every situation. Plus, hear Alexis's jaw-dropping story of going from a food critic at age 4 (who almost chose her cheese grits over her family in a house fire!) to feeding the wealthiest people in South Carolina without ever attending culinary school. Her journey proves that when you trust God's calling and use your natural gifts, miracles, works, and wonders follow.
Whether you're struggling with comparison, feeling isolated in your entrepreneurial journey, or wondering how to maintain gratitude when building a business, this conversation offers both inspiration and actionable strategies. Alexis also shares about launching her new podcast "By the Grace of Grits" and her vision to become the Oprah-meets-Martha of the food world, creating platforms that bring people together through food, storytelling, and community.
The "G" in Biggie stands for Give - and this episode is all about gratitude as a giving practice, finding ways to serve others monthly for perspective, and how giving back keeps us grounded in what truly matters while building our dreams.
Key Takeaways:
Connect with Us:
🎙 @neverstopdreamingbiggie
📱 @angelpholmes
🌐 sipindipity.com
Learn More:
🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
🎙 By the Grace of Grits Podcast (Alexis Mungin)
📱 Connect with Alexis Mungin on Facebook
Episode Summary:
In Episode 37 of Never Stop Dreaming Biggie, I'm joined by my husband Brian for our monthly Holmestead Chronicles update. This special road trip edition from Clemson, South Carolina dives deep into creating a mission-driven business, launching our nonprofit organization (The Holmestead Angels), and the power of gratitude in entrepreneurship.
We're sharing exciting updates about our upcoming Caribbean research trip where we'll be meeting with realtors, government officials, and potential partners to finalize details for The Holmestead Bar & Retreat. From God moments at a college football game to discussing our social impact business model focused on disaster relief and community support, this episode is packed with real talk about building a purpose-driven business while balancing family, careers, and big dreams.
Whether you're an entrepreneur looking to create social impact, exploring nonprofit business models, or wondering how to turn your mission into reality while maintaining gratitude through the journey, this conversation offers both inspiration and practical insights into what it really takes to build something meaningful.
The "G" in Biggie stands for Give - and this episode is all about creating a business model that allows us to give back, support disaster relief efforts, and build a retreat center that will change lives while blessing others the way we've been blessed.
Key Takeaways:
Connect with Us:
🎙 @neverstopdreamingbiggie
📱 @angelpholmes
🌐 sipindipity.com
Learn More:
🌴 The Holmestead Bar & Retreat - thehomesteadangels.org
👩💼 The Brighter Side Society
💝 Become a Holmestead Angel Partner
Episode Summary
In this raw and vulnerable solo episode, Angel Holmes gets brutally honest about over-giving, undercharging, and the trauma responses that keep ambitious women from charging what they're worth. After multiple conversations about this topic and an emotional discussion with husband Brian, Angel knew it was time to address the pattern that cost her $100,000 and led to bankruptcy—and why she's done playing small. From the BevCon conference disaster to underpricing her recent retreat, Angel shares the hard lessons about how over-giving stems from childhood trauma and the belief that you have to give everything away to be loved. She declares 2025 the year of Angel 2.0: no more free events, no more devaluing her 30 years of expertise, and no more guilt about charging what she's worth. The episode also features Biggie Member of the Week Kimberly Sundt, whose eclectic career spans hospitality, interior design, event production, and now helping women take transformative solo personal retreats through her Permission to Pause Collection. Kimberly shares her journey from working with Atlanta Homes & Lifestyles Magazine on massive designer show houses to launching her retreat business in March 2020 (talk about timing!). Together, Angel and Kimberly discuss why getting quiet is essential for hearing your own wisdom, the importance of community even for seasoned entrepreneurs, and why charging your worth isn't selfish—it's necessary for making the impact you're called to make.
CONNECT WITH US:
Instagram: @neverstopdreamingbiggie @thebrightersidesociety and @angelpholmes
Learn more at https://sipindipity.com/neverstopdreamingbiggiemaster
The Brighter Side Society: https://sipindipity.com/brighterside
The Holmestead Bar & Retreat: https://theholmesteadbar.com/
CONNECT WITH THE GUEST:
🌟 Kimberly Sundt - Permission to Pause Collection, Solo Retreat DIY Kits, and Luxury Gift Boxes: https://thepermissiontopausecollection.com/permission-to-pause-current-collection
📍 Based in Beaufort, SC
Key Takeaways:
Have ideas, questions, or comments? Email us at [email protected]
Summary
In this special BONUS episode "Live from the Green Room: When Community Comes Alive," Angel Holmes takes you behind the scenes immediately after an incredible Brighter Side Society Sip & Strategize event at Starlight Motor Inn in Park Circle. Recorded live from the venue's green room, Angel brings together special guests Angela Michelle (singer and social media maven), Coach Dia (fitness instructor and line dancing leader), friend Colleen, and husband Brian for raw, unfiltered reflections on what just happened. From line dancing that got everyone moving to a powerful prayer circle with the band, this episode captures the authentic magic that occurs when ambitious women gather without the "stuffy networking" vibe. Angela shares her dreams of performing while building Magnolia South Creative, Coach Dia reveals her vision of teaching fitness around the world, and Brian offers his unique perspective as "the only guy there" on how women create community differently. The conversation celebrates breaking down walls, showing up even when you don't know anyone, and the power of creating spaces where women can be their authentic selves while building real business relationships. This bonus episode proves that community isn't just about networking—it's about connection, celebration, and making every day "the best day ever."
FOLLOW US:
Instagram: @neverstopdreamingbiggie and @angelpholmes
Learn more at https://sipindipity.com/neverstopdreamingbiggie
The Brighter Side Society: https://sipindipity.com/brighterside
The Holmestead Bar & Retreat: https://neverstopdreamingbiggie.com/the-holmestead-bar-retreat
CONNECT WITH THE GUESTS:
📱 Angela Michelle - Magnolia South Creative
💪 Coach Dia - Nadia Loren
Special Shoutouts:
🎸 Bill and his band at Starlight Motor Inn
🌟 Megan Deschaine - Event host extraordinaire
🏨 Starlight Motor Inn Pool House - Park Circle, Charleston
Takeaways
Chapters
00:00 Welcome from the Green Room
01:15 Tonight Was AMAZING - Event Debrief
02:30 Meet Angela Michelle - Multi-Talented Creative
05:45 Angela's Stormy Monday Performance
07:20 Meet Coach Dia - Line Dancing Queen
10:35 The Power of Movement to Connect
12:50 Colleen's Perspective as the Greeter
15:20 Brian's Take: The Only Guy There
17:40 Bringing Strangers Together
19:25 What's Your Biggie Dream?
21:30 Why This Event Was Different
23:15 Closing & Shoutouts to Starlight Motor Inn
Have ideas, questions, or comments? Email us at [email protected].
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:
Connect with Us:
🎙 @neverstopdreamingbiggie
📱 @angelpholmes
🌐 sipindipity.com
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
Summary
In this transformative solo Episode 33, Angel Holmes tackles a problem every ambitious woman faces: you're organized, your calendar is blocked, your to-do list is perfect—but by 10 AM you're scattered, by 2 PM you're overwhelmed, and by evening you're completely done. Angel reveals why traditional time management systems fail and introduces her game-changing three-step framework for achieving energized success instead of burnout. Drawing from her personal experience running the Charleston Wine and Food Festival (20,000 attendees, 150+ events!) and her COVID business pivot, Angel shares vulnerable stories about isolation, depletion, and the turning point when she discovered energy alignment. She explains why cookie-cutter productivity systems don't work for different brain types, schedules, and life circumstances—and why you're not broken, your system just isn't designed for YOUR energy patterns. Angel walks through her daily structure from morning centering to high-energy creative blocks to evening admin time, proving that working with your natural rhythms changes everything.
The "E" in Biggie stands for Elevate—and this episode is all about elevating your success by mastering your energy, not just your time.
Key Takeaways:
Connect with Us:
🎙 @neverstopdreamingbiggie
📱 @angelpholmes
🌐 sipindipity.com
Learn More:
🌴 The Holmestead Bar & Retreat
👩💼 The Brighter Side Society
🎁 Free Webinar: From Overwhelm to Organized Success at https://sipindipity.myflodesk.com/energizedsuccess
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