Never Stop Dreaming Biggie

We're re-sharing this episode because the message is just as powerful now as it was when we first released it! Due to a recording hiccup with this week's new episode (hey, it happens!), we're bringing back one of our most meaningful conversations to date. In this episode, Brian and I pull back the curtain on The Holmestead Hideaway—our revolutionary Caribbean bar and retreat concept where 100% of profits go to charity. If you've ever dreamed of building a business with purpose, wondered how to create a social impact venture, or want to understand what it takes to launch a giving-focused hospitality experience, this episode reveals the complete vision, mission, and path forward for this legacy project. We share the divine calling behind The Holmestead and the charitable mission that drives everything. This isn't just another bar or retreat; it's a giving bar that will transform lives on Caribbean islands and support disaster relief efforts worldwide through The Holmestead Angels nonprofit. From supporting local island entrepreneurs with grants to providing hospitality training and disaster relief, this project is about building something that matters far beyond profit. In This Episode You'll Discover: Why The Holmestead will be an unforgettable Caribbean experience The complete story of how God called us to create The Holmestead over 10 years What makes a "giving bar" different from traditional hospitality businesses The two charitable legs: 50% to local island communities, 50% to disaster relief How The Holmestead Angels nonprofit was born from Hurricane Helene relief work Real examples of island projects we'll fund (boat upgrades, artist support, entrepreneur grants) Educational programs: bartending, hospitality training, marketing, and sustainability Why we're seeking capital stewards instead of traditional investors The financial structure that prioritizes giving over personal profit How we're integrating faith while remaining inclusive and welcoming to all Behind-the-scenes property search updates The hospitality experience philosophy: making everyone feel like a rockstar Legacy over accumulation: why this project matters more than material wealth How grief and loss shaped our desire to create lasting impact Open invitation for capital stewards who want to be part of this mission Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes and @theholmesteadhideaway 🌐 sipindipity.com 📧 [email protected] Learn More: 🌴 The Holmestead Bar & Retreat Interested in becoming a Capital Steward for The Holmestead Hideaway? Email [email protected]

In this episode of Never Stop Dreaming Biggie, I'm introducing a brand-new segment we're calling "Brian Be Honest" — an unscripted, unfiltered Q&A with my husband Brian, where he has no idea what's coming and (mostly) no chance to edit his answers. This one's personal, playful, and a little bit vulnerable, all at once. Before we get into it, I share where things stand with the Homestead Hideaway — the property we've found, the funding push we're in the middle of, and how you can become one of our "Angels" supporting this legacy project. Then Brian sits down for round one of questions he didn't prep for: our very first date (a strict one-hour interview that almost didn't go his way), his honest fear about taking on something this big, and whether he actually believes we can raise $5 million. The "G" in BIGGIE stands for Grow — and this episode is exactly that: growing through the uncertainty of a huge dream, and being willing to let people see the honest, unpolished parts of building it together. Key Takeaways: Discover the story behind our new "Brian Be Honest" segment and why we started it Get an update on the Homestead Hideaway property and how you can get involved as an Angel supporter Hear the real story of our first date — and the one-hour rule that started it all Learn Brian's honest answer about his biggest fear in building the Homestead from scratch Understand why we believe we can raise $5 million — and the track record behind that confidence Get a behind-the-scenes peek at our frozen cocktail testing (and why I need a real slushy machine) Discover how faith shapes the way Brian and I approach this project and our marriage Hear what makes Brian happiest outside of the business — Clemson football, mountain biking, and family Find out how to submit your own questions for future "Brian Be Honest" episodes Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected] Learn More: 🌴 The Homestead Hideaway 👩‍💼 The Brighter Side Society

In this episode of Never Stop Dreaming Biggie, I'm taking you behind the bar at the Homestead OG — the original house in Park Circle, Charleston, where Brian and I are building something we've dreamed about for years. This one's personal: the bar itself was custom-built by a local carpenter after one too many rental bar bills, and it's dedicated to my dad, Ernie Passailaigue, whose Senate memorabilia sits right at the head of it. I walk you through the philosophy behind our bar program — curated, professional-quality cocktails inspired by island culture, without competing with the local bars we'll one day sit alongside — and test out four signature drinks live, mistakes and all. Along the way I get real about what it actually looks like to build something from scratch: the memory blocks, the supply challenges, the late nights figuring out what works and what doesn't. The "G" in BIGGIE stands for Grow — and that's exactly what this episode is about. Growing through the process, not around it, and being willing to let people see the messy, unfinished parts of building something you love. Key Takeaways: Discover the story behind the Homestead's custom-built bar and why it's dedicated to my dad Learn how a frustrating rental bar situation led to building one from scratch Understand the philosophy behind curating a bar program that complements local island bars instead of competing with them Follow along as I make four signature cocktails live: the Flo-Rida, the Wake Up Call, Out of Office, and the Sweet G Hear why Brian and I built our bar sections around our own spirit preferences — his bourbon, my gin Discover our plans for quarterly guest bartenders who'll train island locals in cocktail-making Get an honest look at what building a hospitality brand actually looks like behind the scenes Understand why every object behind our bar tells a story, and how personal meaning shapes brand identity Learn about our approach to sponsorships and donor-named cocktails Get a preview of what's coming next: the Homestead's charitable mission Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected] To watch the episode with her dad Ernie Passailaigue, visit https://youtu.be/gFm6nvJn6yY Learn More: 🌴 The Holmestead Bar & Retreat 👩‍💼 The Brighter Side Society

In this episode of Never Stop Dreaming Biggie, I'm joined by celebrity stylist Chellie Carlson, founder of the Magnetic Style Method and the Style Society, for a conversation that's about so much more than clothes. Chellie shares her journey from spending 20 years in the intimate apparel industry to launching her own styling business at 40 with almost no resources — and going from unemployment to seven figures in just four years. We talk through what it actually takes to reinvent yourself in midlife, the $3,000 investment in a coach that changed the trajectory of her business, and why she believes most women are one wardrobe reset away from feeling like themselves again. Chellie also opens up about the shame so many of us carry around our bodies and our closets, and how getting dressed with intention can change the way you move through the world. The "E" in BIGGIE stands for Elevate — and that's exactly what this conversation is about. Elevating your standards, your confidence, and the way you show up, starting with something as simple as what you put on your body every day. Key Takeaways: Discover how Chellie went from unemployment to seven figures in four years, starting at age 40 Learn why most women are wearing the wrong bra size — and why that matters more than you'd think Understand the difference between shopping to feel good for a second and dressing with real intention Hear how Chellie's Magnetic Style Method delivers permanent transformation in under three sessions Get her take on why "less is more" when it comes to building a wardrobe you actually love Learn how investing in a personal stylist can save you time, money, and decision fatigue Discover why finding your signature look builds trust with the people around you Hear how Chellie built a seven-figure business and 32,000-person community through word of mouth alone Get her simple daily challenge for getting out of your workout clothes and into pieces that reflect who you're becoming Understand why investing in yourself — whether it's coaching, style, or mindset — is never really optional Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected] Learn More: 👗 Chellie Carlson: @chelliecarlson and https://www.chelliecarlson.com/

In this episode of Never Stop Dreaming Biggie, I'm joined by my youngest son, Chase, for a fun and heartfelt conversation — his second time on the podcast, and this one couldn't have come at a better time. He's heading into his senior year at James Island High School, and we dig into everything from his plans for the future to what he's actually picked up from watching me build businesses. We talk through Chase's plans for Trident Tech and eventually College of Charleston, his interest in business (and maybe running the bar down in the Caribbean one day), and where scuba diving and video games fit into it all. We also get into faith — why the people you surround yourself with matter so much for growing in your relationship with God, and why your faith should feel like any other relationship, not just something you turn to when you need something. After Chase heads out, I go solo to reflect on purpose and what it really means to be "anointed." I share an update on the Homestead Hundred campaign, now at 63 donors, and why every single person's story behind their gift has meant more to me than I expected. The "G" in BIGGIE stands for... actually, this one's less about the framework and more about the proof of it — watching your kids grow into the values you've been living out loud, even when you didn't know they were paying attention. Key Takeaways: Discover Chase's plans for Trident Tech, College of Charleston, and starting his own business Learn what it's really like being the son of an entrepreneur — the good, the funny, and the "he uses ChatGPT as his business partner" Understand why community is essential for growing your faith, not just your business Hear Chase's honest take on senior year, scuba certification, and life goals Get Angel's breakdown of what it means to be "anointed" and find your God-given purpose Learn why asking for what you want is the first step toward receiving it Get an update on the Homestead Hundred campaign and the stories behind the donors Find out why sharing your story — even the small parts — creates a ripple effect you may never fully see Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 [email protected] Learn More: 🌴 The Homestead Hideaway: theholmesteadhideaway.com 👼 The Homestead Angels: homesteadangels.org