Never Stop Dreaming Biggie

Angel Holmes
  • 5.0 (10)
  • ENTREPRENEURSHIP

Never Stop Dreaming BIGGIE is a podcast for ambitious women who want clarity in business and confidence in their next steps. Hosted by business coach and community builder Angel Holmes, each episode blends real-world experience, honest conversations, and practical strategy to help you move forward with intention. From building meaningful communities to creating structure that supports growth, the show explores what it actually takes to build a business without burnout. Through solo episodes and conversations with founders and leaders, you’ll gain actionable insights on focus, mindset, systems, and sustainable success. Whether you’re starting fresh, navigating growth, or craving more alignment in your work, new episodes each week offer grounded guidance and encouragement to keep dreaming — and building — bigger.

  1. Episode 53: Behind the Scenes at Charleston Wine & Food Festival's 20th Anniversary Part 1

    2D AGO

    Episode 53: Behind the Scenes at Charleston Wine & Food Festival's 20th Anniversary Part 1

    In Episode 53 of Never Stop Dreaming Biggie, Angel and Brian Holmes is coming to you LIVE from the Charleston Wine + Food Festival's 20th Anniversary — recorded straight from the Hospitality Hub at High Wire Distilling Company. This is Part 1 of a special multi-part series featuring the OGs who helped build one of the South's most celebrated culinary events, and the real stories behind what it took to make it happen. Angel sits down with Marc Collins (Executive Chef at Circa 1886 for 25 years and the original visionary behind CWFF), Michael Kramer (opening Executive Chef of McCrady's, now chef-owner of Gianna in Greenville), and Scott Blackwell (co-founder of the award-winning High Wire Distilling Company and Guinness World Record holder for the world's biggest cookie). Together they share what it truly means to build something from nothing — with community, curiosity, and tenacity as your only starting capital. The "G" in BIGGIE stands for Give — and this episode is a masterclass in what happens when people show up for each other, for their city, and for a dream that didn't exist yet. Key Takeaways: Discover how one aquarium conversation sparked a 20-year culinary legacyLearn why community — not capital — is the real fuel behind every great buildUnderstand what curiosity and tenacity look like in action over decadesHear how building a business with your spouse actually works (and the hard years in between)Find out why the people no one hears about are always the ones holding everything togetherLearn what 25 years at one restaurant actually teaches you about a citySee how heritage grains, local farmers, and a village of believers built Jimmy Redd WhiskeyUnderstand why showing up for others always comes back around Whether you're just starting out, building your village, or wondering if your wild idea is worth pursuing — this episode is proof that the right people in the right room can change everything. Learn more about Circa 1886: https://circa1886.com/ Learn more about Jianna Greenville: https://jiannagreenville.com/ Learn more about High Wire Distilling Co: https://highwiredistilling.com/ CONNECT WITH ANGEL: 🎙 Never Stop Dreaming Biggie Podcast 📱 Instagram: @neverstopdreamingbiggie | @angelpholmes 🌐 Website: sipindipity.com 📧 Email: angel@sipindipity.com 🌴 The Holmestead: theholmesteadhideaway.com 👩‍💼 The Brighter Side Society & Brighter Week: sipindipity.com/brighter-side-society Take the Free Flow Style Assessment: https://www.tryinteract.com/share/quiz/6980f62c2606173ca6c95a49 Check out Substack: https://angelpholmes.substack.com SUBSCRIBE & SHARE: If this episode reminded you that your dream is always worth building — and that your village is out there waiting — please subscribe, leave a review, and share it with someone who needs to hear these stories. Your support helps us reach more dreamers ready to turn their vision into reality.

    33 min
  2. Episode 52: How I Built a 20-Year Legacy from Zero: The Charleston Wine & Food Festival Origin Story & the System That Made It Possible

    MAR 4

    Episode 52: How I Built a 20-Year Legacy from Zero: The Charleston Wine & Food Festival Origin Story & the System That Made It Possible

    Join Angel Holmes as she shares the untold origin story of the Charleston Wine & Food Festival — now celebrating its 20th anniversary — and the real systems and beliefs that made it possible. This episode is packed with hard-won wisdom, vulnerable storytelling, and practical tools for women entrepreneurs and anyone building something meaningful from the ground up. In This Episode You'll Discover: How a simple meeting with the right people in the room became a 20-year culinary legacy for CharlestonWhy believing in a vision before you have any evidence is the first non-negotiable stepThe village-building strategy that turned a volunteer committee into a world-class festivalWhy creativity without systems will always collapse — and what to do about itHow hiring people smarter than you is the fastest way to grow something bigger than yourselfThe real reason Angel walked away after 10 years — and why she has zero regretsWhy the people behind the scenes are the forgotten heroes of every great thing ever builtWhat Angel learned about relationships, reciprocity, and always leading with how you can serve othersHow losing everything during COVID led to the clearest vision she's ever hadThe brand new Brighter Week system — Angel's personal productivity framework, now available to everyone — and why customized systems beat generic planners every timeWhat "big dreams deserve disciplined weeks" actually means in practice Whether you're just starting to build something from scratch, in the messy middle of growing a business, or rebuilding after a setback, this episode is your reminder that the right people, the right belief, and the right systems can take any dream further than you imagined. TIMESTAMPS: 00:00 Welcome & Episode 52 Intro 02:15 Why the Charleston Wine & Food Festival Matters 05:30 The Aquarium Years & the Sustainable Seafood Project 10:45 How One Chef's Idea Sparked a Festival 15:00 The First Meeting & Building the Planning Committee 20:30 Believing Before You Have Evidence 25:00 Systems, Organization & Hiring Smarter Than Yourself 31:15 The Forgotten Heroes Behind Every Big Event 35:45 Why Angel Left After 10 Years 40:00 Losing Everything During COVID & Starting Over 45:30 Introducing the Brighter Week System 51:00 Big Dreams Deserve Disciplined Weeks — Final Thoughts CONNECT WITH ANGEL: 🎙 Never Stop Dreaming Biggie Podcast 📱 Instagram: @neverstopdreamingbiggie @angelpholmes 🌐 Website: sipindipity.com 📧 Email: angel@neverstopdreamingbiggie.com 🌴 The Holmestead: theholmesteadhideaway.com 👩‍💼 The Brighter Side Society & Brighter Week: sipindipity.com/brighter-side-society Take the Free Flow Style Assessment: https://www.tryinteract.com/share/quiz/6980f62c2606173ca6c95a49 Check out Substack: https://angelpholmes.substack.com SUBSCRIBE & SHARE: If this episode reminded you that your dream is worth building — and that you don't have to do it alone — please subscribe, leave a review, and share it with a woman entrepreneur who needs to hear this story. Your support helps us reach more dreamers ready to turn their vision into their reality. #CharlestonWineAndFood #CWFF #CharlestonSC #CharlestonEvents #EventPlanning #WomenEntrepreneurs #FemaleFounders #NeverStopDreamingBiggie #Entrepreneurship #WomenInBusiness #BusinessPodcast #BuildingALegacy #StartingFromZero #ProductivitySystems #TimeManagement #BrighterWeek #TheBrighterSideSociety #SmallBusinessCharleston #CharlestonBusiness #DreamBig #BusinessSystems #EntrepreneurMindset #CommunityBuilding #WorkLifeBalance #WomenWhoLead

    41 min
  3. Show Up As You Are: Lessons in Business & Community with Sarah Frick

    FEB 25

    Show Up As You Are: Lessons in Business & Community with Sarah Frick

    In Episode 51 of Never Stop Dreaming Biggie, I'm joined by Sarah Frick, founder of The Works — Charleston, SC's most beloved boutique fitness community with six locations across the Lowcountry. This community-driven episode dives deep into what it really takes to build a business rooted in authentic human connection, servant leadership, and the belief that your competitors are actually your community. Sarah has spent 20+ years creating spaces where women don't just come to work out — they come to feel seen, supported, and connected. From fundraising for breast cancer and ALS to championing her team members' own business dreams, Sarah has built something far bigger than a gym. And in this conversation, she gets real about the hard lessons, the leadership challenges, and why showing up as you are is always enough. Whether you're a female entrepreneur building a brick-and-mortar business, a Charleston local curious about The Works, or a business owner figuring out how to scale without losing your soul, this episode will both inspire you and give you practical wisdom you can use today. The "G" in BIGGIE stands for Give — and Sarah Frick is the living definition of what it means to build a business by genuinely giving back to your community. Key Takeaways: Recognize why community-first thinking is the most powerful business strategy you're not usingBuild a team culture so strong your business thrives even when you can't be everywhereUnderstand the real estate and demographic strategy behind smart brick-and-mortar expansionNavigate the hardest leadership challenge — letting go of people who no longer serve the teamLearn why having hard conversations face-to-face is a non-negotiable leadership skillStop fearing your competitors and start building collaborative community insteadCreate giving-back initiatives that are authentically woven into your business modelScale your business without sacrificing the thing that makes it specialBuild systems that allow you to show up for your family and your businessInvest in your people so deeply they invest right back into youDesign a customer experience so warm and welcoming it becomes someone's happy placeShow up as you are — and build a brand that gives others permission to do the same Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 angel@neverstopdreamingbiggie.com Learn More: 🌴 The Holmestead Hideaway https://theholmesteadhideaway.com/ 👩‍💼 The Brighter Side Society https://sipindipity.com/brighter-side-society 💼 One-on-One Coaching https://sipindipity.com/mentorship-2025 📅 The Brighter Week Waitlist & Free Assessment https://quiz.tryinteract.com/#/6980f62c2606173ca6c95a49 📝 Angel's 5% Substack https://angelholmes.substack.com/ Double check which BIGGIE letter you want to use — I went with "G" for Give since it matched Sarah's story so well, but swap it if another letter fits better!

    24 min
  4. Episode 50: The Year of the Horse: Shedding What No Longer Serves You

    FEB 18

    Episode 50: The Year of the Horse: Shedding What No Longer Serves You

    In Episode 50 of Never Stop Dreaming Biggie, I'm sharing a raw, unfiltered conversation about entering life's second half with intention and stepping into the Year of the Horse. This milestone solo episode dives deep into boundaries, burnout recovery, and why high-achieving women must stop giving everything away for free. I hit 52 this year and I'm officially at halftime — that transformative phase where you've spent the first half figuring out who you are and proving yourself, and now it's time to focus on what really matters. After losing my business, rebuilding from rock bottom, and realizing I was depleting myself by constantly over-giving, I'm making some major changes. From cleaning up my email list and social media to launching my 5% Substack where I share the deeper stories, this episode is about shedding what no longer serves you and owning your worth. Whether you're a chronic people-pleaser feeling burnt out from over-giving, a successful woman who struggles to charge what you're worth, or someone ready to make your second half count bigger than your first, this conversation will give you permission to stop playing small and start building the life you actually want. The "B" in BIGGIE stands for Believe — and believing in your vision means believing you deserve to be compensated for the incredible value you bring to the world. Key Takeaways: Recognize the signs of chronic over-giving and how it's actually hurting everyoneImplement the "halftime" mindset shift that changes everything after 50Identify what needs to be shed in the Year of the Horse energyEstablish boundaries with love while protecting your energy and expertiseClean house on email lists, social media followers, and energy drainsLaunch your own "5%" space for deeper, more intimate content sharingTake the free Brighter Week assessment to discover your organizational styleStructure your week to reclaim a full day of your life through better systemsNavigate the transition from free content creator to paid expertBuild sustainable business practices that honor both service and profitCreate community experiences that truly serve your ideal peopleDesign your second half around purpose, profit, and maximum impact Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 angel@neverstopdreamingbiggie.com Learn More: 🌴 The Holmestead Hideaway https://theholmesteadhideaway.com/ 👩‍💼 The Brighter Side Society https://sipindipity.com/brighter-side-society 💼 One-on-One Coaching https://sipindipity.com/mentorship-2025 📅 The Brighter Week Waitlist & Free Assessment https://quiz.tryinteract.com/#/6980f62c2606173ca6c95a49 📝 Angel's 5% Substack https://angelholmes.substack.com/

    18 min
  5. Episode 49: Dreaming BIGGIE Behind the Bar: We Let AI Teach Us Bartending and the Results Were Mixed (Literally)

    FEB 11

    Episode 49: Dreaming BIGGIE Behind the Bar: We Let AI Teach Us Bartending and the Results Were Mixed (Literally)

    In Episode 49 of Never Stop Dreaming Biggie, Brian and I are back together for our February Homestead update — and this time, we let AI teach us how to bartend. The results? Mixed. Literally. This episode is equal parts Valentine's chaos, cocktail experiments, marriage conference highlights, and real talk about where we are with The Holmestead Hideaway. We kicked off the weekend at the Seacoast Marriage Conference where we serve on the prayer team and lead the SYMBIS program. We got to meet Les and Leslie Parrott — the creators of SYMBIS — in person after seven years of teaching their material, and walked away with new tools for our marriage (like the three-squeeze hand trick we probably should have used before hitting record). Then we came home, fired up our AI COO Viva, and attempted to make four classic cocktails: a daiquiri, a Negroni, a Manhattan, and the Harry Maude martini. The daiquiri was a disaster. The Negroni was a showstopper. Brian debuted his signature Holmes Fashion old fashioned with homemade Cheerwine simple syrup, and I learned that he's naturally better at stirring than I am — and I'm not happy about it. Whether you're dreaming of opening your own bar, navigating business with your spouse, or just need a good laugh watching two entrepreneurs fumble through cocktail measurements with questionable jiggers and an AI coach, this episode is for you. We also share major updates on The Holmestead Hideaway in Bequia, our search for capital stewards, dreams of bringing Cheerwine and Waffle House to the Caribbean, and plans for our podcast's one-year anniversary at the Charleston Wine and Food Festival. The "G" in BIGGIE stands for Grow — and growing through challenges (not around them) looks a lot like two people standing at a home bar with bad measurements, a shaker that won't open, and a dream that's bigger than any cocktail fail. Key Takeaways: Discover how AI can serve as your bartending coach and business COO (meet Viva)Learn the proper stirring technique that keeps your cocktails quiet and professionalUnderstand why more ice actually means less dilution in your drinksMaster the classic Negroni with gin, sweet vermouth, and CampariCreate Brian's signature Holmes Fashion old fashioned with Cheerwine simple syrupNavigate learning new skills as a couple without losing your mind (or your marriage)Implement the three-squeeze hand trick from Les and Leslie Parrott's marriage teachingsBuild relationships with brands and creators before using their recipes or productsDevelop your bar menu by starting small and perfecting a few signature drinksExplore the capital steward model for funding passion projects and charity-driven businessesPlan phased business launches from friends-and-family testing to pop-ups to full openingConnect with your community through in-home speakeasy-style soft launches Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 angel@neverstopdreamingbiggie.com Learn More: 🌴 The Holmestead Hideaway https://theholmesteadhideaway.com/ 👩‍💼 The Brighter Side Society https://sipindipity.com/brighter-side-society 💼 One-on-One Coaching https://sipindipity.com/mentorship-2025 📅 The Brighter Week Waitlist & Free Assessment https://quiz.tryinteract.com/#/6980f62c2606173ca6c95a49

    49 min
  6. Episode 48: The Brighter Week: Why Cookie-Cutter Time Management Fails Entrepreneurs

    FEB 4

    Episode 48: The Brighter Week: Why Cookie-Cutter Time Management Fails Entrepreneurs

    In Episode 48 of Never Stop Dreaming Biggie, I'm sharing a raw, unfiltered solo episode recorded on day four of a spiritual fast that changed everything. This is the episode where God downloaded the vision for The Brighter Week—a completely customizable time management and productivity system designed specifically for entrepreneurs and ambitious women who are tired of cookie-cutter systems that don't work for their unique brain, business, or life. This conversation is packed with vulnerable moments, divine revelations, and practical strategies. I share the exact sleepless night where God told me to "cleanse your life and start packing" for The Holmestead project, and how He revealed a system that's already giving me 6-7 hours back every week without the hustle. We dive deep into why every productivity system you've tried has failed (spoiler: they're designed for someone else, not you), how to use AI as your virtual COO, and why you need both mindset and systems to achieve big dreams. Whether you're drowning in to-do lists, exhausted from following other people's routines, or ready to finally create calm and clarity in your business and life, this episode offers the breakthrough you've been praying for. I'm launching The Brighter Week in March with a beta test group from The Brighter Side Society, and you can join the waitlist or take the free personality assessment to discover your unique productivity type. The "B" in BIGGIE stands for Believe—and believing you can have a customized system that actually works for your life (not someone else's) is the first step to getting your time, sanity, and dreams back. Key Takeaways: Discover why traditional time management systems fail entrepreneurs and how to fix itLearn the personality assessment framework that determines your unique productivity styleImplement the exact morning routine that gives you 2-3 hours for prayer, breakfast, and workoutsCreate customizable Notion workspaces with AI prompts designed for your business needsDevelop systems that return 2-7 hours per week without burnout or hustle cultureMaster the art of day-themed business strategy and Sabbath rest for sustainable growthUnderstand how AI can become your virtual COO and business partnerNavigate major life transitions with spiritual clarity and practical organizationBuild lifetime systems with ongoing community support and accountabilityAccess VIP day options for personalized setup and customization helpJoin The Brighter Week beta test or March launch waitlist todayTake the free assessment to discover your productivity personality type Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 angel@neverstopdreamingbiggie.com Learn More: 🌴 The Holmestead Hideaway https://theholmesteadhideaway.com/ 👩‍💼 The Brighter Side Society https://sipindipity.com/brighter-side-society 💼 One-on-One Coaching https://sipindipity.com/mentorship-2025 📅 The Brighter Week Waitlist & Free Assessment https://quiz.tryinteract.com/#/6980f62c2606173ca6c95a49

    18 min
  7. Episode 47: From Imposter Syndrome to 8-Figure Exit: Building a Product Business with Purpose

    JAN 28

    Episode 47: From Imposter Syndrome to 8-Figure Exit: Building a Product Business with Purpose

    In Episode 47 of Never Stop Dreaming Biggie, I'm joined by Lisa Simone Richards for our first guest episode of 2026. Lisa is a former publicist turned product founder who made the bold decision to blow up her 20-year career to launch Pearl Spark Pages and the Female Founders Journal—a guided journal specifically designed to help women entrepreneurs overcome imposter syndrome, build authentic confidence, and celebrate their wins. This conversation is packed with real talk about the messy middle of entrepreneurship. Lisa shares the exact moment she felt like a fraud on stage despite her success, why she walked away from a thriving service-based business, and how she's now building a product company with a crystal-clear 8-figure exit strategy by 2031. We dive deep into how she funded her business through community instead of paid advertising, the power of building in public, and why journaling isn't just wellness—it's a legitimate business strategy that rewires your brain for success. As fellow former publicists, Lisa and I connect on so many levels including working with our spouses in business, the importance of systems and consistency, and why surrounding yourself with the right community is worth more than any course or consultant. Whether you're considering a business pivot, struggling with self-doubt, or wondering how to grow without social media burnout, this episode offers both inspiration and practical implementation strategies. The "B" in BIGGIE stands for Believe—and Lisa's journey from perfectionism and fear to building a business designed for impact and exit is proof that when you believe in yourself and let others into your journey, magic happens. Key Takeaways: Learn why 75% of female leaders experience imposter syndrome and how to push past it permanentlyDiscover the "document, don't create" content strategy that makes social media authentic and sustainableUnderstand how Lisa funded 40% of her Kickstarter campaign through community investment aloneMaster the art of building a business with your spouse without losing your mindImplement the BRAGGS framework for morning confidence rituals that actually workCreate daily celebration habits using "Today I'm proud of myself for" promptsNavigate the pivot from service-based to product-based business with confidenceBuild intentional community that supports your growth instead of just consuming contentDevelop a clear exit strategy and business goals that keep you focusedLeverage publicity and storytelling skills to grow without paid advertisingControl your inner narrative using Emma Greed's wisdom about training your brainPour into community before taking from it—the secret to organic business growth Connect with Lisa Simone Richards: 📓 Female Founders Journal https://www.femalefoundersjournal.com 🛍️ Pearl Spark Pages https://www.pearlsparkpages.com 📱 @pearlsparkpages Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 angel@neverstopdreamingbiggie.com Learn More: 🌴 The Holmestead Hideaway https://theholmesteadhideaway.com/ 👩‍💼 The Brighter Side Society https://sipindipity.com/brighter-side-society 💼 One-on-One Coaching https://sipindipity.com/mentorship-2025 Resources Mentioned: https://sipindipity.com/resources

    43 min
  8. Episode 46: Overcoming Imposter Syndrome: From Fear to Fearless in Business

    JAN 21

    Episode 46: Overcoming Imposter Syndrome: From Fear to Fearless in Business

    In Episode 46 of Never Stop Dreaming Biggie, I'm getting real about the number one thing holding entrepreneurs back: lack of confidence. If you've ever struggled with imposter syndrome, felt like you're not qualified enough, or played small when you know you're meant for bigger things, this solo episode will show you how to overcome fear and build the unshakeable confidence you need to succeed. I'm sharing my personal journey from losing everything in bankruptcy at age 50 to reclaiming my power and embracing my identity as a queen in business. You'll hear the prophetic revelation that changed how I see myself, why Mel Robbins' high-five habit actually works, and how my Word of the Year—Fearless—is transforming my entire approach to entrepreneurship and The Holmestead launch. This isn't just motivational fluff. I'm giving you practical, actionable confidence-building strategies you can implement today: daily rituals that rewire your brain, why fear is NOT from God, how to be your own biggest cheerleader without being cocky, and the critical importance of surrounding yourself with confident people who believe in you. Plus, I'm getting vulnerable about almost giving up on the podcast and The Brighter Side Society, and the mindset shift that turned everything around and brought my biggest membership month ever. The "B" in BIGGIE stands for Believe—and if you don't believe in yourself, no one else will either. This episode is your permission slip to stop playing small and own the unique gifts God created you with. Key Takeaways: Understand why confidence is the #1 differentiating factor for successful entrepreneursLearn the difference between true confidence and flashy overcompensation from insecurityDiscover Mel Robbins' high-five habit and why it builds unshakeable self-beliefMaster the "If it's in you, it's for you" mindset that eliminates imposter syndromeCreate your Word of the Year to transform your confidence and business approachImplement daily confidence rituals including prayer, journaling, and affirmationsRecognize signs of low confidence in yourself and others (and how to fix them)Surround yourself with confident people who will lift you up and believe in your visionUnderstand why giving up is the #1 reason entrepreneurs fail—and how to push throughLearn how to be your own best friend and biggest cheerleader without arroganceRewire your brain around fear using faith-based principles and Joyce Meyer's wisdomBuild belief systems that attract the right opportunities and people into your business Connect with Us: 🎙 @neverstopdreamingbiggie 📱 @angelpholmes 🌐 sipindipity.com 📧 angel@neverstopdreamingbiggie.com Learn More: 🌴 The Holmestead Hideaway 👩‍💼 The Brighter Side Society https://sipindipity.com/brighter-side-society 💼 One-on-One Coaching https://sipindipity.com/mentorship-2025 ✨ Luvie Smith Dream Sessions Books and other free resources: https://sipindipity.com/resources

    22 min
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5
out of 5
10 Ratings

About

Never Stop Dreaming BIGGIE is a podcast for ambitious women who want clarity in business and confidence in their next steps. Hosted by business coach and community builder Angel Holmes, each episode blends real-world experience, honest conversations, and practical strategy to help you move forward with intention. From building meaningful communities to creating structure that supports growth, the show explores what it actually takes to build a business without burnout. Through solo episodes and conversations with founders and leaders, you’ll gain actionable insights on focus, mindset, systems, and sustainable success. Whether you’re starting fresh, navigating growth, or craving more alignment in your work, new episodes each week offer grounded guidance and encouragement to keep dreaming — and building — bigger.

Information

  • Creator
    Angel Holmes
  • Years Active
    2025 - 2026
  • Episodes
    53
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Angel Holmes
  • Show Website
    Never Stop Dreaming Biggie

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