"Live from Charleston: The Holmes Boys Take the Mic"

SummaryIn 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 @angelpholmesLearn More🌴 The Holmestead Bar & Retreat👩‍💼 The Brighter Side Society📧 Email: [email protected]🌐 Website: sipindipity.comTakeawaysDiscover the three Caribbean islands being considered for The Homestead Bar & RetreatLearn complete details about The Brighter Side Society membership ($75/month)Master strategies for overcoming imposter syndrome through community supportUnderstand how family business dynamics strengthen entrepreneurial venturesExplore the disaster relief mission driving The Homestead Bar conceptNavigate international business planning and island selection criteriaRecognize the importance of sailing communities for bar location successApply manifestation techniques through faith and consistent visualizationBuild supportive partnerships that fuel rather than limit your dreamsCreate authentic family business content that connects with audiencesChapters00:00 Live Setup & Caribbean Bar Introduction02:30 Meet Brian & Chase: The Holmes Boys05:45 Island Hopping Plans: Bequia, Barbados, Grenada08:20 Chase's Entertainment Director Job Interview12:15 The Brighter Side Society Membership Breakdown18:30 Homestead Bar Timeline & Investment Details22:10 Overcoming Imposter Syndrome as Female Entrepreneurs28:45 Family Business Dynamics & Partner Support32:20 Community Building & Women Supporting Women35:50 Caribbean Trip Planning & Attorney Guidance38:15 Closing Thoughts & Community Appreciation