Live from Charleston: The Holmes Boys Take the Mic

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.

Instagram

@neverstopdreamingbiggie and @angelpholmes

Learn More

🌴 The Holmestead Bar & Retreat

👩‍💼 The Brighter Side Society

📧 Email: [e-mail]

🌐 Website: sipindipity.com

Takeaways

• Discover the three Caribbean islands being considered for The Homestead Bar & Retreat
• Learn complete details about The Brighter Side Society membership ($75/month)
• Master strategies for overcoming imposter syndrome through community support
• Understand how family business dynamics strengthen entrepreneurial ventures
• Explore the disaster relief mission driving The Homestead Bar concept
• Navigate international business planning and island selection criteria
• Recognize the importance of sailing communities for bar location success
• Apply manifestation techniques through faith and consistent visualization
• Build supportive partnerships that fuel rather than limit your dreams
• Create authentic family business content that connects with audiences

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