Episode 6 of Never Stop Dreaming BIGGIE reveals Angel and Brian’s biggest secret yet – The Homestead Bar & Retreat

“It was all a dream…” but what happens when your spouse becomes a podcast celebrity and you’re ready to reveal the biggest secret you’ve been keeping?

In this week’s episode of Never Stop Dreaming BIGGIE, fan-favorite Brian “The Director of No Fun” Holmes returns by popular demand to finally spill the beans on our Caribbean venture that’s been years in the making. After becoming an overnight sensation in our most downloaded episode ever, Brian’s back with humor, heart, and some serious concerns about bugs in cereal.

When Your Husband Becomes Charleston’s Favorite Podcast Guest

Let me tell you, nothing prepared me for what happened after Brian’s first podcast appearance. People were literally stopping him at Natalie Dupree’s memorial service – Charleston’s culinary elite recognizing my husband and saying, “Brian! We love Brian!” Meanwhile, he’d never met any of these people in his life.

I kept joking that he should carry a Sharpie for autographs. Brian went from the guy who couldn’t get his headphones plugged in to Charleston’s most beloved podcast guest practically overnight. The episode shot to #1 for the month, and suddenly everyone wanted to know when the “Director of No Fun” was coming back.

Well, the wait is over – and this time, he’s helping me reveal our biggest dream yet.

The Secret We’ve Been Keeping: The Homestead Bar & Retreat

For months, Brian and I have been quietly working on something that combines my 30+ year love affair with the Caribbean, our shared faith journey, and a business model that puts giving back at its core. Today, I’m finally ready to share it with you:

We’re building The Homestead Bar & Retreat in the Caribbean.

This isn’t just another island bar. This is an upscale sanctuary where sailboats dot the harbor, charitable giving drives every decision, and the “woohoo” crowd need not apply (sorry, bachelorette parties!).

How a Teenage Rebellion Became a Lifelong Passion

The Caribbean dream started when I was 13 years old. My dad surprised my sister and me with a trip to Guadalupe with our grandfather’s caregiver. I was absolutely furious – I wanted clothes for my birthday, not some random island vacation. I was such a brat about it (deservedly so, I’ll admit).

But something magical happened on that island. There was no drinking age (which immediately improved my attitude at 13!), we stayed with local kids who spoke French and English, we hiked waterfalls, went to discotheques, and had complete freedom to explore. When I came home, I told my dad, “I was so wrong about that trip. I don’t ever want to leave the Caribbean.”

From that moment on, I spent every possible vacation in the islands. I got married there (one of my marriages!), celebrated anniversaries there, explored the majority of Caribbean destinations. The islands became my sanctuary, my inspiration, my happy place.

When Dreams Meet Divine Inspiration

Fast forward to BevCon a few years ago. I was walking through that conference feeling a calling – not just a business idea, but a spiritual pull – to create something meaningful in the Caribbean. A place that would be unlike anything that existed down there.

When I met Brian and told him about this dream during what was basically our job interview first date, his response was simple: “Who am I to kill that dream?”

That’s when I knew he was the right partner for this journey.

The Vision: More Than Just Paradise

The Homestead Bar & Retreat represents everything we believe about business, community, and faith:

Our Island Criteria:

• Sailboat communities: Picture a beautiful cove dotted with sailboats and yachts, with little dinghies bringing guests to our dock each morning
• Hurricane-resistant locations: We’re looking south of St. Kitts – islands like Antigua, Dominica, Grenada, Trinidad, and the Grenadines
• English-speaking preferred: For business ease (though we’re open to French islands with the right connections)
• Stable, less corrupt governments: We want to work with good people in manageable political environments
• No cruise ship crowds: This isn’t that kind of destination

The Homestead Experience:

• Upscale atmosphere: Think sophisticated sailing community, not spring break party zone
• Charitable focus: ALL proceeds benefit disaster relief and causes close to our hearts (hello, José Andrés and World Central Kitchen!)
• Retreat space: Private bungalows and pavilions for intimate gatherings, spiritual retreats, and meaningful connections
• Community membership: “Friends of the Homestead” get special access and perks
• Limited access: You need to be on our list – this maintains the intimate, special atmosphere we’re creating

The Director of No Fun Keeps It Real

While I’m dreaming of sunset cocktails and sailboat arrivals, Brian’s asking the practical questions that make dreams actually work:

Brian’s Concerns (and they’re valid!):

• “We’re gonna have soap, right?” (His non-negotiable requirement)
• Bugs in cereal (apparently weevils are just “extra protein”)
• Reliable infrastructure and internet connectivity
• Not having to play our current neighborhood game of “fireworks or gunshots?”

But here’s what I love about Brian – he’s not trying to shut down the dream. He’s asking the questions that will make it successful. His role isn’t to be a dream killer; it’s to be the practical counterpart to my visionary energy.

As he says, “Less corrupt. We want good people.” Simple, but exactly right.

Faith as Our Foundation

What makes this venture different from every other Caribbean bar is that it’s rooted in our faith journey. This dream came through prayer, through feeling called to create something that serves a higher purpose.

We’re not just building a business – we’re creating a space where meaningful connections happen, where every dollar spent helps disaster relief efforts, where people can retreat from the chaos of life and reconnect with what matters.

As I told Brian, “This dream came about because of God. It really did. And it’s happening because of God.”

The Journey Ahead

We’re not naive about the challenges. We have an amazing Caribbean attorney (shoutout to Matt Norton in Charleston!), we’re learning from people like LeGrand Elebash who lived in St. Kitts, and we’re preparing for the reality of island life.

This year, we’ll be island-hopping to scout locations. We’ll be sharing our journey every step of the way through @TheHomesteadBar on social media and monthly updates on this podcast.

What We Need From You:

• Caribbean connections (especially in our target islands)
• Recommendations for places to stay while we scout
• Business contacts in the islands
• Your prayers and support as we take this leap of faith

The Bigger Picture

The Homestead represents something larger than a business venture. It’s about creating spaces where ambitious people can retreat, recharge, and reconnect with their purpose. It’s about building a business model that prioritizes giving back over maximum profit. It’s about showing that faith and entrepreneurship can work together beautifully.

Most importantly, it’s about proving that dreams backed by prayer, practical planning, and the right partner can become reality – even when they involve moving to a Caribbean island and dealing with potential bugs in your cereal.

Behind Every Dream Is an Advisory Team

We can’t wait to announce our advisory committee – a group of incredible humans who believe in this vision and are helping us make it happen. God is our chairman of the board, Brian and I are the co-founders, and we’re surrounded by some truly special friends who bring expertise and wisdom to this journey.

(Gary Crunkleton, you’re definitely part of the opening weekend!)

Your Part in This Story

Whether you become a “Friend of the Homestead,” follow our journey on social media, or just cheer us on from afar, you’re part of what makes big dreams possible. Community support matters more than you know.

Brian might joke about doing this podcast “less often,” but the truth is, these monthly updates with him have become a favorite part of our journey. Watching the practical meet the passionate, seeing dreams take shape through real planning and faith – that’s what Never Stop Dreaming BIGGIE is all about.

Ready to follow our Caribbean adventure? Connect with us @TheHomesteadBar on Instagram and submit your questions for Brian’s next appearance. Trust me, anything goes with the Director of No Fun!

The best is yet to come (literally – that’s what the sign behind Brian says), and we can’t wait to share every step of this journey with you.

Listen to Never Stop Dreaming BIGGIE every Wednesday wherever you get your podcasts. Connect with Angel Holmes on Instagram @angelpholmes and join our community at @neverstopdreamingbiggie.

Have Caribbean connections or island recommendations? We’d love to hear from you! Reach out through our social media channels or email angel@neverstopdreamingbiggie.com