The Giving Bar Revolution: How We’re Building a Caribbean Legacy That Changes Lives

Why We’re Creating The Holmestead Hideaway Giving Bar in the Caribbean (And Why It Matters)

It was all a dream… but what if I told you that some dreams are actually callings? Our giving bar in the Caribbean—The Holmestead Hideaway—is more than a business venture. It’s a revolutionary hospitality model where 100% of profits go to charity, combining world-class experiences with meaningful impact on island communities and disaster relief efforts worldwide.

In episode 45 of Never Stop Dreaming Biggie, Brian and I finally pulled back the curtain on the project that’s been consuming our hearts, minds, and prayers for the past year. This isn’t just another bar or retreat. This is about legacy, impact, and answering a call that’s been growing louder for over a decade.

The 10-Year Journey to Creating Our Caribbean Giving Bar

The seeds of The Holmestead giving bar were planted long before I even knew what they would become. It started during my BevCon days when I realized my superpower wasn’t just event planning—it was creating experiences that brought people together in meaningful ways.

Then came the Caribbean trips. Island after island, I kept feeling like something was missing. By midweek, I’d be craving a space that combined incredible hospitality, authentic connection, and that indefinable magic that makes you feel alive.

The pieces started coming together:

• A visit to a New York bar with a menu featuring all my favorite people
• Attending Sother Teague’s giving bar where 100% of proceeds went to charity
• Working with the incredible team at Edmunds Oast and learning from the best in hospitality
• Building The Brighter Side Society and seeing the power of intentional community

But it wasn’t until recently—through loss, grief, and watching people I love leave this earth—that the mission became crystal clear: We’re not here to accumulate. We’re here to give.

What is a Giving Bar? Understanding This Revolutionary Caribbean Business Model

A giving bar operates differently than traditional hospitality businesses in the Caribbean or anywhere else. Every dollar that comes through the door—after operational expenses—goes directly to charitable causes.

But The Holmestead Hideaway isn’t just about giving money. It’s about creating an experience so extraordinary that guests walk away saying, “That was the greatest place I’ve ever been… and I helped change lives just by being there.”

Imagine walking into our Caribbean giving bar where:

• Every detail tells a story (yes, even the cocktail napkins)
• The bartenders are world-class professionals who’ve come to share their craft
• The menu features batched cocktails perfected over months (shoutout to the Holmes Fashion!)
• The vibe makes you feel like an absolute rockstar
• And knowing that your night out just funded an island entrepreneur’s dream or supported disaster relief efforts

That’s The Holmestead giving bar experience.

Our Two Charitable Missions: How Our Caribbean Giving Bar Creates Impact

Mission 1: Caribbean Island Community Support (50% of profits)

Half of everything our giving bar makes goes directly back to the Caribbean island community where we’re located. This includes:

Grants for Local Caribbean Entrepreneurs Remember the sweet 80-something-year-old woman we met driving her boat called “Blessing”? She needed just a couple thousand dollars to upgrade so her sons could take over the business. That’s exactly the kind of project our Caribbean giving bar will fund.

Caribbean Artist and Artisan Support We’ve already connected with an incredible local artist whose work will be featured throughout The Holmestead. But beyond that, we want to support his dreams—whether that’s opening a gallery, creating a workshop space, or expanding his reach.

Caribbean Infrastructure and Agriculture Projects From community gardens to sustainable farming initiatives, our giving bar will support projects that make the island stronger and more self-sufficient.

Education and Training Programs in the Caribbean This is where my heart really comes alive. We’re bringing world-class bartending and hospitality training to Caribbean islands. We’re teaching marketing for entrepreneurs, entrepreneurship, and business strategy. Brian will lead sustainability and engineering workshops.

We’re not coming in as outsiders who think we know better. We’re coming as partners who want to learn from island culture while sharing the skills and resources we have access to.

Mission 2: Disaster Relief Worldwide (50% of profits)

The other half of our giving bar profits goes to The Holmestead Angels—our nonprofit focused on disaster relief, with a special emphasis on hurricanes and natural disasters affecting Caribbean islands and coastal communities.

This mission was born from personal experience. I lived through Hurricane Hugo in high school. I saw my community devastated. I experienced what it’s like to go days without power, water, or communication. That trauma never really leaves you, but it can be transformed into purpose.

When Hurricane Helene hit Asheville last year, I couldn’t not respond. I organized a relief mission, rallied a team, raised money, and we went. That’s when The Holmestead Angels was truly born.

Our Caribbean giving bar partners with organizations like:

• World Central Kitchen (who does incredible work feeding people in crisis)
• Operation Drop (who can literally drop supplies into hard-to-reach areas)
• Local relief organizations in Caribbean communities we serve

When disaster strikes—whether in the Caribbean, the Carolinas, or anywhere else—we’ll be there.

Why Capital Stewards, Not Investors for Our Caribbean Giving Bar

Here’s where we’re doing things differently with our giving bar in the Caribbean.

Traditional investors want returns. They want profit. They want to make money. And that’s completely legitimate for most businesses.

But we’re not building The Holmestead giving bar to get rich. We’re building it to change lives in the Caribbean and beyond.

That’s why we’re seeking capital stewards—people who have the financial means to support this vision and who are looking for legacy over profit.

What does that mean for our Caribbean giving bar model?

For Capital Stewards:

• You’re investing in impact, not just returns
• Your name can be permanently attached to this legacy (think naming rights for parts of the property)
• You’ll receive some financial return as our giving bar generates profit
• You get VIP access to The Holmestead in the Caribbean for you and your family
• You’re part of something that will outlive all of us

For Us:

• We maintain the mission integrity—giving stays the priority
• We partner with people who share our values
• We’re not micromanaged by investors focused only on profit margins
• We can make decisions based on Caribbean community impact, not just revenue

If you or someone you know has been looking for a way to create lasting impact while being part of an incredible Caribbean hospitality experience, we’d love to talk.

The Faith Factor in Our Caribbean Giving Bar (And Why Everyone is Welcome)

I’m going to be real with you: this giving bar project is rooted in faith. Brian and I believe God has been orchestrating every step of this journey. From the people we’ve met to the Caribbean properties we’ve found to the timing of everything—we’ve seen miracle after miracle.

But here’s what’s equally important: The Holmestead giving bar welcomes everyone.

Our faith teaches us to love. Period. Not love with conditions. Not love only people who believe what we believe. Just love.

So whether you’re Christian, Jewish, Buddhist, Muslim, atheist, agnostic, or anything else—you’re welcome at our Caribbean giving bar. Whether you’re straight, gay, trans, or anywhere on the spectrum—you’re welcome. Whatever your background, your story, your beliefs—you’re welcome.

Some of my best friends are Jewish. We want them hosting events and retreats at our giving bar. We’ll celebrate Pride. We’ll honor different faith traditions. We’ll create space for everyone to feel seen, valued, and loved.

Because at the end of the day, that’s what this Caribbean giving bar is about. Love. Connection. Humanity.

The Timeline for Our Caribbean Giving Bar (Yes, Really)

Here’s the crazy part: this giving bar in the Caribbean could launch in 2026. Like, starting next month.

We’ve found the property (no, we’re not saying where yet—don’t want anyone snatching it up!). We’ve been meeting with:

• Land designers
• Interior designers
• Attorneys
• Caribbean island advisors
• Hospitality consultants

The pieces are coming together faster than we ever imagined. If we secure our capital stewards soon, we could literally be hosting friends and family for “test runs” at our giving bar within months.

The bar could be operational. The experiences could be happening. The giving could begin.

That’s not hype. That’s where we actually are with our Caribbean giving bar project.

What Makes Our Caribbean Giving Bar Different

Beyond the giving bar model, here’s what sets The Holmestead apart in the Caribbean:

Curated Experiences If you’ve been to any event I’ve produced—BevCon festival events, community gatherings—you know I don’t do basic. Every detail is intentional. Every element tells a story. Every moment is designed to make you feel special at our Caribbean giving bar.

World-Class Talent We’re bringing the best bartenders, chefs, artists, and hospitality professionals to this Caribbean project. People who are at the top of their craft and want to be part of something meaningful.

Caribbean Community Integration This isn’t a resort that exists separate from the local Caribbean community. Our giving bar is embedded in it, supporting it, learning from it, and growing with it.

Sustainable Practices in the Caribbean Brian’s background in engineering means we’re building our giving bar with sustainability at the core. Solar power, water conservation, waste reduction—all of it matters in protecting the Caribbean environment.

Story-Driven Design From the moment you arrive at our Caribbean giving bar, you’re stepping into a story. The Holmes Fashion cocktail. The captain’s hats. The locally-made art. The menu featuring our favorite people and places. Every element connects.

The Bigger Picture: Caribbean Giving Bar Impact

Here’s what keeps me up at night (in the best way) about our giving bar in the Caribbean:

Imagine a young woman on the Caribbean island who has a dream to start a catering business but doesn’t have the $2,000 she needs for equipment. She applies for a Holmestead giving bar grant. She gets it. She launches. Her business thrives. She employs others. She sends her kids to college.

Imagine a hurricane devastating a Caribbean island. The Holmestead Angels mobilizes. We send funds. We send supplies. We send people. We help rebuild.

Imagine Caribbean islanders who’ve never had professional hospitality training suddenly learning from the best bartenders in the world at our giving bar. They go on to open their own establishments. They raise the standard across the entire island.

Imagine guests who come to our Caribbean giving bar for a vacation and leave transformed—not just because the experience was incredible, but because they were part of something that mattered.

That’s what we’re building in the Caribbean.

Your Role in This Caribbean Giving Bar Story

Even if you’re not a capital steward, you’re part of this giving bar journey.

You can:

• Share this Caribbean giving bar vision with people who might want to be involved
• Follow the journey on Instagram @neverstopdreamingbiggie
• Plan to visit our giving bar when we open (and bring everyone you know)
• Support The Brighter Side Society, which is teaching women entrepreneurs how to build meaningful businesses
• Pray for us, send good vibes, or just believe in what we’re creating in the Caribbean

The “G” in Biggie stands for Give. And giving isn’t just about money—it’s about sharing vision, spreading hope, and believing in something bigger than yourself.

Listen to Episode 45: The Caribbean Giving Bar Story

Want to hear the full story of our giving bar in the Caribbean? Brian and I get real, vulnerable, and excited in this podcast episode. You’ll hear:

• The Holmes Fashion cocktail saga (Brian’s been perfecting it!)
• My Ford’s Gin batching class at Starlight Inn
• The Blessing boat story that still makes me emotional
• Why we’re building this Caribbean giving bar despite not having “Buco’s money”
• The role faith has played in every miracle along the way
• Why legacy matters more than accumulation
• And so much more about our giving bar mission

Listen to Episode 45 now

Let’s Build This Caribbean Giving Bar Together

If this giving bar in the Caribbean vision resonates with you, I want to hear from you.

If you know someone who might want to be a capital steward for our Caribbean giving bar, introduce us.

If you’re an entrepreneur building something meaningful, join The Brighter Side Society.

If you just want to follow along and cheer us on, subscribe to the Never Stop Dreaming Biggie podcast and follow @neverstopdreamingbiggie on Instagram.

This Caribbean giving bar is happening. The Holmestead Hideaway is becoming reality. And you get to be part of the story.

Because here’s the truth: dreams aren’t just for sleeping. They’re blueprints for the legacy you’re about to build.

Let’s dream Biggie together.

---

Connect with Angel:

• 🎙 Never Stop Dreaming Biggie Podcast
• 📱 Instagram: @neverstopdreamingbiggie @angelpholmes
• 🌐 Website: sipindipity.com
• 📧 Email: angel@neverstopdreamingbiggie.com
• 🌴 The Holmestead Bar & Retreat
• 👩‍💼 The Brighter Side Society

Interested in becoming a Capital Steward for our Caribbean giving bar? Email us today

---