Episode 2 of Never Stop Dreaming BIGGIE

“It was all a dream…” but what happens when that dreamer meets someone who asks, “Okay, but how much will that cost?”

In this week’s hilarious and heartwarming episode of Never Stop Dreaming BIGGIE, I’m excited to introduce you to the man who keeps my feet on the ground while supporting my head-in-the-clouds dreams: my husband, Brian Holmes, affectionately known as “The Director of No Fun.”

Every Dreamer Needs Their Balance

While I hold the title of Director of Fun in our company Sipindipity, Brian has earned his stripes as the Director of Financial Responsibility (though we all know why he’s really called the Director of No Fun!). The kids have it right when they describe him as “cheap with a lot of rules” – but here’s the thing: every big dreamer needs someone like Brian.

When you’re building something meaningful, whether it’s a business, a community, or in our case, a Caribbean retreat, you need people who complement your strengths and fill in your gaps. Brian brings the practical wisdom, the financial oversight, and the “let’s think this through” energy that turns wild dreams into achievable realities.

The Charleston Native Who Said Yes to Caribbean Dreams

Brian grew up right here in Charleston (making us one of the few remaining native couples in our beloved city!), studied at Clemson, and now works as an engineer focusing on environmental work. His biggest influence? His father – something we deeply have in common, as my dad has been equally instrumental in shaping who I am.

But here’s what made me fall in love with this practical, spreadsheet-loving man: when I shared my vision for a Caribbean bar and retreat on one of our first dates, he didn’t hesitate. He looked at this crazy woman with her wild dreams and said, “Who am I to argue with that dream? Count me in.”

That’s the kind of partner every entrepreneur needs – someone who sees your vision and chooses to build it with you.

The “WAIT” Method: Our Secret Communication Hack

In the episode, we reveal one of our favorite relationship tools: the “WAIT” method. When either of us says “wait” during a conversation, it’s actually code for “Why Are You Talking?” – our gentle (okay, sometimes not so gentle) reminder to stop rambling and check if we’re actually adding value to the conversation.

Fair warning: I hear this code word way more than Brian does. But hey, that’s what happens when you’re a verbal processor married to someone who thinks before he speaks!

Finding Your Purpose (Even When It’s Still Evolving)

One of the most authentic moments in our conversation was when Brian admitted he’s still figuring out his true purpose – something I think resonates with so many of us. His current mission? “To leave the people that I have relationships with, and my company, and my family, and my neighborhood better than I found it.”

Sometimes the most profound purposes are the simplest ones. Not everyone needs to start a revolutionary company or change the world on a massive scale. Sometimes your purpose is being the steady, reliable force that helps others achieve their dreams.

Why Diversity Matters in Your Dream Team

Brian dropped some serious wisdom in this episode: “You’ve got to know your strengths and weaknesses and you’ve got to fill your life, business, whatever, with the people that fill in the gaps and complete the circle of what you need to be successful. Don’t surround yourself with similar people.”

This is HUGE for anyone building something big. If you’re naturally a visionary, you need the practical implementer. If you’re the creative type, you need the organized systems person. If you’re the eternal optimist, you need someone who can spot potential problems before they become disasters.

A Sneak Peek at The Homestead

While we’re keeping most of the details under wraps for now, this episode gives you the first taste of our biggest BIGGIE dream: The Homestead Bar & Retreat. Our goal is to open in 2028, and we’re currently in the exciting phase of exploring different Caribbean islands to find our perfect location.

This isn’t just a business venture for us – it’s a calling to create a space where people can come and feel loved, where we can integrate our faith with hospitality, and where dreams are nurtured alongside great food and stunning sunsets.

The Power of the Practical Dreamer

What I love most about Brian’s perspective is that he’s not a dream-crusher – he’s a dream-builder who happens to love spreadsheets. He doesn’t say “that’s impossible.” He says “that sounds amazing, now let’s figure out how to make it happen responsibly.”

Every entrepreneur needs someone asking the tough questions:

• How will we fund this?
• What’s our timeline?
• What are the potential risks?
• How do we measure success?

These aren’t fun questions, but they’re necessary ones. They’re the questions that turn “someday maybe” into “here’s our plan.”

Your Turn to Dream BIGGIE

As you listen to this episode, I want you to think about your own dream team. Who are the people filling in your gaps? Who’s asking you the practical questions? And if you don’t have a “Brian” in your circle yet, how can you start building relationships with people who complement your strengths?

Remember, dreaming BIGGIE isn’t just about the size of your vision – it’s about building the right team, asking the right questions, and taking practical steps toward making those dreams reality.

The “B” in BIGGIE stands for “Believe” – believe in your vision, even when others don’t see it yet. But sometimes believing means surrounding yourself with people who help turn that belief into a concrete plan.

What’s Next

Next month, Brian and I will be back to share more details about The Homestead project and take you behind the scenes of what it really looks like to build a dream from the ground up. We’ll talk about the islands we’re considering, the vision we’re creating, and yes, probably some spreadsheets too.

Until then, keep dreaming BIGGIE, but don’t forget to ask yourself: who’s your Director of No Fun, and how are they helping turn your dreams into reality?

Listen to the full episode wherever you get your podcasts, and don’t forget to subscribe so you don’t miss our monthly updates about The Homestead journey!

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Connect with us:

• Instagram: @neverstopdreamingbiggie and @angelpholmes
• Website: sipindipity.com
• Email: angel@neverstopdreamingbiggie.com
• Join The Brighter Side Society for more dream-building support