From Vacant Building to Boutique Hotel: A Real-Time Hospitality Investment Journey

In this episode of the Brand & Market Podcast, I’m pulling back the curtain on a brand new project that’s currently unfolding in real time. What started as curiosity about an empty building in my hometown has turned into the early stages of exploring a boutique hotel development opportunity.

This episode is a little different from the usual strategy-focused conversations. Instead, I’m walking you through the actual thought process, research, and decision-making behind evaluating a hospitality investment — from the mindset shifts that led me here to the early due diligence on the property itself.

If you’ve ever wondered what it really looks like to explore a larger hospitality project — especially before there’s even an offer on the table — this episode gives you a behind-the-scenes look at the process.

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A Shift in Mindset: Human Design, Intuition, and “Engineering Luck”

Before diving into the property itself, I share two unexpected ideas that have recently shaped the way I approach business decisions.

Through my membership in Action Academy, I’ve been exposed to new perspectives on entrepreneurship that go beyond traditional hustle culture.

One of those ideas is human design, a personality framework based on your birth information that highlights how you naturally operate in the world.

According to my human design profile, I’m a Projector and Seer, which means:

• I work best when I allow space between projects rather than constantly pushing forward.
• My intuition is a powerful decision-making tool.
• I tend to thrive when opportunities come through invitations rather than forced outreach.

For someone who previously identified strongly with the “hard work solves everything” mentality, this insight was surprisingly freeing.

Another concept that challenged my thinking was quantum surfing, introduced by guest speaker Monica Lawrence inside Action Academy.

One study she referenced examined the difference between the top 1% of successful individuals and the remaining 99%. The surprising conclusion?

The most consistent differentiator wasn’t intelligence, connections, or effort.

It was luck.

But the real insight wasn’t that luck is random — it’s that people can create more opportunities for luck to happen.

One example from the research involved a study comparing people who considered themselves lucky with those who considered themselves unlucky.

Participants were asked to count the number of images in a newspaper.

The “unlucky” group approached the task rigidly, counting each image one by one.

The “lucky” group became curious along the way, allowing themselves to explore side articles — and in doing so, they stumbled across a page that clearly stated the total number of images in the paper.

Because they stayed open to exploration, they completed the task faster and more accurately.

The takeaway?

Curiosity creates opportunity.

And that idea plays a huge role in the story I’m about to share.

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Why I’m Leaning Into the “Boots on the Ground” Perspective

Recently, a listener left feedback describing this podcast as “boots on the ground.”

At first, I wasn’t sure how to take that.

Part of me worried it meant I sounded inexperienced.

But the more I thought about it, the more I realized that’s actually the value of this show.

You’re not just hearing polished success stories after everything is figured out.

You’re hearing the process while it’s happening.

So instead of waiting until this project is complete, I’m bringing you along for the journey from the very beginning.

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The Opportunity: An Assisted Living Facility Turned Boutique Hotel?

While visiting my hometown near Charlottesville, Virginia, I kept noticing a building that had been sitting vacant for several years.

It was previously an assisted living facility, located in a small downtown area about 15 minutes from where I grew up.

At the time, it felt like one of those “interesting someday” ideas.

But now — with more experience in hospitality and a larger network — I started looking at the building differently.

Instead of seeing an empty facility, I saw potential for something else.

A boutique hotel.

The property already had many of the structural features hospitality developers look for:

• Over 20 existing residential rooms
• Private bathrooms in every room
• Extensive plumbing infrastructure
• ADA accessibility
• Elevator access
• A large footprint with room for expansion

The building itself is 23,500 square feet on five acres, located right in the center of a small downtown area.

And across the street?

An additional two to two-and-a-half acres of undeveloped land.

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Why the Location Is So Interesting

What makes this opportunity particularly compelling is the surrounding region.

Within about 15 miles of the property, there are numerous wineries that host weddings and events.

But here’s the key detail:

There are very few nearby accommodations for guests attending those events.

The closest hotels are roughly 40–45 minutes away.

That means wedding guests, visitors, and travelers in the area often have limited lodging options.

From an investor’s perspective, that gap in the market is worth paying attention to.

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The First Site Visit

In early January, we conducted our first site visit.

At that point, we weren’t even sure we’d be able to get inside.

The building had been vacant for nearly three years, and we didn’t know what condition it would be in.

But once we were able to walk through the property, we were pleasantly surprised.

The current owner had continued maintaining the building even while it sat empty.

• Utilities were still active.
• Heat was running.
• Landscaping was maintained.

Even more interesting was discovering a former medical office space inside the building that served residents when it operated as an assisted living facility.

Instead of seeing that as unused space, we immediately began imagining a new possibility.

What if that space became a spa?

In a region already known for wineries, hospitality, and wellness destinations, that addition could complement the hotel experience perfectly.

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The Due Diligence Process

At this stage, the project is still very much in the research phase.

Because the building isn’t currently generating revenue, traditional hospitality underwriting methods don’t apply.

Instead, we’re evaluating the opportunity through a combination of:

• Renovation cost estimates
• Market research
• Regional ADR (Average Daily Rate) data
• Occupancy rates from nearby properties
• Tourism demand from wineries and events

Another major factor is that part of the property sits within a historic district.

That opens the door to potential historic renovation tax credits, which could significantly impact the financial structure of the project.

These tax credits often require a detailed approval process and specific renovation standards, so that’s another layer of due diligence we’re currently navigating.

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The Role I Would Play in the Project

If this project moves forward, my role would likely center around two key areas:

Local Market Insight

Because this town is where I grew up, I have familiarity with:

• The local community
• Regional tourism patterns
• Nearby vendors and contractors
• Zoning considerations and city relationships

That kind of on-the-ground knowledge can be extremely valuable in early-stage hospitality projects.

Branding and Marketing

Of course, branding is where I naturally focus.

One fascinating discovery in our research is the history of the town itself.

The area was historically known as a crossroads for travelers, largely due to a railroad line that once ran through the town.

For generations, people stopped there to rest, gather, and exchange ideas.

That legacy of hospitality is woven into the town’s identity — which opens up powerful storytelling opportunities if this building becomes a hotel.

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What Happens Next

Right now, we’re still gathering information.

That includes:

• More accurate renovation estimates
• Further market research
• Understanding potential tax credit opportunities
• Evaluating financing structures
• Determining a potential offer price

It’s a research-heavy phase, but it’s also an exciting one.

Because at this stage, the possibilities are wide open.

And if there’s one lesson from this episode, it’s that sometimes the best opportunities start with simple curiosity.

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This project may or may not ultimately come together.

But sharing the process — the research, the ideas, the questions — is exactly what “boots on the ground” looks like.

Entrepreneurship rarely happens in neat, predictable steps.

Sometimes it starts with noticing an empty building and asking one simple question:

What could this become?

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🎧 Want to hear the full story?
Listen to this episode of the Brand & Market Podcast to hear the complete behind-the-scenes journey.