How This Entrepreneur Built His First Hotel

The rise and fall of Airbnb’s popularity has created a unique opportunity for investors to innovate in the short-term rental space. For Andrew Llewellyn, CEO and Founder of Super Stays STR, this shift opened the door to reimagining large-group accommodations. What started as an idea to convert an old office building into a bakery quickly evolved into Swepson Guesthouse—a 10,000-square-foot boutique property with 15 bedrooms, 10 bathrooms, and 21 beds, now hosting up to 42 guests in downtown Louisville, Kentucky.

In this article, we’ll break down Andrew’s transformation of Swepson Guesthouse into a profitable hospitality business and provide actionable steps for anyone looking to follow a similar path in commercial real estate investing.

Finding the Right Opportunity

Andrew’s story highlights a key principle for aspiring commercial real estate investors—adaptability. Initially, Andrew’s plan was to expand a wholesale bakery business into a commercial space. However, unexpected construction costs and zoning challenges led him to pivot and transform the property into a boutique hospitality business.

For investors transitioning from residential to commercial real estate, this approach illustrates the importance of identifying flexible-use properties that can adapt to changing strategies and market demands.

Why Flexible-Use Properties Matter

For the aspiring commercial investor, flexibility offers two major advantages:

Reduced Risk - Properties with mixed-use potential provide multiple exit strategies, whether through residential, office, or hospitality conversions. This safeguards against losses if the original business plan doesn’t pan out.
Value-Add Opportunities - Adaptive reuse properties allow investors to unlock hidden value by modernizing and repositioning underutilized spaces. These projects often yield higher returns than traditional real estate plays.

Key Features of Flexible-Use Properties

Mixed-Use Zoning - Look for properties that already allow for both commercial and residential applications. These zoning designations reduce permitting challenges and enable multi-purpose transformations.
Structural Versatility - Focus on buildings with open floor plans, high ceilings, and modular layouts. These features simplify renovations and expansions.
Prime Locations - Properties near business districts, entertainment hubs, or tourist attractions provide a built-in customer base for short-term rentals or boutique hotels.
Historical Character - Older buildings often qualify for tax incentives and attract premium tenants due to their unique architectural appeal.

How to Identify Adaptable Properties

1. Research Emerging Markets

Focus on cities or neighborhoods experiencing growth in tourism, tech startups, or business relocations.
Tools like CoStar or LoopNet can help you locate commercial listings in high-demand areas.

2. Evaluate Building Features

Inspect floor plans for layouts that can easily be divided into units, suites, or event spaces.
Check for compliance with ADA (Americans with Disabilities Act) requirements and existing utilities like HVAC, plumbing, and electrical capacity.

3. Analyze Multiple Revenue Models

Model different scenarios, such as:
- Short-term rentals for groups (e.g., bachelor parties, corporate retreats).
- Long-term leases for office or residential tenants.
- Hybrid models combining event rentals and hospitality stays.

4. Assess Regulatory Feasibility

Engage local zoning authorities early to confirm whether short-term rentals or boutique hotels are permitted.
Budget for potential zoning variances if the property requires rezoning.

2. Designing for Large Group Experiences

The short-term rental market has become increasingly saturated with single-family Airbnb listings, making it harder for investors to stand out and command premium pricing. Instead of competing in this crowded space, Andrew Llewellyn identified a high-demand, underserved niche—large group accommodations—and designed Swepson Guesthouse to cater specifically to this audience.

This approach serves as a blueprint for aspiring commercial real estate investors looking to transition from traditional residential rentals to scalable, hospitality-focused properties that generate higher returns.

Why Focus on Large Group Niches?

For investors moving into commercial real estate, targeting group travel niches like corporate retreats, wedding parties, sports teams, and family reunions offers three key advantages:

Reduced Competition - Most properties aren’t equipped to handle groups of 15–40 guests, leaving a supply gap in many markets.
Premium Pricing - Large groups are often willing to pay more for exclusive-use spaces that provide privacy, comfort, and custom experiences—leading to higher nightly rates and longer bookings.
Repeat Business - Corporate retreats and family reunions are recurring events, providing built-in demand for future bookings.

Key Features for Large Group Properties

Andrew designed Swepson Guesthouse with scalable, group-focused layouts to maximize occupancy and guest satisfaction. Here’s what made it work:

Modular Layouts for Flexibility
- Five apartment-style units that can be booked individually for smaller groups or combined for full-building buyouts.
- Configurations to suit corporate retreats during the week and social events on weekends, offering maximum flexibility.
Corporate Retreat Capabilities
- A third-floor conference setup with AV equipment, large tables, and private spaces for brainstorming sessions.
- Easy transitions from formal meetings to casual gatherings, making it ideal for work-play balance.
Entertainment-Focused Amenities
- Open-concept living spaces for group activities like game nights, dinners, and cocktail hours.
- Spaces adaptable for bachelor/bachelorette parties, including beer pong setups and multiple kitchens for entertaining.
Privacy and Exclusivity
- Entire-building rentals for exclusive use, offering privacy and reducing disruptions—something hotels often can’t provide.
- Layouts designed to encourage togetherness while also offering separate suites for downtime.

How Investors Can Tap Into Large Group Travel Niches

1. Understand Your Target Audience

Research the types of groups visiting your area—weddings, sporting events, corporate offsites, or seasonal festivals.
Identify gaps in the market, such as a lack of large rental homes or properties with dedicated meeting spaces.

2. Build Flexible Floor Plans

Invest in multi-unit properties or large buildings with open layouts that can be divided or combined.
Focus on features like multiple kitchens, bathrooms, and living rooms to accommodate comfort and privacy.

3. Incorporate Amenities for Group Stays

Add features like conference tables, projectors, and breakout areas for business retreats.
Equip kitchens for catering and provide game rooms or bars for social events.

4. Offer Concierge Services

Provide trip-planning assistance for large groups to streamline logistics.
Partner with local businesses for services like catering, guided tours, and event planning to enhance the guest experience.

3. Financial and Market Analysis

A key factor in the success of Andrew’s Swepson Guesthouse was his financial discipline and ability to adapt to market signals. Instead of going all-in on a single concept, Andrew designed a flexible investment strategy that allowed him to test the waters and pivot as needed.

His initial underwriting treated the property as five separate Airbnb units, providing a fallback plan in case the large-group rental concept didn’t perform as expected. However, once market demand validated his niche group-travel model, he scaled operations and focused entirely on the boutique hospitality approach—yielding premium pricing and consistent income.

This process highlights an essential lesson for aspiring investors: financial analysis and market testing must precede full-scale development. By balancing conservative projections with creative vision, Andrew minimized risk while unlocking high-profit potential.

Why Financial Flexibility Matters for Investors

For aspiring commercial investors—especially those transitioning from residential real estate—financial flexibility is critical.

1. Minimizes Risk of Failure

Starting small or incorporating fallback plans protects against market volatility or unproven concepts.
Allows for course corrections if initial projections prove inaccurate.

2. Enables Scalability

Testing multiple models (e.g., individual rentals, corporate retreats, event bookings) identifies the most profitable niche before committing extensive resources.
Successful testing builds confidence for future expansions.

3. Attracts Financing

Well-developed financial models and contingency plans make lenders and investors more likely to provide funding.
Proven cash flow during testing periods reduces perceived risk.

Breaking Down Andrew’s Financial Model

1. Conservative Underwriting

Andrew originally modeled the Swepson Guesthouse as five individual Airbnb units, treating each as a standalone short-term rental.
This conservative approach ensured that the property would remain profitable even if the large-group niche failed to attract consistent bookings.

2. Testing Market Demand

Rather than making assumptions, Andrew listed units on Airbnb to test pricing and occupancy rates.
By tracking performance metrics (e.g., inquiries, weekend bookings, group-size requests), he validated demand before fully transitioning to the group-travel concept.

3. Flexible Renovation Budget

With an initial renovation cost of $450,000, Andrew prioritized upgrades that enhanced revenue potential (e.g., multiple kitchens, living spaces, and flexible layouts).
He avoided over-investing in luxury finishes and focused on functional, high-impact improvements to keep costs manageable.

4. Premium Pricing Strategy

Once demand was validated, Andrew raised nightly rates to reflect the premium experience offered by Swepson Guesthouse—an exclusive-use property with custom concierge services.
This pricing structure resulted in higher margins and consistent income, far outpacing revenue from standard short-term rentals.

4. Key Lessons for Real Estate Investors

Andrew’s transformation of Swepson Guesthouse into a high-performing, boutique hospitality business is more than just a success story—it’s a roadmap for commercial real estate investors looking to scale their portfolios. His approach demonstrates how flexibility, creativity, and strategic positioning can help investors outperform traditional short-term rental models and generate premium returns.

Below, we break down the five key lessons investors can apply to replicate Andrew’s success.

1. Start with Adaptable Properties

Mixed-use spaces and flexible layouts provide the foundation for scalable, creative projects. Andrew’s decision to convert a historic office building into modular apartment-style suites highlights the importance of selecting properties that support multiple revenue strategies.

Why It Works:

Risk Mitigation: Adaptable properties can pivot between short-term rentals, long-term leases, and corporate housing if market conditions shift.
Scalability: Flexible layouts make it easier to expand services or divide spaces as demand changes.
Market Positioning: Unique layouts create a competitive edge compared to cookie-cutter hotel rooms.

Action Steps:

Look for mixed-use zoning and older buildings that can be reconfigured without major structural changes.
Prioritize multi-unit buildings that can accommodate multiple income streams (e.g., event spaces, rentals, or coworking areas).
Analyze the potential for future expansions to capitalize on growth opportunities.

2. Target Underserved Markets

Rather than competing in the crowded single-family Airbnb market, Andrew focused on large group bookings—a niche often ignored by traditional hotels and short-term rental owners.

Why It Works:

Less Competition, Higher Margins: Large groups value privacy and shared spaces, enabling investors to charge premium rates.
Built-in Demand: Weddings, corporate retreats, sports teams, and family reunions create recurring business opportunities.
Scalable Concept: Once proven, group-focused layouts can be replicated in other markets, forming the foundation for a multi-property portfolio.

Action Steps:

Conduct local market research using tools like AirDNA to identify niche audiences—such as sports teams, wedding parties, or tech company offsites.
Create modular layouts that can adapt to different needs (e.g., split suites for smaller groups or combined spaces for full-building rentals).
Test demand by marketing to niche audiences through specialized platforms and partnerships with local event planners.

3. Focus on Guest Experiences

Andrew didn’t just provide a place to stay—he offered memorable, curated experiences that set Swepson Guesthouse apart. From custom itineraries and bourbon tastings to concierge services, his focus on elevating guest experiences helped him charge premium prices and build repeat bookings.

Why It Works:

Differentiation: Unique guest experiences distinguish boutique properties from hotels and generic Airbnbs.
Loyalty & Referrals: Guests are more likely to return and recommend the property to others when they receive concierge-level service.
Higher Revenue Per Stay: Guests pay more for personalized experiences that simplify planning and maximize enjoyment.

Action Steps:

Add concierge services like itinerary planning, group dinners, and private tours to enhance the stay.
Partner with local businesses (restaurants, event planners, and tour operators) to provide custom packages for guests.
Highlight guest experiences in marketing campaigns and website content to attract premium bookings.

4. Streamline Operations

Managing a large hospitality space can be complex, but Andrew focused on efficiency and scalability by simplifying inventory, standardizing furnishings, and prioritizing staff retention.

Why It Works:

Cost Savings: Bulk ordering and standardized supplies reduce costs and simplify replacements.
Consistency: Guests experience the same high-quality service across all bookings, boosting reviews and reputation.
Staff Productivity: Trained and retained staff improve operational efficiency and reduce turnover costs.

Action Steps:

Use hospitality management software to handle bookings, cleaning schedules, and guest communications.
Stock extra inventory of frequently used items (plates, furniture, décor) to prevent disruptions due to damage or wear and tear.
Invest in staff training programs and culture-building activities to retain employees and maintain service quality.

5. Market Beyond Airbnb—Own Your Audience

While Airbnb provided initial exposure, Andrew quickly shifted focus to direct bookings through his website to increase profitability and control the guest experience.

Why It Works:

Lower Fees, Higher Profits: Avoid third-party platform fees and capture more revenue per booking.
Repeat Customers: Build relationships with past guests by offering exclusive discounts and direct communication.
Brand Authority: A standalone website and SEO-optimized content establish credibility and attract organic traffic.

Action Steps:

Build a professional website with direct booking capabilities and integrate payment processing tools.
Focus on SEO strategies by targeting niche keywords (e.g., “Louisville corporate retreats” or “large group rentals in Louisville”).
Leverage email marketing to stay connected with past guests and promote seasonal offers.
Partner with local event planners and travel agents to secure direct referrals.

Final Thoughts: Build Smarter, Scale Faster

Success in commercial real estate doesn’t come from following trends—it comes from anticipating needs and creating unique experiences that others overlook.

By starting small, testing demand, and scaling strategically, investors can:

Reduce risk.
Maximize profits.
Create repeatable systems.

For aspiring investors looking to build long-term wealth, the CRE Accelerator Mastermind provides the step-by-step guidance needed to analyze markets, develop scalable concepts, and streamline operations.

Ready to make your move? Start by identifying underserved niches, building adaptable layouts, and focusing on premium guest experiences—just like Andrew did with Swepson Guesthouse.

Learn more about the CRE Accelerator Mastermind