We Transformed a Boring Office Into a Modern Airbnb for 42 Guests (Booked SOLID) | Andrew Llewellyn

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00:00 - Meet Andrew Llewellyn & Smart Stay’s Big Idea
00:54 - Redefining Group Hospitality & Hosting in Kentucky
03:36 - Starting Out: From Ice Cream Shops to Rentals
06:59 - Commercial Space to Short-Term Rental Success
09:29 - Transforming an Office into a Boutique Hotel
10:28 - Financing the Dream: Banks, Challenges, & SBA
13:57 - Who Books These Stays? Target Guests & Events
16:31 - Group Booking Strategies & Sales Process
18:30 - Managing Bookings, Occupancy & Flexible Listings
22:25 - Navigating Market Trends & Booking Windows
24:57 - Peak Season, Slow Season & Local Events
26:20 - Challenges of Hosting Large Groups
27:54 - Creating Unique Local Experiences for Guests
29:20 - Partnerships, Bourbon Tours, and Personal Touches
30:29 - Marketing, OTAs, and Return Guest Strategy
33:14 - Turnover Secrets: Cleaning & Staffing Efficiency
35:51 - Advice for Aspiring Hosts & Finding a Mentor
36:38 - Final Thoughts: Thinking Big & Niche Strategies
37:28 - Episode Wrap Up & Where to Learn More


What happens when an ice cream shop owner decides to reinvent hospitality in the heart of bourbon country? ????????


In this episode, we sit down with Andrew Llewellyn, the creative force behind some of Louisville’s most exciting group-focused short-term rentals. From transforming forgotten commercial buildings into stylish hangout destinations to curating unforgettable experiences for bachelor parties, corporate retreats, and bourbon-loving travelers, Andrew has mastered the art of blending comfort, design, and storytelling.


Tune in as Jason and Andrew dive into how a bold vision — and a little Kentucky grit — can turn overlooked spaces into thriving hospitality hubs. You’ll hear about the power of niche marketing, the importance of creating experiences (not just accommodations), and what it really takes to stand out in today’s competitive short-term rental world.


Whether you’re an aspiring host, an entrepreneur, or just love a great reinvention story, this conversation will leave you inspired to think bigger about what’s possible in hospitality.




Things we discussed in this episode:


Andrew Llewellyn’s journey from ice cream shops to short-term rentals.
Repurposing commercial buildings for large-group lodging.
Hosting bachelor parties and corporate retreats under one roof.
Integrating unique local experiences, especially bourbon-centric activities.
Overcoming challenges with permits, city officials, and securing bank financing.
Booking trends, windows, and group sales strategies.
Handling guest communications for large groups and ensuring personalized hospitality.
Innovative cleaning processes, staff management, and keeping costs down.
Marketing approaches using SEO, OTAs, and targeting conventions.
Advice for aspiring hosts: mentorship, vision, and niching for business success.


Get in touch with Andrew:


Instagram - ⁠https://www.instagram.com/iamandrewllewellyn/⁠
Facebook - ⁠⁠⁠https://www.facebook.com/Superstayslouisville/⁠
Website - ⁠⁠⁠https://andrewllewellyn.com/⁠
⁠https://superstaysstr.com/⁠


#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals
#GroupTravel #Hospitality #LouisvilleKY #BourbonTrail #VacationRental #TravelPodcast #Entrepreneurship #SmartStays




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