How one entrepreneur built a thriving large-group rental on the Kentucky Bourbon Trail—after 40 banks said no

What happens when you blend ice cream, muffins, and entrepreneurship with a healthy dose of persistence? For Andrew Llewellyn, the result was a 10,000-square-foot short-term rental in Louisville that now welcomes milestone celebrations, bachelor parties, and corporate retreats.

Andrew’s story didn’t start with real estate. He first ran ice cream shops and a food truck before pivoting during COVID. When plans for a bakery fell through, he turned to Airbnb—transforming a building into a one-of-a-kind large-group property that can host up to 42 guests.

But success didn’t come easy. Andrew faced major challenges:

• Financing hurdles: 40 banks turned him down before one finally said yes.
• Renovation struggles: Managing construction while running another business pushed him to his limits.
• Operations at scale: Turning over a property for 42 guests required building a systemized cleaning team from the ground up.

Through it all, Andrew learned to stay focused on the guests he wanted to serve. By targeting milestone events and corporate groups, he created a property that delivers exactly what his customers need—and commands premium rates.

Today, Andrew balances parent-child listings to maximize occupancy, leans on dynamic pricing to stay competitive, and uses blogging and SEO to grow direct bookings. His advice to other hosts? Keep going. Persistence pays off, even when the obstacles feel overwhelming.

Whether you host a single-family home or are eyeing your own large-scale project, Andrew’s journey proves that clarity, systems, and tenacity can turn big dreams into reality.s.

Download a transcript of this episode.

Resources:

• PriceLabs – Dynamic pricing software that automatically adjusts your rates based on real-time demand.
• SuperStay STR – Andrew’s direct booking site for large group stays in Louisville, Kentucky.
  Minoan – Outfit your short-term rental with guest-loved brands at insider pricing.
•  Avalara – Book a demo to save $100
• #STRShareSunday: @vistaaframe
• Submit your property for our next #STRShareSunday at strshare.com

#STRShareSunday

@vistaaframe

This stunning black A-frame in Flagstaff has completely stolen our hearts! Perched high in towering pines with panoramic views, it’s the perfect blend of remote mountain retreat and convenient location — just 10 minutes to downtown Flagstaff and 20 minutes to Snowbowl.

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