What does it take to turn a 10,000-square-foot building into a thriving short-term rental that can host up to 42 guests? For Andrew Llewellyn, the answer included grit, rejection, and relentless problem-solving.

In this episode, Sarah and Annette sit down with Andrew to hear how he went from running ice cream shops and a food truck to becoming a real estate developer along Kentucky’s Bourbon Trail. Andrew shares how he convinced a bank to back his vision (after 40 rejections), why he leans on parent-child listings to maximize occupancy, and the systems his team uses to pull off back-to-back turnovers for massive groups.

You’ll learn:

• How Andrew pivoted from muffins to multi-unit rentals during COVID.
• Why defining your ideal guest avatar matters for large group stays.
• How to set up parent-child listings that increase revenue and flexibility.
• What it takes to build cleaning systems that can handle 42-guest turnovers.
• Why direct bookings and SEO fuel long-term sustainability.
• Andrew’s hard-won advice for dealing with city regulations and securing financing.

This conversation is packed with inspiration and actionable strategies—whether you host a one-bedroom cottage or are dreaming about your own large-scale project.

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.

Mentioned in this episode:

Minoan | Visit MinoanExperience.com and tell them TFV sent you!