From Wedding Venue Dreams to Airbnb Success: Our Kentucky Property Pivot

What do you do when your dream property faces 18 zoning restrictions? You pivot.

In this episode, I take you behind the scenes of our Kentucky property—originally intended to be a luxury wedding venue and now a thriving short-term rental on the Bourbon Trail. From unexpected zoning drama to interior design choices that tell a brand story, this one’s a ride.

I share the real estate misadventures that shaped our approach to short-term rentals, how we branded The Commonwealth with themed rooms inspired by U.S. commonwealths, and the specific guest experience strategies we use to maintain a 5-star Superhost status—even while managing remotely.

Time-stamps:

The first short-term rental story (1:04)

Our dreams for the Kentucky property (2:26)

Deciding to make the property a short-term rental (4:07)

Lessons learned from the Kentucky property (6:10)

From wedding venue to short-term rental (9:51)

Building the brand within the rental walls (11:34)

Power Hour (15:06)

Opening for bookings and maintaining 5-star status (16:01)

Running the rental remotely (18:27)

Our ideal guest avatar (21:01)

Next steps for the property (25:05)