AI is changing short-term rental marketing—but not always for the better.

In this episode of the STR Investing Podcast, Taylor sits down with Conrad, founder of BuildUp Bookings, to break down what actually drives bookings in today’s crowded STR market.

They discuss how overused AI messaging can turn guests away, where automation still adds real value, and why authentic communication is becoming a competitive advantage for Airbnb hosts and property managers. Conrad shares practical insights from nearly a decade in STR marketing, helping operators rethink how they attract, convert, and retain guests.

Key topics covered:

• AI vs human messaging in STR marketing
• How to improve bookings without sounding automated
• Guest psychology and conversion fundamentals
• Marketing mistakes hurting Airbnb performance

If you want more bookings without relying on spammy AI tactics, this episode delivers clear, actionable insight.

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com