
AI-Generated Direct Bookings
From STR Investing, The Podcast by Taylor Jones & Mark Lumpkin
May 29, 2026 · 29 min · Episode 83
About this episode
The episode discusses how AI is transforming the short-term rental industry through automation and direct booking technology.
AI is moving faster than most short-term rental hosts realize. In this episode of the STR Investing Podcast, Mark Lumpkin welcomes back Boostly founder Mark Simpson for a deep dive into how AI agents, automation, and direct booking technology are changing the future of hospitality. Mark Simpson shares how he went all-in on AI at the beginning of 2026, replacing repetitive manual tasks with AI agents that now help run parts of his business 24/7. What started as simple experiments quickly turne...
People in this episode
Host: Mark Lumpkin
Guest: Mark Simpson
Topics covered
- AI in hospitality
- short-term rentals
- automation
- direct bookings
- business technology
Keywords
- AI agents
- hospitality
- automation
- direct booking technology
- short-term rental
Mentioned in this episode
Organizations: Boostly
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