AI-Generated Direct Bookings

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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