STR Investing, The Podcast
Unlock financial freedom through short-term rental investing with hosts Taylor Jones and Mark Lumpkin. Each week, they sit down with the biggest names in the STR industry to uncover what’s working right now — from acquisitions and design to operations, marketing, and scaling portfolios.
Taylor has helped acquire and manage over 500+ STRs, while Mark brings years of hands-on experience transforming properties into high-performing investments.
Together, they break down real strategies, real numbers, and real stories that help investors grow smarter and faster.
Whether you’re buying your first Airbnb or expanding a multi-market portfolio, this show is your roadmap to building wealth and freedom through short-term rentals.
Subscribe and start turning your STR goals into results.
STR Investing, The Podcast
AI-Generated Direct Bookings
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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 turned into real revenue, operational efficiencies, and entirely new systems for managing guests, marketing, and direct bookings.
Throughout the conversation, they discuss the difference between basic AI chat tools and true AI agents, how operators can use AI without losing the hospitality element, and why most hosts are still thinking too small when it comes to automation.
They also break down:
- AI agents and how they actually work
- Using automation to increase direct bookings
- Why hospitality still matters more than AI
- The future of Airbnb algorithms and booking platforms
- AI tools that save operators hours every week
- How hosts can leverage guest data more effectively
- The importance of owning your customer relationships
- Real examples of AI-generated revenue growth
Mark also shares details about Boostly Connect, the new platform designed to help hosts better manage guest data, automate outreach, and improve direct booking performance.
If you’re trying to stay ahead in the short-term rental industry, this is an episode you don’t want to miss.
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Episode Sponsored By:
STR Search
STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
