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
The Robots Are Coming For You!
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In this episode, Mark Lumpkin sits down with Jay Ullrich, STR operator, tech founder, and CEO of HostBuddy.ai - to unpack his journey from cold-calling landlords and scrubbing his own units to managing 45+ short-term rentals and launching one of the most advanced AI guest communication tools in the industry.
Jay shares:
- How he built a thriving STR property management company without outbound sales
- What he learned scaling from 1 arbitrage unit to 45+ managed homes in San Diego
- Why HostBuddy.ai was born out of late-night guest message fatigue, and how it works
- How today’s AI tools can help you reduce stress, automate communication, and increase profits
- Why HostBuddy stands out from every other AI chatbot in the space
- The challenges of scaling and how to maintain trust as you grow
- How to test HostBuddy live on their site (no signup required!)
Whether you’re just starting in cohosting or you’re managing dozens of units, this episode is packed with firsthand experience and future-focused insights that can save you time, money, and headaches.
Try HostBuddy's AI for yourself → https://hostbuddy.ai
Connect with Jay: jay@hostbuddy.ai | @hostbuddy_ai on Instagram
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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
