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
More Money, Less Problems
Mark Lumpkin sits down with Nick Swanson and Alex from Chetu, a technology firm that has spent 25 years helping hotels, operators, and brands navigate digital transformation. Together, they unpack how AI is changing hospitality and what short term rental operators can do right now to stay ahead.
Nick and Alex break down what agentic AI actually is, how it is already being used behind the scenes in hotels and restaurants, and why the next wave of tools will feel more like talking to a real person than fighting a phone tree. They also explain how STR hosts can use AI to refresh listings, improve Airbnb ranking, mine historic guest data, streamline pricing, and elevate guest communication without hiring a huge team.
They share the story of Chetu's journey from tiny startup to a global company, and why AI is exposing digital weak spots that were papered over by old “transformation” slides. The conversation also tackles the big question on everyone’s mind: AI versus virtual assistants. Will AI replace VAs, or work alongside them
In this episode, you will learn:
- What agentic AI is and how it fits into hospitality
- Practical ways AI can increase bookings and guest satisfaction in STRs
- How to use AI to automate repetitive workflows and free your team to do higher value work
- Why historic guest data is a goldmine that humans will never fully unlock on their own
- How to think about cost, data security, and using off the shelf tools versus custom builds
If you are serious about using AI to grow your short term rental business, this episode will give you a clear, grounded starting point.
__
Episode Sponsored By:
STR Search
STR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
