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STR Investing, The Podcast

STR Investing, The Podcast

By: Taylor Jones & Mark Lumpkin
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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.


© 2026 STR Investing, The Podcast
Economics Personal Finance
Episodes
  • Monday Market Data: Breakdown of Yosemite, CA Amenities Market
    Jun 1 2026

    Yosemite is one of the most visited national parks in America, attracting more than 4 million visitors every year. But when it comes to short-term rentals, the opportunity may be even bigger than most investors realize.

    In this week’s Monday Market Data Report, Mark Lumpkin breaks down the Yosemite STR market, including travel demand, regulations, seasonality, and the amenities that separate average properties from true standouts.

    Here's what the data shows:

    • Fire Pits → 64% of listings
    • Hot Tubs → 61%
    • Pools → 13%
    • Home Gyms → 13%
    • Game Rooms → 10%
    • Saunas → 8%
    • Playgrounds → 6%
    • Waterfront → 4%
    • Pickleball Courts → 1%

    The takeaway?

    Most Yosemite rentals stop at a fire pit and hot tub. The investors who add game rooms, pools, saunas, or pickleball courts create true unicorn properties with very little competition.

    If you're looking for a mountain market where differentiation still matters, Yosemite deserves a closer look.

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    9 mins
  • AI-Generated Direct Bookings
    May 29 2026

    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


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    29 mins
  • Monday Market Data: Breakdown of Galveston, TX Market
    May 25 2026

    Mark Lumpkin breaks down the short-term rental market in Galveston — one of the fastest-growing and most competitive beach markets on the Gulf Coast.

    With over 6,000 active listings and supply up more than 50% in just two years, Galveston has become a major target for STR investors. But despite the competition, there’s still a clear path to winning.

    In this episode, Mark covers:

    • The travel demand driving Galveston tourism
    • Why cruise traffic creates consistent STR bookings
    • The amenities that are now mandatory to compete
    • And the rare amenities that can still create a true “unicorn” property

    Here’s what the market looks like today:

    • Pools → 35% of listings
    • Fire pits → 29%
    • Waterfront → 27%
    • Hot tubs → 20%

    Those are expected.

    The real opportunity comes from the amenities almost nobody has:

    • Pickleball courts → 2.2%
    • Mini golf → 1.5%
    • Movie theaters → <1%
    • Saunas → almost nonexistent

    The takeaway?
    If you want to stand out in Galveston, you need more than just a pool and a beach house.

    Show More Show Less
    8 mins
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