STR Investing, The Podcast

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.

  1. 2d ago

    AI-Generated Direct Bookings

    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 workUsing automation to increase direct bookingsWhy hospitality still matters more than AIThe future of Airbnb algorithms and booking platformsAI tools that save operators hours every weekHow hosts can leverage guest data more effectivelyThe importance of owning your customer relationshipsReal examples of AI-generated revenue growthMark 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. __ 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

    29 min

  2. 6d ago

    Monday Market Data: Breakdown of Galveston, TX Market

    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.

    8 min

  3. May 22

    STR Lessons From Surviving a Million Dollar COVID Loss

    What happens when a short-term rental operator loses over $1,000,000 during COVID? In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Jason Baxter to talk about the highs, lows, and future of the short-term rental industry. Jason shares how he accidentally got started in Airbnb over 10 years ago, scaled to a portfolio of 50 lofts in Montreal, and then watched everything collapse during the COVID shutdowns in Canada. Facing bankruptcy, Jason rebuilt from the ground up by leaning into technology, automation, hospitality, and smarter booking strategies. In this episode, they dive into: The early days of Airbnb automationSurviving a million-dollar loss during COVIDThe biggest mistakes STR hosts make with techWhy hospitality still matters more than AIHow Airbnb algorithms really workPricing strategy and booking optimizationThe future of direct bookings and alternative platformsWhy “short-term rentals are a long-term game”Jason also explains how the right positioning and strategy helped one property grow from $65,000/year to over $210,000/year in bookings. If you’re an STR investor, property manager, or host trying to scale smarter, this is an episode you don’t want to miss. __ 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

    34 min

  4. May 18

    Monday Market Data: Breakdown of Charleston, SC Market

    Mark Lumpkin breaks down the short-term rental market in Charleston — one of the most desirable and tightly regulated STR markets in the Southeast. Charleston is a heavyweight market:  Over 8 million annual visitors More than $14 billion in tourism impact Strong ADRs and occupancy  And some of the strictest STR regulations in the country In this episode, Mark dives into:  Why Charleston continues to attract massive tourism demand  Where travelers are coming from and why they visit  The importance of weddings, bachelorette groups, and food tourism  Why Charleston’s strict regulations actually create opportunity  What investors need to know before buying in the market The data shows that Charleston isn’t just another beach destination — it’s a premium travel market with strong demand, limited supply, and travelers willing to spend. If you can secure the right property in the right zoning area, Charleston can be an incredibly powerful STR market.

    9 min

  5. May 15

    Smart Locks, Smarter Stays with Amber Baron

    Smart locks are no longer optional in short-term rentals. In this episode, Mark Lumpkin sits down with Amber Baron from Dormakaba to talk about why access control is one of the most overlooked parts of the guest experience — and how bad systems can completely ruin a stay. They break down: Why check-in is one of the most important moments in hospitalityThe biggest mistakes hosts still make with property accessWhy physical keys are creating massive operational headachesHow smart lock systems integrate with PMS software and automationThe importance of backup systems and emergency access plansHow remote operators can manage properties more securelyWhere AI and smart access technology are headed nextReal stories from the field — including a property manager literally Kool-Aid-manning through a door to save a guest stayIf you own, manage, or plan to scale short-term rentals, this episode is packed with practical insights on security, operations, and creating a smoother guest experience. Listen now and learn why access is the new front desk in hospitality. __ 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

    37 min

  6. May 11

    Monday Market Data: Breakdown of Chattanooga, TN Market

    Chattanooga might be one of the biggest STR opportunities flying under the radar. In this week’s Monday Market Data Report, Mark Lumpkin breaks down why Chattanooga is still in the early innings of the amenity arms race — and how investors can create a true “unicorn” property with surprisingly little competition. The numbers are eye-opening: Only 18% of listings have hot tubsOnly 3.8% have swimming poolsLess than 1% have movie theaters, saunas, mini golf, or pickleball courtsTranslation? Most properties in Chattanooga still look basic. That creates massive opportunity for investors willing to buy the right property, add strategic amenities, and stand out in a market that hasn’t fully matured yet. In this episode, Mark breaks down: Why Chattanooga’s tourism market keeps growingThe events and attractions driving travel demandWhich amenities are becoming mandatoryWhich amenities almost nobody has yetHow to create a top-performing STR without competing against thousands of heavily amenitized propertiesIf you’ve been looking for a market where you can still get ahead of the curve instead of fighting oversaturation, this episode is worth your attention. __ 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

    7 min

  7. May 8

    Building my First Micro Resort

    AI is changing business faster than ever — and short-term rentals are no exception. Mark Lumpkin sits down with Nick Korwin to talk about building a luxury micro resort from the ground up while working full-time in the AI and autonomous vehicle industry. Nick shares: How he transitioned from traditional rentals into short-term rentalsWhy he chose to build a micro resort instead of buying more housesThe lessons learned developing raw land into luxury cabinsHow he’s using AI to automate parts of his STR businessWhy unique stays continue to outperform average rentalsThe realities of scaling while still working a W2 jobHow technology is reshaping hospitality and operationsThe biggest mistakes investors make when developing propertiesThey also dive deep into the future of AI, automation, hospitality, and what STR operators should be paying attention to over the next few years. If you’ve ever thought about building something bigger than a traditional Airbnb — or wondered how AI could give you an edge in business — this episode is packed with insights. __ 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

    37 min

  8. May 1

    STR Marketing Without Airbnb

    STR software is evolving fast - but the best operators know the real edge isn’t just automation. In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Amber Knight from bookingcloud.com to break down where the industry is headed—and what most hosts are still getting wrong. Amber shares her journey from helping scale early-stage operations at Vacasa to building new technology that drives visibility, bookings, and revenue for short-term rental operators. They dive into: • How automation is reshaping the STR industry • Why most hosts are still behind on direct booking strategy • The real role of AI in your business (and what it can’t replace) • How top operators are driving more visibility and bookings • Why guest experience is still the ultimate differentiator As Amber puts it: you can automate processes—but you can’t automate how a guest feels.  If you’re managing properties, building a brand, or trying to scale your STR business, this episode will challenge how you think about tech, marketing, and hospitality. Listen now and start building a more profitable, experience-driven STR business. __ 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

    33 min
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About

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.

Information

  • Creator
    Taylor Jones & Mark Lumpkin
  • Years Active
    2025 - 2026
  • Episodes
    120
  • Rating
    Clean
  • Copyright
    © 2026 STR Investing, The Podcast
  • Show Website
    STR Investing, The Podcast

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