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.

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    8 mins
  • STR Lessons From Surviving a Million Dollar COVID Loss
    May 22 2026

    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 automation
    • Surviving a million-dollar loss during COVID
    • The biggest mistakes STR hosts make with tech
    • Why hospitality still matters more than AI
    • How Airbnb algorithms really work
    • Pricing strategy and booking optimization
    • The future of direct bookings and alternative platforms
    • Why “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.

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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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    34 mins
  • Monday Market Data: Breakdown of Charleston, SC Market
    May 18 2026

    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.

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    9 mins
  • Smart Locks, Smarter Stays with Amber Baron
    May 15 2026

    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 hospitality
    • The biggest mistakes hosts still make with property access
    • Why physical keys are creating massive operational headaches
    • How smart lock systems integrate with PMS software and automation
    • The importance of backup systems and emergency access plans
    • How remote operators can manage properties more securely
    • Where AI and smart access technology are headed next
    • Real stories from the field — including a property manager literally Kool-Aid-manning through a door to save a guest stay

    If 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.

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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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    37 mins
  • Monday Market Data: Breakdown of Chattanooga, TN Market
    May 11 2026

    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 tubs
    • Only 3.8% have swimming pools
    • Less than 1% have movie theaters, saunas, mini golf, or pickleball courts

    Translation?

    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 growing
    • The events and attractions driving travel demand
    • Which amenities are becoming mandatory
    • Which amenities almost nobody has yet
    • How to create a top-performing STR without competing against thousands of heavily amenitized properties

    If 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.

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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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    7 mins
  • Building my First Micro Resort
    May 8 2026

    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 rentals
    • Why he chose to build a micro resort instead of buying more houses
    • The lessons learned developing raw land into luxury cabins
    • How he’s using AI to automate parts of his STR business
    • Why unique stays continue to outperform average rentals
    • The realities of scaling while still working a W2 job
    • How technology is reshaping hospitality and operations
    • The biggest mistakes investors make when developing properties

    They 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.

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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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    37 mins