From Handwritten Checks to Managing 115+ STRs Across 14 States w/ Landon Schlabach

In this episode, Landon Schlabach shares his remarkable journey from flipping houses to building a thriving short-term rental property management company. Starting with just a few homeowners and handwritten checks, Landon scaled his operations to managing over 115 homes across 14 states—with deep roots in the Amish and Mennonite communities.

We dive into:

• Why he pivoted away from rental arbitrage early on
• How the pandemic became an unexpected growth accelerator
• The scrappy early days of doing everything solo
• How a remote cabin in Pennsylvania changed everything
• Why not every investor is in it for cash flow—and why that’s okay
• His approach to building relationships, earning trust, and growing organically

Whether you're just getting started or scaling your STR business, Landon's story is packed with lessons on grit, trust, and jumping in before everything’s perfect.

🎧 Tune in for one of the most down-to-earth origin stories in the space.

→ Learn more about Landon and his team: bnbbreeze.co/our-team
→ Attend Landon’s upcoming STR Summit in 2025 (use code strcribs10 for a discount): The STR Summit – Keys to Cash Flow

What if your short-term rental could save you hundreds of thousands in taxes and generate serious cash flow? That’s exactly what happened to Derek Gisreal. In this episode of STR Investing, Derek shares how a single investment—originally just a tax strategy—became a full-fledged short-term rental business.

We cover:

• The tax loophole that saved him nearly $200K
• How he tripled the revenue of an existing STR
• Using a cash-out refi to scale faster
• The power of personalized guest experiences—handwritten notes, welcome screens, and more
• Partnering with developers to create STR-ready homes

Derek and his wife turned their passion for travel and design into a profitable STR business. Tune in to hear their journey and get practical tips to optimize your own rental!

Are you tired of high OTA fees eating into your short-term rental profits? In this episode, Mark Lumpkin sits down with direct booking expert Mark Simpson, founder of Boostly, to uncover the secrets to maximizing direct bookings while keeping a balanced approach to Airbnb, Booking.com, and other platforms.

Mark shares valuable insights on:

• The real percentage breakdown of direct vs. OTA bookings and why 65% direct is the sweet spot.
• Why going 100% direct booking can be just as risky as relying entirely on OTAs.
• Simple but powerful strategies to drive direct bookings—including a game-changing messaging tactic that can land you instant reservations.
• The biggest mistakes hosts make with pricing and why some direct booking sites charge more than Airbnb (and how to fix it!).
• The top tools and tactics for increasing direct bookings, including Get Directo and other must-have resources.
• How to structure your OTA listings to drive traffic to your direct booking site without breaking platform rules.

Mark Simpson has helped set up over 1,000 direct booking websites, and he’s here to share his playbook on how to make your short-term rental business thrive.

Connect with Mark Simpson and get the exact template he uses to generate bookings: DM him “template” on Instagram @boostlyuk.

Don’t forget to like, subscribe, and share this episode with your fellow hosts.

Let’s take control of our bookings!

Host Taylor sits down with tax strategist Nathan Sosa to break down the biggest tax advantages available to short-term rental investors. They dive deep into key strategies, including material participation, real estate professional status, cost segregation, bonus depreciation, and the game-changing 1031 exchange.

Whether you’re a first-time investor or managing a growing portfolio, this episode is packed with expert insights to help you maximize deductions, optimize cash flow, and legally minimize your tax burden.

Don’t leave money on the table—tune in and learn how to make tax laws work in your favor!

In this episode, new host Mark Lumpkin sits down with industry veteran Paul Kromidas, who transformed his career at Airbnb into launching a highly successful short-term rental business.

Paul explains how he overcame “imaginary barriers”—a common mindset among parents and aspiring investors—and embraced bold, calculated risks to build an asset-heavy, cash-flow–rich model. He offers actionable insights on raising capital, balancing host and guest experiences, and leveraging innovative strategies in today’s evolving market.

Whether you’re just starting out or looking to scale your portfolio, Paul’s journey provides a powerful roadmap to achieving long-term success in short-term rentals.

Check out his website here: https://www.summeros.com/

Taylor Jones sits down with Connor Cushman, a sharp short-term rental agent and investor, to explore his innovative "slow burster" strategy—a refined twist on the traditional buy, rehab, rent, refi, repeat model. Connor explains how blending the steady fundamentals of long-term rentals with the high revenue and cash flow of short-term rentals lets you hold a property for a full year of proven performance, thereby transforming equity and opening doors to premium refinancing or sale opportunities.

Drawing on his experiences in North Georgia’s competitive market, he breaks down the importance of smart property selection, strategic amenity upgrades, and keeping an eye on market fundamentals like interest rates and ROI. Whether you’re a budding investor or a seasoned pro looking to 10x your results, this conversation is packed with actionable insights to elevate your STR game.

Join us for Mark Lumpkin’s very first episode as the newest host of the STR Investing Podcast! In this debut, Mark interviews Rachel Vigil, a hands-on short-term rental owner and the founder of Up Close Marketing—to discuss how she bootstrapped her way into buying her first cabin, then expanded into properties in Big Bear and Maui. Rachel shares her secrets on delivering exceptional guest experiences through small, thoughtful touches that lead to stellar reviews and repeat bookings. She also reveals how her new company provides hosts with free, high-quality products to delight visitors.

Tune in as Mark dives headfirst into the world of STR podcasting, gleaning real-life lessons in hospitality, financing, and long-term wealth building from an investor who’s living proof that success in vacation rentals is within anyone’s reach.

Check out her website here: https://www.upclosemktg.com/

In this episode of the STR Investing Podcast, host Taylor interviews seasoned short-term rental entrepreneur Josh Hatter, who has scaled from a single one-bedroom condo to managing over 100 listings and operating boutique hotels. Josh shares how early challenges pushed him to build a business centered on solid fundamentals, rather than relying on a “quick win” mentality. He unpacks the importance of accurate underwriting, avoiding emotional decisions, and knowing when to invest in the right team and technology to support sustainable growth. Josh also offers a preview of his new educational venture aimed at helping investors bypass industry hype and access proven, expert-driven strategies.

Whether you’re just starting out or looking to refine your approach, this episode provides a reality check on what it takes to succeed in a more mature, data-driven short-term rental market.