STR Investing, The Podcast

Taylor is joined by Galiano Tiramani, co-founder of Boxabl—the groundbreaking housing company known for building foldable, factory-made homes that can be deployed in under a day. From military housing to backyard ADUs and Airbnb-ready tiny homes, Galiano walks through how Boxabl is shaping the future of modular living and short-term rental opportunities.What you’ll learn in this episode:How the “Casita” unit is built, shipped, and set up in as little as one hourThe RV loophole that bypasses permitting and building code bottlenecksWays Boxabl homes are already being used for disaster relief, workforce housing, and STRsPlans to expand into larger homes, townhouses, and multi-unit developmentsWhy Boxabl is considering becoming its own real estate developerHow ADU-friendly laws in states like California and Arizona are opening doors for investorsIdeas for turning Boxabl units into high-performing Airbnb properties, roadside motels, or couples’ getaway communitiesIf you’re in real estate, hospitality, or just love innovation—this is one to bookmark.Connect with Boxabl: Email: hello@boxabl.com Website: boxabl.com

We sit down with Chris Van Arnam, an STR operator who’s not just building high-performing short-term rentals in the Smoky Mountains, but doing it while living halfway across the world in Italy.Chris walks us through how he built a 10-cabin portfolio rooted in data, operational efficiency, and design differentiation. He opens up about why he sold off part of his portfolio, how he pivoted into new construction, and what it’s really like managing from a different continent.We unpack:How Chris sourced and scaled his first 10 propertiesThe power of data when choosing a marketWhy operational density matters—and how to achieve itWhat makes a short-term rental truly “differentiated”The hard lessons from new construction vs. heavy renosBuilding a property management company (even when you didn’t plan to)How to operate a U.S.-based STR portfolio from Europe with precisionWhether you're just getting started or are in the thick of growing your portfolio, this episode is packed with real-world insights from someone who’s quietly built a scalable STR business from scratch.🎧 Tune in, take notes, and get ready to think differently about scale, systems, and strategy.

From Handwritten Checks to Managing 115+ STRs Across 14 States w/ Landon SchlabachIn 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 onHow the pandemic became an unexpected growth acceleratorThe scrappy early days of doing everything soloHow a remote cabin in Pennsylvania changed everythingWhy not every investor is in it for cash flow—and why that’s okayHis approach to building relationships, earning trust, and growing organicallyWhether 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 $200KHow he tripled the revenue of an existing STRUsing a cash-out refi to scale fasterThe power of personalized guest experiences—handwritten notes, welcome screens, and morePartnering with developers to create STR-ready homesDerek 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.