STR Investing, The Podcast

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.__Episode Sponsored By:STR SearchSTR 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

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__Episode Sponsored By:STR SearchSTR 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

Derek Gisriel, a property manager and STR investor from San Antonio, turned his love for travel into a booming rental business. He shares how a tax strategy morphed into significant cash flow, including a tax loophole that saved him nearly $200K. Discover his secrets for tripling revenue through personalized guest experiences, like handwritten notes and thoughtful touches. Derek emphasizes the importance of human connection over automation and discusses strategic growth in property management, including partnerships that boost their portfolio.

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!__Episode Sponsored By:STR SearchSTR 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

In this episode, tax strategist Nathan Sosa shares his expertise on maximizing tax benefits for short-term rental investors. He explains crucial strategies like material participation and real estate professional status that help optimize deductions. Listeners will learn about cost segregation, bonus depreciation, and the powerful 1031 exchange. Nathan’s insights are designed to guide both novice and seasoned investors in legally minimizing their tax burdens and ensuring they make the most of their investments. Don’t miss these wealth-building tips!

Paul Kromidas, a former Airbnb employee turned short-term rental entrepreneur, shares his journey of overcoming mindset barriers and taking bold risks. He discusses the importance of capital raising and balancing host-guest experiences in a competitive market. Paul also emphasizes the need to choose the right properties for investment and the evolution of his business model towards innovative, software-driven solutions. His insights on integrating family life with entrepreneurial duties offer valuable lessons for aspiring investors.

Taylor Jones chats with Connor Cushman, a savvy short-term rental agent and investor focused on North Georgia. Connor shares his 'slow burster' strategy, blending long-term rental stability with short-term profit potential. He emphasizes the significance of smart property selection and innovative amenities that attract guests, like beautifully designed outdoor spaces. Discover how to navigate market trends and enhance guest experiences for maximum profitability, whether you're just starting or looking to boost your investment results.

Discover how Rachel turned her passion into a thriving short-term rental portfolio while juggling motherhood and a full-time job. She shares insights on crafting unforgettable guest experiences with thoughtful amenities that lead to repeat bookings. Learn about her innovative marketing strategies to boost occupancy rates and the importance of personal touches in hospitality. Rachel also reveals practical tips for remote property management and entertaining anecdotes about travel quirks, all while debunking myths in vacation rental investments.

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.__Episode Sponsored By:STR SearchSTR 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

In this episode, we’re diving into the world of short-term rentals with Gil from Crafted Stays. Gil shares his journey, from launching his first Airbnb to becoming fully immersed in the business, discussing how a single night of high bookings ignited his passion for STRs. We explore the mindset shift that led him to expand quickly, leveraging skills from his tech background and previous roles in hospitality to optimize the guest experience. Gil and Taylor discuss the importance of understanding your ideal guest, building a differentiated product, and utilizing effective, simple strategies for direct bookings. This episode is packed with insights on staying competitive in STRs by focusing on core customer needs, design, and efficient operations. If you’re ready to take your STR game to the next level, this episode is for you!Tune in to hear practical advice and inspiring stories from two seasoned STR operators.__Episode Sponsored By:STR SearchSTR 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