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...

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...

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...

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 ex...

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 a...

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...

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 insi...

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 p...

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 experien...

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...

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 h...

In this episode of the STR Investing Podcast, host Taylor welcomes Jay Bowman, a seasoned real estate investor with over 20 years of experience, to discuss his journey into short-term rentals. Jay shares how a conversation with a friend about the impressive earnings potential of Airbnb sparked his transition from long-term and college rentals to short-term rentals. He delves into his approach of p...

In this episode, host Taylor welcomes Max Gagliardi, an oil and gas entrepreneur who cracked the code on luxury short-term rentals. Max reveals how he transformed his real estate side hustle into a thriving business, building high-end properties that attract premium guests and skyrocket revenue. From nailing down cost basis strategies to developing jaw-dropping, waterfront properties, Max shares t...

In this episode of the STR Investing Podcast, host Taylor dives into a comprehensive discussion with Eric Moeller from Freewyld. Eric shares his extensive journey in the short-term rental industry, starting with his early days in rental arbitrage, through his evolution into property management, and now leading Freewyld. With a focus on creating exceptional guest experiences, Eric highlights the sh...

In this episode of the STR Investing Podcast, Taylor chats with Brett, a young short-term rental entrepreneur who started his journey before even reaching the legal drinking age. Brett shares how he transitioned from aspiring realtor to successful short-term rental investor, highlighting his first major deal—a set of cabins in Hocking Hills, Ohio, which he transformed into a thriving venture by le...

In this episode of the STR Investing, The Podcast, host Taylor Jones welcomes Ben Wolff, the man behind "unique stays" and a pioneer in the short-term rental market.  Ben shares his journey from humble beginnings in New York City to creating extraordinary treehouse hotels and innovative outdoor hospitality experiences. He delves into the game-changing power of influencer collaborations,...

In this episode of the STR Investing Podcast, host Taylor Jones welcomes Tyann Marcink, dubbed the "Queen of Guest Experience," to discuss her journey in turning overlooked properties into successful short-term rentals.   Tyann's transformation of the drug house into a lucrative Airbnb involved extensive renovations and strategic upgrades, turning the dilapidated property into a des...

Welcome to another episode of STR Investing, The Podcast, hosted by Taylor Jones. In this episode, we are thrilled to have Allen Meringolo join us to dive deep into the strategies and insights on how to transform your Airbnb expenses into lucrative revenue streams. Allen, an experienced short-term rental expert, shares his proven methods for maximizing profits, cutting unnecessary costs, and lever...

Join us for an insightful episode featuring Rob Leventhal, a seasoned short-term rental investor with a remarkable journey and effective real estate tactics. In this episode, Rob shares his experience in building a successful short-term rental portfolio, including his strategic decisions, challenges, and triumphs. Learn about the importance of return on equity, the power of 1031 exchanges, and how...

In this episode of STR Investing, we welcome Eric Goldreyer, founder of BNB Finder—a direct booking platform designed to help guests find their next short-term rental without the high fees of traditional OTA platforms. Eric shares his inspiring journey from BedandBreakfast.com to Turnkey Vacation Rentals and now BNB Finder. We dive into the benefits of direct bookings, professional property manage...

Sabrina x2 on this episode! Join us for an insightful episode of STR Investing, where Sabrina Guler welcomes Sabrina Calnan, an expert in short-term rental revenue management and listing optimization.  Sabrina Calnan shares her journey from the corporate world to mastering the art of Airbnb, discussing strategies to maximize revenue for individual hosts and property managers.  This episode is pack...

In this episode of STR Investing, Taylor Jones welcomes Jeremy Werden to share his incredible journey from investing in his first short-term rental just three years ago to now owning a portfolio of 25 Airbnb listings and 7 boats, generating over $1,000,000 per year. Jeremy built his portfolio from scratch with minimal startup capital, documenting his entire journey while growing an audience of 200...

In this episode of STR Investing , host Taylor Jones interviews Aidan Groll and dives deep into innovative financing strategies that will help you acquire short-term rentals without the need for a hefty down payment. Learn how savvy investors are leveraging creative solutions to secure properties at half the current interest rate. If you're eager to expand your STR portfolio, this episode is...

In this unique episode of STR Investing, host Sabrina Guler departs from the usual interview format to answer some of the most frequently asked questions she receives. Sabrina shares insights from her transition from working at Apple to starting her journey in short-term rental investing. Covering topics from her first property purchase challenges to strategic advice for new investors, this episod...

In this insightful episode of "STR Investing," host Sabrina welcomes Brooke Rigolini, head of property management at Techvester, to dive deep into the nuances of property management within the short-term rental industry. Brooke shares her extensive background in hospitality and property management, emphasizing the importance of guest experience and proactive communication. Listeners will...