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.

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.

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 purchasing distressed properties, navigating Louisville's evolving regulations, and converting duplexes into high-performing short-term rentals. Jay also provides insights into the challenges of hospitality as an asset class and his future plans to explore other markets and unique investment opportunities.

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 the exact tactics he’s used to scale fast in a cutthroat market. Tune in to learn how design, marketing, and direct bookings could be the key to multiplying your income and building your own resort community.

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 shift from mere rental transactions to prioritizing hospitality, especially post-COVID. He also touches on the challenges of adopting new technologies in the industry and the strategic pivot towards integrating hospitality with real estate to enhance guest engagements and property management.

Join Eric and Taylor as they explore the nuances of sustaining growth and innovation in the evolving landscape of short-term rentals.

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 leveraging data and marketing.

He also discusses his strategic shift to unique, high-demand properties and his effective direct booking approach using social media and content creators to enhance visibility and profitability.

Tune in for insights on finding undervalued properties, the power of content marketing, and the evolving landscape of short-term rentals.

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, recounting a remarkable story where a single influencer helped generate $25,000 in direct bookings without any upfront cost. Ben discusses the evolution of the market, the critical role of content marketing, and the strategies that transformed his business.

Tune in to learn how Ben's unique approach to social media and direct bookings can revolutionize your own rental business.

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 desirable vacation rental. This impressive feat highlights her ability to see potential where others might not and underscores the profitability of creative real estate investments.

Tune in and learn from Tyann Marcink's incredible journey to elevate your short-term rental game.