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.