Join us for Mark Lumpkin’s very first episode as the newest host of the STR Investing Podcast! In this debut, Mark interviews Rachel—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.

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.