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 insights on raising capital, balancing host and guest experiences, and leveraging innovative strategies in today’s evolving market.

Whether you’re just starting out or looking to scale your portfolio, Paul’s journey provides a powerful roadmap to achieving long-term success in short-term rentals.

Check out his website here: https://www.summeros.com/

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 proven performance, thereby transforming equity and opening doors to premium refinancing or sale opportunities.

Drawing on his experiences in North Georgia’s competitive market, he breaks down the importance of smart property selection, strategic amenity upgrades, and keeping an eye on market fundamentals like interest rates and ROI. Whether you’re a budding investor or a seasoned pro looking to 10x your results, this conversation is packed with actionable insights to elevate your STR game.

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 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.

Check out her website here: https://www.upclosemktg.com/

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.