How do you scale from managing fewer than 10 short-term rentals to 30+ properties—and more than $300K in monthly gross bookings?

In this episode of the STR Pros Podcast, host Jeremy sits down with Ryan Shapiro to unpack Ryan’s journey of building and scaling his short-term rental property management business.

Ryan shares how he went from getting his first listings and leaving his job to managing a growing portfolio of 30+ properties. He and Jeremy discuss the strategies, systems, delegation, and mindset shifts that helped make that growth possible—and why scaling successfully isn't always about adding as many properties as possible.

They also dive into one of the biggest lessons they've learned in the STR industry: quality inventory matters.

From Airbnb arbitrage and co-hosting to building operational systems and choosing properties that create memorable guest experiences, Jeremy and Ryan share practical insights for anyone looking to build a more profitable and sustainable short-term rental business.

In this episode, you'll learn:

• How Ryan scaled from fewer than 10 to 30+ STR properties
• What helped his portfolio reach $300K+ in monthly gross bookings
• Why mastering the basics is still one of the best ways to grow
• How to delegate guest messaging, maintenance, and daily operations
• Why 20% of your properties can create 80% of your headaches
• When it makes sense to walk away from difficult properties
• The pros and cons of Airbnb rental arbitrage
• Why quality inventory can matter more than total unit count
• How Ryan approaches luxury co-hosting in Florida
• How systems and the right team can help you scale without handling everything yourself

Whether you're an Airbnb host, STR investor, co-host, or property manager, this episode is packed with lessons for building a short-term rental business that can grow without taking over your life.

Subscribe to the STR Pros Podcast for more conversations with Jeremy and other STR operators about Airbnb investing, co-hosting, property management, vacation rentals, operations, and scaling a profitable short-term rental business.

Jordan McDonough is a Co-Founder of Somerled Designs (a short term rental design company). Her and Jeremy sit down and have a convo about how she has helped build a design power-house with 60 employees in two years.

Learn how she built her company and how her clients are having success launching high-potential Airbnb's.

In this episode of the Short Term Rental Pros Podcast, Jeremy welcomes guest Zach, who shares his unique perspective on short-term rentals and his recent transition into a new role with Journey, a next-generation loyalty program. Zach discusses the acquisition of his previous company, Stay Watched, by Journey, and sheds light on the new platform's vision of combining vacation rentals and boutique hotels into a unified loyalty program. They delve into the importance of crafting unique, luxurious, and high-value experiences for guests, the shifting landscape of consumer expectations towards luxury, and the significant role of social media in direct marketing for short-term rentals. Key takeaways include building a strong hospitality brand, leveraging social proof, and focusing on fewer but highly differentiated units to create exceptional guest experiences.

In this comprehensive episode of the Short Term Rental Pros podcast, Jeremy recounts a period filled with remarkable events and significant challenges. From dealing with the aftermath of two hurricanes affecting properties in Florida and North Carolina, to attending the Chicago Marathon and VRMA conference, Jeremy shares personal stories and key lessons on resilience, the importance of flood insurance, and community support. The episode highlights insights from major conferences discussing networking, AI, and short-term rental software innovations. Additionally, it delves into the creation and growth of BNBCalc, a tool aimed at enhancing short-term rental portfolios, and the ambitions behind it. Jeremy also reflects on his encounters with major companies and a high-profile interview involving Tim Walz, navigating logistics with the Secret Service. Moving between personal anecdotes, industry advancements, and future aspirations, the episode underscores the power of mission-driven investments, consistency, and seizing unique opportunities in the rental industry.

In this episode of the Short Term Rental Pros Podcast, Jeremy sits down with Emir Dukic shares his extensive journey and insights in the short-term rental industry. Emir, who started as a civil engineer, transitioned into the tech startup world before venturing into real estate. He co-founded Rabbu, a platform aiming to be the 'Zillow' of short-term rentals by providing investment data, agent, and lender connections. Emir recounts his personal history from emigrating from Bosnia to settling in the U.S., his early entrepreneurial ventures, and developing Rabbu. Rabbu offers tools for property management and investment, focusing now on data and lead generation for real estate agents and lenders. Despite industry challenges amplified by recent market conditions, Emir emphasizes the sustained growth and demand in the short-term rental space and Rabbu's role in professionalizing the asset class. Throughout the conversation, Emir shares the strategic pivots Rabbu undertakes to adapt to industry changes and market demands.

In this episode of the Short Term Rental Pros Podcast, host Jeremy interviews Jay Ulrich, a successful operator of approximately 37 properties. Jay shares his journey from being a civil engineer to becoming a full-time short-term rental entrepreneur. He discusses the dynamics of scaling a property management company and co-founding HostBuddy AI, a software that aims to streamline communication for rental hosts through powerful AI tools. Jay reveals insights on property management models, current market trends in San Diego, and how HostBuddy enhances guest communication, increasing efficiency and guest satisfaction. The episode emphasizes the importance of strong relationships with property owners and the innovative use of technology in the short-term rental space.

In this episode of the Short Term Rental Pros Podcast, host Jeremy sits down with with Andrew, a key figure behind Wheelhouse, a software designed for pricing and revenue management in the short-term rental market. The discussion covers the impact of COVID-19 on the industry and how Wheelhouse adapted by restructuring their business model to focus on software development. Andrew delves into the nuances of managing urban versus rural short-term rentals, the challenges and strategies for scaling a rental portfolio, and the impact of new technologies like electric cars and social media on the hospitality industry. He highlights Wheelhouse’s offerings, including their advanced revenue management tools and how these tools can help property managers increase efficiency and scale their businesses. The conversation also touches on predictions for the future of the industry, emphasizing the importance of local data and the evolving landscape of short-term rentals.

In this episode of the Short Term Rental Pros Podcast, Jeremy interviews Ryan, a young entrepreneur from Montreal, Canada, who has rapidly scaled his co-hosting business to manage properties in Florida and North Carolina. Ryan shares his background in sales, the pivotal shift from purchasing to co-hosting, and his unique approach to client acquisition and property management. He outlines his cold calling strategies, the importance of providing white-glove service, and the benefits of building in public. Despite initial challenges, Ryan's relentless pursuit and innovative marketing tactics have positioned him as a rising star in the short-term rental industry.

In this episode of the Short Term Rental Pros Podcast, host Jeremy welcomes back Kyle, a rapidly growing star in the rental property scene. Kyle has expanded his portfolio from one to six mega properties since last November, focusing on barn-style accommodations across the Midwest. The duo discusses his journey from working a W2 job to managing a flourishing rental business, the unique amenities of each property, the challenges and strategies behind scaling, and the importance of leveraging local community banks and social media for growth. They also outline future plans to optimize operations and further expand the business. Tune in for insights into investing, scaling, and managing short term rentals for large groups.

In this episode of the Short Term Rental Pros Podcast, Jeremy welcomes guest Jeff Iloulian, founder of HostGPO. They delve into Jeff’s extensive experience in short-term rentals since 2014, exploring industry changes and trends, including the impact of regulatory shifts, the rise of co-hosting, and the strategic importance of choosing markets. Jeff discusses HostGPO's value in providing discounts for short-term rental supplies and their recent fundraising success. They also cover the significance of industry events, such as VRMA, and Jeff shares insights for succeeding with short-term rentals in 2024. This episode is packed with tips and trends for both new and experienced short-term rental operators.