Short Term Rental Pros Podcast

What happens when you step away from the podcast for two years and come back with a completely different perspective on short-term rentals? In this episode of the STR Pros Podcast, host Jeremy Werden returns to the microphone to share what has changed in his life, his businesses, and his approach to short-term rental investing and property management since the podcast went on hiatus. Jeremy gives...

How do you actually get property management clients in the short-term rental industry? In this episode of the STR Pros Podcast, host Ryan Shapiro sits down with Marcus, an active-duty Air Force member and short-term rental property manager who built his business from the ground up while balancing a demanding military career. Marcus started his STR journey after partnering with his dad to build a l...

A great Airbnb doesn't start when the guest arrives—it starts with what happens after the previous guest checks out. In this episode of the STR Pros Podcast, host Ryan Shapiro sits down with Ashley, Ryan's Head of Cleaning and the owner of Be Clean 360, to break down what it really takes to build a professional, reliable, and scalable cleaning operation for short-term rentals. Ashley shares her ex...

In this episode of the Short-Term Rental Pros Podcast, co-host Ryan Shapiro sits down with Jackson Sterns, a 24-year-old entrepreneur and short-term rental operator who is building and scaling multiple businesses at the same time. Jackson has grown his STR management business to 17–18 properties, with a goal of reaching 50, while also running a growing boat rental business with seven boats and a s...

In this episode of the Short-Term Rental Pros Podcast, host Jeremy Werden sits down with Rajan Chida, a 22-year-old entrepreneur and real estate developer documenting his journey of building a short-term rental development from the ground up. Rajan's journey started far outside traditional real estate. While in college, he built a successful shoe-flipping business, saving aggressively until he was...

In this episode of the Short-Term Rental Pros Podcast, host Jeremy Werden sits down with three standout STR operators and creators: Rajan Chida, Kyle Miklasz, and Ryan Shapiro for an unfiltered conversation about building, marketing, and scaling short-term rental businesses. Rajan Chida shares the story behind Royal Oak Retreat, a luxury cabin project he launched while still in college. After purc...

What separates creators who consistently grow from those who struggle to get views? In this episode of the STR Pros Podcast, host Ryan Shapiro sits down with content creator and social media strategist Rajan Chida to break down the strategies behind creating content that captures attention, builds trust, and drives business growth. Rajan shares the exact frameworks he's used to grow on social medi...

In this episode of the STR Pros Podcast, Jeremy sits down with Leo Walton, Co-Founder of Truvi (formerly Superhog), one of the most respected voices in the short-term rental industry. Before co-founding Truvi, Leo helped grow onefinestay from a single luxury rental in London into a global vacation rental brand. Today, he works with property managers and vacation rental operators around the world t...

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...

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...

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 insur...

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...

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...

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 nu...

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...

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 o...

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...

In this episode of the Short Term Rental Pros Podcast, Jeremy welcomes Brian Meyer to discuss his unique business model that combines short term rentals with houseboats. Brian shares his journey from growing up on the Eastern Shore of Maryland to founding Flow Home, a company offering luxurious floating homes as short-term rental properties. They touch on Brian's background in paddleboarding and t...

In this episode of the Short Term Rental Pros podcast, host Jeremy and Patryk dive into high-level conversations about the short-term rental industry. They discuss the importance of being in the right rooms, share experiences from recent conferences, and explore the dynamics of their successful property management ventures. The episode also highlights Patryk's acquisition of a well-known co-host c...

In this episode of the Short Term Rental Pros Podcast, host Jeremy is joined by Matt and Lori to discuss their progress over the past year in the short term rental market. The episode covers various expert discussions featuring speakers like Patrick Swiatek and John Bianchi. Matt and Lori share their experiences transitioning from property arbitrage to co-hosting, the benefits of investing in Flor...

In this episode of the Short Term Rental Pros Podcast, host Jeremy is joined by John Bianchi to discuss a range of topics vital for success in the Airbnb market. Despite a challenging trip to the studio due to a nationwide computer virus, Bianchi shares his expertise on leveraging a data-driven approach to identify profitable properties and stresses the importance of having a reliable team to exec...

Jeremy sits down with Seb, a successful short-term rental investor. Seb shares his journey from dealing with flight debacles to investing in short-term rentals. He discusses his background as a professional athlete from Uruguay, his transition to finance, and how he and his wife started their real estate business in Maine. Seb details various investment strategies, including flips, long-term, and...

In this episode Jeremy is joined by Mark and Xander, two highly successful real estate agents from the Poconos. They delve deep into their personal journeys into the short-term rental (STR) market, share insights on regulations and market idiosyncrasies in the Poconos, and discuss tips for succeeding in the ever-evolving STR landscape. From winter tourism trends to the impact of amenities like pet...

In this episode Jeremy interviews Natalie Palmer, a prominent figure in the short-term rental space and host of the No Vacancy Podcast. Natalie shares her journey of managing ten condos within a single complex, operating them like a boutique hotel and the efficiencies gained through centralized operations. They discuss the benefits of scaling in one location, the operational challenges in rural ma...