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 able to purchase his first investment property at just 21. Soon after, a partnership with his longtime friend Renzo led him to a much bigger challenge: purchasing 2.5 acres in Virginia for $37,000 and developing a four-unit short-term rental project called Royal Oak Retreat—despite having virtually no development experience.

What makes Rajan's story even more interesting is how he has built the entire journey in public. His social following grew from roughly 20,000 followers to more than 185,000, allowing him to attract contractors, mentors, investors, creators, and opportunities simply by documenting the process.

Jeremy and Rajan break down what it's really like to develop an STR from scratch, build an audience, and turn attention into a potential business advantage.

In this episode, you'll learn:

Whether you're an aspiring real estate investor, Airbnb host, STR developer, content creator, or entrepreneur, this episode offers a behind-the-scenes look at what happens when you combine real estate, hospitality, social media, and the willingness to build in public.

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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 purchasing land for $37,000 and building the first cabin for roughly $380,000 all-in, Rajan has used social media storytelling and influencer marketing to drive significant direct bookings. He also breaks down what he's learned about identifying the right audience, building a personal brand, and turning attention into actual revenue.

Kyle Miklasz, founder of Big Sky Barn House and Wild Wild Warehouse, shares how he has built a portfolio of unique Airbnb destinations across eight states. His strategy is anything but traditional—transforming abandoned barns and warehouses into one-of-a-kind experiential stays. Kyle discusses the launch of his latest property in rural Iowa, which generated nearly $300,000 in gross bookings within its first eight weeks, and explains how he uses social media as another distribution channel for his properties.

Ryan Shapiro, co-host of the Short-Term Rental Pros Podcast and a luxury co-hosting operator in Northeast Florida, joins the conversation to share his perspective on experiential stays, property management, and the realities of operating a growing STR portfolio.

Together, Jeremy, Rajan, Kyle, and Ryan dive into what it really takes to turn unique properties into high-performing short-term rentals.

In this episode, you'll learn:

Whether you're an Airbnb host, property manager, real estate investor, co-host, or aspiring STR entrepreneur, this episode offers a candid look at what it takes to build properties people actually want to book—and a business that can scale beyond the founder.

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Three days. A small group of STR founders, hosts, and brand builders. Real numbers, real playbooks, and real conversations you won’t find online.

Bring your biggest bottleneck. Leave with a plan — and a room of people who will hold you accountable.

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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 media, including how to find your niche, craft hooks that stop the scroll, document your journey, and turn everyday business moments into engaging content. He also explains why quality beats quantity, how to test different hooks using Trial Reels, and the mindset required to build a long-term personal brand.

Whether you're an Airbnb host, short-term rental operator, entrepreneur, real estate investor, or anyone looking to grow a business online, this episode is packed with actionable advice you can apply immediately.

In this episode, you'll learn:

If you're looking to grow your audience, attract more customers, and build a brand through content, this conversation with Rajan Chida is a master class you won't want to miss.

Follow the STR Pros Podcast for more conversations with the entrepreneurs, operators, and industry leaders shaping the future of short-term rentals and modern business.

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 to help them reduce risk, build trust with guests, and grow more resilient businesses.

Together, Jeremy and Leo explore the future of the STR industry—from direct bookings and revenue management to AI, guest screening, and hospitality technology. They discuss why understanding your ideal guest is one of the biggest competitive advantages in today's market, how operators can build systems that scale, and why successful businesses focus on solving real operational challenges instead of chasing every new trend.

In this episode, you'll learn:

Whether you're an Airbnb host, co-host, vacation rental owner, property manager, or real estate investor, this episode is packed with practical insights to help you build a stronger, more profitable, and future-ready short-term rental business.

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.