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 listeners a behind-the-scenes look at the past couple of years—from getting married and becoming a father to growing BNBCalc, buying and selling short-term rental properties, refining his investment strategy, and launching a new revenue management business focused on high-grossing properties.

A major theme of the conversation is why Jeremy has become increasingly focused on high-revenue, experiential short-term rentals rather than simply growing his property count. He shares examples of unique properties he's invested in and explains why creating a memorable, differentiated guest experience can be a powerful part of an STR strategy.

Jeremy also breaks down how he's approaching revenue management for high-performing and one-of-a-kind Airbnb properties. He discusses pricing strategy, historical pacing, seasonal demand, marketing, identifying revenue gaps, and why traditional market-based pricing tools aren't always enough for unique properties.

In this episode, you'll learn:

Jeremy also reflects on how becoming a husband and father has changed his priorities and how he's thinking differently about business, investing, time, and building a life around the things that matter most.

Whether you're a short-term rental investor, Airbnb host, property manager, co-host, or real estate entrepreneur, this episode offers an inside look at Jeremy's evolving strategy for building, operating, and maximizing high-performing vacation rental properties.

🎙️ Follow the STR Pros Podcast for more conversations, strategies, and real-world lessons from people building businesses in the short-term rental industry.

Property Management Mastermind:

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Need help buying a property:

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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 luxury cabin in Broken Bow. After learning the business largely through trial and error, he began helping other property owners—and eventually developed a repeatable system for acquiring clients, closing deals, and scaling a property management business.

In this conversation, Marcus breaks down the client acquisition and sales strategies that helped him grow, including cold calling, discovery calls, follow-up systems, referrals, email, SMS, direct mail, Facebook/Meta ads, and automated lead nurturing. He also explains how he uses GoHighLevel, AI, call recording, and automation to streamline his sales process and stay organized while managing limited time.

Marcus and Ryan also get into the details of his cold-call script, how to handle objections, why the goal of the first call isn't necessarily to close the client, how to structure a multi-step sales process, and why consistent follow-up can make a major difference.

They also dive into Facebook ads for short-term rental property management, including lead forms vs. landing pages, creative testing, strong offers, ad budgets, and building a backend system capable of converting incoming leads.

In this episode, you'll learn:

• How Marcus got his first short-term rental management clients

Whether you're a short-term rental property manager, Airbnb host, co-host, real estate investor, or entrepreneur looking to grow an STR business, this episode offers a practical look at how to build a client acquisition system instead of relying entirely on referrals.

🎙️ Follow the STR Pros Podcast for more conversations with short-term rental operators and industry experts sharing the strategies, systems, and lessons behind building and scaling successful STR businesses.

Save Your Spot! Join Our Lakefront Retreat at Hyco Lake Mastermind:

⁠⁠⁠https://www.investstr.com/lake-front-retreat⁠⁠⁠

Property Management Mastermind:

⁠⁠⁠str-pros.com⁠⁠⁠

Need help buying a property:

⁠⁠⁠investstr.com⁠⁠⁠

Save 25% on BNB Calc. Use our exclusive discount through the link below:

⁠⁠⁠⁠https://bnbcalc.com?fpr=strpros⁠

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 experience working in vacation rental cleaning since 2015 and explains why luxury Airbnb turnovers require much more than simply cleaning a house. From detailed training and standardized systems to inspections, inventory management, maintenance reporting, welcome baskets, and in-house linen service, she explains the processes that help keep Ryan's portfolio of approximately 30 Florida properties operating at a high standard.

Ryan and Ashley also discuss one of the biggest challenges facing Airbnb hosts and property managers: finding cleaning teams that don't just show up, but actually take ownership of the property and understand how their work impacts the guest experience.

In this episode, you'll learn:

• How to find and train high-quality Airbnb cleaners
• Why standardized cleaning systems are critical when scaling an STR portfolio
• How professional turnovers can help protect 5-star reviews
• Why cleaners should be the eyes and ears of your property
• How to identify and report maintenance issues before guests do
• The advantages of keeping the same cleaner assigned to each property
• How cleaning software and automation can eliminate scheduling headaches
• Why Ashley prefers managing linens in-house instead of outsourcing linen service
• The real difference between low-cost, average, and professional Airbnb cleaners
• How welcome baskets and small details can elevate the guest experience
• Why paying more for the right cleaning operation can actually save money long term
• How property managers and cleaning companies can work together as one operational team

If you're an Airbnb host, short-term rental owner, co-host, property manager, or STR operator, this conversation will give you practical insight into building the systems and service standards needed to deliver a consistently great guest experience.

🎙️ Follow the STR Pros Podcast for more conversations with successful short-term rental operators, entrepreneurs, and industry experts sharing the strategies, systems, and lessons behind profitable STR businesses.

Save Your Spot! Join Our Lakefront Retreat at Hyco Lake Mastermind:

⁠⁠https://www.investstr.com/lake-front-retreat⁠⁠

Property Management Mastermind:

⁠⁠str-pros.com⁠⁠

Need help buying a property:

⁠⁠investstr.com⁠⁠

Save 25% on BNB Calc. Use our exclusive discount through the link below:

⁠⁠⁠https://bnbcalc.com?fpr=strpros⁠

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 subscription-based model. His experience gives him a unique perspective on sales, client acquisition, operations, and what it takes to build systems that can support rapid growth.

Ryan and Jackson go behind the scenes of what it really takes to scale a short-term rental management company—from cold calling and acquiring property owners to hiring sales reps, implementing a CRM, and creating automated systems for follow-ups, messaging, remarketing, and guest reviews.

They also talk honestly about the challenges that come with growth, including difficult clients, managing a team, knowing when to let clients go, and the constant ups and downs of entrepreneurship.

In this episode, you'll learn:

• How to acquire new STR management clients

• Sales strategies for growing a co-hosting business

• How to scale toward 20+ properties

• When to hire your first sales representative

• Why CRMs and automation become critical as you grow

• How to build systems and processes that scale

• Lessons from managing difficult clients

• How to balance multiple businesses at once

• The importance of starting sooner and failing faster

• What it takes to build a business with the goal of reaching 50+ properties

Whether you're an Airbnb host, co-host, property manager, or entrepreneur looking to grow your STR business, this episode offers a candid look at the sales, systems, and mindset behind scaling a successful short-term rental operation.

Save Your Spot! Join Our Lakefront Retreat at Hyco Lake Mastermind:

⁠https://www.investstr.com/lake-front-retreat⁠

Property Management Mastermind:

⁠str-pros.com⁠

Need help buying a property:

⁠investstr.com⁠

Save 25% on BNB Calc. Use our exclusive discount through the link below:

⁠⁠https://bnbcalc.com?fpr=strpros⁠

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.

Save Your Spot! Join Our Lakefront Retreat at Hyco Lake Mastermind:

https://www.investstr.com/lake-front-retreat

Property Management Mastermind:

str-pros.com

Need help buying a property:

investstr.com

Save 25% on BNB Calc. Use our exclusive discount through the link below:

⁠https://bnbcalc.com?fpr=strpros⁠

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.

This isn’t a conference. It’s a mastermind.

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.

🌊 A lakefront retreat, not a conference room.

👉 Apply for a spot: https://www.investstr.com/lake-front-retreat

🎁 Save 25% on BNB Calc

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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.