Short Term Rental Pros Podcast

In this episode of the Short-Term Rental Pros Podcast, Jeremy sits down with Michael Klein, a leading short-term rental broker in the Poconos, to explore how investors can find better deals, build distinctive vacation rentals, and maximize both rental revenue and property value.

Recorded at Michael's custom-built six-bedroom lakefront property, this conversation dives into the strategy behind designing a short-term rental from the ground up. From indoor pools and resort-style amenities to layouts built for large groups, Michael explains why creating a memorable guest experience can help a property stand out in an increasingly competitive market.

The discussion also covers the changing investment landscape, the value of off-market deals, and how to move decisively when a promising property becomes available.

Michael shares the numbers behind his new construction project, including the $100,000 land purchase, an approximately $1.2 million construction cost, and a pre-construction appraisal of roughly $1.6 million. He discusses his goal of generating around $300,000 in annual rental revenue once the property is operating. These figures reflect the project's reported costs, appraisal, and target—not a confirmed operating result.

In this episode, you'll learn:

• Why some investors are choosing custom construction over existing properties
• How to design a short-term rental around guest experience and revenue potential
• Which amenities can help a property stand out, including indoor pools and game rooms
• How to identify underserved guest demographics in a market
• Why off-market deals can create opportunities in competitive markets
• How to evaluate land, construction costs, appraisals, and potential returns
• Why taking action on a good deal matters—and how contingencies can protect buyers
• How lakefront locations and proximity to major population centers influence demand
• Why larger properties can appeal to group travelers
• How to think about appreciation alongside cash flow and tax benefits
• Why planning new construction early can create more opportunities for investors

Whether you're an Airbnb investor, real estate entrepreneur, broker, or short-term rental operator, this episode offers practical insights into finding opportunities, building differentiated properties, and making smarter investment decisions.

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, Ryan Shapiro sits down with Alex to break down how he and his partner went from starting with zero properties to managing roughly 70 live short-term rentals in just months.

Alex's journey is anything but traditional. After playing professional tennis and spending years competing at the highest level, he transitioned into the short-term rental industry and went all-in on building an Airbnb management business.

Today, Vol Hosting manages around 55 properties across the Smoky Mountains and East Tennessee, while its sister operation, Gulf Coast Hosting, manages around 25 properties along Florida's Gulf Coast.

So what's behind the rapid growth?

The answer might be much simpler than you think.

Alex shares how he used cold calling, massive outreach volume, genuine curiosity, and a focus on helping property owners to build relationships and acquire new clients. At one point, he was making 150–200 calls per day, using every conversation as an opportunity to learn more about owners, competitors, and the market.

The conversation also covers the importance of building the right partnership, knowing when to focus on sales instead of systems, using technology and AI to streamline operations, and developing the mindset required to keep pushing when growth gets difficult.

In this episode, you'll learn:

• How to grow an Airbnb management business from zero
• Why cold calling is still one of the most powerful STR growth strategies
• How to make 150–200 calls a day without sounding like a salesperson
• How to approach property owners by focusing on their problems
• Why curiosity and listening can be more powerful than pitching
• How to turn conversations into long-term client relationships
• When to prioritize sales over systems and automation
• How to build a strong business partnership
• How professional athletics can translate into entrepreneurship
• How to use AI and technology to handle more operational work
• Why perseverance and consistency matter more than complicated strategies
• How young entrepreneurs can compete in the short-term rental industry

If you're trying to grow an Airbnb management company, acquire more property owners, or build a scalable STR business, this episode is packed with practical lessons on sales, discipline, relationships, and taking massive action.

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 special episode of the Short-Term Rental Pros Podcast, Jeremy Werden brings together two of the leading names in short-term rental design for a candid conversation about how smart design, strategic amenities, and value-add renovations can transform an Airbnb's revenue and overall property value.

Recorded live at the STR Pros retreat in North Carolina, the episode features Ashita of Ashita Interiors and Blue Delgado of Funk It Design, two successful STR designers and investors who have helped launch hundreds of short-term rental properties.

Ashita Interiors has designed more than 400 properties, specializing in value-add renovations, hospitality-driven design, landscaping, and maximizing unfinished spaces. Blue Delgado, co-founder of Funk It Design, has helped launch 300+ properties, focusing on maximizing the potential of short-term rental investments through creative design, data, and unique guest experiences.

Together, they break down how investors should think about design as an investment—not just an expense.

The conversation includes real-world case studies, including properties that went from roughly $140K–$160K in annual revenue to $350K+, as well as a property purchased for $1.3M that was renovated and ultimately appraised at $2.75M.

In this episode, you'll learn:

• Which Airbnb amenities can actually drive revenue
• How to decide where to invest your renovation budget
• Why pools, hot tubs, saunas, pickleball, and outdoor entertainment can matter
• How to identify high-value unfinished spaces like garages, basements, and attics
• How design can increase both STR revenue and property value
• How to use data without blindly trusting market projections
• Why designing for your target guest is critical
• How to create amenities and experiences that competitors can't easily replicate
• The difference between virtual design, installation, and white-glove design services
• How professional STR design is priced
• Why planning for future amenities can save you money later
• How value-add renovations can create appreciation and tax advantages
• Real examples of investors dramatically increasing property revenue through design

Whether you're an Airbnb host, STR investor, property manager, or real estate entrepreneur, this episode will help you think differently about design, amenities, revenue, and the true ROI of a short-term rental property.

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

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:

⁠⁠⁠⁠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

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

Want to make smarter decisions when analyzing potential short-term rental investments? BNB Calc helps STR investors analyze properties and estimate their potential returns.

Use our exclusive 25% off discount through the link below:

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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.