Scaling a short-term rental business from one guest house to 150+ properties in just a few years is no small feat. In this episode, we sit down with Michael Vialpando, Co-Founder & CTO of Renjoy, to uncover the strategies, challenges, and technology that fueled their rapid growth.

Michael shares his journey from house hacking and DIY property management to building a fully systematized, tech-driven STR business. We also dive deep into AI, automation, and operational efficiencies—and why the STR industry is evolving faster than ever.

Whether you’re an aspiring STR host or an established operator, this episode is packed with insights to future-proof your business.

What You’ll Learn:

• How house hacking and creative financing built the foundation for growth

• Why scaling beyond a few units requires a mindset shift

• The biggest operational breaking points when growing a STR portfolio

• How automation and AI are reshaping guest communication and operations

• The tech stack Renjoy uses to manage 150+ properties efficiently

• Why focusing on the right markets matters more than ever

• How STR regulations, demand, and revenue trends are shifting in 2024

  
  

The future of STR management is changing—are you keeping up?

Scaling a hospitality business isn’t just about taking on more properties—it’s about building systems, automating processes, and knowing when to let go. In this episode, we sit down with Gianrene Padilla, managing partner at HMG Hospitality Management Group and co-founder of Viva Puerto Rico Shorter Rental Alliance, to explore how he transformed a one-property hustle into a scalable hospitality operation.

Gianrene shares his real-world experiences of going from a bootstrapped startup to an efficient, process-driven business, including the challenges of giving up control, the power of delegation, and how to build a company that runs without you being glued to it 24/7.

If you’re a short-term rental operator, property manager, or hospitality entrepreneur, this episode will give you the strategies you need to streamline and scale—without losing your sanity.

What You’ll Learn:

• How to transition from day-to-day operator to strategic entrepreneur

• The key systems and automations every short-term rental business needs

• How to delegate tasks effectively and avoid bottlenecks in your operations

• The difference between a business owner and an entrepreneur—and why it matters

• Why balancing guest satisfaction and owner relationships is crucial for long-term success

• The biggest mistakes that prevent property managers from scaling

• How to build a hospitality brand that stands out in a crowded market

Tune in now to learn how to scale smarter, not harder!

Scaling a hospitality business isn’t just about taking on more properties—it’s about building systems, automating processes, and knowing when to let go. In this episode, we sit down with Gianrene Padilla, managing partner at HMG Hospitality Management Group and co-founder of Viva Puerto Rico Shorter Rental Alliance, to explore how he transformed a one-property hustle into a scalable hospitality operation.

Gianrene shares his real-world experiences of going from a bootstrapped startup to an efficient, process-driven business, including the challenges of giving up control, the power of delegation, and how to build a company that runs without you being glued to it 24/7.

If you’re a short-term rental operator, property manager, or hospitality entrepreneur, this episode will give you the strategies you need to streamline and scale—without losing your sanity.

What You’ll Learn:

• How to transition from day-to-day operator to strategic entrepreneur

• The key systems and automations every short-term rental business needs

• How to delegate tasks effectively and avoid bottlenecks in your operations

• The difference between a business owner and an entrepreneur—and why it matters

• Why balancing guest satisfaction and owner relationships is crucial for long-term success

• The biggest mistakes that prevent property managers from scaling

• How to build a hospitality brand that stands out in a crowded market

Tune in now to learn how to scale smarter, not harder!

How do you go from a high-paying corporate job to building a thriving vacation rental business? In this episode, we sit down with Shannon St.Val, the founder of Elevate Vacation Rentals, who shares her journey from finance and consulting to scaling a multi-million dollar short-term rental operation.

Shannon reveals how she made $80,000 passively in her first year, navigated strict New York City regulations, and survived the financial hit of COVID-19 while still paying every landlord on time. From rental arbitrage to real estate ownership, she breaks down the creative financing strategies that allowed her to acquire properties and build long-term wealth.

If you're looking for real estate investing strategies, insights into short-term rental management, or the mindset needed to pivot and scale, this episode is for you.

What You'll Learn:

• How Shannon turned a side hustle on Airbnb into a full-time business

• The exact steps she took to replace her corporate salary

• How she scaled to 15 rental properties—and what happened next

• The New York City short-term rental regulations and how she adapted

• How she survived losing $200,000 in savings during COVID

• The lease-to-purchase strategy that helped her acquire a $3 million property

• Why SOPs, efficiency, and team delegation are crucial in real estate

• How she leverages VA teams and keeps operations lean

• Her mindset shifts, business lessons, and what she wishes she had done differently

Listen now to hear Shannon’s full story and her best insights for short-term rental success!

How do you go from a high-paying corporate job to building a thriving vacation rental business? In this episode, we sit down with Shannon St. Val, the founder of Elevate Vacation Rentals, who shares her journey from finance and consulting to scaling a multi-million dollar short-term rental operation.

Shannon reveals how she made $80,000 passively in her first year, navigated strict New York City regulations, and survived the financial hit of COVID-19 while still paying every landlord on time. From rental arbitrage to real estate ownership, she breaks down the creative financing strategies that allowed her to acquire properties and build long-term wealth.

If you're looking for real estate investing strategies, insights into short-term rental management, or the mindset needed to pivot and scale, this episode is for you.

Listen now to hear Shannon’s full story and her best insights for short-term rental success!

In this episode of The Hospitality Edge Podcast, we sit down with Taylor Labno, the Vice President of Operations and Marketing at Vacay Mama and a seasoned real estate broker based in Destin, Florida. Taylor shares her journey from California's retail management to becoming a leader in the short-term rental (STR) industry in Florida. She explores the essential aspects of owner education and financing strategies that are crucial for success in the vacation rental market.

What You'll Learn:

Whether you're a first-time vacation rental owner or an experienced investor looking to optimize your portfolio, this episode provides the knowledge and tools you need to thrive in the competitive STR market.

Tune in now to gain invaluable insights from Taylor Labno on mastering owner education and financing strategies for successful short-term rentals!

In this episode of The Hospitality Edge Podcast, we sit down with Taylor Labno, the Vice President of Operations and Marketing at Vacay Mama and a seasoned real estate broker based in Destin, Florida. Taylor shares her journey from California's retail management to becoming a leader in the short-term rental (STR) industry in Florida. She explores the essential aspects of owner education and financing strategies that are crucial for success in the vacation rental market.

What You'll Learn:

The key elements of educating vacation rental owners for successful property management.

Various financing options available for short-term rental investments.

Strategies to navigate market challenges such as seasonality and legislative impacts.

Effective communication techniques to build trust with property owners and partners.

Pricing strategies and common pitfalls to avoid for maximizing STR revenue.

Whether you're a first-time vacation rental owner or an experienced investor looking to optimize your portfolio, this episode provides the knowledge and tools you need to thrive in the competitive STR market.

Tune in now to gain invaluable insights from Taylor Labno on mastering owner education and financing strategies for successful short-term rentals!

In this episode of The Hospitality Edge, we sit down with Hunter Harrelson, owner of Beach Ball Properties, to uncover the secrets behind his impressive success in managing and scaling over 350 vacation rental properties. Hunter shares his journey from acquiring a small property management business to building a thriving company that prioritizes owner retention and operational excellence.

Whether you're just starting in vacation rentals or managing hundreds of properties, this episode is packed with actionable advice, insights, and real-world strategies to grow and sustain your business while keeping owners happy and engaged.

Join us as we dive into the strategies and stories behind one of the most successful vacation rental management companies in the market today.

Tune in to learn how you can master owner retention, scale your operations, and stand out in the competitive world of short-term rentals!

In this episode ofThe Hospitality Edge, we sit down with Hunter Harrelson, owner of Beach Ball Properties, to uncover the secrets behind his impressive success in managing and scaling over 350 vacation rental properties. Hunter shares his journey from acquiring a small property management business to building a thriving company that prioritizes owner retention and operational excellence.

Whether you're just starting in vacation rentals or managing hundreds of properties, this episode is packed with actionable advice, insights, and real-world strategies to grow and sustain your business while keeping owners happy and engaged.

What You'll Learn:

• How Hunter scaled from 20 to 350+ properties without compromising service quality.

• The key strategies behind building strong owner relationships and fostering retention.

• Why local marketing and community engagement are essential for growth.

• How to manage operational challenges like cleaning and customer service at scale.

• The importance of setting boundaries and delegating tasks effectively as a leader.

• How to leverage transparency and education to retain property owners long-term.

• Lessons learned about adapting and evolving systems as your business grows.

• Insights into the future of the vacation rental industry and the role of technology.

Join us as we dive into the strategies and stories behind one of the most successful vacation rental management companies in the market today.

Tune in to learn how you can master owner retention, scale your operations, and stand out in the competitive world of short-term rentals!

In this compelling episode of The Hospitality Edge podcast, we sit down with Nick Falcone, CEO of NDM Hospitality, to explore the dynamic journey of building a successful multifaceted hospitality business. From humble beginnings as founding franchisees of BurgerFi to pioneering branded vacation rental resorts, Nick shares invaluable insights into strategic business model evolution, technological innovation, and effective revenue management. Discover how NDM Hospitality leveraged proprietary technology and exceptional owner relations to outpace industry giants and create a unique niche in the competitive world of short-term rentals and hospitality.

What You'll Learn:

Join us for an eye-opening conversation that delves deep into the strategies and innovations driving success in the hospitality industry. Whether you're an entrepreneur, developer, or hospitality professional, Nick Falcone's experiences offer actionable lessons and inspiration for your own journey.