In this episode of The Hospitality Edge, we dive into what it really takes to thrive in a high-risk, high-reward short-term rental market. Sebastian Humbert, co-owner and founder of Tropicalia Puerto Rico, shares the raw truth about platform dependency, business reinvention, and building a resilient rental operation on an island where the lights don’t always stay on — literally.
From Hurricane Maria to Airbnb delistings, Sebastian has weathered it all. His experience isn’t just a survival story — it’s a masterclass in smart adaptation.
What You'll Learn:
The real dangers of relying too heavily on Airbnb
How to adapt your STR model in unpredictable markets
Why Sebastian shifted from arbitrage to full-service management
How to set expectations with property owners from day one
What makes a guest experience truly unforgettable — even during a power outage
Simple, scalable strategies to stand out in a saturated listing market
How to prepare your business for the next OTA algorithm shift
Whether you're just starting out or scaling past 50+ units, this episode will change the way you think about platforms, risk, and resilience in the short-term rental space.
What separates burnt-out landlords from strategic investors managing $70M+ portfolios? For Rodney Rivera—CEO of Ion Mortgage & Lending and CEO/COO of Ion Property Management—it all comes down to knowledge. In this episode, Rodney shares how deep research, creative financing, and long-term thinking helped him build and scale his real estate empire. Forget chasing cash flow at all costs—Rodney makes the case for appreciation, disciplined operations, and smarter decision-making as the real path to wealth.
💡 What You’ll Learn:
Why research is the most underrated asset in real estate success
How Rodney used DSCR loans to scale faster than traditional investors
The overlooked advantages of forced appreciation in multifamily properties
When cash flow is overrated — and what really builds wealth
What most new STR investors get wrong in saturated markets
How to identify the wrong property management clients (and say no)
In this episode of The Hospitality Edge Podcast, we sit down with Austin Spitzenberger, Founder of Blue Door Retreats and Partner at LazyH Retreats.
Austin shares his journey of scaling his property management business, from managing just a few properties to successfully scaling to 100+ properties. He reveals the key strategies that allowed him to scale his business efficiently, emphasizing the importance of strategic partnerships and transitioning from co-hosting to full property management. Tune in to learn valuable insights that can help you grow your own property management business!
What you'll learn:
How to scale your property management business from 10 to 100 properties.
The importance of strategic partnerships and how they can accelerate growth.
Why transitioning from co-hosting to full property management is a game changer.
The biggest mistakes property managers make and how to avoid them.
How to self-assess your strengths and weaknesses as an entrepreneur for better decision-making.
Key strategies for streamlining operations and delegating effectively.
In this episode of The Hospitality Edge, we sit down with Robin Bass – Chief Visionary Officer and Founder of Premier Properties, a luxury property management company known for its outstanding service, loyal team, and rapid growth.
Robin opens up about the leadership philosophy that changed everything: kindness. From building lasting vendor relationships to scaling to 40 luxury properties without burning out, she shares how empathy and authenticity have shaped her business success.
If you've ever wondered how to lead with integrity, keep your team motivated, and grow a business without compromising your values—this one’s for you.
What You’ll Learn:
➡ How kindness became Robin’s competitive edge in business
➡ The systems she uses to keep 40 properties running smoothly
➡ Why “people over profit” isn’t just a feel-good mantra—it’s a strategy
➡ How to build a team that stays loyal and inspired
➡ The surprising leadership shift that helped Robin scale fast
➡ How to navigate boundaries while being relationship-driven
➡ What most people get wrong about growth and success
🎧 Hit play now to discover how leading with heart can lead to serious results—and why kindness might just be your ultimate business advantage.
In our latest episode of The Hospitality Edge Podcast, we sit down with Jeff Jenson, CEO of Buckingham Luxury Vacation Rentals and serial entrepreneur, to discuss the secrets behind scaling a successful vacation rental business.
What you’ll learn:
Why most property managers fail and how to avoid common pitfalls
How AI is transforming guest experiences and operational efficiency
Key strategies for boosting rental income and scaling your property business
This episode is packed with actionable insights from a seasoned industry leader who has been through the ups and downs of property management. Don't miss out on Jeff’s invaluable advice to take your business to the next level!
In this episode of the The Hospitality Edge Podcast, we sit down with Jack Zoppa, CEO of Haven Vacation Rentals, to explore the transformative power of ownership and accountability in leadership. Jack shares his unique journey from starting at the ground level to managing over 240 properties, offering valuable insights into the vacation rental industry.
What You'll Learn:
The importance of 100% ownership in leadership and business success.
Strategies for navigating challenges and turning setbacks into opportunities.
How to cultivate a resilient mindset as a young leader.
Actionable tips for building a strong team culture and enhancing accountability.
Insights into operational best practices that drive growth in the hospitality sector.
Join us for an inspiring conversation that will empower you to lead with intention and drive success in your own ventures!
When short-term rental operators hit 30–50 units, most stall — or burn out. Why? Because they never learn to truly leverage people, systems, or strategy. In this episode, Sean Rakidzich, Founder of Million Dollar Renter & Host of Airbnb Automated, shares the brutal lessons he learned scaling an STR business past 100 units and the hidden risks most operators don’t see coming until it’s too late.
With nearly 300,000 subscribers on YouTube and a career consulting for REITs and major operators, Sean breaks down how to scale profitably — not just aggressively.
What you’ll learn:
Why most STR businesses collapse under their own weight after 30 units
How to use leverage the right way — from staffing to systems to strategy
What “scale gravity” and “inertia” mean — and why they kill your margins
How to spot the real bottlenecks in your business before they stall your growth
The lessons Sean learned losing over $500,000 on a bad portfolio
When (and how) to go from operator to CEO in your business
Why design, structure, and delegation matter more than ever post-COVID
Whether you're just getting started or managing dozens of properties, this episode will challenge your assumptions — and give you the roadmap to scale without breaking your business.
Buying a vacation rental management company is exciting — but what happens next can make or break your success.In this episode, we dive deep into the real challenges new owners face after an acquisition: keeping the staff, the property owners, and the business you just bought.
Renée Triplett, Owner at Easy Vacation Services and Breathe Easy Rentals, shares her experience of acquiring two rental management companies — and the key lessons she learned about building trust, avoiding turnover, and protecting the portfolio you worked so hard to acquire.
If you're planning to buy a property management business (or already have), this episode is your survival guide.
What You’ll Learn:
Why staff and property owners often leave after an acquisition — and how to prevent it
The critical mistakes new owners make during the transition
How to build immediate trust with employees you didn’t hire
Buying your way into the short-term rental industry might sound easier than starting from scratch — but it comes with a whole different set of challenges. In this episode, we sit down with someone who didn’t just start a vacation rental company… he acquired two of them without any industry experience.
Gene Triplett, Owner of Easy Vacation Services & Breathe Easy Rentals, dives into what it really takes to buy and grow an STR business, from finding the right deal to navigating financial risk, team building, and budgeting for seasonal cash flow.
Whether you're a property manager, operator, or real estate investor eyeing the STR space, this episode will give you real-world insights into what happens after the deal closes.
What you’ll learn:
The pros and cons of buying vs. building an STR business
How to source deals and negotiate with brokers
The role of SBA loans and seller financing in acquisitions
Why team-building is more important than doing it all yourself
How to evaluate management contracts and deal structures
Budgeting strategies to survive the off-season
What most new owners underestimate when entering the space
How to protect yourself with earnouts (aka clawbacks)
Ready to grow your STR portfolio the smart way? Start here.
Most short-term rental operators hit a wall around 50 units. Scaling beyond that? It’s where quality starts slipping, operations break, and owners walk away.
But not this time.
In this episode, we dive with Steven Chrobak, Owner of Myrtle Beach Destinations, into the playbook of an operator who built a 100+ unit portfolio in under two years — without ever living in the market he manages.
From military precision to guest-first thinking, he shares the systems, mindset, and strategic decisions that set his company up for sustainable scale. Whether you’re at 5 units or 55, this episode will shift how you think about growth, operations, and owner acquisition.
What You’ll Learn:
- How to scale to 100+ STR units without sacrificing guest experience
- Why most operators fail when they hit 50 units — and how to avoid it
- The mindset shift that allowed him to grow fast and stay profitable
- How military leadership principles shaped his approach to operations
- The #1 thing that attracts new homeowners (hint: it’s not sales)
- What to build today if you plan to double your portfolio next year
- Why turning away the wrong units is key to protecting your reputation
What happens when a seasoned Wall Street portfolio manager enters the short-term rental game? In this episode, we sit down with Andy Newman, CEO of Newman Hospitality, to unpack the surprising parallels between financial portfolio management and building a successful STR (short-term rental) business.
With over a decade of experience in both banking and vacation rentals, Andy shares what most STR operators overlook — and how applying investment discipline, risk management, and diversification principles can be the difference between scaling sustainably and burning out.
Whether you’re an investor, operator, or just STR-curious, this episode delivers practical insights and honest reflections you won’t hear anywhere else.
What You'll Learn:
The “1,500-Mile Rule” for reducing market and seasonality risk in your STR portfolio
Why most people buy vacation rentals in the wrong places — and how to fix it
The marketing mistake that slowed Andy’s growth for 5 years
How to diversify STR investments like a true portfolio manager
Why Vacasa’s national scaling strategy failed — and what’s working instead
How to evolve from operator to CEO (and build a team that stays)
What does it really take to grow a short-term rental business from one unit to over 100 listings—without raising a single dollar from outside investors? In this episode, we sit down with Joshua Hatter, CEO of Curated Vacation Properties and Founding Director of KEYS Collective, who did exactly that.
From building a property management company during COVID to acquiring boutique hotels and navigating commercial financing, this conversation is packed with honest insights, hard lessons, and practical strategies for anyone looking to scale in the world of short-term rentals.
Whether you're just starting out or aiming to take your STR business to the next level, this episode will give you a behind-the-scenes look at what it actually takes to grow sustainably—without giving up equity.
What You’ll Learn:
Why he left corporate America (and what held him back for too long)
How to secure commercial financing without a W2
The difference between DSCR loans and true commercial lending
Key lessons from managing over 100+ properties
How to hire, partner, and build a team that actually scales
Scaling a vacation rental business is one thing — staying in control while managing 200+ properties is another.
In this episode, we dive deep with Philip Wilburn, Co-Founder & CEO of Hoste, into what it actually takes to grow to 200+ vacation rentals without letting quality, operations, or your sanity fall apart. You'll hear real lessons from someone who's done it — including the mistakes that almost broke the business, what they would do differently, and how they built a structure that can grow without losing control.
If you're growing your short-term rental business and want to avoid costly mistakes, this is a must-listen.
What You’ll Learn:
- How to scale your property management company without losing control
- Why core operations like cleaning & maintenance are make-or-break for growth
- How to avoid the biggest mistakes when scaling beyond 50, 100, or 200+ units
- The key to structuring your team for sustainable growth
- When to pause growth and fix operations before adding more properties
- Lessons on building (or not building) custom tech like owner portals
- The metrics and warning signs that show if your business is ready to scale
In this episode of The Hospitality Edge, we sit down with Heidie Henriksen, Executive Director of VRNation and Co-Founder of ASTRHO, to dive deep into the evolving landscape of the vacation rental industry — and why bridging the gap between rental owners (RBOs) and professional property managers is more critical than ever.
Heidie shares how VRNation is leading a movement to unite the industry, elevate standards, and support hosts of all sizes — from individual owners to large-scale managers.
Whether you're an experienced property manager or a rental-by-owner figuring it out as you go, this episode is packed with insights on what’s changing, what mistakes to avoid, and how to stay ahead in today’s competitive short-term rental market.
What You’ll Learn:
The key differences between rental-by-owners (RBOs) and property managers — and why it matters
The biggest challenges rental owners face today (and why many are struggling to get bookings)
Why professionalizing the industry is crucial for long-term success (even for small hosts)
How VRNation's new national strategy is changing the game for hosts and managers alike
The truth about OTA diversification — should you be on more platforms, or focus on a few?
How advocacy and upcoming regulations are shaping the future of short-term rentals
The surprising reasons why working together (RBOs + managers) may be the best path forward
If you want to know where the industry is heading and how to protect your rental business, this is an episode you can't miss.
In this episode of The Hospitality Edge, we sit down with Dunniela Kaufman, CEO of Sojourn DC, to explore the behind-the-scenes journey of growing a hospitality brand into a full-service property management company. Starting from managing a single building on Capitol Hill to operating over 320 properties, Dunniela shares candid insights on how Sojourn scaled organically without outside funding, navigated COVID-19, and pioneered a flexible rental model that combines short-term and mid-term stays.
We also dive deep into the operational and legal challenges of running a growing property management business, and what it really takes to deliver a consistent guest experience at scale.
Whether you're a short-term rental operator, property manager, or entrepreneur, this episode is packed with real-world lessons on growth, operations, and brand-building in a rapidly evolving industry.
What You'll Learn:
How to scale a property management company organically — without raising capital
The evolution from hospitality brand to full-service property management, including in-house operations
Why and how flex leasing (short-term and mid-term rentals) creates more value for owners and guests
Key lessons from navigating COVID-19 and how to adapt in times of crisis
The legal and liability considerations every operator should think about, especially with longer stays
Why building a consistent guest experience is crucial — and how to achieve it, even with hundreds of properties
The tech challenges of managing diverse rental types — and what’s still missing from current software solutions
Tune in to hear how Sojourn is redefining what it means to be a hospitality brand and property manager — and what it takes to grow and thrive in today’s market.
Handling unhappy clients is one of the hardest challenges in any business—but what if you could turn frustration into loyalty? In this episode, we dive deep into the strategies that transform conflict into long-term trust and repeat business.
Luke Rzepiennik, Co-Founder and Director of Sales & Marketing of Renjoy, shares real-life experiences from scaling a short-term rental business, revealing hard-earned lessons on managing client expectations, handling complaints, and navigating the fine line between customer satisfaction and operational efficiency.
Whether you're in property management, hospitality, or any service-based industry, this episode is packed with actionable insights to help you build stronger relationships and retain clients—no matter how tough the situation.
What You’ll Learn:
- The #1 mistake businesses make when dealing with unhappy clients- How to identify the real reason behind a complaint (hint: it’s not always about money)- The proven strategy to de-escalate conflicts and rebuild trust- Why saying "yes" to every client request can hurt your business- The secret to balancing customer service and profitability- How to systemize owner relations so issues don’t repeat themselves
Tune in for a deep dive into client relationships, conflict resolution, and the psychology of customer loyalty!
In this episode of The Hospitality Edge, we sit down with Jacob Mueller, co-founder and CEO of Renjoy, a property management company that’s grown to manage nearly 200 properties. Jacob shares the key lessons he's learned in scaling a business quickly, from managing a huge volume of transactions to navigating the complexities of financial systems and operational efficiency. He also opens up about the challenges of maintaining quality control while growing and the tough decisions that come with leading a rapidly expanding business.
Whether you're managing short-term rentals or building any fast-growing business, this episode is packed with valuable insights on navigating growth without sacrificing quality.
What you’ll learn:
The critical financial systems you need in place when scaling a property management business
Why outsourcing your financial structure can backfire—and how to fix it
The challenges of managing 30,000 transactions a month and how to stay organized
How to balance rapid growth with maintaining quality control
The key mistake that led to a painful lesson on financial maturity
Why scaling isn’t just about growth, but about creating sustainable systems
How to build an operational foundation that can handle a large portfolio of properties
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!