The Hospitality Edge

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!