Send us a message!

VRMA International 2025 is in the books and if you were there, you probably felt it too: this year hit differently.

More people, deeper conversations, and a sense that the vacation rental industry is entering a new chapter. But what actually stuck after the applause faded?

In this episode, Alex & Annie sit down with Tim Rosolio, Ela Mezhiborsky, and Jessica Gillingham to reflect on what stood out most, not just from the sessions, but from the conversations around the show. 

From global distribution shifts and OTA quality standards to how AI is reshaping operations, trust, and discoverability, this is a candid look at what’s changing and what it means for property managers on the ground.

We discuss:
1️⃣ The state of global distribution with Tim Rosolio
2️⃣ Trust, verification, and real-world AI risks with Ela Mezhiborsky
3️⃣ Marketing visibility and the future of discoverability with Jessica Gillingham

Whether you joined the crowd in Vegas or followed along from afar, this conversation will catch you up on the bigger picture.

Connect with Tim:
LinkedIn: https://www.linkedin.com/in/tim-rosolio-434b2a98/

Connect with Ela:
LinkedIn: https://www.linkedin.com/in/elamezhiborsky/ 

Connect with Jessica:
LinkedIn: https://www.linkedin.com/in/jessicagillingham/ 

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #vrma2025

Send us a message!

In this episode, Alex & Annie head to Florida’s scenic 30A to sit down with Dylan Bozarth, General Manager of 30A Escapes, for a real conversation about leadership, culture, and what it takes to build a team that truly lasts in the fast-paced vacation rental world.

Dylan shares how his decade-long journey at 30A Escapes has shaped a people-first approach to property management. One that values work-life balance, communication, and genuine hospitality as the keys to long-term success.

We discuss:
1️⃣ The challenges of managing vacation rentals along the 30A corridor
2️⃣ How leadership and team structure can prevent burnout
3️⃣ Creative ways to engage and communicate with homeowners
4️⃣ Why defining core values transforms company culture
5️⃣ The importance of collaboration among local property managers
6️⃣ Insights on market shifts post-2021 and preparing for sustainable growth

This episode is a reminder that growth starts with your people and that sustainable success in hospitality is built from the inside out.

Connect with Dylan:

LinkedIn: https://www.linkedin.com/in/dylan-bozarth-6225b8338/

Website: https://www.30aescapes.com/ 

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #culture

Send us a message!

When everything you’ve built disappears overnight, how do you begin again?

In this episode, we sit down with Angela “Angie” Leone, founder of Coconut Condos in Maui, to share a story of loss, faith, and rebirth after the devastating Lahaina wildfires.

Just days after finding a buyer for her thriving vacation rental company, Angie’s world changed forever. The wildfires destroyed her office, her vehicles, and 45 of the 50 homes she managed — a lifetime of work gone in an instant.

But what followed wasn’t the end of her story.

Through faith, family, and community, Angie found a way forward, creating new meaning, new strength, and a renewed sense of purpose in the ashes.

She opens up about:

1️⃣ The day Lahaina burned  and how her family faced unimaginable loss together

2️⃣ The “5 Fs” that became her foundation for resilience: Faith, Family, Fitness, Friends, and Focus

3️⃣ The healing power of cold plunges, saunas, and daily routines

4️⃣ Building the Lahaina Dreamers Cohort:  a community helping women rediscover purpose after tragedy

5️⃣The power of faith, perseverance, and post-traumatic growth

Connect with Angie:

LinkedIn: https://www.linkedin.com/in/angela-leone-549295a4/ 

Website: https://www.coconutcondos.com/ 

Exclusive Offers for Alex & Annie Listeners:

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #hospitality

Send us a message!

Big news to kick off the month! 🚀

In this first-of-the-month bonus episode, Alex & Annie sit down with the Boom founders, Moran,  Shahar, and Alon Goldboim, to talk about Boom’s recent $12.7 million funding round and what it means for the future of the short-term rental (STR) industry.

The Goldboim brothers share how they built Boom, the world’s first AI-powered Property Management System (AiPMS), and how their newest innovation, BAM (Business Agentic Manager), is redefining what true AI automation looks like for property managers.

From their vision of “business-as-a-software” to the story behind their investor partnerships, this conversation dives deep into the future of AI-driven STR operations, profitability, and guest experience — and why Boom’s approach to AI is fundamentally different from every other PMS on the market.

We cover:

1️⃣ The story behind Boom’s $12.7M funding raise and what it enables next

2️⃣ How the Goldboim brothers combined real estate, tech, and AI expertise to build Boom

3️⃣ What Agentic AI means and how BAM helps operators move from reacting to predicting

4️⃣ Why Boom’s all-in-one design gives AI a true advantage over bolt-on solutions

5️⃣ The future of “business as a software” and how AI will power every part of STR operations

Learn more about Boom:

LinkedIn: https://www.linkedin.com/company/boom-now/ 

Website: https://www.boomnow.com/ 

Connect with the Boom Brothers:

Moran Goldboim: https://www.linkedin.com/in/moran-goldboim-9bb9b118/
Shahar Goldboim: https://www.linkedin.com/in/shahar-goldboim-80820b95/v
Alon Goldboim: https://www.linkedin.com/in/alon-goldboim-56821880/ 

Exclusive Offers for Alex & Annie Listeners:

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout: https://www.lodgify.com/ 

Offer valid until December 31, 2025.

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #AIinhospitality

Send us a message!

In this episode, we’re joined by Kerri Gibson, CEO and Co-Founder of Chalets Hygge, a hospitality brand inspired by the Scandinavian idea of hygge — finding joy and contentment in life’s quieter moments.

After years in the corporate tech world, Kerri took a much-needed step back to rediscover what truly mattered. That pause led her to create a business grounded in balance, creativity, and genuine human connection.

What began as a single renovation project has grown into a collection of cozy retreats and a thriving brand where 70% of bookings come directly from guests. With Lodgify at the core of her tech stack, Kerri has built systems that simplify operations while keeping guest relationships personal and meaningful.

We discuss:

1️⃣ How a personal sabbatical evolved into a purpose-led hospitality brand

2️⃣ Building trust through authenticity and storytelling

3️⃣ Why repeat guests are the strongest driver of direct bookings

4️⃣ How Lodgify helps her maintain genuine connection at scale

5️⃣ Lessons from expanding into a boutique motel guided by the same values

Connect with Kerri:

LinkedIn: https://www.linkedin.com/in/kerri-gibson-cpa/
Website: https://chaletshygge.com/ 

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #directbookings

Send us a message!

As hospitality companies race to scale, many face a difficult trade-off: grow fast or stay personal. 

But Zzzing, a leading hospitality brand based in Malta, is proving you can do both.

In this episode, we’re joined by Sab Mulligan, Head of Teams at Zzzing, to explore how they’ve scaled rapidly by using AI not to replace the human touch, but to protect and enhance it.

Through a thoughtful blend of technology, team culture, and brand consistency, Zzzing is setting a new benchmark for what modern hospitality can look like.

We cover:

1️⃣ How Zzzing scaled from 40 to nearly 500 properties without compromising guest experience
2️⃣ How Boom allows their team to grow fast without worrying about the tech stack
3️⃣ Why they embraced AI as a teammate (not a replacement) for human hospitality
4️⃣ How they use AI to automate routine tasks and free up teams for more meaningful guest interactions
5️⃣ How they maintain consistency across properties while delivering personalized, local experiences
6️⃣ How they balance rapid operational growth with a deep commitment to guest care

Whether you manage a small portfolio or lead a growing hospitality brand, this episode offers actionable insights into scaling with intention and staying human in an AI-driven world.

Connect with Sab:

LinkedIn: https://www.linkedin.com/in/sabrinamulligan/ 

Website: https://www.zzzing.com/ 

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #AIinhospitality

Send us a message!

In this episode, Alex & Annie are joined by Marissa Galle, founder of Click Media, to explore the real impact of photography, video, and social content on brand perception and booking behavior.

Marissa shares how vacation rental operators can move beyond generic listings and start using visual storytelling to connect with guests, stand out on OTAs, and bring more personality into their marketing. From FPV drone shots to content repurposing strategies, she breaks down what works and why.

We cover:

1️⃣ What “visual storytelling” means in a modern vacation rental business
2️⃣ How to turn property photos into content that inspires trust and excitement
3️⃣ The biggest mistakes operators make with social media and video
4️⃣ Why showing your team is just as important as showing your homes
5️⃣ How Click is making it easier to access high-quality media services at scale

If you’re looking for fresh ways to strengthen your brand and drive more direct demand, this episode is packed with practical ideas to help you do just that.

Connect with Marissa:
LinkedIn: https://www.linkedin.com/in/marissagalle/
Website: https://letsgoclick.com/ 

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #storytelling

Send us a message!

As the vacation rental industry matures, growth has become the holy grail for many property management companies. But what happens when scaling too fast starts doing more harm than good?

In this episode, Ashley Ching, Founder & CEO of Inhaven, joins us to unpack her in-depth research on why many large property management companies fail and what separates the ones that last.

Drawing insights from over 100 executive interviews across the hotel, restaurant, and vacation rental sectors, Ashley reveals the five pillars of successful hospitality management  and how losing sight of them leads to the downfall of even the biggest brands.

We cover:

1️⃣ Why diseconomies of scale are real in hospitality and how to avoid them
2️⃣ The five pillars that define sustainable hospitality businesses
3️⃣ Why curated portfolios and empowered local teams matter more than size
4️⃣ What Vacasa and Aimbridge’s struggles teach us about over-expansion
5️⃣ How Inhaven is helping property managers raise the standard for quality and consistency

Ashley also shares how her background with Tiffany & Co. and The Home Depot shaped her approach to brand standards and guest experience and how those same principles can guide operators in today’s competitive landscape.

Connect with Ashley:
LinkedIn: https://www.linkedin.com/in/ashley-ching-7569a5240/
Website: https://inhaven.com/ 

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #propertymanagement

Send us a message!

This year marks 40 years of the Vacation Rental Management Association (VRMA), a milestone that comes at a pivotal time for the industry. 

In this episode, Alex & Annie sit down with Anne Gardner, Executive Director of VRMA, to explore how the association is entering a new chapter of growth, engagement, and industry leadership.

Anne reflects on her first year as Executive Director and shares how listening to members, strengthening communication, and re-energizing volunteer leadership have reshaped VRMA’s direction. From transforming the design of its events to amplifying advocacy and expanding education for managers of every size, VRMA is building a foundation for the next 40 years.

In this conversation, we cover:

1️⃣ Why listening to members has been central to VRMA’s renewal.
2️⃣ How this year’s 40th anniversary conference in Las Vegas is setting a new standard for engagement, education, and networking.
3️⃣ The role of smaller operators in the future of professional property management.
4️⃣ How VRMA is working with local associations, DMOs, and even hotel groups to strengthen advocacy and industry collaboration.
5️⃣ What’s ahead for VRMA as it continues to evolve with the needs of its members.

Whether you’re a longtime member or new to the vacation rental space, this episode offers valuable insight into how VRMA is leading the industry into its next era.

Connect with Anne:
LinkedIn: https://www.linkedin.com/in/anne-gardner-mba-cae/

Connect with VRMA:
LinkedIn: https://www.linkedin.com/company/vrma/
Website: https://www.vrma.org/

✨ Exclusive Offers to Alex & Annie Listeners:

Use code AAVRMA25LV to receive 15% off as a property manager attending VRMA, October 12–14 at Caesars Forum, Las Vegas.

Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #vrma

Send us a message!

When Airbnb changes its policies, the ripple effect can shake operators everywhere. For many, the problem is deeper than one policy update. Relying too heavily on a single platform leaves businesses vulnerable, and the cracks are starting to show.

In this episode, Mark Simpson, CEO and founder of Boostly, shares why now is the time for vacation rental operators to double down on direct bookings. Drawing from more than a decade of helping hosts grow beyond OTAs, Mark brings practical steps that any operator can put into action.

We cover:
1️⃣ Why overreliance on OTAs creates long-term risk for property managers
2️⃣ How to turn guest data into a foundation for repeat bookings
3️⃣ Simple strategies that work even without a large marketing budget
4️⃣ Ways to use referrals, user-generated content, and email campaigns to build stronger relationships with guests
5️⃣ What Boostly is creating to make direct bookings more accessible and effective

Mark also opens up about the importance of creativity in marketing, sharing real stories of campaigns that cut through the noise at conferences and online. His approach proves that building direct channels is not only possible but powerful.

Connect with Mark:
LinkedIn: https://www.linkedin.com/in/mrmarksimpson/
Website: https://boostly.co.uk/

✨ Exclusive Offer to Alex & Annie Listeners:

Get free onboarding when you partner with Xplorie! Valid through November 30, 2025.

👉 https://hubs.ly/Q03B9lmX0  

Free Market Assessment from Track (valued at $400)

Get 3–5 actionable insights tailored to your business. Meet one-on-one with an expert to evaluate your market, identify opportunities, and build a winning strategy.

👉 https://calendly.com/dstephens-tnsinc 

Considering an exit strategy? 

Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.

👉 Contact [email protected] 

#vacationrentals #shorttermrentals #directbookings