Advertise on podcast: Alex and Annie: The Real Women of Vacation Rentals

Nashville was buzzing, and VRMA 2026 brought some of the industry's biggest conversations to the forefront! From major OTA changes and AI developments to industry consolidation and predictions for 2027, this year's conference sparked some fascinating discussions about the future of vacation rentals. And of course, Alex & Annie were right in the middle of it all. In this special episode, we're taking you straight to the VRMA show floor for a mix of industry insight, candid conversations, and a little unexpected fun. We caught up with some of our industry partners and put them on the spot with three burning questions: Where do hospitality professionals actually go on vacation? If their company were a band, who would they be? And the most entertaining question of all: "Rumor has it..." We even kept an unofficial tally, and let's just say the beach won, Bali had a moment, and classic rock is apparently alive and well in vacation rentals. Beyond the laughs and show-floor banter, we also sat down for separate conversations with Jeff Hurst of Furnished Finder, Ian Ackland of Booking.com, and Joel Schoen of Escapia, each bringing a unique perspective on the industry's evolving landscape. Their discussions explore Vrbo's fee changes, opportunities in midterm rentals, industry consolidation, AI, and the future of vacation rental technology and distribution. From the latest industry developments to the unexpected moments that made Nashville memorable, this episode captures the energy, insights, and personalities of VRMA 2026. Episode Chapters: 03:40 - Three burning questions: industry rumors, rock bands, and dream vacations 18:57 - Jeff Hurst on Furnished Finder and the growth of midterm rentals 21:40 - Vrbo's fee changes and the evolving OTA landscape 23:45 - Will AI transform vacation rental distribution? 33:58 - Ian Ackland on Booking.com, trust, and industry partnerships 41:20 - What's next for vacation rental industry consolidation? 45:01 - Joel Schoen on Escapia's latest innovations 47:58 - AI, customer support, and the human side of vacation rental technology Whether you joined us in Nashville or missed the conference this year, tune in for an inside look at the conversations, personalities, and ideas making waves across the vacation rental industry. ✨ Exclusive Offers to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list Build a direct booking site designed to get found and convert with CraftedStays. Turn more visitors into direct bookings with less manual work. 👉 Get started: https://craftedstays.co/alexannie/ #vacationrentals #shorttermrentals #VRMA2026 Send us a message!

Your revenue may be up in 2026, but how much of that growth came from a stronger strategy, and what can you learn from those results heading into 2027? As vacation rental operators begin planning for the year ahead, understanding what drove their performance becomes especially important. In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie welcome back Julie Brinkman, CEO of Beyond, for a timely conversation about evaluating revenue performance, identifying missed opportunities, and building a more effective strategy for 2027. Julie explains why portfolio-wide revenue numbers can hide important differences in performance across properties, markets, and inventory types. She shares how operators can use segmentation, historical trends, and market comparisons to understand where their strategies worked and where adjustments may be needed. Through real questions from vacation rental operators, Julie offers practical guidance on setting realistic revenue targets, strengthening owner conversations, and making smarter decisions before the next booking season begins. Episode Chapters 00:00 – Welcome to Revenue Reality Check, presented by Beyond 03:56 – How to evaluate your 2026 revenue performance 07:14 – Using performance data to retain and acquire homeowners 12:22 – Rethinking distribution, direct bookings, and AI search 16:03 – Turning guest data into repeat booking opportunities 20:04 – Why one revenue strategy doesn't work for every property 24:03 – Identifying inventory that may be holding your portfolio back 26:04 – The danger of lowering rates too early 29:46 – Using search demand to make better pricing decisions 30:51 – Setting 2027 revenue targets using historical performance 33:16 – When should you start planning your 2027 revenue strategy? As operators prepare for another year of changing demand and booking behavior, Julie encourages a closer examination of the decisions behind their results and the opportunities available to improve performance. Tune in to this episode of Revenue Reality Check, presented by Beyond, for insights to help you approach 2027 with a more informed and adaptable revenue strategy. Connect with Julie Brinkman LinkedIn: https://www.linkedin.com/in/jrbrinkman/ Connect with Beyond Website: https://beyondpricing.com/ LinkedIn: https://www.linkedin.com/company/beyond-pricing/ Instagram: https://www.instagram.com/beyondpricing/ #vacationrentals #shorttermrentals #revenuemanagement Send us a message!

Growing a vacation rental portfolio brings new opportunities, but maintaining the quality and consistency that made the business successful becomes increasingly challenging as operations expand. In this episode, Alex & Annie catch up with Brandon Hall, Founder and CEO of Hallson Hospitality, for an on-location conversation in Nashville about the company's next chapter of growth. Brandon shares the news of Hallson Hospitality's merger with Epicbnb, a partnership expected to bring their combined portfolio to approximately 175 properties. He explains how their shared commitment to hospitality standards, strong guest reviews, and thoughtful operations made the merger a natural fit. As the company prepares for its next phase, Brandon shares how Hallson Hospitality is investing in better systems, centralized property information, and AI-powered tools to help teams work more efficiently and maintain service standards across a larger portfolio. Episode Chapters: 02:32 - Welcome to Nashville: Inside Hallson Hospitality's Star Piano Suites 03:14 - Blending boutique hotel service with luxury vacation rentals 04:48 - Why design, branding, and consistency matter to the guest experience 07:12 - Brandon Hall's approach to responsible vacation rental growth 09:50 - Hallson Hospitality's merger with Epicbnb and expansion to 175 properties 11:59 - Expanding into boutique hospitality with Germantown Inn 13:34 - Scaling operations while maintaining quality and service standards 14:08 - How Hallson is using AI and centralized property data to support its team 18:51 - Improving information accuracy across a growing portfolio 19:44 - Integrating the merger and exploring future growth opportunities From strategic partnerships and brand consistency to technology and operational readiness, this episode offers an inside look at how Hallson Hospitality is approaching expansion while keeping the guest experience at the center of its growth strategy. Connect with Brandon: LinkedIn: https://www.linkedin.com/in/brandonhall/  Learn more about Hallson Hospitality: Instagram: https://www.instagram.com/hallson.co/  Website: https://hallson.co/  Facebook: https://www.facebook.com/hallsonco  ✨ Exclusive Offers to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/ List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions. 👉 Get started: https://partners.vacationfinder.com/alexandannie Learn more about dormakaba’s vacation & short-term rental access solutions: 👉 Website: https://dk.world/Vacation26  #vacationrentals #shorttermrentals #guestexperience Send us a message!

Your property management system says one thing. Your revenue management platform says another. Your accounting reports tell a different story. So which numbers can you actually trust? As AI becomes more integrated into vacation rental operations, inconsistent data across systems presents a growing challenge for property managers. In this episode, Alex & Annie sit down with John An, Founder and CEO of TechTape, to explore why disconnected systems and conflicting data can lead to misleading reports, unreliable AI insights, and costly business decisions. John also introduces Tidewell by TechTape, a solution designed to bring fragmented data from existing systems into one consistent, trusted foundation. They explore how cleaner, more connected data can give operators greater visibility into their business and support more informed decisions while building a stronger foundation for AI. Episode Chapters: 02:43 - How John's experience as an operator led to TechTape 05:07 - Introducing Tidewell and the problem it solves 06:31 - Why vacation rental systems report different numbers 08:34 - The risks of using AI with inconsistent data 10:29 - Finding operational opportunities through connected data 13:58 - Why consistent definitions of revenue and occupancy matter 16:09 - Making enterprise-level data infrastructure accessible to smaller operators 19:11 - Maintaining historical data through PMS migrations 23:09 - Improving maintenance reporting with connected data 28:18 - Integrating existing software and data sources 31:11 - Building a trustworthy foundation for AI automation Connect with John An: LinkedIn: https://www.linkedin.com/in/john-s-an/  TechTape: https://www.gettechtape.com/  Tidewell: https://www.gettechtape.com/tidewell/  ✨ Exclusive Offers to Alex & Annie Listeners: Get 3 months of Tidewell FREE with your property management system connected, for up to 20 properties. Bring your vacation rental data together and start building a more reliable foundation for reporting, business insights, and AI. 👉 Learn more about Tidewell: https://www.gettechtape.com/tidewell/ Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list #vacationrentals #shorttermrentals #AI Send us a message!

A high-end vacation rental and a premium nightly rate don't always guarantee well-behaved guests. And when a stay ends with serious property damage, getting the home back in shape can be only part of the headache. In Episode 4 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Alexandra “Ali” Chaney of 30A Beach Stays & Vacations, alongside Amanda Martins and Zach Grimes of Safely, for a candid conversation about the unpredictable side of vacation rental management. Ali brings firsthand stories of unexpected guest incidents and the challenges of managing damage claims, while Amanda and Zach share insights from Safely's experience helping operators navigate these situations. Together, they explore the realities of guest-related risks, the challenges of recovering costs through booking platforms, and how the right protection and processes can help property managers safeguard the homes entrusted to them. We discuss: 12:55 - Why luxury properties are not immune to destructive guest behavior 14:53 - The challenges of recovering damage costs through booking platforms 21:52 - How the right protection can support homeowner confidence 24:08 - What operators can learn from real guest damage incidents 27:47 - Why documentation and a clear claims process matter 30:14 - How different types of insurance and damage protection work together 36:48 - Where guest waivers fit into a broader protection strategy From shocking guest stories to practical insights on damage protection, this episode offers plenty for property managers to think about before the next stay goes sideways. Connect with Ali: https://www.alexandanniepodcast.com/guests/alexandra-chaney/  Connect with Zach: LinkedIn: https://www.linkedin.com/in/zach-grimes-9242b478/  Connect with Amanda: LinkedIn: https://www.linkedin.com/in/amandakatmartins/  Learn more about Safely: Website: https://safely.com/alex-and-annie LinkedIn: https://www.linkedin.com/company/safely-stay/ Instagram: http://instagram.com/safely/ Facebook: https://www.facebook.com/safelyprotection  This Episode's Cocktail: Ali's Special A classic margarita with a fresh citrus twist. Ingredients: TequilaTriple secSour mixFresh lime juice, optionalFresh orange juice, optionalIceHow to make it: Combine the tequila, triple sec, and sour mix in a shaker with ice. Add fresh orange and lime juice if desired. Shake well and pour into your favorite glass. #vacationrentals #shorttermrentals #damageclaims Send us a message!

A guest books a beautiful vacation rental, has an incredible stay, and leaves with memories worth sharing. But when they tell others about their experience, whose brand do they remember? In this episode, Alex & Annie sit down with Michelle Gilliland, VP of Sales at Savvy, to explore what it takes to build a recognizable brand in a market where OTAs dominate traveler attention. Drawing from nearly 15 years of experience in the vacation rental industry, Michelle brings a unique perspective on how brands can differentiate themselves, create stronger connections with travelers, and build lasting recognition. The conversation offers a look at Savvy's approach to branding and distribution, along with insights that challenge property managers to think more intentionally about how their businesses are discovered, experienced, and remembered. Episode Chapters: 03:06 - Michelle Gilliland's background at Vrbo, Expedia Group, and Savvy 03:43 - Why property managers deserve greater brand visibility 06:21 - Airbnb's direct booking links and what they mean for operators 12:33 - Why consistency matters throughout the guest experience 17:00 - Should the vacation rental industry establish clearer hospitality standards? 21:48 - Making it easier for travelers to connect directly with property managers 24:58 - Collaboration, community, and building local brand awareness 26:05 - Behind Savvy's unconventional "Death of the Middleman" marketing campaign 31:17 - How referral incentives can encourage more bookings 33:26 - Savvy's approach to brand visibility, distribution, and guest relationships 37:58 - Building a business that is less dependent on major OTAs If you're looking to strengthen your vacation rental brand and stand out in an increasingly competitive market, this is a conversation worth tuning into. Connect with Michelle: LinkedIn: https://www.linkedin.com/in/michellegilliland/ ✨ Exclusive Offers to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list Learn more about dormakaba’s vacation & short-term rental access solutions: 👉 Website: https://dk.world/Vacation26  #vacationrentals #shorttermrentals #directbookings Send us a message!

The way travelers discover vacation rentals is changing. Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent. In this episode, Alex & Annie sit down with Gil Chan, Founder and CEO of CraftedStays, to explore what this shift means for vacation rental operators and the direct booking websites they have spent years building. Gil shares how his experience as a property manager, combined with his background in e-commerce and product development, led him to build CraftedStays around a problem he saw firsthand: vacation rental websites often lack the infrastructure needed to support a seamless, measurable direct booking journey. The conversation also dives into how AI search is changing website strategy, what CraftedStays has learned from its research into AI visibility, and why content, structured data, reviews, and strong local expertise may become even more important as the search journey evolves. Episode Chapters: 05:39 - Why direct bookings are still complicated 06:56 - What vacation rental websites can learn from e-commerce 16:52 - Building a website platform that can evolve faster 18:55 - CraftedStays’ relationship with Google and the development of Aria 22:56 - From Google search to conversational travel discovery 28:34 - Reviews, structured data, and helping AI understand your business 32:07 - What CraftedStays learned from 24,000 AI search queries 36:53 - Using AI to create and optimize direct booking landing pages 48:13 - Where independent operators can compete with OTAs in AI search 50:12 - How to audit your visibility across AI search platforms 55:35 - Why there is no “page two” in AI search Want to dig deeper into AI search? CraftedStays has created a free AI Search Guide for vacation rental operators that breaks down what property managers should be paying attention to as search continues to evolve. 👉 Explore the guide: https://craftedstays.co/ai-search-for-vacation-rentals/ Connect with Gil: LinkedIn: https://www.linkedin.com/in/thegilbertchan/ Learn more about CraftedStays: Website: https://craftedstays.co/alexannie/ ✨ Exclusive Offer to Alex & Annie Listeners: Build a direct booking site designed to get found and convert with CraftedStays. Turn more visitors into direct bookings with less manual work. 👉 Get started: https://craftedstays.co/alexannie/ Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/ Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list #vacationrentals #shorttermrentals #directbookingwebsite Send us a message!

In this fourth episode of First of the Month Wrangle, presented by Lasoh, we are joined by Orlie Benjamin, Founder and CEO of Lasoh, and Eric Goldreyer, Founder and CEO of Savvy, to unpack one of the latest conversations surrounding Airbnb and direct booking. Airbnb has been testing a program that allows some hosts and co-hosts to drive their own demand to an Airbnb listing in exchange for a reduced platform fee. The company may be calling it direct booking, but Orlie and Eric argue that the definition gets more complicated when the reservation still happens on Airbnb and the operator does not fully control the guest relationship. That question opens the door to a much bigger conversation about what direct booking actually means, who owns the guest relationship, and what operators gain or give up depending on where that relationship lives. Episode Chapters 00:57 - What Airbnb is testing with “direct booking” 05:53 - Is Airbnb’s direct booking link really direct? 08:30 - If you are doing the marketing, who owns the guest? 13:02 - Guest data, remarketing, and the customer relationship 23:30 - Why direct booking has a trust problem 26:23 - Why your guest list is part of the value of your business 29:05 - Owning versus renting the customer 30:02 - The opportunity in referrals and repeat guests 39:31 - Solving the discovery problem for direct booking 41:56 - How AI, AEO, and GEO are changing travel search 49:04 - Why there will never be only one booking channel 51:31 - Building around customer feedback and relationships For vacation rental operators thinking seriously about reducing OTA dependence, strengthening guest relationships, and building more value beyond the next reservation, this episode offers a useful look at what “direct” really means and what it takes to build a business around the customer relationship.  Learn more about Lasoh: Website: https://tinyurl.com/52nvyw8t LinkedIn: https://www.linkedin.com/company/lasoh/ Facebook: https://www.facebook.com/people/Lasohio/61575721958679/ Instagram: https://www.instagram.com/lasoh.io Connect with Orlie: LinkedIn: https://www.linkedin.com/in/orliebenjamin/ Facebook: https://www.facebook.com/profile.php?id=61585160391720 Instagram: https://www.instagram.com/orlie.benjamin/  Learn more about Savvy: Website: https://www.savvy.com/ LinkedIn: https://www.linkedin.com/company/stay-savvy/ Instagram: https://www.instagram.com/savvy_stay Facebook: https://www.facebook.com/savvystays  Connect with Eric: LinkedIn: https://www.linkedin.com/in/ericgoldreyer/  ✨ Exclusive Offer to Alex & Annie Listeners:  Turn every guest interaction into more revenue with Lasoh. Get 20% off Lasoh products with code AlexandAnnie. Valid through November 30, 2026. 👉 Learn more: https://explore.lasoh.io/alex-annie #vacationrentals #shorttermrentals #directbookings Send us a message!

A guest can spend months planning a vacation, travel all day, arrive with tired kids and luggage in tow, and then have the entire experience unravel at one very important moment: the front door. In this episode, Alex is joined by Dawn Keathley of Dormakaba and Matt Seyed of Secure Lodging Systems for a conversation about an often overlooked part of the vacation rental experience: guest access. They explore why getting guests through the door reliably is about much more than choosing a lock. Access sits at the intersection of guest experience, property security, owner trust, and day-to-day operations. Drawing from both the manufacturing and implementation sides of the industry, Dawn and Matt share what reliable access looks like in practice and why the right system needs to hold up to constant turnover while still making arrival simple for guests and manageable for teams. Reliable access is easy to overlook precisely because guests should not have to think about it. A failure at the front door, however, can quickly become the moment they remember most. Episode Chapters: 06:17 – What makes Dormakaba different in access control 08:18 – What makes vacation rental access different from other industries 09:30 – Working with homeowners, HOAs, and associations 10:51 – Managing access across complex condo and resort environments 17:20 – How vacation rental access control has evolved 18:20 – The challenges with hard keys and inconsistent lock systems 19:55 – Commercial-grade vs. residential-grade locks 21:43 – Phasing access-control upgrades across a portfolio 22:55 – Why the vacation starts at the front door 24:00 – Access control and the professionalization of vacation rentals 25:26 – What happens when operators cut corners on guest access 31:53 – Evaluating doors, common areas, pool gates, and guest workflows 33:14 – New access technology built for vacation rentals Learn more about dormakaba’s vacation & short-term rental access solutions: Website: https://dk.world/Vacation26  Connect with Dawn: LinkedIn: https://www.linkedin.com/in/dawnkeathley/  Connect with Matt: LinkedIn: https://www.linkedin.com/in/matt-s-2a05751b6/  ✨ Exclusive Offer to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business?  Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/  Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list #vacationrentals #shorttermrentals #guestexperience Send us a message!

Alex & Annie are taking the podcast on the road for a special on-location episode from Montego Bay, Jamaica.  This time, they’re stepping inside Call Center Solutions to see the operation firsthand, meet the people behind it, and get a closer look at what it takes to build a hospitality team that can support vacation rental businesses from hundreds of miles away. Throughout the visit, Alex and Annie sit down with members of the CCS team across operations, HR, IT, and leadership to hear what the business looks like from the people running it every day. One theme keeps surfacing along the way: the importance of culture, connection, and making remote team members feel like a true extension of the companies they support. Episode Chapters: 00:00 – Alex & Annie arrive at Call Center Solutions in Montego Bay 02:49 – How CCS started in Jamaica and grew beyond the original experiment 06:50 – What onboarding and training a remote hospitality team actually looks like 11:36 – Meet the operations team: culture, customer service, and what makes a great agent 20:47 – Inside HR: hiring, employee support, and building a team people want to stay with 29:42 – The IT and infrastructure keeping the operation running 34:21 – Beachside reflections on culture, connection, and hospitality 41:30 – Beyond reservations: how CCS supports more of the operation 45:16 – How property managers can get started with a CCS team Come along for a behind-the-scenes look at Call Center Solutions, the team they've built in Montego Bay, and a few uniquely Jamaican moments along the way. Connect with Call Center Solutions: Website: https://www.ccssuccess.com/  LinkedIn: https://www.linkedin.com/company/my-call-center-solutions/  Instagram: https://www.instagram.com/call.center.solutions/  ✨ Exclusive Offers to Alex & Annie Listeners: Build a direct booking site designed to get found and convert with Crafted Stays. Turn more visitors into direct bookings with less manual work. 👉 Get started: https://craftedstays.co/alexannie/ Thinking about the next chapter for your vacation rental business?  Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/  Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list #vacationrentals #shorttermrentals #guestexperience Send us a message!

In this episode, Alex & Annie sit down with Vinny Dicarlo, CEO of Ciirus, and Josh Parry, Chief Product Officer, for a conversation about the philosophy that has shaped the company over nearly two decades. Founded as a family business, Ciirus has taken a deliberately measured approach to growth. Rather than building around outside investment or pressure to scale at all costs, Vinny and Josh explain how the company has focused on long-term customer relationships, continued investment in its technology, and human support that keeps the team closely connected to the property managers it serves. That approach opens up a broader conversation about what operators should expect from a technology partner today. Vinny and Josh share why they believe there are limits to how much vacation rental operations can be automated, where AI can genuinely help, and why human involvement still matters in an industry where every property, owner, guest, and stay can look different. Episode Chapters: 11:14 - Building customer relationships designed to last 17:15 - Why Ciirus has chosen measured growth over growth at all costs 18:28 - How independent ownership shapes investment in customers and technology 22:38 - Why vacation rental operations cannot automate everything 27:39 - Building a global team around specialized talent 32:49 - Helping property managers get more from their technology 38:14 - Why customer and employee satisfaction matter together 39:55 - Ciirus’ new mobile app, owner tools, and Booking.com integration 46:03 - How LoveRentals helps property managers expand their capabilities 54:59 - Finding vacation rental demand beyond the major OTAs 57:55 - Reaching guests through travel agents, wholesalers, and international markets 1:02:24 - What is next for the Ciirus platform If you are evaluating your tech stack, thinking about sustainable growth, or looking for new ways to reach guests, this episode offers a closer look at what a strong technology partnership can bring to your business. Connect with Josh & Vinny Josh Parry: https://www.linkedin.com/in/josh-parry-47165997/  Vinny Dicarlo: https://www.linkedin.com/in/vincenzo-dicarlo/  Connect with Ciirus Website: https://ciirus.com/ ✨ Exclusive Offers to Alex & Annie Listeners: Alex & Annie listeners can receive their first three months of Ciirus subscription fees waived when joining the platform. Visit https://ciirus.com/ and let the team know you heard about Ciirus through the Alex & Annie Podcast. Thinking about the next chapter for your vacation rental business?  Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/  List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions. 👉 Get started: https://partners.vacationfinder.com/alexandannie  #vacationrentals #shorttermrentals #vacationrentaltechnology Send us a message!

In this episode, Annie is joined by Jinnie Randolph for a conversation with Cristiana Carpini, founder of the Women in Vacation Rental European Conference (WVREC), and Neely Khan, founder of Kahani. Together, they explore the value of creating spaces where women can build trust, share openly, and form meaningful relationships that support both personal and professional growth. Cristiana shares the thinking behind WVREC, while Neely reflects on what made the first gathering feel so different and why that environment gave her the confidence to share a deeply personal story publicly for the first time. They also look ahead to WVREC 2026 in Barcelona, how the event is evolving, and the larger community Cristiana and Neely hope to continue building around it. Episode Chapters: 02:20 - The story behind the Women in Vacation Rental European Conference 09:23 - Why trust and vulnerability shaped the first WVREC 16:19 - Why Cristiana is keeping the event women-focused 18:28 - How deeper connections can lead to collaboration and opportunity 21:52 - What to expect from WVREC 2026 in Barcelona 24:52 - Cristiana and Neely’s upcoming storytelling project 28:00 - Making the case for investing in professional development 34:27 - What surprised Cristiana most about the first conference 40:31 - Final details for WVREC 2026 Connect with Cristiana: LinkedIn: https://www.linkedin.com/in/cristiana-carpini-hospitality/ Connect with Neely: LinkedIn: https://www.linkedin.com/in/neelykhan/  Learn more about WVREC: https://wvrec.eu/  ✨ Exclusive Offer to Alex & Annie Listeners: Build a direct booking site designed to get found and convert with Crafted Stays. Turn more visitors into direct bookings with less manual work. 👉 Get started: https://craftedstays.co/alexannie/ Thinking about the next chapter for your vacation rental business?  Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/  List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions. 👉 Get started: https://partners.vacationfinder.com/alexandannie  #vacationrentals #shorttermrentals #hospitality Send us a message!

Welcome to Episode 300 of the Alex & Annie Podcast! 🎉  Three hundred conversations, countless aha moments, plenty of industry debates, and a front-row seat to some of the biggest shifts vacation rentals have seen over the last several years. This is such a huge milestone for us ⭐ To celebrate, we knew we wanted to bring back someone who has been part of the Alex & Annie journey since the early days. We’re fortunate to have several people who have supported us along the way, and for this milestone, longtime friend of the show Terry Whyte returns for a conversation about how far the vacation rental industry has come and where it may be headed next. Terry revisits predictions from his past appearances, including his views on technology, all-in-one platforms, loyalty, and distribution. He shares what he got right, what he would revise today, and how AI has changed the conversation. Through it all, Terry keeps coming back to the fundamentals: quality properties, strong technology, smart distribution, customer care, and real human hospitality. And because this is Episode 300, Alex & Annie also reflect on the journey so far and share a glimpse of what comes next for the podcast. Here’s to 300 episodes and the next chapter of Alex & Annie. 🥂 Episode Chapters 02:30 - Revisiting Terry’s past industry predictions 03:26 - How AI changed the vacation rental tech conversation 06:29 - Why technology is becoming more fragmented 08:29 - Where automation ends and human hospitality matters 16:31 - Why growth does not always mean adding more doors 18:35 - Why distribution matters more than ever 19:37 - Direct bookings, website traffic, and marketing 24:39 - Rethinking loyalty in vacation rentals 29:40 - Terry’s advice for operators today 30:39 - What will separate thriving property managers in the future 33:37 - The risk of relying on a single OTA 35:49 - Terry reflects on the Alex & Annie Podcast 39:44 - The industry shift that changed Terry’s business 41:23 - What comes next for Alex & Annie Connect with Terry: LinkedIn: https://www.linkedin.com/in/terry-whyte-4540633b/  ✨ Exclusive Offer to Alex & Annie Listeners: Build a direct booking site designed to get found and convert with Crafted Stays. Turn more visitors into direct bookings with less manual work. 👉 Get started: https://craftedstays.co/  Thinking about the next chapter for your vacation rental business?  Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/  List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions. 👉 Get started: https://partners.vacationfinder.com/alexandannie  #vacationrentals #shorttermrentals #hospitality Send us a message!

In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie are joined again by Julie Brinkman, CEO of Beyond, to talk about why owner retention deserves the same level of attention as pricing, pacing, and acquisition. Julie breaks down the metrics property managers should be watching, how unrealistic revenue expectations can create problems later in the relationship, and why adding new properties does not always tell the full story of business growth. She also answers real operator questions around high churn, founder-dependent owner relationships, and what retention can mean for the long-term value of a property management company. Episode chapters: 01:43 - Building owner trust through consistent communication 05:03 - The owner retention metrics property managers should understand 12:19 - When growth hides a leaky owner bucket 15:49 - Revenue projections and owner expectations 22:30 - Added 40 properties, lost 26: is that really growth? 27:00 - Transferring founder trust as the company scales 32:10 - What high owner churn can mean for a future sale 35:10 - Using portfolio data to identify where attention is needed Tune in for Episode 3 of Revenue Reality Check, brought to you by Beyond, and take a closer look at what owner churn may be telling you about the health of your business. Connect with Julie: LinkedIn: https://www.linkedin.com/in/jrbrinkman/  Connect with Beyond: Website: https://beyondpricing.com/ LinkedIn: https://www.linkedin.com/company/beyond-pricing/  Instagram: https://www.instagram.com/beyondpricing/  Facebook: https://www.linkedin.com/company/beyond-pricing/  #vacationrentals #shorttermrentals #strindustry Send us a message!

In this episode, Alex & Annie sit down with Jeremy Gall, Founder and CEO of Breezeway, to explore how the continued professionalization of vacation rentals is raising the bar for operations. Jeremy shares what led him to tackle one of the industry's most complex challenges: coordinating the people, properties, and workflows behind great hospitality. The conversation explores how rising guest expectations, greater owner scrutiny, and advances in technology are changing what it takes to operate well, and where vacation rental operations may be headed next. Episode Chapters: 04:10 - Building a company property managers want to work with 12:00 - The early days of Breezeway and connecting operational workflows 14:40 - Why property managers should think differently about their relationship with the property 18:35 - How rising guest expectations are changing vacation rental standards 22:00 - Reviews, owner expectations, and the professionalization of the industry 25:11 - The growing importance of cleaners and third-party service providers 29:01 - Could robots eventually handle vacation rental turnovers? 33:31 - How AI is changing vacation rental operations 39:52 - Why Breezeway continues to go deeper on operations As vacation rentals continue to mature, the operators who can deliver consistently behind the scenes will be better positioned to meet rising expectations from both guests and owners. Connect with Jeremy: LinkedIn: https://www.linkedin.com/in/jeremiahgall/  Connect with Breezeway: Website: https://hubs.la/Q04tyWJL0  ✨ Exclusive Offer to Alex & Annie Listeners: Get 20% off your first three months of Breezeway if you sign up by September 30.  👉 Get started here: https://hubs.la/Q04tyWJL0  Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list Thinking about the next chapter for your vacation rental business?  Connect with Monarch Collective to explore what growth could look like with the right platform behind you. 👉 Learn more: https://gomonarch.com/partnerships/  #vacationrentals #shorttermrentals #directbookings Send us a message!