Alex and Annie: The Real Women of Vacation Rentals

Alex and Annie
  • 5.0 (35)
  • Business
  • Updated Weekly

With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.

  1. 4h ago ·  Video

    1st of the Month Wrangle: Is Airbnb’s “Direct Booking” Really Direct? with Orlie Benjamin and Eric Goldreyer

    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!

    1st of the Month Wrangle: Is Airbnb’s “Direct Booking” Really Direct? with Orlie Benjamin and Eric Goldreyer

  2. 1d ago ·  Video

    Shut the Front Door: Why Guest Access Can Make or Break a Stay, with dormakaba

    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 Keathly 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!

    Shut the Front Door: Why Guest Access Can Make or Break a Stay, with dormakaba

  3. Sep 24 ·  Video

    Jamaican Me Crazy: Alex & Annie Live from Montego Bay, with Call Center Solutions

    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!

    Jamaican Me Crazy: Alex & Annie Live from Montego Bay, with Call Center Solutions

  4. Sep 16 ·  Video

    Building Vacation Rental Tech for Customers, Not Investors with Vinny Dicarlo and Josh Parry of Ciirus

    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!

    Building Vacation Rental Tech for Customers, Not Investors with Vinny Dicarlo and Josh Parry of Ciirus

  5. Sep 9 ·  Video

    Creating Space for Women to Connect, Grow & Lead with Cristiana Carpini & Neely Khan

    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!

    Creating Space for Women to Connect, Grow & Lead with Cristiana Carpini & Neely Khan

  6. Sep 2 ·  Video

    300th Episode Special: What’s Changed in Vacation Rentals and What Comes Next with Terry Whyte

    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!

    300th Episode Special: What’s Changed in Vacation Rentals and What Comes Next with Terry Whyte

  7. Sep 1 ·  Video

    Revenue Reality Check: Your Biggest Revenue Risk Isn’t Pricing, It’s Owner Churn with Julie Brinkman of Beyond

    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!

    Revenue Reality Check: Your Biggest Revenue Risk Isn’t Pricing, It’s Owner Churn with Julie Brinkman of Beyond

  8. Aug 26 ·  Video

    Why the Future of Vacation Rentals Starts with Better Operations with Jeremy Gall of Breezeway

    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!

    Why the Future of Vacation Rentals Starts with Better Operations with Jeremy Gall of Breezeway
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5
out of 5
35 Ratings

About

With more than 35 years of combined experience in vacation rentals, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity, seeking to find the one story, idea, strategy or decision that led to their guests big A-HA moment. Join them, as they highlight the REAL stories behind the people and brands that have built vacation rentals into the 100 BILLION dollar industry it is today.

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