Alex and Annie: The Real Women of Vacation Rentals

Hosted by Alex and Annie

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280

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Jun 2026

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EN-US

About the show

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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60 recent

June 15, 2026Episode 28541 min

Pour Decisions: When Vacation Brain Hits Summer Stays, with Amanda Martins of Safely

Send us a message!Welcome to the second episode of Pour Decisions: When Stays Go Sideways, presented by Safely.In this episode, Alex and Annie are joined again by Amanda Martins, VP of Business Development at Safely, for another round of real guest stories, summer stay surprises, and practical takeaways for short-term rental operators.This conversation is all about “vacation brain” and the strange, messy, and sometimes costly decisions guests make when they are out of their normal routine.From poolside surprises to hot tub chaos and grill-related mishaps, this episode brings the stories, the laughs, and the reminders operators can use before the next stay goes sideways.We discuss:05:38 - Why summer season can bring more guest-related damage08:38 - How vacation brain shows up in real short-term rental claims18:53 - What operators can learn from pool, hot tub, and grill-related incidents25:29 - Why clear amenity instructions can help reduce preventable issues10:24 - How protection programs can support owner trust08:20 - Why guest involvement is not always required in many damage claims11:49 - How Safely helps property managers explain coverage to homeowners38:30 - Why operators should think about preparation before the busy season gets messyConnect with Amanda:LinkedIn: https://www.linkedin.com/in/amandakatmartins/Learn more about Safely:Website: https://safely.com/alex-and-annieLinkedIn: https://www.linkedin.com/company/safely-stay/Instagram: http://instagram.com/safely/Facebook: https://www.facebook.com/safelyprotectionThis episode’s cocktail: Hugo Spritz with a twistA refreshing summer spritz inspired by Annie’s favorite vacation drink, with Amanda’s optional vodka twist.Ingredients:ProseccoElderflower liqueurFresh limeFresh mintClub sodaVodka, optionalHow to make it:Build over ice in a wine glass. Add elderflower liqueur, lime, mint, and vodka if using. Top with Prosecco and club soda, then stir gently.Best enjoyed responsibly and preferably nowhere near a hot tub full of seafood.#vacationrentals #shorttermrentals #vacationbrain

June 10, 2026Episode 28458 min

Trust Accounting Isn’t Back Office: It’s the Foundation, with Ed Ulmer of Barefoot

Send us a message!In this episode, we are joined by Ed Ulmer, CEO of Barefoot, for a conversation about trust accounting, vacation rental technology, and what operators need from their systems as their businesses become more complex. Ed shares how his background in tourism, destination marketing, real estate, and software all shaped the way he looks at vacation rental management today. For him, the industry has always come back to one core idea: trust. The conversation takes a deep dive into why trust accounting should not be treated as a back-office function. When vacation rental companies manage properties on behalf of owners, they are also managing funds, contracts, obligations, and expectations. As companies grow, that complexity only increases. Episode Chapters:03:18 - Ed’s path from tourism, real estate, and software into vacation rental technology11:56 - Why vacation rental management is built on trust17:37 - What trust accounting really means for property managers25:24 - Why managing owner and guest funds gets more complex as companies grow27:27 - How state regulations and real estate requirements impact vacation rental operators30:10 - Why loyalty programs are harder to build in vacation rentals than in hotels33:48 - How PMS technology can support concierge services, rewards, and guest retention39:17 - What operators should consider when choosing a PMS47:55 - How AI and natural language search may change the booking experienceFor operators evaluating their technology, this episode offers a practical look at why the systems behind the business matter just as much as the guest-facing experience. Connect with Ed & Barefoot:LinkedIn: https://www.linkedin.com/in/ed-ulmer-150596/ Website: https://www.barefoot.com/ Facebook: https://www.facebook.com/mybarefoot ✨ Exclusive Offer to Alex & Annie Listeners: Manage your vacation rental business with more control and confidence using Barefoot. Alex & Annie listeners get 10% off monthly fees through 2026.👉 Get started: https://www.barefoot.com/alex-and-annie 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 guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ #vacationrentals #shorttermrentals #trustaccounting

June 3, 2026Episode 28354 min

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

Send us a message!The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet.In this episode, we are joined by John Suzuki, Chief Technology Evangelist at Staylist, for a conversation about the evolution of vacation rental technology, the pace of innovation, and what this next chapter could mean for property managers.John brings a long-term perspective on how far the industry has come, along with a thoughtful look at where it may be headed as AI becomes more deeply connected to the way operators work, serve guests, and build their businesses.Episode Chapters:02:46 - John’s 20-Year Journey in the Vacation Rental Industry03:31 - How Vacation Rentals Moved From Phone and Fax Reservations Into the Mainstream of Travel04:47 - Why John Came Back to the Industry After Retiring09:20 - How AI Is Changing Property Management Technology10:53 - Why Property Managers Need Systems That Help Them Move Faster21:22 - The Importance of Connected Operations, Accounting, Reservations, Housekeeping, Maintenance, and Guest Communication27:17 - How AI Can Support Call Tracking, Reservation Inquiries, and Guest Service28:43 - Why Guest Data Will Play a Bigger Role in Travel Personalization35:06 - The Ethical and Security Questions Surrounding AI42:54 - How Robotics Could Affect Hospitality, Housekeeping, and the Workforce46:16 - Why Professionals Need to Stay Curious and Keep Learning48:55 - How AI Can Help Property Managers Get Back to the Human Side of HospitalityIf you are trying to understand what AI means for the future of vacation rentals, this conversation offers both perspective and practical insight from someone who has seen the industry evolve through multiple waves of change. Connect with John:Website: https://www.johnsuzuki.com/ ✨ Exclusive Offer to Alex & Annie Listeners: Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.👉 Get started: https://hospitable.com/partners/alex-annie Reach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ 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 #ai

June 1, 2026Episode 28237 min

1st of the Month Wrangle: Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Send us a message!In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered.This time, the conversation focuses on a simple but important question: can we stop marketing properties and start marketing to people?For many vacation rental operators, marketing often defaults to the property itself. A home needs bookings, a calendar has gaps, or a listing needs more visibility, so the message becomes centered around the unit. While property marketing still has a place, Orlie explains why stronger results often come from understanding the guest first.That means looking beyond the booking and thinking about who the guest is, why they are traveling, what they care about, and how operators can use that information to create more relevant communication.The conversation also explores why guest data is only valuable when operators can actually use it. Orlie breaks down how Lasoh is building a guest marketing system that helps operators collect, organize, and activate guest data through AI-supported campaigns, smarter segmentation, and more personalized messaging.Instead of expecting teams to manually sort through data, build every campaign from scratch, and figure out what message should go to which guest, Lasoh is working to make that process more accessible. The goal is to help operators create more meaningful marketing, drive repeat bookings, and grow revenue without adding more pressure to already busy teams.Episode Chapters01:16 - Stop marketing properties and start marketing to people01:41 - Why guest-first marketing needs better data03:53 - Property management systems vs. guest marketing systems06:47 - Turning guest data into action with Lasoh08:24 - Using AI to create revenue-driving campaigns12:28 - Smarter segmentation and fewer, better emails15:54 - How AI agents support vacation rental marketing18:40 - Saving time and growing revenue without adding more work23:42 - One-to-all, one-to-some, and one-to-one marketing26:44 - Lasoh’s founding member program30:35 - What founding members can expectThis episode is a valuable listen for anyone thinking about how to make vacation rental marketing more relevant, more efficient, and more connected to the people behind each stay.Learn more about Lasoh:Website: https://lasoh.io/ LinkedIn: https://www.linkedin.com/company/lasoh/ Facebook: https://www.facebook.com/people/Lasohio/61575721958679/ Instagram: https://www.instagram.com/lasoh.ioConnect 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/ ✨ Exclusive Offer to Alex & Annie Listeners: Turn every guest interaction into more revenue with Lasoh.Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through July 31, 2026.👉 Learn more: https://explore.lasoh.io/alex-annie#vacationrentals #vacationrentalmarketing #directbookings

May 27, 2026Episode 28150 min

Why InvitedHome Bet on Ski Markets Instead of Bigger Scale with CEO James Smith

Send us a message!In this episode, we are joined by James Smith, CEO of InvitedHome, for a conversation about focused growth, luxury vacation rental operations, and what it takes to build a more sustainable business in high-end destinations.James shares how InvitedHome evolved from a broader multi-market vacation rental company into a luxury brand focused on ski markets. After operating across different types of destinations, the company made the decision to narrow its focus and go deeper in the markets where it could build stronger operations, deeper owner relationships, and more consistent guest experiences.That shift became one of the central themes of the conversation: bigger is not always better. James explains why going deeper in the right markets can be stronger than expanding everywhere at once, and why sustainable growth requires the right homes, the right owners, strong teams, and the operational discipline to support the experience being promised.Episode Chapters:04:00 - Choosing Focus Over Footprint05:39 - The Challenge of Scaling Luxury Vacation Rentals16:59 - Working with the Right Owners20:04 - What Consistency Means in Luxury21:32 - AI, Technology, and High-Touch Service27:36 - Direct Bookings and Luxury Travel Advisors39:22 - Regulation in Ski Markets46:12 - Why Undercharging Can Hurt the BusinessConnect with James:LinkedIn: https://www.linkedin.com/in/jamesalansmith/ Connect with InvitedHome:Website: https://invitedhome.com Instagram: https://www.instagram.com/invitedhome/Facebook: https://www.facebook.com/InvitedHomeLinkedIn: https://www.linkedin.com/company/invitedhome/✨ Exclusive Offer to Alex & Annie Listeners: Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.👉 Get started: https://hospitable.com/partners/alex-annie Reach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ #vacationrentals #shorttermrentals #skimarkets

May 20, 2026Episode 28046 min

Smarter Staffing, Stronger Service, Better Guest Experiences with Paul Wohlford and Amanda Szubert of Call Center Solutions

Send us a message!In this episode, we are joined by Paul Wohlford and Amanda Szubert of Call Center Solutions to talk about staffing, guest services, AI, and the growing need for reliable support in vacation rental operations.Paul and Amanda share how Call Center Solutions grew out of a real hospitality staffing challenge and how their nearshore team in Montego Bay, Jamaica now supports vacation rental and hotel companies with reservations, outbound calls, after-hours support, back-office work, and more.The conversation also explores why human connection still plays such an important role in hospitality, even as AI becomes a bigger part of guest communication. Paul and Amanda break down how operators can use technology to support their teams while still creating the kind of guest experience that builds trust, drives bookings, and keeps people coming back.We discuss:05:59 - How Call Center Solutions got its start in the hospitality space05:59 - Why staffing continues to be a challenge for reservation and guest service teams12:00 - How nearshore support can help operators improve consistency and coverage10:20 - The role of redundancy during storms, outages, and operational disruptions14:40 - Where AI fits into guest communication and agent support16:01 - Why human connection still matters in vacation rental hospitality13:20 - The importance of training, knowledge bases, and quality assurance44:41 - How support teams can help identify gaps in the booking experience28:21 - What operators should consider when outsourcing guest servicesConnect with CCS:Website Link: https://www.ccssuccess.com/LinkedIn Link: https://www.linkedin.com/company/my-call-center-solutions/Facebook Link: https://www.facebook.com/ccssuccessInstagram Link: https://www.instagram.com/call.center.solutions/Connect with Paul:Email: paulw@ccssuccess.comConnect with Amanda:LinkedIn: https://www.linkedin.com/in/amanda-szubert-8b26a033/ ✨ Exclusive Offer to Alex & Annie Listeners: Improve efficiency and customer engagement with Call Center Solutions.Get all setup and implementation fees waived when you let them know you heard about CCS from Alex & Annie.👉 Get started: https://www.ccssuccess.com/ Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.👉 Get started: https://hospitable.com/partners/alex-annie Reach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ #vacationrentals #shorttermrentals #guestservices

May 13, 2026Episode 27957 min

Direct Bookings Aren’t Dead, But Your Strategy Might Be | with Chris Walker of Direct Booking Tools

Send us a message!Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there.In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools.Chris shares what he has learned from nearly two decades in property management and how his experience as an operator led to the creation of Direct Booking Tools.Through his own property management experience, Chris saw how important it is for guests to clearly understand the value of booking direct at the moment they are making a decision. Operators may know that value, but it has to be visible, trustworthy, and easy for guests to act on.We discuss:00:06:13 - Why trust is central to direct booking conversion00:09:43 - How price transparency can influence guest decisions00:15:16 - What website traffic can reveal about booking behavior00:28:12 - How operators can use data to improve pricing decisions00:49:26 - Why direct booking strategy needs more than awareness00:28:12 - How to strengthen conversations with owners using real data00:42:31 - Why Chris believes quality and intentional growth still matter Whether you are trying to increase direct bookings, improve website conversion, or better understand how guests are making booking decisions, this episode offers a practical look at what operators can do to turn more interest into revenue.Connect with Chris:LinkedIn: https://www.linkedin.com/in/chriswalkerhhi/ Website: https://directbookingtools.com/✨ Exclusive Offer to Alex & Annie Listeners: Strengthen your direct booking strategy with Direct Booking Tools.Alex & Annie listeners get 50% off for the first 3 months.👉 Get started: https://directbookingtools.com/alex-annie-landing-page/ Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.👉 Get started: https://hospitable.com/partners/alex-annie Reach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.👉 Access the offer here: https://explore.lasoh.io/alex-annie #vacationrentals #shorttermrentals #directbookings

May 6, 2026Episode 27859 min

How Marriott Vacations Worldwide Thinks About Loyalty with President, Mike Flaskey

Send us a message!In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide.Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value.The conversation looks at the timeshare and vacation club model through a hospitality lens, including how major brands build trust, keep owners engaged, and create value beyond the initial sale or stay.Alex, Annie, and Mike also explore what short-term rental operators can learn from Marriott Vacations Worldwide, especially when it comes to consistency, brand standards, guest experience, and creating reasons for people to stay connected over time.Episode Chapters:02:32 - Why Mike returned to the industry and joined Marriott Vacations Worldwide10:06 - How Marriott Vacations Worldwide thinks about loyalty11:02 - The role of Marriott Bonvoy in brand affinity and direct bookings18:53 - What vacation rental operators can learn from timeshare19:30 - How brand standards help build guest trust28:20 - Why lifetime value matters in the customer journey29:00 - Viewing vacation ownership as a subscription business31:09 - Using experiences to strengthen loyalty and engagement40:11 - How Marriott Vacations Worldwide is using AI in sales training41:41 - How AI is changing digital search and hospitality marketing47:52 - Why prepaid vacations create resilience51:43 - What is ahead for Marriott Vacations WorldwideConnect with Mike:LinkedIn: https://www.linkedin.com/in/mike-flaskey-13496094 Instagram: https://www.instagram.com/thevacationdr/reels/ Connect with Marriott Vacations Worldwide:Marriott Vacation Club: https://www.instagram.com/marriottvacationclub/ Westin Vacation Club: https://www.instagram.com/westinvacationclub/ Sheraton Vacation Club: https://www.instagram.com/sheratonvacationclub/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.👉 Get started: https://hospitable.com/partners/alex-annieReach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.👉 Access the offer here: https://explore.lasoh.io/alex-annie #vacationrentals #shorttermrentals #timeshare

May 1, 2026Episode 27740 min

Introducing Revenue Reality Check Presented by Beyond, with CEO Julie Brinkman

Send us a message!Revenue strategy does not happen on autopilot.Markets shift, booking windows move, owners ask harder questions, and guests become more price sensitive. For vacation rental managers, the strategy that worked last month may need a second look today.That is the focus of Revenue Reality Check, a 6-part bimonthly series brought to you by Beyond. Each episode takes a closer look at the pricing decisions, demand trends, owner conversations, and revenue moves property managers should be paying attention to right now.For the first episode, Alex & Annie are joined by Julie Brinkman, CEO of Beyond, to talk about one of the biggest topics in revenue management today: AI.Julie shares how AI is already helping operators make sense of large amounts of data, reduce repetitive work, and give revenue managers more time to focus on strategy. She also explains why human oversight still matters, especially when it comes to pricing decisions, owner communication, and the revenue line of the business. For Julie, the opportunity is in using AI to support stronger decisions while keeping operators involved in the strategy.We discuss:00:37 - Why revenue strategy needs regular review03:01 - How AI is being used in vacation rental revenue management08:39 - Where automation can help reduce repetitive work11:12 - Why owner communication needs market context19:21 - How AI may affect OTAs, direct bookings, and listing visibility28:22 - Julie’s Stop, Start, and Scale advice for using AI thoughtfully31:43 - What operators should watch as World Cup demand developsTune in for the first episode of Revenue Reality Check, brought to you by Beyond, and follow along as we look at the trends, data, and revenue decisions vacation rental managers should be paying attention to now.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

April 29, 2026Episode 2761 hr 3 min

Does Vacation Rental Software Still Have Room to Grow? With Hospitable CEO Pierre-Camille Hamana

Send us a message!In this episode, Alex & Annie sit down with Pierre-Camille Hamana, founder and CEO of Hospitable, to talk about the evolution of vacation rental software and why adoption across the industry still has so much room to grow.Pierre-Camille shares how his own experience as an Airbnb host in Brussels led to the creation of Smartbnb, which later became Hospitable. What started as a solution for repetitive guest messaging has grown into a broader property management platform supporting communication, operations, channel management, direct bookings, payments, and more.The conversation also explores why many hosts and operators still hesitate to adopt property management software, how Hospitable is working to make software more accessible, and what AI could mean for guest communication, support, direct bookings, and the future of vacation rental distribution.In this episode, we discuss:02:27 - How Pierre-Camille’s experience as an Airbnb host led to the creation of Hospitable04:22 - Why guest messaging became the starting point for a larger software platform09:45 - How Hospitable evolved from Smartbnb into a broader property management system20:16 - Why software adoption remains low across parts of the short-term rental industry21:55 - The challenges that keep smaller hosts and operators from adopting software23:44 - Hospitable’s approach to making property management software more accessible17:47 - How self-managers can grow into co-hosts or professional property managers41:47 - The role of AI in guest messaging, customer support, and software usability44:07 - Why AI should make tools easier to use, not simply add more complexity53:07 - What AI agents could mean for OTAs, direct bookings, and property discovery53:07 - Why strong owner service, guest experience, and operational consistency still matter as technology evolvesConnect with Pierre-Camille:LinkedIn: https://www.linkedin.com/in/pchamana/ Connect with Hospitable:Website: https://hospitable.com/partners/alex-annie LinkedIn: https://www.linkedin.com/company/hospitable/ Instagram: https://www.instagram.com/hospitable_com/ Facebook: https://www.facebook.com/hospitable/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.👉 Get started: https://hospitable.com/partners/alex-annieReach more guests across top travel sites with BookingPal.Alex & Annie listeners get onboarding fees waived + 20% off the first two months.👉 Get started: https://alex-and-annie-offer.bookingpal.com/ Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.👉 Access the offer here: https://explore.lasoh.io/alex-annie #vacationrentals #shorttermrentals #pms