Alex and Annie: The Real Women of Vacation Rentals

Alex and Annie

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. 4d ago ·  Video

    From Fighting Regulations to Shaping Better Policy with Tyann Marcink Hammond

    Advocacy often stays on the back burner until a regulation directly threatens the business. For Tyann Marcink Hammond, that moment came when vacation rentals in parts of Missouri were reclassified from residential to commercial properties, causing some tax bills to rise dramatically. In this episode, Tyann returns to share how that experience pulled her deeper into vacation rental advocacy and showed her why operators need to get involved before policy decisions are finalized. She explains how relationships with local officials, Realtors, tourism organizations, legislators, and fellow property managers can help shape clearer, more reasonable regulations. Tyann also shares how collaboration in Missouri has supported progress on state legislation and the development of a model short-term rental ordinance. The conversation also covers Kansas City’s preparations for the 2026 FIFA World Cup, including how vacation rentals helped address the city’s lodging needs and the resources created to help new hosts operate responsibly. We discuss: 03:31 - Why vacation rental operators need to pay attention to local policy 04:46 - How property tax changes affected Missouri vacation rentals 14:05 - Why relationships are essential to effective advocacy 20:28 - How operators can get involved in shaping local regulations 25:51 - What Kansas City’s World Cup preparations can teach other destinations 36:43 - How last-minute bookings are changing operational planning  42:16 - Why human connection still plays an important role in vacation rental marketing  If you want to better understand how local decisions are made and how operators can have a meaningful voice in the process, this episode is for you. Connect with Tyann: LinkedIn: https://www.linkedin.com/in/tyannmarcink/  ✨ Exclusive Offer to Alex & Annie Listeners:  Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list 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  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 #regulations Send us a message!

    From Fighting Regulations to Shaping Better Policy with Tyann Marcink Hammond

  2. Jul 8 ·  Video

    The Direct Booking Movement Has a Discovery Problem, with Eric Goldreyer of Savvy

    Direct booking has been part of the vacation rental conversation for years, but one challenge remains hard to solve. Travelers are not always searching that way. In this episode, Alex & Annie sit down with Eric Goldreyer, CEO and founder of Savvy, to talk about why direct booking has struggled to become a consumer habit and what needs to change for travelers to find, trust, and use it more easily. Eric shares how Savvy evolved from BNB Finder into a book-direct marketplace for professional property managers. The conversation gets into why lower fees alone are not enough to change booking behavior, how OTAs have shaped traveler expectations, and why direct booking needs a better discovery path if it is going to scale. Episode Chapters: 06:21 - How professional property managers can build stronger guest relationships 06:53 - Why repeat business starts with owning guest data 07:56 - Why direct booking has struggled to reach the consumer 09:04 - How traveler behavior has been shaped by OTAs 18:16 - Why property managers still need OTAs while building a stronger direct strategy 20:55 - How destination content can support discovery and conversion 27:05 - Why property managers cannot rely on direct booking websites alone 33:28 - How trust, reviews, verification, and clear pricing influence conversion 34:18 - Why saving money is not always enough to win the booking 42:00 - What AI and structured data could mean for the future of travel search If you are a vacation rental operator trying to reduce OTA dependency, build more repeat business, or understand how travelers are discovering and booking stays today, this episode is for you. Connect with Eric LinkedIn: https://www.linkedin.com/in/ericgoldreyer/  Connect with 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  ✨ Exclusive Offer to Alex & Annie Listeners:  Reach more direct-booking travelers with Savvy. List your professionally managed properties for free. 👉 Get started here: https://savvy.com/list 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  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!

    The Direct Booking Movement Has a Discovery Problem, with Eric Goldreyer of Savvy

  3. Jul 1 ·  Video

    Revenue Reality Check: What to Do When Revenue Plans Do Not Go as Planned with Julie Brinkman of Beyond

    Revenue strategy always starts with a plan, but the market does not always follow it. A major event may not pace the way it did last year, certain property types may start falling behind, owners may get nervous about open dates, and new channel updates can quickly add more complexity to an already busy season. In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie are joined once again by Julie Brinkman, CEO of Beyond, for a practical conversation about what vacation rental operators should do when revenue plans do not go as expected. Julie breaks down how property managers can respond to soft pacing, underperforming inventory, owner pressure, cancellation policy changes, paid placement opportunities, and shifting demand without jumping straight into reactive pricing decisions. Julie also answers real revenue questions from operators in Nashville, Myrtle Beach, and Park City, covering what to do when a major event underperforms, how to handle inventory that is telling two different stories, and how to help owners understand the strategy when they want rates lowered too soon. We discuss: 01:30 - Why revenue backup plans matter during a busy season 02:24 - Airbnb cancellation policy changes and what flexibility means for operators 05:38 - Direct bookings, OTA visibility, and finding the right channel mix 11:24 - VRBO paid placement and why marketing needs to align with revenue 16:39 - When a major event weekend does not pace as expected 23:46 - When part of the portfolio is falling behind 31:28 - Helping nervous owners understand the pricing strategy 37:51 -Stop, Start, and Scale: building more proactive revenue plans Tune in for this episode of Revenue Reality Check, brought to you by Beyond, and learn how to build better revenue backup plans for the moments when the market does not go according to plan. 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: What to Do When Revenue Plans Do Not Go as Planned with Julie Brinkman of Beyond

  4. Jun 24 ·  Video

    From National Scale to Local Strength: Bob Milne on Vacasa, Casago, and First Chair Destinations

    In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Bob Milne, President and COO of First Chair Destinations. Bob has spent decades in the vacation rental industry, with leadership experience across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair Destinations. His career has taken him from building a local vacation rental company in Colorado to helping lead large-scale portfolios across some of the most recognizable names in the industry. Now, with First Chair Destinations, Bob is returning to a more focused, locally grounded model of vacation rental management. Throughout the conversation, Bob shares what he has learned from building and scaling vacation rental companies, what the industry can take away from the Vacasa to Casago transition, and why the future of vacation rental management still depends on strong local teams, trusted owner relationships, and consistent guest hospitality. He also discusses the role of technology, AI, distribution, OTAs, private equity, and consolidation in shaping what comes next for the industry. Episode Chapters: 03:22 - Bob’s path through Steamboat, Wyndham, Vacasa, Casago, and First Chair 06:26 - What the Vacasa to Casago transition revealed about the industry 10:25 - How First Chair is approaching its next chapter 15:29 - What rapid growth has taught the vacation rental industry 16:18 - Why local teams still matter in a scaled industry 17:05 - How hospitality can get lost as companies grow 23:56 - What operators can learn from the Vacasa to Casago transition 27:51 - What consolidation could mean for the industry 30:06 - Where AI can support vacation rental operations 33:16 - Building a hospitality-first culture across local teams 40:47 - Why OTAs still play a major role in distribution 46:56 - How owner expectations around channel visibility are changing 49:34 - Why the future of vacation rentals is still local 51:57 - How guest expectations are changing Connect with Bob: LinkedIn: https://www.linkedin.com/in/robertemilne/  Website: https://www.firstchair.com/  ✨ 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/  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 #local Send us a message!

    From National Scale to Local Strength: Bob Milne on Vacasa, Casago, and First Chair Destinations

  5. Jun 17 ·  Video

    The Great AI Debate: Direct Bookings, Websites, and the Future of Search with Richard Vaughton and Mark Simpson

    AI is changing the way travelers search, compare, and book vacation rentals. But what does that mean for direct bookings, local brands, and the websites operators have spent years building? In this episode, Alex and Annie are joined by Richard Vaughton of Yes Consulting and Mark Simpson of Boostly for The Great AI Debate. After taking this conversation to the stage at the Host Planet Roadshow in London, Richard and Mark continue the discussion around what AI could mean for vacation rental marketing, website strategy, and guest acquisition. Richard argues that AI will reshape websites, search, and distribution in ways the industry has not fully prepared for yet. Mark makes the case that strong website infrastructure, brand strategy, PMS connectivity, and niche positioning still matter, especially for operators who want to grow direct bookings. Together, they explore whether AI search will create new opportunities for independent vacation rental companies or make it even harder to compete with OTAs. Episode Chapters: 05:29 - How AI is changing the future of vacation rental websites 07:10 - The debate between WordPress websites and AI-built websites 10:00 - Why website design alone is not enough to drive direct bookings 28:25 - How Airbnb, Vrbo, Booking.com, and Expedia continue to shape guest behavior 36:29 - Why broad search terms are becoming harder for local operators to compete for 18:00 - How AI search could make niche positioning more important 21:53 - The growing role of TikTok, creators, and social media in travel discovery 46:03 - Why brand trust still matters in an AI-driven search environment 48:22 - How PMS data, integrations, and distribution may evolve 53:22 - What vacation rental operators should be thinking about now as search changes As guest behavior shifts, vacation rental operators are being pushed to think more carefully about how people find them, what makes their brand memorable, and how they can stay visible beyond the major booking platforms.  Connect with Richard: LinkedIn: https://www.linkedin.com/in/richardvaughton/  Website: https://yes.consulting/  Connect with Mark: LinkedIn: https://www.linkedin.com/in/mrmarksimpson/  Website: https://boostly.co.uk/  ✨ 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/  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 #ai Send us a message!

    The Great AI Debate: Direct Bookings, Websites, and the Future of Search with Richard Vaughton and Mark Simpson

  6. Jun 15

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

    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 damage 08:38 - How vacation brain shows up in real short-term rental claims 18:53 - What operators can learn from pool, hot tub, and grill-related incidents 25:29 - Why clear amenity instructions can help reduce preventable issues 10:24 - How protection programs can support owner trust 08:20 - Why guest involvement is not always required in many damage claims 11:49 - How Safely helps property managers explain coverage to homeowners 38:30 - Why operators should think about preparation before the busy season gets messy 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: Hugo Spritz with a twist A 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 Send us a message!

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

  7. Jun 10

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

    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 technology 11:56 - Why vacation rental management is built on trust 17:37 - What trust accounting really means for property managers 25:24 - Why managing owner and guest funds gets more complex as companies grow 27:27 - How state regulations and real estate requirements impact vacation rental operators 30:10 - Why loyalty programs are harder to build in vacation rentals than in hotels 33:48 - How PMS technology can support concierge services, rewards, and guest retention 39:17 - What operators should consider when choosing a PMS 47:55 - How AI and natural language search may change the booking experience For 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 Send us a message!

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

  8. Jun 3

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

    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 Industry 03:31 - How Vacation Rentals Moved From Phone and Fax Reservations Into the Mainstream of Travel 04:47 - Why John Came Back to the Industry After Retiring 09:20 - How AI Is Changing Property Management Technology 10:53 - Why Property Managers Need Systems That Help Them Move Faster 21:22 - The Importance of Connected Operations, Accounting, Reservations, Housekeeping, Maintenance, and Guest Communication 27:17 - How AI Can Support Call Tracking, Reservation Inquiries, and Guest Service 28:43 - Why Guest Data Will Play a Bigger Role in Travel Personalization 35:06 - The Ethical and Security Questions Surrounding AI 42:54 - How Robotics Could Affect Hospitality, Housekeeping, and the Workforce 46:16 - Why Professionals Need to Stay Curious and Keep Learning 48:55 - How AI Can Help Property Managers Get Back to the Human Side of Hospitality If 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 Send us a message!

    From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki
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34 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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