Alex and Annie: The Real Women of Vacation Rentals

Alex and Annie
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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. 1st of the Month Wrangle: What's Missing from Vacation Rental Marketing, with Lasoh CEO Orlie Benjamin

    1D AGO

    1st of the Month Wrangle: What's Missing from Vacation Rental Marketing, with Lasoh CEO Orlie Benjamin

    Send us a message! We’re kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing. Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relationships with every guest. Together, they explore what it really takes to build stronger guest relationships, improve direct booking performance, and think more strategically about marketing in vacation rentals. In this first episode, Orlie shares the thinking behind Lasoh and the problem she believes the industry still has not solved. While many of the core systems in vacation rentals are designed to manage properties, pricing, and distribution, far fewer are built to help operators understand guests, strengthen relationships, and market in a way that creates long-term value. The conversation looks at what happens when hospitality gets overshadowed by operations, why guest data matters far beyond the initial booking, and why marketing deserves a bigger role in growth strategy. Episode Chapters: 01:56 - Why Orlie Benjamin built Lasoh for vacation rental marketing 04:19 - What’s missing from most vacation rental PMS platforms 07:58 - Vacation rental tech vs. hotel tech: where the gaps still exist 09:47 - Asset management vs. guest experience in hospitality 11:01 - Why hospitality gets harder to scale in vacation rentals 13:42 - Why revenue management and marketing should work together 16:33 - The real levers of growth: customers, spend, and repeat stays 21:03 - How Lasoh helps operators capture guest data and personalize marketing 25:46 - Guest-first marketing vs. inventory-first marketing This episode sets the tone for the series ahead and offers a valuable perspective for anyone looking to build a more thoughtful, guest-centered marketing strategy. ✨ Exclusive offer for Alex & Annie listeners ✨ Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Access the offer here: https://explore.lasoh.io/alex-annie  Valid through May 31, 2026. 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/lasoh.io/ #vacationrentals #vacationrentalmarketing #directbookings

    35 min
  2. The Realities of Operating in a Legacy Vacation Rental Market, with Tom Stewart of Resort Realty

    MAR 25

    The Realities of Operating in a Legacy Vacation Rental Market, with Tom Stewart of Resort Realty

    Send us a message! In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie to talk about the realities of running a vacation rental business in the Outer Banks, one of the most established and distinctive markets in the industry. They get into what makes the market different, from its geography and seasonality to its mix of inventory and long-standing operating norms. Tom also shares what it takes to keep a legacy operation strong as market conditions change. The conversation explores weather and erosion challenges, guest and owner communication, selective growth, direct bookings, linen and laundry logistics, dynamic pricing, onboarding complexity, and the reset in owner expectations after the COVID boom.  If you work in vacation rentals, especially in a mature or highly seasonal market, this episode offers a practical look at what long-term success requires behind the scenes.  Episode Chapters: 04:20 - Tom Stewart’s path into vacation rentals 08:18 - What makes the Outer Banks such a unique vacation rental market 11:37 - Weather, erosion, road access, and operating through disruption 20:56 - Why legacy markets function differently from newer STR markets 25:05 - Professionally managed inventory and Resort Realty’s direct booking mix 27:18 - Growth vs. scale and why selective inventory matters 30:41 - Laundry, linens, and simplifying operations at scale 36:13 - How Resort Realty approaches dynamic pricing 44:16 - Expanding into long-term rentals and building steadier cash flow 49:01 - Why onboarding large homes is more complex than it looks 54:15 - How owner expectations changed after the COVID boom 58:43 - Why pricing and demand look different now 1:00:38 - Tom’s advice for people getting into vacation rental operations Connect with Tom: LinkedIn: https://www.linkedin.com/in/tom-s-8b607938/  Website: https://www.resortrealty.com/  ✨ Exclusive Offer to Alex & Annie Listeners: Streamline your short-term rental operations with Hostfully. Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value). 👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/  Reach more guests across top travel sites with BookingPal. Alex & Annie listeners get onboarding fees waived + 20% off the first two months. 👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/ #vacationrentals #shorttermrentals #outerbanks

    1h 2m
  3. How Booking.com and It’s A Penalty Are Addressing Human Trafficking in Hospitality

    MAR 18

    How Booking.com and It’s A Penalty Are Addressing Human Trafficking in Hospitality

    Send us a message! Human trafficking is a complex and often misunderstood issue, and one that exists across communities, including within hospitality. In this episode, we’re joined by Betsy Steckler, Regional Director of Partner Services at Booking.com, and Jennifer Easterday, Head of Human Rights at Booking.com, to talk about how their teams are approaching human trafficking through awareness, education, and partner support. From building training programs to equipping operators with practical tools, they share how Booking.com is working to help partners better understand the signs, respond appropriately, and create safer environments for both guests and communities. We then continue the conversation with Philippa King, Deputy CEO of It’s A Penalty, a global non-profit organization focused on raising awareness and preventing human trafficking through large-scale campaigns tied to major events like the Super Bowl and the upcoming World Cup. Philippa shares how these campaigns work, why major events create both risk and opportunity, and how collaboration between platforms, organizations, and local communities plays a critical role in prevention. Across both conversations, a few themes stand out: the importance of awareness, the need for practical action, and the role that individuals, teams, and communities can play in recognizing and responding to potential risks. While the issue is complex, the conversation highlights practical ways to better understand it and take action when something doesn’t feel right. Episode Chapters: 03:00 – Booking.com partner services and human rights overview 05:30 – Human trafficking awareness in hospitality 08:30 – Understanding human trafficking in lodging and guest environments 10:30 – How operators and teams can stay informed 13:00 – Signs of human trafficking in guest stays 18:00 – Reporting suspicious activity and escalation process 22:30 – Training and resources for hospitality teams 30:36 – It’s A Penalty overview and mission 31:00 – How It’s A Penalty campaigns started 34:10 – Human trafficking risks during major events 36:20 – Types of human trafficking explained 40:30 – Real-world example of trafficking in a rental property 43:00 – Why human trafficking is often hidden in plain sight 45:30 – Practical steps for awareness and prevention 47:10 – World Cup preparation and risk awareness Connect with Betsy: LinkedIn: https://www.linkedin.com/in/betsysteckler/ Connect with Jennifer: LinkedIn: https://www.linkedin.com/in/jennifereasterday/ Connect with Philippa: LinkedIn: https://www.linkedin.com/in/philippa-king-04307b4a/ Website: https://itsapenalty.org/ ✨ Exclusive Offer to Alex & Annie Listeners: Streamline your short-term rental operations with Hostfully. Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value). 👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ Reach more guests across top travel sites with BookingPal. Alex & Annie listeners get onboarding fees waived + 20% off the first two months. 👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/  #vacationrentals #shorttermrentals #humantrafficking

    50 min
  4. London Calling: A Preview of the Short Stay Summit with Leo Walton & Sarah Nan DuPre

    MAR 11

    London Calling: A Preview of the Short Stay Summit with Leo Walton & Sarah Nan DuPre

    Send us a message! In this episode, we’re joined by Leo Walton, Co-founder of Truvi, and Sarah Nan DuPre, Strategic Partnerships Director at AirDNA. Leo and Sarah are also the co-hosts of The Check-In Podcast, and they join us for a conversation about the upcoming Short Stay Summit in London and the industry conversations surrounding it. Leo and Sarah will be serving as emcees for this year’s event, and they share why the Short Stay Summit has become such an important gathering for the industry, especially as regulation, technology, and market dynamics continue to evolve across different regions. If you’re curious about the conversations shaping the industry today, this episode offers a preview of what to expect from one of the sector’s most talked-about gatherings. Episode Chapters: 06:34 – What attendees can expect from this year’s Short Stay Summit in London 07:06 – What makes the Short Stay Summit different from other industry events 14:43 – Why bringing operators and policymakers together matters 14:56 – Key conversations happening across the short-term rental industry 25:13 – Differences between US and European operator mindsets 25:13 – How operators approach technology and tech stacks in different markets 30:35 – The growing role of AI in hospitality operations Connect with Leo: LinkedIn: https://www.linkedin.com/in/leo-walton-aa59bb25/ Website: https://truvi.com/  Connect with Sarah: LinkedIn: https://www.linkedin.com/in/sarah-nan-dupre-86815828/  Explore Short Stay Summit: Website: https://www.shortstaysummit.org/  ✨ Exclusive Offer to Alex & Annie Listeners: Streamline your short-term rental operations with Hostfully. Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value). 👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/  Reach more guests across top travel sites with BookingPal. Alex & Annie listeners get onboarding fees waived + 20% off the first two months. 👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/  #vacationrentals #shorttermrentals #shortstaysummitlondon

    41 min
  5. The Future of Vacation Rental Distribution with Blake Warner of BookingPal

    MAR 4

    The Future of Vacation Rental Distribution with Blake Warner of BookingPal

    Send us a message! Distribution in the vacation rental industry has never been more complex. Property managers today are balancing major OTAs, niche platforms, emerging luxury channels, and an increasingly layered tech stack, all while trying to deliver exceptional guest experiences. In this episode, Alex & Annie sit down with Blake Warner, CEO of BookingPal, to talk about how distribution is evolving and what it takes to build scalable infrastructure in a rapidly maturing industry. Blake shares how BookingPal operates at the center of the ecosystem, connecting property managers, PMS platforms, and global channels, and offers his perspective on where the industry is heading. The conversation explores how distribution strategies are expanding beyond the traditional OTA landscape, the opportunities emerging in luxury and niche channels, and why technology innovation must balance efficiency with simplicity. Drawing from his background in investment banking and capital markets, Blake also discusses the realities of scaling technology companies in the vacation rental space and why consolidation across the tech landscape may be inevitable. Episode Chapters: 03:01 Introducing Blake Warner, CEO of BookingPal 03:44 Blake’s background in investment banking and capital markets 04:26 What BookingPal sees across distribution channels heading into 2026 06:07 The realities of running a channel management business 12:32 New BookingPal features and product developments for 2026 15:30 Is vacation rental tech getting better or more complex? 17:05 The explosion of software tools in the STR tech stack 20:03 How many channels the average property manager distributes to 21:21 Which distribution channels are gaining traction 22:53 Luxury platforms and the blurring lines in the ecosystem 24:41 Why helping managers focus on hospitality still matters most 28:13 Travel agents, discovery, and how distribution expands the market 30:05 Why it’s difficult for vacation rental companies to go public 35:44 How the industry has evolved since pre-COVID Connect with Blake: LinkedIn: https://www.linkedin.com/in/blakewarner/ Website: https://bookingpal.com/ ✨ Exclusive Offer to Alex & Annie Listeners: Streamline your short-term rental operations with Hostfully. Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value). 👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/  Reach more guests across top travel sites with BookingPal. Alex & Annie listeners get onboarding fees waived + 20% off the first two months. 👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/  #vacationrentals #shorttermrentals #distribution

    43 min
  6. 1st of the Month Bonus: Intentional Growth in a Rapidly Evolving STR Market with Carly Traub

    MAR 1

    1st of the Month Bonus: Intentional Growth in a Rapidly Evolving STR Market with Carly Traub

    Send us a message! Growth in short-term rentals often gets framed as a numbers game. More properties, more markets, more tech, and more scale. But what if growth isn’t about doing more but choosing better? In this 1st of the Month Bonus episode, Alex & Annie sit down with Carly Traub, Co-Founder and CEO of Lazy Sunday Rentals, to talk about what it really looks like to build a business intentionally in a fast-moving, information-heavy industry. Carly launched her company in 2022 alongside her husband, starting with a single property and quickly scaling to a growing portfolio. Like many operators, she said yes to everything early on. Over time, she realized that not all growth is aligned growth. This conversation explores the shift from reactive expansion to thoughtful refinement. Episode Chapters: 04:53 Moving from channel-dependent to brand-driven 06:15 Why saying “yes” to everything works at first and why it eventually doesn’t 07:15 Maximizing your existing tech stack before adding more tools 6:26 Evaluating return on time, not just return on money 18:23 Building a direct booking strategy that reflects your identity 27:58 How to define the kind of guest experience you actually want to deliver 31:59 Why smaller operators need a seat at the DMO table 41:26 The realities of operating in a “hot” investment market 45:29 Unrealistic investor expectations and the myth of easy remote hosting If you’re building in a crowded market and want growth that fits your vision, this episode will help you pause, refocus, and move forward with intention. Connect with Carly: LinkedIn: https://www.linkedin.com/in/carly-traub-6a402325/  Website: https://lazysundayrentals.com/  ✨ Exclusive Offer to Alex & Annie Listeners: Streamline your short-term rental operations with Hostfully. Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value). 👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ #vacationrentals #shorttermrentals #intentionalgrowth

    49 min
  7. The Virtual Property Management Model Explained with Tim Hubbard of Corzly

    FEB 25

    The Virtual Property Management Model Explained with Tim Hubbard of Corzly

    Send us a message! In this episode, Alex & Annie sit down with Tim Hubbard, CEO of Corzly, to break down how a virtual property management model actually works and what it takes to make it successful. Tim started in long-term rental investing before shifting into short-term rentals more than a decade ago. As his portfolio grew across multiple states, and eventually internationally, he built the systems needed to manage properties remotely. That operational backbone became Corzly, a virtual management partner now supporting property managers in more than 40 cities. Tim shares how their white-label backend model works, how they collaborate with on-the-ground teams, and where AI fits into real workflows. Not just automated check-in messages, but layered operational processes that involve owners, cleaners, early check-in requests, and revenue decisions. Episode Chapters: 1:04 – From Long-Term Rentals to a 40-City Virtual Operation 4:02 – The Idea Behind “Core Operations” 5:28 – What Virtual Property Management Actually Means 6:08 – Why 10–60 Unit Managers Are Their Sweet Spot 7:22 – Running the Backend Without Owning the Listings 11:17 – How Much Can You Really Automate With AI? 11:58 – The Early Check-In Example That Shows How Complex Workflows Get 15:55 – 225 Units Today… 10X Growth This Year? 19:58 – The Hardest Part of Scaling Across Markets 22:21 – Building Culture With a Fully Global Team 27:44 – Developing a 20-Unit Resort in Medellín 29:08 – Two Years of Permitting and What It Took to Launch If you are exploring growth, efficiency, or a different structure for your management business, this episode offers a clear look at another way to build. Connect with Tim: LinkedIn: https://www.linkedin.com/in/tim-hubbard-str/ Website: https://corzly.com/  ✨ Exclusive Offer to Alex & Annie Listeners: Streamline your short-term rental operations with Hostfully. Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value). 👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ #vacationrentals #shorttermrentals #propertymanagement

    35 min
  8. Boss Lady Energy: How Krista Goodrich and Kymberlee Nguyen Built Salty Dog Vacations

    FEB 18

    Boss Lady Energy: How Krista Goodrich and Kymberlee Nguyen Built Salty Dog Vacations

    Send us a message! In this episode, Alex & Annie sit down with Krista Goodrich and Kymberlee Nguyen, the duo behind Salty Dog Vacations, to talk about what it really takes to build a vacation rental company that guests remember and a team that is proud to be part of it. They share how Salty Dog grew from early investing decisions in Daytona Beach into a full-scale operation, and how their approach to branding goes beyond design choices. It shows up in the details, the guest experience, and the way they protect their people. The conversation also expands into Krista’s work in local advocacy and zoning, their broader mission to help more women build wealth through real estate, and how their community has grown through retreats and education. Episode Chapters: 08:20 – How local rules, zoning, and community involvement shape what it takes to operate responsibly 15:07 – Building a brand guests remember: personality, pet-friendly touches, and guest joy 19:37 – Krista’s “Boss Lady Investor” work, and why real estate education needs to feel accessible 25:00 – How retreats and community experiences can become part of a bigger platform, not just a side project 33:32 – What it looks like to build a company culture where your team feels protected and respected 35:44 – The moment they fired an owner, and why that decision mattered for the business long term 40:25 – Why consistency matters more than “cute ideas,” especially once you are scaling If you’re trying to build a stronger guest experience and a business that holds up as you grow, this one’s worth a listen. Connect with Kym & Krista: LinkedIn: https://www.linkedin.com/in/krista-goodrich-2823198/ Podcast: https://www.thebossladyinvestor.com/ Website: https://mysaltydogvacation.com/ ✨ Exclusive Offer to Alex & Annie Listeners: Streamline your short-term rental operations with Hostfully. Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value). 👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ #vacationrentals #shorttermrentals #bossladyenergy

    48 min
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5
out of 5
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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