Alex and Annie: The Real Women of Vacation Rentals

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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

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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

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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

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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

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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