Alex and Annie: The Real Women of Vacation Rentals

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Not every guest stay ends with a five-star review.
Some leave behind a mess. Some turn into a serious operational headache. And some become the kind of story you end up telling for years.
That is the idea behind Pour Decisions: When Stays Go Sideways, a special series presented by Safely. 
In this series, Alex & Annie sit down with the Safely team and industry guests to unpack the kinds of guest incidents that rarely make it into the marketing copy but often leave the biggest operational impact. Through real stories, practical insight, and a little cocktail-fueled commiseration, the series explores what went wrong, how it was handled, and what operators can do to better protect their homes, teams, and owners.
About Episode 1:
In this kickoff episode, Alex & Annie are joined by Amanda Martins, Vice President of Business Development at Safely, to introduce the series and set the stage for the conversations ahead. Amanda shares what Safely sees behind the scenes when guest-related damage claims come in and why these stories can be some of the most useful lessons in the business.
The episode also dives into one recent case involving a large home that became the site of a 50-person party, complete with police involvement, extensive damage, smoke remediation, and a long list of cleanup issues. Amanda walks through what happened, the documentation that helped support the claim, and what operators should be thinking about when it comes to guest screening, damage protection, liability, and owner communication.
It is a practical conversation that sets the tone for the series ahead, showing how real guest incidents can reveal where systems hold up, where they fall short, and what operators can do to better protect their business before the next stay goes sideways.
In this episode:
01:41 - Meet Amanda Martins of Safely
03:34 - Why Alex & Annie launched this special series with Safely
08:34 - A real story involving a party that caused major property damage
15:01 - How Safely’s claims process works
16:31 - What happens if an operator does not have damage protection
19:01 - When operators should involve police or pursue legal action
24:06 - Why guest screening can help deter the wrong bookings
28:28 - Protecting homeowners and reducing business risk
30:20 - How Safely works alongside homeowner insurance
36:55 - Why this matters for operators of every size
Have a story to share?
We want to hear your worst guest stories. If you have a stay that went completely sideways and a lesson to go with it, submit it for a chance to be featured on a future episode.
Submit your story here: https://form.jotform.com/261032817700044
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/ 
This episode’s cocktail: Checkout 75
A little classy, a little dangerous, and apparently best enjoyed seated.
Ingredients:
1 oz tequila
0.5 oz GranGala
0.5 oz fresh squeezed lime juice
0.5 oz fresh squeezed orange juice
Sparkling wine, such as prosecco or a dry brut, to top
How to make it:
Shake the tequila, GranGala, lime juice, and orange juice with ice. Strain into your favorite wine glass, then top with bubbly.
Amanda’s final tip:
Don’t stand up too fast when finished.
#vacationrentals #shorttermrentals #guesthorrorstories

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What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place?
In this episode, we are joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through a model built on local leadership, shared support, and strong operational foundations.
Instead of forcing every market into the same mold, Awayday supports growth through shared resources across accounting, HR, revenue management, business development, and technology, while local teams continue to lead the day-to-day business. Jakob also shares how that approach influences the way Awayday evaluates partners, supports local operators, and balances growth with owner and guest experience.
This conversation offers a clear look at how Awayday is building scale through stronger operations and support without losing the local identity at the core of each business.
Episode Chapters:
00:00 - Intro to Awayday CEO Jakob Dwyer
01:14 - Jakob Dwyer’s background in vacation rentals and RealJoy’s growth
05:52 - How Awayday scales local vacation rental companies
10:50 - Why local market knowledge matters in vacation rental growth
13:07 - What Awayday looks for in a vacation rental partner
18:17 - Founder transitions, succession planning, and exit options
23:15 - Why strong vacation rental operations matter more than growth at all costs
27:01 - Awayday’s onboarding process and value creation strategy
31:41 - Shared services, local leadership, and centralized support
37:05 - How Awayday is thinking about AI in vacation rental operations
46:11 - SOPs, company culture, and empowering vacation rental teams
50:57 - Awayday’s growth strategy for 2026 and beyond
58:43 - Why every team member plays a role in company growth
This episode is brought to you by Awayday. If you are interested in being part of a company that values local leadership, strong operations, and long-term growth, connect with Jakob at [email protected].
Connect with Jakob:
LinkedIn: https://www.linkedin.com/in/jakob-dwyer-19516033/ 
Connect with Awayday:
Website: https://www.awayday.com/
LinkedIn: https://www.linkedin.com/company/awayday-vacation-rentals/ 
✨ 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 #localidentity

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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