Alex and Annie: The Real Women of Vacation Rentals

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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 review
03:01 - How AI is being used in vacation rental revenue management
08:39 - Where automation can help reduce repetitive work
11:12 - Why owner communication needs market context
19:21 - How AI may affect OTAs, direct bookings, and listing visibility
28:22 - Julie’s Stop, Start, and Scale advice for using AI thoughtfully
31:43 - What operators should watch as World Cup demand develops
Tune 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

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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 Hospitable
04:22 - Why guest messaging became the starting point for a larger software platform
09:45 - How Hospitable evolved from Smartbnb into a broader property management system
20:16 -  Why software adoption remains low across parts of the short-term rental industry
21:55 - The challenges that keep smaller hosts and operators from adopting software
23:44 - Hospitable’s approach to making property management software more accessible
17:47 - How self-managers can grow into co-hosts or professional property managers
41:47 - The role of AI in guest messaging, customer support, and software usability
44:07 - Why AI should make tools easier to use, not simply add more complexity
53:07 - What AI agents could mean for OTAs, direct bookings, and property discovery
53:07 - Why strong owner service, guest experience, and operational consistency still matter as technology evolves
Connect 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-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 #pms

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In this special episode, Alex and Annie sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Vrbo, for a behind-the-scenes look at Vrbo’s Vacation Rentals of the Year program and what it takes to earn that recognition.
Recorded on location at Lakefront Escape on Squam Lake, New Hampshire, one of this year’s winning properties, the episode offers both a platform perspective and a firsthand look at the kind of hospitality Vrbo is celebrating.
Tim shares how Vrbo selects winners from millions of properties across its global network, using a mix of performance data, guest reviews, local market insight, and hospitality storytelling to identify homes that deliver standout guest experiences.
The conversation then shifts to David Rose, owner of Lakefront Escape, who shares how he transformed a dated lake house into an award-winning retreat designed with intention, warmth, and usability in mind.
From intuitive in-home tech and thoughtful labels to tailored recommendations and architectural details, this episode highlights how exceptional hospitality is built through the details.
In this episode, we cover:
03:50 - Why Vrbo created the Vacation Rentals of the Year program
04:39 - How Vrbo selects its Vacation Rentals of the Year
08:04 - What makes a vacation rental experience feel personal and memorable
13:35 - Meet David Rose and the story behind Lakefront Escape
16:42 - Why intuitive technology matters more than flashy features
23:00 - How David Rose designed Lakefront Escape for connection, comfort, and discovery
25:20 - Why David chose self-management and how Vrbo supports pricing and promotion
26:43 - How personalized recommendations can elevate the guest stay
30:34 - How labels, notes, and in-home guidance reduce guest friction
32:21 - The Japanese design influence behind the home’s guest experience
35:27 - How design, layout, and local insight help create repeat guests
This episode captures both the criteria behind Vrbo’s recognition and the real-world hospitality choices that help a property earn it.
Connect with:
David Rose / Lakefront Escape
https://www.squamlakehouse.com/ 
Tim Rosolio / Vrbo
https://www.linkedin.com/in/tim-rosolio-434b2a98/ 
✨ 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/ 
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 #vrbovacationrentalsoftheyear

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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