Alex and Annie: The Real Women of Vacation Rentals

Welcome to Episode 300 of the Alex & Annie Podcast! 🎉 
Three hundred conversations, countless aha moments, plenty of industry debates, and a front-row seat to some of the biggest shifts vacation rentals have seen over the last several years.
This is such a huge milestone for us ⭐
To celebrate, we knew we wanted to bring back someone who has been part of the Alex & Annie journey since the early days.
We’re fortunate to have several people who have supported us along the way, and for this milestone, longtime friend of the show Terry Whyte returns for a conversation about how far the vacation rental industry has come and where it may be headed next.
Terry revisits predictions from his past appearances, including his views on technology, all-in-one platforms, loyalty, and distribution. He shares what he got right, what he would revise today, and how AI has changed the conversation.
Through it all, Terry keeps coming back to the fundamentals: quality properties, strong technology, smart distribution, customer care, and real human hospitality.
And because this is Episode 300, Alex & Annie also reflect on the journey so far and share a glimpse of what comes next for the podcast.
Here’s to 300 episodes and the next chapter of Alex & Annie. 🥂

Episode Chapters
02:30 - Revisiting Terry’s past industry predictions
03:26 - How AI changed the vacation rental tech conversation
06:29 - Why technology is becoming more fragmented
08:29 - Where automation ends and human hospitality matters
16:31 - Why growth does not always mean adding more doors
18:35 - Why distribution matters more than ever
19:37 - Direct bookings, website traffic, and marketing
24:39 - Rethinking loyalty in vacation rentals
29:40 - Terry’s advice for operators today
30:39 - What will separate thriving property managers in the future
33:37 - The risk of relying on a single OTA
35:49 - Terry reflects on the Alex & Annie Podcast
39:44 - The industry shift that changed Terry’s business
41:23 - What comes next for Alex & Annie
Connect with Terry:
LinkedIn: https://www.linkedin.com/in/terry-whyte-4540633b/ 

✨ Exclusive Offer to Alex & Annie Listeners:
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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/ 

List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.
👉 Get started: https://partners.vacationfinder.com/alexandannie 

#vacationrentals #shorttermrentals #hospitality
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In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie are joined again by Julie Brinkman, CEO of Beyond, to talk about why owner retention deserves the same level of attention as pricing, pacing, and acquisition.
Julie breaks down the metrics property managers should be watching, how unrealistic revenue expectations can create problems later in the relationship, and why adding new properties does not always tell the full story of business growth. She also answers real operator questions around high churn, founder-dependent owner relationships, and what retention can mean for the long-term value of a property management company.
Episode chapters:
01:43 - Building owner trust through consistent communication
05:03 - The owner retention metrics property managers should understand
12:19 - When growth hides a leaky owner bucket
15:49 - Revenue projections and owner expectations
22:30 - Added 40 properties, lost 26: is that really growth?
27:00 - Transferring founder trust as the company scales
32:10 - What high owner churn can mean for a future sale
35:10 - Using portfolio data to identify where attention is needed
Tune in for Episode 3 of Revenue Reality Check, brought to you by Beyond, and take a closer look at what owner churn may be telling you about the health of your business.
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!

In this episode, Alex & Annie sit down with Jeremy Gall, Founder and CEO of Breezeway, to explore how the continued professionalization of vacation rentals is raising the bar for operations.
Jeremy shares what led him to tackle one of the industry's most complex challenges: coordinating the people, properties, and workflows behind great hospitality. The conversation explores how rising guest expectations, greater owner scrutiny, and advances in technology are changing what it takes to operate well, and where vacation rental operations may be headed next.
Episode Chapters:
04:10 - Building a company property managers want to work with
12:00 - The early days of Breezeway and connecting operational workflows
14:40 - Why property managers should think differently about their relationship with the property
18:35 - How rising guest expectations are changing vacation rental standards
22:00 - Reviews, owner expectations, and the professionalization of the industry
25:11 - The growing importance of cleaners and third-party service providers
29:01 - Could robots eventually handle vacation rental turnovers?
33:31 - How AI is changing vacation rental operations
39:52 - Why Breezeway continues to go deeper on operations
As vacation rentals continue to mature, the operators who can deliver consistently behind the scenes will be better positioned to meet rising expectations from both guests and owners.
Connect with Jeremy:
LinkedIn: https://www.linkedin.com/in/jeremiahgall/ 
Connect with Breezeway:
Website: https://hubs.la/Q04tyWJL0 
✨ Exclusive Offer to Alex & Annie Listeners:
Get 20% off your first three months of Breezeway if you sign up by September 30. 
👉 Get started here: https://hubs.la/Q04tyWJL0 
Reach more direct-booking travelers with Savvy.
List your professionally managed properties for free.
👉 Get started here: https://savvy.com/list
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 vacation rental industry has changed dramatically over the years.
The technology is smarter, distribution is broader, competition is stronger, and AI is reshaping how operators work. But some of the most important parts of the business have not changed at all.
In this special reshare, Alex & Annie step into the guest seats with Tim Rosolio of Expedia Group’s Powering Travel Podcast for a conversation about what thoughtful growth looks like as the vacation rental industry continues to mature.
Recorded at one of Vrbo’s Vacation Rentals of the Year in New Hampshire, they reflect on what decades in the industry have taught them about building strong businesses, choosing technology intentionally, reaching new travelers, and keeping hospitality at the center of it all.
Episode Chapters:
02:11 - How Alex and Annie found their way into vacation rentals
06:28 - What has stayed constant as the industry has changed
09:10 - Growth at all costs vs. building a strong business
10:55 - What smaller operators need before they scale
15:52 - Has the vacation rental tech stack become too complicated?
20:00 - Expanding demand through new traveler segments and distribution
24:30 - The role of DMOs in introducing travelers to vacation rentals
28:03 - AI, technology, and the changing meaning of human touch
Whether you caught the original episode on Powering Travel or are hearing this conversation for the first time, this is a timely look at how the vacation rental industry is evolving and what operators should keep in focus as they grow.
Connect with Tim:
LinkedIn: https://www.linkedin.com/in/tim-rosolio-434b2a98/

Powering Travel Podcast:
Apple Podcast: https://podcasts.apple.com/us/podcast/powering-travel/id1620056867 
Spotify: https://open.spotify.com/show/4gaaqGF4oxYzdhIF4MZzZv?si=58490146cf3a4b37 
#vacationrentals #shorttermrentals #hospitality 
Send us a message!

When an owner asks for more detail, questions why something was handled differently, or wonders why they were not told about an incident sooner, the question is usually about more than the immediate issue.
They want to know their property is in good hands.
In Episode 3 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Amanda Martins and Rachel Alday for a candid conversation about the moments that put owner trust, guest relationships, and an operator’s decision-making to the test.
From serious property incidents and liability concerns to difficult emails and guest complaints, Rachel and Amanda share what years of experience have taught them about responding when emotions are high and the stakes are even higher.
Episode Chapters:
02:25 - What Owners Really Mean When They Ask for More Detail
08:20 - Why Documentation Matters After a Serious Incident
17:07 - Why Consistency Builds Owner Trust
24:07 - Turning Guest Complaints Into Service Recovery
28:41 - When a Guest Complaint Becomes a Liability Issue
33:28 - How to Show Empathy Without Accepting Liability
37:47 - Why Reacting Too Quickly Can Make Things Worse
42:00 - Why You Need the Right Processes and Partners Before Something Goes Wrong 
If you have ever received an email that made you want to respond immediately, only to realize five minutes later that deleting the draft was probably the better decision, this episode is for you.
Connect with Rachel Alday
LinkedIn: https://www.linkedin.com/in/rachelalday/
Connect with Amanda Martins
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: The Owner Manual
A Pour Decisions twist on an Old Fashioned made with bourbon, honey, bitters, and orange.
Stir it. Don’t shake it. And maybe finish the drink before replying to that owner email.
#vacationrentals #shorttermrentals #ownerrelations
Send us a message!