Alex and Annie: The Real Women of Vacation Rentals

In this episode, Annie is joined by Jinnie Randolph for a conversation with Cristiana Carpini, founder of the Women in Vacation Rental European Conference (WVREC), and Neely Khan, founder of Kahani.

Together, they explore the value of creating spaces where women can build trust, share openly, and form meaningful relationships that support both personal and professional growth. Cristiana shares the thinking behind WVREC, while Neely reflects on what made the first gathering feel so different and why that environment gave her the confidence to share a deeply personal story publicly for the first time.

They also look ahead to WVREC 2026 in Barcelona, how the event is evolving, and the larger community Cristiana and Neely hope to continue building around it.

Episode Chapters:
02:20 - The story behind the Women in Vacation Rental European Conference
09:23 - Why trust and vulnerability shaped the first WVREC
16:19 - Why Cristiana is keeping the event women-focused
18:28 - How deeper connections can lead to collaboration and opportunity
21:52 - What to expect from WVREC 2026 in Barcelona
24:52 - Cristiana and Neely’s upcoming storytelling project
28:00 - Making the case for investing in professional development
34:27 - What surprised Cristiana most about the first conference
40:31 - Final details for WVREC 2026

Connect with Cristiana:

LinkedIn: https://www.linkedin.com/in/cristiana-carpini-hospitality/

Connect with Neely:

LinkedIn: https://www.linkedin.com/in/neelykhan/ 

Learn more about WVREC: https://wvrec.eu/ 

✨ Exclusive Offer to Alex & Annie Listeners:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/alexannie/

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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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:

Build a direct booking site designed to get found and convert with Crafted Stays.

Turn more visitors into direct bookings with less manual work.

👉 Get started: https://craftedstays.co/ 

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

Send us a message!

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

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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

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Vacation rental search is changing fast.

Organic traffic is declining, AI Overviews are taking up more space in Google, and travelers are increasingly using tools like ChatGPT, Gemini, and Claude to research where to stay.

For property managers, that creates a new challenge: how do you stay visible when the way people search is no longer as straightforward as ranking on page one of Google?

In this episode, Alex & Annie are joined by Vanessa Humes, VP of Sales and Marketing at ICND, and Jill McGee, Senior Digital Marketing Specialist, to unpack what this shift means for vacation rental brands and their direct booking strategies.

They explore why SEO is still very much alive, how AI is changing the path travelers take before reaching a website, and why the fundamentals of trust, authority, useful content, and strong website structure may matter more than ever.

The conversation also looks at what operators should actually be paying attention to as new terms like AEO and GEO enter the marketing vocabulary, whether emerging AI optimization tactics are worth the hype, and how the metrics used to measure digital marketing success may need to evolve along with search.

In this episode, we discuss:

06:45 - Why declining organic traffic does not mean SEO is losing its value

07:33 - How AI is changing the way travelers research and discover vacation rentals

26:14 - What SEO, AEO, and GEO mean for vacation rental marketers

10:32 - Why trust, reviews, structured data, and strong content still matter

36:27 - How property managers can create content with stronger booking intent

23:41 - Why AI-driven traffic may be smaller but more qualified

29:00 - Which new AI optimization tactics deserve attention and which may be more hype than substance

48:20 - How operators should think about search visibility heading into 2027

If you are trying to understand where SEO fits in an AI-driven search landscape and what your vacation rental brand should be doing now to stay discoverable, this episode is worth a listen.

Connect with Vanessa:

LinkedIn: https://www.linkedin.com/in/vanessa-humes-549b528/ 

Connect with Jill:
LinkedIn: https://www.linkedin.com/in/jill-highsmith-mcgee-940908179/

Connect with ICND:

Website: https://bit.ly/3THIq8J 

LinkedIn: https://www.linkedin.com/company/intercoastal-net-designs/ 

Free Resource from ICND:

Download ICND’s AI Visibility Case Study to learn how vacation rental companies can adapt to AI-driven search.

👉 https://bit.ly/4qu6Df3

✨ Exclusive Offer to Alex & Annie Listeners: 

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!

What makes a vacation rental business attractive to a buyer?

Door count may get attention, but it does not tell the full story. Sustainable growth, clean financials, a trusted local brand, strong employees, and direct booking performance can all influence how a business is evaluated.

In this episode, Alex & Annie sit down with Igor Simkin, CEO of Monarch Collective, for a candid look at what owners should understand before exploring a sale. Igor shares what Monarch looks for in a company, where sellers are often unprepared, and why the conversation should begin long before an owner is ready to step away.

They also explore what happens after the transaction, from protecting the local brand and retaining employees to helping founders choose the role they want in the company’s next chapter.

Episode Chapters:

 05:22 - Why Monarch Collective was created and the opportunity it saw in the market
 08:07 - Preserving local brands, teams, and community relationships
 11:12 - Anchor acquisitions versus tuck-in acquisitions
 11:51 - The qualities Monarch looks for in an established business
 13:57 - When owners should begin preparing for a potential sale
 16:14 - Creating a transition plan around the founder’s goals
 22:16 - The performance indicators buyers consider
 25:03 - Financial readiness, valuation, and common seller blind spots
 28:04 - Building a shared data layer across different technology platforms
 33:43 - How Monarch is approaching AI across operations and marketing
 38:13 - What an acquisition can mean for employees and local leadership
 46:48 - How owners can get feedback before they are ready to sell

Connect with Igor:

Email: [email protected]

LinkedIn: https://www.linkedin.com/in/igor-simkin-4902993/ 

Connect with Monarch Collective:

Website: https://gomonarch.com/

Thinking about the next chapter for your vacation rental business?

Connect with Monarch Collective to explore what your options could look like and how to prepare before the time comes.

👉 Learn more: https://gomonarch.com/partnerships/

✨ Exclusive Offer to Alex & Annie Listeners: 

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

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 

#vacationrentals #shorttermrentals #propertymanagement #businessvaluation #mergersandacquisitions

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In this third episode of First of the Month Wrangle, presented by Lasoh, we are joined by Orlie Benjamin, Founder and CEO of Lasoh, and Patti Ziegler, Orlie’s longtime mentor and former leader at Scotts Miracle-Gro.

Before building Lasoh, Orlie worked with Patti across direct-to-consumer marketing, brand building, innovation, and partnerships. That experience shaped how she thinks about customer relationships, distribution, and the value of knowing the people behind each purchase.

That same thinking applies in vacation rentals. OTAs may help bring guests in, but operators still need a way to understand who those guests are, stay connected, and create reasons for them to book again.

Orlie and Patti also share the mentorship behind that journey, including what it means to take a chance on someone, recognize when a role is no longer the right fit, and support a person as they move toward something bigger.

We discuss:

00:51 - Meet Patti Ziegler and learn how she worked with Orlie

02:04 - Building a direct-to-consumer brand from zero to one

03:19 - How established brands create new pathways to the customer

08:39 - What retail distribution can teach operators about OTAs and direct bookings

11:50 - How direct-to-consumer thinking shaped Lasoh

13:36 - The mentorship behind Orlie’s move into entrepreneurship

21:46 - How a career pivot brought Orlie closer to her purpose

28:33 - What vacation rental operators can learn from full-funnel marketing

30:46 - Why awareness, conversion, and guest loyalty all need attention

36:23 - Building a business in a way that still supports people

40:22 - Why the guest experience is central to Orlie’s work in vacation rentals

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/orlie.benjamin/ 

Connect with Patti:

LinkedIn: https://www.linkedin.com/in/patti-ziegler-4649173/ 

✨ Exclusive Offer to Alex & Annie Listeners: 

Turn every guest interaction into more revenue with Lasoh.

Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through September 30, 2026.

👉 Learn more: https://explore.lasoh.io/alex-annie

#vacationrentals #vacationrentalmarketing #directbookings

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Nearly 300 episodes in, the Alex & Annie Podcast is entering one of its most exciting chapters yet.

In this special mid-year episode, Alex & Annie are joined by Jinnie Randolph, who has been working behind the scenes to help shape the show’s content, partnerships, strategy, and future growth.

Jinnie shares her journey through vacation rental marketing, technology, and operations, along with the full-circle story of how she went from longtime listener and sponsor partner to becoming an important part of the Alex & Annie team.

Together, Alex, Annie, and Jinnie reflect on the conversations and industry themes that have defined 2026 so far. They discuss the rapid evolution of AI, the continued importance of human connection, and why intentional growth, consistency, and education have become increasingly important across the vacation rental industry.

They also take listeners behind the scenes of the show’s evolution into Aha Moments Media. Alex & Annie share how the Growth Blueprint has shaped this year’s content and how new recurring series, roundtables, on-site interviews, private podcasts, and thought leadership opportunities are helping the platform grow beyond its original format.

Episode Chapters:

04:19 – How Jinnie became part of the Alex & Annie Podcast team

11:24 – The industry themes shaping the first seven months of 2026

16:14 – How AI and human connection are evolving together

22:25 – Why smaller operators need better access to credible education

15:56 – The Growth Blueprint behind this year’s podcast content

13:11 – How the show is expanding into Aha Moments Media

27:30 – New series, roundtables, partnerships, and storytelling formats

31:31 – What nearly 300 episodes have taught Alex and Annie about consistency

36:46 – Alex’s decision to dedicate more time to the podcast

38:49 – Annie’s work with Booking.com and smaller vacation rental operators

49:00 – What the team is building for the rest of 2026 and beyond

Tune in for a candid look at where the show has been, what is changing, and why the second half of 2026 could be its most exciting yet. 

Enjoying the Alex & Annie Podcast?

Leave a rating to help more vacation rental professionals discover the show:

https://alexandanniepodcast.com/review

✨ Exclusive Offer to Alex & Annie Listeners: 

Reach more direct-booking travelers with Savvy.

List your professionally managed properties for free.

👉 Get started here: https://savvy.com/list

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 

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 #hospitality

Send us a message!