Alex and Annie: The Real Women of Vacation Rentals

In this episode, Alex & Annie sit down with Vinny Dicarlo, CEO of Ciirus, and Josh Parry, Chief Product Officer, for a conversation about the philosophy that has shaped the company over nearly two decades.
Founded as a family business, Ciirus has taken a deliberately measured approach to growth. Rather than building around outside investment or pressure to scale at all costs, Vinny and Josh explain how the company has focused on long-term customer relationships, continued investment in its technology, and human support that keeps the team closely connected to the property managers it serves.
That approach opens up a broader conversation about what operators should expect from a technology partner today. Vinny and Josh share why they believe there are limits to how much vacation rental operations can be automated, where AI can genuinely help, and why human involvement still matters in an industry where every property, owner, guest, and stay can look different.
Episode Chapters:
11:14 - Building customer relationships designed to last
17:15 - Why Ciirus has chosen measured growth over growth at all costs
18:28 - How independent ownership shapes investment in customers and technology
22:38 - Why vacation rental operations cannot automate everything
27:39 - Building a global team around specialized talent
32:49 - Helping property managers get more from their technology
38:14 - Why customer and employee satisfaction matter together
39:55 - Ciirus’ new mobile app, owner tools, and Booking.com integration
46:03 - How LoveRentals helps property managers expand their capabilities
54:59 - Finding vacation rental demand beyond the major OTAs
57:55 - Reaching guests through travel agents, wholesalers, and international markets
1:02:24 - What is next for the Ciirus platform
If you are evaluating your tech stack, thinking about sustainable growth, or looking for new ways to reach guests, this episode offers a closer look at what a strong technology partnership can bring to your business.
Connect with Josh & Vinny
Josh Parry: https://www.linkedin.com/in/josh-parry-47165997/ 
Vinny Dicarlo: https://www.linkedin.com/in/vincenzo-dicarlo/ 
Connect with Ciirus
Website: https://ciirus.com/
✨ Exclusive Offers to Alex & Annie Listeners:
Alex & Annie listeners can receive their first three months of Ciirus subscription fees waived when joining the platform.
Visit https://ciirus.com/ and let the team know you heard about Ciirus through the Alex & Annie Podcast.

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 #vacationrentaltechnology
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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
Send us a message!

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!