Alex and Annie: The Real Women of Vacation Rentals
Episodes
282 episodes
From National Scale to Local Strength: Bob Milne on Vacasa, Casago, and First Chair Destinations
In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Bob Milne, President and COO of First Chair Destinations.Bob has spent decades in the vacation rental industry, with leadership experience...
.jpg)
The Great AI Debate: Direct Bookings, Websites, and the Future of Search with Richard Vaughton and Mark Simpson
AI is changing the way travelers search, compare, and book vacation rentals. But what does that mean for direct bookings, local brands, and the websites operators have spent years building?In this episode, Alex and Annie are joined by Ri...
.png)
Pour Decisions: When Vacation Brain Hits Summer Stays, with Amanda Martins of Safely
Welcome to the second episode of Pour Decisions: When Stays Go Sideways, presented by Safely.In this episode, Alex and Annie are joined again by Amanda Martins, VP of Business Development at Safely, for another round of rea...
.png)
Trust Accounting Isn’t Back Office: It’s the Foundation, with Ed Ulmer of Barefoot
In this episode, we are joined by Ed Ulmer, CEO of Barefoot, for a conversation about trust accounting, vacation rental technology, and what operators need from their systems as their businesses become more complex. Ed shares how hi...
From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki
The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet.In this episode, we are joined by John Suzuki, Chief Technology Evangelist at ...
.png)
1st of the Month Wrangle: Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin
In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it tak...
.png)
Why InvitedHome Bet on Ski Markets Instead of Bigger Scale with CEO James Smith
In this episode, we are joined by James Smith, CEO of InvitedHome, for a conversation about focused growth, luxury vacation rental operations, and what it takes to build a more sustainable business in high-end destinations.James shares h...
Smarter Staffing, Stronger Service, Better Guest Experiences with Paul Wohlford and Amanda Szubert of Call Center Solutions
In this episode, we are joined by Paul Wohlford and Amanda Szubert of Call Center Solutions to talk about staffing, guest services, AI, and the growing need for reliable support in vacation rental operations.Paul and Amanda share how Cal...
Direct Bookings Aren’t Dead, But Your Strategy Might Be | with Chris Walker of Direct Booking Tools
Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there.In this episode, we are joined by Chri...
.png)
How Marriott Vacations Worldwide Thinks About Loyalty with President, Mike Flaskey
In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide.Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations World...
.jpg)
Introducing Revenue Reality Check Presented by Beyond, with CEO Julie Brinkman
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 l...
.png)
Does Vacation Rental Software Still Have Room to Grow? With Hospitable CEO Pierre-Camille Hamana
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-Cami...
.png)
Vrbo Vacation Rentals of the Year: A TRUE Fireside Chat with Tim Rosolio
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.
Pour Decisions: When Stays Go Sideways, with Amanda Martins of Safely
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: W...
.png)
How Awayday Is Scaling Without Losing Local Identity, with CEO Jakob Dwyer
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 thro...
.png)
1st of the Month Wrangle: What's Missing from Vacation Rental Marketing, with Lasoh CEO Orlie Benjamin
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 vacati...
The Realities of Operating in a Legacy Vacation Rental Market, with Tom Stewart of Resort Realty
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 ...
How Booking.com and It’s A Penalty Are Addressing Human Trafficking in Hospitality
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
.png)
London Calling: A Preview of the Short Stay Summit with Leo Walton & Sarah Nan DuPre
In this episode, we’re joined by Leo Walton, Co-founder of Truvi, and Sarah Nan DuPre, Strategic Partnerships Director at AirDNA. Leo and Sarah are also the co-hosts of The Check-In Podcast, and they join us for a conversation abo...
.png)
The Future of Vacation Rental Distribution with Blake Warner of BookingPal
Distribution in the vacation rental industry has never been more complex. Property managers today are balancing major OTAs, niche platforms, emerging luxury channels, and an increasingly layered tech stack, all while trying to deliver exception...
.jpg)
1st of the Month Bonus: Intentional Growth in a Rapidly Evolving STR Market with Carly Traub
Growth in short-term rentals often gets framed as a numbers game. More properties, more markets, more tech, and more scale.But what if growth isn’t about doing more but choosing better?In this 1st of the Month Bonus episode, Alex ...
The Virtual Property Management Model Explained with Tim Hubbard of Corzly
In this episode, Alex & Annie sit down with Tim Hubbard, CEO of Corzly, to break down how a virtual property management model actually works and what it takes to make it successful.Tim started in long-term rental investing before shi...
Boss Lady Energy: How Krista Goodrich and Kymberlee Nguyen Built Salty Dog Vacations
In this episode, Alex & Annie sit down with Krista Goodrich and Kymberlee Nguyen, the duo behind Salty Dog Vacations, to talk about what it really takes to build a vacation rental company that guests remember and a team that is proud to be ...
Jeff Hurst on Why Midterm Rentals Are Gaining Ground in a Mature STR Market
Midterm rentals are moving from a side option to a real strategy. In this episode, Alex & Annie sit down with Jeff Hurst, CEO of Furnished Finder and former HomeAway and Expedia Group leader, to explain why 30+ day stays are gaining tractio...
.png)
Are DMOs and Vacation Rentals Finally Ready to Work Together? with Stuart Butler and Adam Stoker
Destination marketing is in a pressure test.Short-term rentals have become a major part of how people travel, yet many DMOs still struggle with how (or whether) to include them. At the same time, AI is speeding up the research-to-bookin...
