Alex and Annie: The Real Women of Vacation Rentals
Episodes
273 episodes
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...
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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...
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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...
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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...
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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...
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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
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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...
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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...
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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...
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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...
1st of the Month Bonus: Bridging the Gap Between Resorts and Vacation Rental Channels with Jetstream CEO Emmanuel Lavoie
Condo-hotels and resort-style properties sit in a tricky middle ground. They are not traditional hotels, but they are not quite vacation rentals either. Many still run on hotel tech stacks, charge hotel-style commissions, and operate with hotel...
Behind the Sheets: Operational Considerations Behind Linen Choices in STRs
In this episode, we are joined by Deepak Mehrotra, founder and CEO of California Design Den, for a practical discussion on how linen decisions affect short-term rental operations over time.Drawing from more than 20 years in textile manuf...
Stop Calling It Luxury: Setting the Standard in Vacation Rentals with Nir Maimon
Last week with Moriya Rockman, we explored luxury through the lens of growth, relationships, and what it takes to scale a high-end portfolio without losing the hospitality at the center. This week, Nir Maimon brings the conversation to the defi...
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From One Swiss Chalet to a Global Luxury Portfolio with Moriya Rockman of Smiling House Luxury
In this episode, we sit down with Moriya Rockman, founder of Smiling House Luxury, to explore how a single personal vacation home in the Swiss Alps became the starting point for a global luxury vacation rental portfolio.Moriya shares her...
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Culture Over Features: Building a Human-First Tech Company with Frank Bosi of Hostfully
In this episode, Alex & Annie sit down with Frank Bosi, Senior Director of Partnerships at Hostfully, to unpack what it really takes to build a tech company that people trust.Frank’s journey began in luxury hotels long ...
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1st of the Year Special Episode: Charging into 2026 — The Year of the Horse
Welcome to the 1st of the year special episode. Alex & Annie are kicking off 2026 by looking back at the moments that shaped 2025, the lessons they’re carrying forward, and the intentions guiding the year ahead.They share how the pod...
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From Rocks to Remarkable: The Making of Destin Dreamers, with Arlen Busenitz
In this episode, Alex & Annie sit down with Arlen Busenitz to talk about his unconventional path from a Kansas farm to pastoring a small-town church, volunteering as an EMT, working with NASA through a defense contractor, and ultimately bec...
Sarah Bradford Unfiltered: Fix These Vacation Rental Mistakes Before 2026
In this unfiltered conversation, Sarah Bradford joins us once again to break down the most common and costly mistakes she sees vacation rental operators still making today.Drawing from more than two decades in the industry and her...
DARM 2025 Fireside Chats: What the Industry Is Finally Saying Out Loud
This episode was recorded live at DARM 2025, right in the middle of the event, while the conversations were still unfolding and the energy was still fresh. Alex & Annie sit down for two fireside chats with Alex Cisneros (StayTer...
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