Property Management Episodes

Send us a message! 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 across Steamboat Resorts, Wyndham Vacation Rentals, Vacasa, Casago, and now First Chair Destinations. His career has taken him from building a local vacation rental company in Colorado to helping lead large-scale portfolios across some of the most recogn...

Send us a message! 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 & Annie are joined by Richard Vaughton of Yes Consulting and Mark Simpson of Boostly for The Great AI Debate. After taking this conversation to the stage at the Host Planet Roadshow in London, Richard and Mark continue the discussion around what AI could mean for vacat...

Send us a message! 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 how InvitedHome evolved from a broader multi-market vacation rental company into a luxury brand focused on ski markets. After operating across different types of destinations, the company made the decision to narrow its focus and go deeper in t...

Send us a message! 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 Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools. Chris shares what he has learned from nearly two decades in property management and how his experience as an operator led to the creation of Direct Booking Tools. ...

Send us a message! 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 Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value. The conversation looks at the timeshare and vacation club model through a hospitality lens, including how major brands build trust, keep owners engaged, and cre...

Send us a message! 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-Camille shares how his own experience as an Airbnb host in Brussels led to the creation of Smartbnb, which later became Hospitable. What started as a solution for repetitive guest messaging has grown into a broader property management platform support...

Send us a message! 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. Recorded on location at Lakefront Escape on Squam Lake, New Hampshire, one of this year’s winning properties, the episode offers both a platform perspective and a firsthand look at the kind of hospitality Vrbo is celebrating. Tim shares h...

Send us a message! 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: When Stays Go Sideways , a special series presented by Safely . In this series, Alex & Annie sit down with the Safely team and industry guests to unpack the kinds of guest incidents that rarely make it into the marketing copy but often leave the biggest...

Send us a message! 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 through a model built on local leadership, shared support, and strong operational foundations. Instead of forcing every market into the same mold, Awayday supports growth through shared resources across accounting, HR, revenue management, business...

Send us a message! 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 vacation rentals: marketing. Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relatio...

Send us a message! 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 what makes the market different, from its geography and seasonality to its mix of inventory and long-standing operating norms. Tom also shares what it takes to keep a legacy operation strong as market conditions change. The conversation expl...

Send us a message! 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 & Annie sit down with Carly Traub, Co-Founder and CEO of Lazy Sunday Rentals, to talk about what it really looks like to build a business intentionally in a fast-moving, information-heavy industry. Carly launched her company in 2022 alongside her hu...

Send us a message! 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 shifting into short-term rentals more than a decade ago. As his portfolio grew across multiple states, and eventually internationally, he built the systems needed to manage properties remotely. That operational backbone became Corzly, a virtual manag...

Send us a message! 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 part of it. They share how Salty Dog grew from early investing decisions in Daytona Beach into a full-scale operation, and how their approach to branding goes beyond design choices. It shows up in the details, the guest experience, and the w...

Send us a message! 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 traction as many STR markets move into a more mature phase. Jeff breaks down what makes midterm rentals different from short-term rentals, what demand is actually driven by, and why midterm can be a strong fit for operators looking for stability, f...

Send us a message! 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-booking journey and forcing destinations to rethink what “relevance” even means. In this episode, Alex and Annie sit down with Stuart Butler (President of Visit Myrtle Beach) and Adam Stoker (President of Brand Revolt) to unpack what’s getting in the...

Send us a message! 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 mindsets. Meanwhile, guests are increasingly searching on vacation rental channels, homeowners are asking why they cannot find their units online, and off-site managers charging half the commission are pulling inventory away. In our Feb...

Send us a message! 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 manufacturing, Deepak shares how California Design Den evolved from supplying major retailers to working directly with short-term rental operators. The conversation focuses on how linen choices shift as portfolios grow, and why decisions that seem ...

Send us a message! 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 definition itself, what “luxury” should mean, how it should be verified, and why the category loses trust when the label gets used too loosely. “Luxury” has become one of the most overused words in vacation rentals, and that is exactly the p...

Send us a message! 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 journey from accidental host to global founder, including why she and her husband chose to stay hands-on operators while scaling internationally. She explains how staying close to hospitality standards shaped every stage of growth, from prope...

Send us a message! 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 before short-term rentals became a professionalized industry. That hospitality foundation now shapes how he approaches partnerships, leadership, and growth inside one of the most culture-driven PMS brands in the space. This conversation explores why culture s...

Send us a message! 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 becoming CEO of Destin Dreamers. Before he was running a luxury vacation rental company on Florida's Emerald Coast, Arlen was hauling 500-pound rocks in a 1976 Jeep pickup to pay for college. It's an unlikely origin story but one that laid the ...

Send us a message! 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 experience building, scaling, and ultimately selling two successful vacation rental companies, Sarah revisits pivotal moments that shaped her leadership, operations, and decision-making. This episode is practical, direct, and rooted in real situatio...

Send us a message! 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 (StayTerra) and Dennis Goedheid (Casiola) to talk through what’s showing up in the industry right now, and what operators are being asked to decide even when the path forward is not perfectly clear. If you were at DARM, this conversation will likely put words t...