Podcast Episodes

Growing a vacation rental portfolio brings new opportunities, but maintaining the quality and consistency that made the business successful becomes increasingly challenging as operations expand. In this episode, Alex & Annie catch up with Brandon Hall, Founder and CEO of Hallson Hospitality, for an on-location conversation in Nashville about the company's next chapter of growth. Brandon shares the news of Hallson Hospitality's merger with Epicbnb, a partnership expected to bring their comb...

Your property management system says one thing. Your revenue management platform says another. Your accounting reports tell a different story. So which numbers can you actually trust? As AI becomes more integrated into vacation rental operations, inconsistent data across systems presents a growing challenge for property managers. In this episode, Alex & Annie sit down with John An, Founder and CEO of TechTape, to explore why disconnected systems and conflicting data can lead to misleadi...

A high-end vacation rental and a premium nightly rate don't always guarantee well-behaved guests. And when a stay ends with serious property damage, getting the home back in shape can be only part of the headache. In Episode 4 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Alexandra “Ali” Chaney of 30A Beach Stays & Vacations, alongside Amanda Martins and Zach Grimes of Safely, for a candid conversation about the unpredictable side of vacation ...

A guest books a beautiful vacation rental, has an incredible stay, and leaves with memories worth sharing. But when they tell others about their experience, whose brand do they remember? In this episode, Alex & Annie sit down with Michelle Gilliland, VP of Sales at Savvy, to explore what it takes to build a recognizable brand in a market where OTAs dominate traveler attention. Drawing from nearly 15 years of experience in the vacation rental industry, Michelle brings a unique perspective o...

The way travelers discover vacation rentals is changing. Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent. In this episode, Alex & Annie sit down with Gil Chan, Founder and CEO of CraftedStays, to explore what this shift means for vacation rental operators and the direct booking websites they have spent years b...

In this fourth episode of First of the Month Wrangle, presented by Lasoh, we are joined by Orlie Benjamin, Founder and CEO of Lasoh, and Eric Goldreyer, Founder and CEO of Savvy, to unpack one of the latest conversations surrounding Airbnb and direct booking. Airbnb has been testing a program that allows some hosts and co-hosts to drive their own demand to an Airbnb listing in exchange for a reduced platform fee. The company may be calling it direct booking, but Orlie and Eric argue that the ...

A guest can spend months planning a vacation, travel all day, arrive with tired kids and luggage in tow, and then have the entire experience unravel at one very important moment: the front door. In this episode, Alex is joined by Dawn Keathley of Dormakaba and Matt Seyed of Secure Lodging Systems for a conversation about an often overlooked part of the vacation rental experience: guest access. They explore why getting guests through the door reliably is about much more than choosing a lock...

Alex & Annie are taking the podcast on the road for a special on-location episode from Montego Bay, Jamaica. This time, they’re stepping inside Call Center Solutions to see the operation firsthand, meet the people behind it, and get a closer look at what it takes to build a hospitality team that can support vacation rental businesses from hundreds of miles away. Throughout the visit, Alex and Annie sit down with members of the CCS team across operations, HR, IT, and leadership to hear what...

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 te...

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 a...

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 ...

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 op...

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...

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 m...

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 opera...

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 ...

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, ...

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 sam...

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 impo...

What does it take to build a vacation rental company that can grow, evolve, and remain successful for nearly seven decades? In this episode, Alex & Annie sit down with Rick Elliott and Brandon Cox of Elliott Realty to explore the people, systems, leadership decisions, and business fundamentals behind the company’s longevity. Elliott Realty has been part of the Myrtle Beach vacation rental industry since 1959. Over those 67 years, the company has navigated new technology, changing traveler ...

Advocacy often stays on the back burner until a regulation directly threatens the business. For Tyann Marcink Hammond, that moment came when vacation rentals in parts of Missouri were reclassified from residential to commercial properties, causing some tax bills to rise dramatically. In this episode, Tyann returns to share how that experience pulled her deeper into vacation rental advocacy and showed her why operators need to get involved before policy decisions are finalized. She expla...

Send us a message! Direct booking has been part of the vacation rental conversation for years, but one challenge remains hard to solve. Travelers are not always searching that way. In this episode, Alex & Annie sit down with Eric Goldreyer, CEO and founder of Savvy, to talk about why direct booking has struggled to become a consumer habit and what needs to change for travelers to find, trust, and use it more easily. Eric shares how Savvy evolved from BNB Finder into a book-direct market...

Send us a message! Revenue strategy always starts with a plan, but the market does not always follow it. A major event may not pace the way it did last year, certain property types may start falling behind, owners may get nervous about open dates, and new channel updates can quickly add more complexity to an already busy season. In this episode of Revenue Reality Check, presented by Beyond, Alex & Annie are joined once again by Julie Brinkman, CEO of Beyond, for a practical conversation ab...

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 reco...