Podcast Episodes

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...

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 va...

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 real guest stories, summer stay surprises, and practical takeaways for short-term rental operators. This conversation is all about “vacation brain” and the strange, messy, and sometimes costly decisions guests make when they are out of their normal routine. From poolsid...

Send us a message! 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 his background in tourism, destination marketing, real estate, and software all shaped the way he looks at vacation rental management today. For him, the industry has always come back to one core idea: trust. The conversation takes a deep dive i...

Send us a message! 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 Staylist, for a conversation about the evolution of vacation rental technology, the pace of innovation, and what this next chapter could mean for property managers. John brings a long-term perspective on how far the industry has come, along wit...

Send us a message! 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 takes to make it more effective, more personal, and more guest-centered. This time, the conversation focuses on a simple but important question: can we stop marketing properties and start marketing to people? For many vacation rental operators, marketing ...

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 i...

Send us a message! 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 Call Center Solutions grew out of a real hospitality staffing challenge and how their nearshore team in Montego Bay, Jamaica now supports vacation rental and hotel companies with reservations, outbound calls, after-hours support, back-office w...

Many vacation rental operators are working on their direct booking strategy, 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. T...

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, an...