Operations Episodes

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...

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 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! 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, bu...

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 e...

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 alongsi...

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 ma...

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 se...

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 th...

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 t...

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 si...

Send us a message! In this episode, we are joined by Jim DeVos, industry veteran, former co-owner of Best Beach Getaways, for the first public reveal of VR Works — the backend system he spent years building to fix the operational pain points he couldn’t ignore. Jim breaks down how VR Works evolved from an internal solution into a fully integrated platform, how it nearly doubled their profit, and why an operator-first mindset shaped every design decision. He also explains the onboarding and pr...

Send us a message! In this episode, Alex & Annie head to Florida’s scenic 30A to sit down with Dylan Bozarth, General Manager of 30A Escapes, for a real conversation about leadership, culture, and what it takes to build a team that truly lasts in the fast-paced vacation rental world. Dylan shares how his decade-long journey at 30A Escapes has shaped a people-first approach to property management. One that values work-life balance, communication, and genuine hospitality as the keys to long-ter...

Send us a message! As hospitality companies race to scale, many face a difficult trade-off: grow fast or stay personal. But Zzzing, a leading hospitality brand based in Malta, is proving you can do both. In this episode, we’re joined by Sab Mulligan, Head of Teams at Zzzing, to explore how they’ve scaled rapidly by using AI not to replace the human touch, but to protect and enhance it. Through a thoughtful blend of technology, team culture, and brand consistency, Zzzing is setting a new...

Send us a message! In this week’s episode, we’re joined by Adrienne Clark (President & COO) and Caleb Yaryan (Chief Product Officer) of Xplorie, a trusted partner for vacation rental operators looking to enhance guest satisfaction while gaining a competitive edge. For nearly 30 years, Xplorie has been connecting lodging providers with local attractions in more than 70 destinations across the U.S., creating seamless, curated activity experiences that guests value. But more than just a perks pr...

Send us a message! In this episode, we’re joined by Simon Seroussi, Co-Founder of SuiteOp, a guest experience and operations platform built by operators, for operators. With a background in both hospitality tech and short-term rental management, Simon shares how SuiteOp was born from firsthand experience growing a 400-unit portfolio and the operational chaos that came with it. From automating smart locks to unifying guest portals, task management, and upsells, SuiteOp is designed to simplify ev...

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we’re thrilled to welcome back Alex Shapiro, CEO and co-founder of CanMonkey. Alex joins us to share exciting updates on how his company has continued to revolutionize trash management for vacation rentals and beyond. CanMonkey, which started as a bootstrap idea in 2018, now operates in 28 states and services over 5,000 properties across 350 cities. With innovative solutions, a gig-based workforce, and a deep understanding o...

In this special re-air of one of our most popular episodes, Alex & Annie brings together a powerhouse panel of industry experts, known as the OGs of the Panhandle. Our guests—James Olin, Steve Caron, Lino Maldonado, and Paul Wohlford—share invaluable insights from their decades-long journeys in the vacation rental industry, reflecting on where it all started, where it is now, and where it’s headed. Episode Highlights: The Early Days: Travel back with our panel as they recount the challenges a...

In this week’s episode, we welcome back Dennis Goedheid, founder and CEO of Casiola Vacation Homes. Dennis returns to share exciting updates on his company's growth, including the launch of a new franchise model. Since its inception, the franchise has rapidly expanded into key markets, including Aruba, where Casiola has seen tremendous success. Dennis also dives into the challenges and opportunities in the vacation rental space, from navigating property management in international markets to ...

Exclusive offer for Alex & Annie listeners: Mention "Alex & Annie" when you sign up with Boom to get 50% off your onboarding fee and 1 month FREE. Visit boomnow.com to claim this limited-time deal! In this week’s episode, we’re joined by Eric Moeller, the visionary founder and CEO of Freewyld, a brand creating nature-inspired cabin communities. Eric takes us on his entrepreneurial journey from real estate investment to building luxury short-term rental brands and developing Freewyld. ...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: ⁠http://get.hostaway.com/alexandannie In this insightful episode of Alex & Annie: The Real Women of Vacation Rentals, we are thrilled to welcome Mark Lumpkin, Director of Sales for STR Cribs. Mark shares his journey from a Florida local with a passion for real estate to leading a company that transforms vacant properties into stunning, resort-style short-term rentals ac...

Exclusive offer for Alex & Annie listeners: Get $400 off your onboarding fee when you partner with Hostaway using this link: http://get.hostaway.com/alexandannie Join Alex & Annie as they dive into an enlightening conversation with Margenett Moore-Roberts and Gia Sharp, key figures in the short-term rental advocacy scene in New York City. This episode explores their personal journeys, the challenges posed by current rental regulations, and their relentless efforts through RHOAR (Restore Ho...