Consolidation, Mergers & Acquisitions 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 reco...

Send us a message! What does it take to scale luxury vacation rentals while protecting the legacy of the brands that built them? In this episode, Alex & Annie welcome back Scott Wiseman, CEO of Nocturne Luxury Villas, for an inside look at how Nocturne approaches acquisitions in the luxury vacation rental space. Instead of treating acquisitions as one-size-fits-all deals, Scott explains how his team works with founders to create personalized exit plans that honor their legacy, protect employee...

Send us a message! In this episode, we sit down with two industry powerhouses: Dennis Goedheid , CEO of Casiola, and Shahar Goldboim , CEO of Boom and founder of DesignedVR, to unpack the story behind their groundbreaking new partnership. As the vacation rental industry continues to mature, operators are finding new ways to grow that prioritize sustainability, clarity, and control. This conversation explores the revenue-sharing agreement between DesignedVR and Casiola, a creative alternative ...

In this week’s episode, we’re thrilled to welcome back Tom Goodwin, CEO of Mountain Laurel Chalets and host of "For the Love of Gatlinburg" Podcast. Tom shares insights into his family-run vacation rental business in Gatlinburg, which has been a beloved destination for over 50 years. We dive into his journey of preserving the essence of Gatlinburg through his podcast and discuss how it celebrates the community's rich heritage and unique stories. Tom also gives an update on Mountain Laurel ...

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 special re-air of one of our most popular episodes, Alex & Annie revisit our insightful conversation with Tom Goodwin, CEO of Mountain Laurel Chalets. Tom’s remarkable journey in the vacation rental industry, from unexpected beginnings to building a brand rooted in community, continues to inspire. Tom's Journey: Discover how Tom's unexpected entry into the vacation rental world, through his wife's family-run business in Gatlinburg, evolved into a thriving venture. His initial 18-month...

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we are joined by Ian Carter, the former CEO of Hilton International and current Chair of the Board for Watches of Switzerland, Eataly, The Boston University School of Hospitality and Administration, and Boom. Ian shares his remarkable career journey, from his early days at General Electric to leading Hilton International through its historic merger with Hilton Hotels Corporation. We also dive into the vacation rental mark...

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 Welcome to our August 1st of the month bonus episode! Today, we welcome back Simon Lehmann, a seasoned expert in the vacation rental industry and the co-founder and CEO of AJL Atelier. With over two decades of experience, Simon has been at the forefront of innovation and strategy, guiding countless property management companies throu...

In this episode of Alex & Annie: The Real Women of Vacation Rentals, we're joined by Scott Wiseman, CEO of Nocturne Luxury Villas. Scott brings a wealth of experience from his journey through the hospitality industry, from hotels to luxury tour operators, and now leading the charge in high-end vacation rentals. Scott's journey in hospitality began at 15 after a transformative family vacation to Acapulco. His career has spanned from hotels to luxury tour operators, including leadership roles a...

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 week’s episode of Alex & Annie: The Real Women of Vacation Rentals, we're joined by two powerhouse guests in the vacation rental space - Jason Sprenkle, CEO of Keydata, and Jacobie Olin, President of C2G Advisors. Jason has over 20 years of experience in vacation rentals, previously running 360 Blue in the Panhandle area. ...

In this episode, we welcome Lynell Gordon – vacation rental expert, partner at Inhabit, and host of "How We Grow: the vacation rental show." Lynell shares her powerful personal journey and how the practice of writing down goals and intentions has positively shaped both her life and career. Meet Lynell: Lynell's vacation rental expertise shines through her work with Inhabit and her podcast, "How We Grow: the vacation rental show." Her dedication to sharing industry knowledge and personal exper...

In this episode of "Alex and Annie, The Real Women of Vacation Rentals," we embark on a fascinating journey into the vacation rental industry with a panel of seasoned experts known as the OGs of the Panhandle. Our guests, including trailblazers like Jim Olin, Steve Caron, Lino Maldonado, and Paul Wolford, share their personal journeys from the industry's early days to the dynamic landscape it occupies today. The Early Days: Dive into the challenges and triumphs of being pioneers in the vacati...

In this captivating episode of “Alex and Annie: The Real Women of Vacation Rentals, we sit down with Tom Goodwin, a seasoned professional in the vacation rental industry, to explore his remarkable journey and the transformative power of community and branding in business. Tom's Journey: Discover how Tom's unexpected entry into the vacation rental world, through his wife's family-run business in Gatlinburg, evolved into a thriving venture. His initial 18-month commitment turned into an 11-year...

In this insightful episode, hosts Alex and Annie dive deep into the world of vacation rentals with a special guest, Sarah Bradford, co-host of Sarah and T Podcast, and former owner of two successful vacation rental companies in the picturesque landscapes of Colorado. Journey Through Experience: Sarah begins by unraveling her rich background in the vacation rental industry, providing listeners with an intimate look into her entrepreneurial journey. She candidly shares her experiences in sellin...

In this episode of Alex & Friends, Leslie Sonnier joins Alex for an in-person conversation set against the backdrop of Myrtle Beach. From a chance meeting three years ago in matching dresses at a conference, to reflecting on the emotional process of selling Rebl Rentals, a thriving vacation rental business in Scottsdale, Arizona, this episode is a rollercoaster of memories, lessons, and the excitement of new beginnings. Creating Memorable Experiences and Impact on Families: The conversation emp...

In this episode, Alex and Annie are joined by Mike Reinman, Owner of Casago Kona & Owner/GM of Casago Redwood Coast. Mike sold Redwood Coast Vacation Rentals to Vacasa at the end of 2019. After speaking with Casago CEO Steve Schwab, Mike decided to return to the industry and purchase a STR business in Kona. This is where his partnership with Casago began, and what laid the foundation for his next venture with Casago Redwood Coast. Mike started in the short-term rental industry by converting his...

Welcome to another first of the month bonus episode where it’s all about advocacy and legislative issues with Tiffany Edwards, a strategic consultant specializing in short-term vacation rental organizations. Tiffany's expertise spans across various markets, assisting in navigating STVR regulations, state legislation, stakeholder engagement, and grassroots campaigns. Her remarkable achievements include receiving the 2021 VRMA President's Award for her exceptional work in reopening STVRs post-COVI...

Simon Lehmann is back for our May 1st of the Month Bonus Episode! As one of the world’s foremost experts on short-term rentals and vacation rentals, Simon is always first to spot emerging trends in our industry. In this episode, we delve into the current state of acquisitions within vacation rentals and how the economy is influencing these deals, along with what companies should be thinking about if they’re considering selling. Join us to gain valuable insights into the world of vacation rental...

In today’s episode, Alex and Annie are joined by Christina Thoreson, who with her husband Thor, built Chattanooga Vacation Rentals into a sizable and well-run outfit in Tennessee prior to selling in 2022. Christina recalls their early struggles including not knowing how to run housekeeping and maintenance, and struggling to figure out the legal and operational aspects of the business. Christina and Thor were early adopters of technology, and although they went through a series of software cha...

In today’s episode, Alex and Annie sit down with Graham Donoghue, the CEO of Sykes Holidays Cottages Group. When Graham was brought on Sykes, the brand was lacking a narrative and a story. They were large and profitable but departments were siloed with no real rallying cry to drive the company forward. Today, Sykes has 25 brands in its portfolio and 24,000 properties under management in the UK and New Zealand, making the brand a major player in the vacation rental industry. One interesting th...

Elevate a Vacation Guest’s Experience In today’s episode, Alex and Annie welcome Mike Flaskey, Former CEO of Diamond Resorts International and Founder of Mike Flaskey Entertainment, as he gives his second public interview since leading the sale of Diamond Resorts to Hilton Grand Vacations in June 2021. COVID profoundly affected Diamond but innovation allowed them to rebound quickly. Mike shares how they did this and how they pioneered a new way to be evaluated on multiples of EBITDA. He ta...

Scott Bunce, COO of Cabins for You joins us today for a look behind the curtain of their innovative enterprise that manages properties in the Smoky Mountains and Georgia mountains, with plans to expand into the Florida Panhandle on the horizon. Scott's extensive background in hotel revenue management has made him a top choice for panels at vacation rental conferences, and in today's episode he shares his thoughts on the impact of revenue management on our industry. Inventory growth - and loss o...

It's the 1st of the Month! Tune in as we recap the previous month and look ahead to the next, discussing industry trends, pacing, events and more. Simon Lehmann of AJL Consulting joins us each month for "Simon Says", where we discuss the latest hot-button issue facing the vacation rental and short term rental industry. Simon Says: Alex & Annie's Careers are a Changin' Tune in for not one but TWO major announcements from Alex & Annie, which we were happy to share alongside Simon who has been a m...

Robin Craigen and his wife Heather had a unique beginning in their hospitality journey that started on the high seas with their luxury yacht charter business. During this time, they developed a formula for creating exceptional guest experiences that would later lead them to trade their swim trunks and flippers for snow suits and ski poles. They moved to Steamboat Springs and opened a ski chalet business with just 2 properties, applying the same principles they learned from the yacht business to ...