Podcasts about vacation rentals

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 well, and where vacation rental operations may be headed next.Episode Chapters:04:10 - Building a company property managers want to work with12:00 - The early days of Breezeway and connecting operational workflows14:40 - Why property managers should think differently about their relationship with the property18:35 - How rising guest expectations are changing vacation rental standards22:00 - Reviews, owner expectations, and the professionalization of the industry25:11 - The growing importance of cleaners and third-party service providers29:01 - Could robots eventually handle vacation rental turnovers?33:31 - How AI is changing vacation rental operations39:52 - Why Breezeway continues to go deeper on operationsAs vacation rentals continue to mature, the operators who can deliver consistently behind the scenes will be better positioned to meet rising expectations from both guests and owners.Connect with Jeremy:LinkedIn: https://www.linkedin.com/in/jeremiahgall/ Connect with Breezeway:Website: https://hubs.la/Q04tyWJL0 ✨ Exclusive Offer to Alex & Annie Listeners:Get 20% off your first three months of Breezeway if you sign up by September 30. 

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 mature.Recorded at one of Vrbo's Vacation Rentals of the Year in New Hampshire, they reflect on what decades in the industry have taught them about building strong businesses, choosing technology intentionally, reaching new travelers, and keeping hospitality at the center of it all.Episode Chapters:02:11 - How Alex and Annie found their way into vacation rentals06:28 - What has stayed constant as the industry has changed09:10 - Growth at all costs vs. building a strong business10:55 - What smaller operators need before they scale15:52 - Has the vacation rental tech stack become too complicated?20:00 - Expanding demand through new traveler segments and distribution24:30 - The role of DMOs in introducing travelers to vacation rentals28:03 - AI, technology, and the changing meaning of human touchWhether you caught the original episode on Powering Travel or are hearing this conversation for the first time, this is a timely look at how the vacation rental industry is evolving and what operators should keep in focus as they grow.Connect with Tim:LinkedIn: https://www.linkedin.com/in/tim-rosolio-434b2a98/ Powering Travel Podcast:Apple Podcast: https://podcasts.apple.com/us/podcast/powering-travel/id1620056867 Spotify: https://open.spotify.com/show/4gaaqGF4oxYzdhIF4MZzZv?si=58490146cf3a4b37 #vacationrentals #shorttermrentals #hospitality Send us a message!

In this episode, we interview Seth Borko of Skift Research to talk all things travel trends, the experience economy, vacation rentals, guest behavior, local experiences, AI discoverability, flipping the traditional booking funnel, and a lot MORE!Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellSeth BorkoSkift ResearchLiving The Dream Divers

Explore Inhaven: https://inhaven.com/ Connect with Ashley: https://www.linkedin.com/in/ashley-ching-inhaven-b56a843/ Connect with Zach: https://www.linkedin.com/in/zacharybusekrus/ Check out Lodgify and get an exclusive discount: https://www.lodgify.com/behind-the-stays/  — Meet Ashley Ching — founder of Inhaven, former head of global merchandising operations at Tiffany & Co., and the person behind what might be the most important piece of research the vacation rental industry has produced in years. Here's the question Ashley keeps asking: every other hospitality industry — hotels, airlines, restaurants, car rentals — has a language of trust. Quality tiers that tell the consumer what they're buying before they arrive. Vacation rentals don't. And that single missing layer is behind almost every structural problem the industry can't seem to solve — from review manipulation to failed scaling attempts to the reason you still can't build a transferable property management brand. Ashley walks us through the Reasonable Hospitality framework her team developed alongside property managers and Steve Joyce, the former CEO of Choice Hotels. We dig into why service standards matter more than furnishings in determining where you fall on the quality spectrum, this care coverage ratio concept that quantifies what "boots on the ground" actually means, and why every attempt to put standards at the individual property level has failed. She makes a compelling case that most operators calling themselves luxury probably aren't — and that's not an insult, because only 3% of US hotel supply is actually luxury, and there's excellence at every tier. We talk about the luxury fallacy, why a Hampton Inn with an 8.2 rating doesn't mean it's better than a Ritz-Carlton with a 7.8, and what this industry could look like in ten years if it finally gets the foundation right. —   Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world's top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.   Your host is Zach Busekrus, Head of Growth at Journey. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we'd love for you to apply to join our Alliance at journey.com/alliance.

Most hosts pick their next STR on a gut feeling, a beachfront view or a cozy cabin. Garrett Brown from BiggerPockets took a different approach… He built a data comparison today across 5 property archetypes, scoring cash flow, appreciation, and long-term risk. In this episode, we break down which property type won, and why management matters more than location: The property type most investors overlook actually scored highest on cash flow. Why lakefront properties deliver strong appreciation but almost no day-1 cash flow? The 1 management decision worth $18,000 a year on the same property. Why the highest-ceiling property type also carries the widest range of outcomes. The property type that scored lowest despite the strongest nightly rates. If this episode helped, subscribe, leave a review, and share it with someone weighing their next short-term rental purchase. We'll catch you again real soon. Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/  

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 Jill McGee, Senior Digital Marketing Specialist, to unpack what this shift means for vacation rental brands and their direct booking strategies.They explore why SEO is still very much alive, how AI is changing the path travelers take before reaching a website, and why the fundamentals of trust, authority, useful content, and strong website structure may matter more than ever.The conversation also looks at what operators should actually be paying attention to as new terms like AEO and GEO enter the marketing vocabulary, whether emerging AI optimization tactics are worth the hype, and how the metrics used to measure digital marketing success may need to evolve along with search.In this episode, we discuss:06:45 - Why declining organic traffic does not mean SEO is losing its value07:33 - How AI is changing the way travelers research and discover vacation rentals26:14 - What SEO, AEO, and GEO mean for vacation rental marketers10:32 - Why trust, reviews, structured data, and strong content still matter36:27 - How property managers can create content with stronger booking intent23:41 - Why AI-driven traffic may be smaller but more qualified29:00 - Which new AI optimization tactics deserve attention and which may be more hype than substance48:20 - How operators should think about search visibility heading into 2027If you are trying to understand where SEO fits in an AI-driven search landscape and what your vacation rental brand should be doing now to stay discoverable, this episode is worth a listen.Connect with Vanessa:LinkedIn: https://www.linkedin.com/in/vanessa-humes-549b528/ Connect with Jill:LinkedIn: https://www.linkedin.com/in/jill-highsmith-mcgee-940908179/ Connect with ICND:Website: https://bit.ly/3THIq8J LinkedIn: https://www.linkedin.com/company/intercoastal-net-designs/ Free Resource from ICND:Download ICND's AI Visibility Case Study to learn how vacation rental companies can adapt to AI-driven search.

In this episode, we interview Dunniela Kaufman of Sojourn to talk all things building a hospitality brand, growing from 6 to 430 vacation rental units, short-term vs. mid-term rentals, changing homeowner and guest expectations, creating consistent brand standards, balancing profitability with a better guest experience, using AI to support human hospitality, and a lot MORE!Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellDunniela KaufmanSojourn DC

Vacation rental markets were some of the biggest winners of the housing boom several years ago. But where are those real estate markets today?   New data suggests that many of the operators who chased cash flow in the Airbnb gold rush are now looking to cut their short-term rentals loose. As it turns out, running a profitable Airbnb is much harder than it looks. So, does that make this the perfect time to buy?   Our resident short-term rental expert, Garrett Brown, joins the show to break down exactly what's happening and why it could be worth making a few “disrespectful” offers on these types of properties in 2026.   Sellers are highly motivated, and more properties are hitting the market, but investors must be able to distinguish the “good” rental properties from the homes that should never have been vacation rentals in the first place. We'll get into market analysis, the amenities that actually drive bookings, and why the next wave of successful short-term rental investors will win with hospitality—not hype. In This Episode We Cover The exact type of operator being squeezed out of vacation rental markets The two types of short-term rentals that are still wildly profitable in 2026 Why there are so many motivated sellers in the short-term rental space right now Garrett's favorite short-term rental markets to target in 2026 The number one thing you must do when entering a new Airbnb market And So Much More! Links from the Show Join the Future of Real Estate Investing with Fundrise Join BiggerPockets for FREE Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets Sign Up for the Investor Brief Newsletter Find an Investor-Friendly Agent in Your Area Investing in Short-Term Rentals: A Beginner's Guide & How to Get Started Garrett's BiggerPockets Profile Dave's BiggerPockets Profile Watch Garrett on BiggerStays! Parcl: Trouble in Paradise: America's Vacation-Home Sellers Are the Most Motivated in Housing AirDNA BNBCalc Buy the Book, Smarter Short-Term Rentals Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and https://www.biggerpockets.com/blog/on-the-market-449. Interested in learning more about today's sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

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, where sellers are often unprepared, and why the conversation should begin long before an owner is ready to step away.They also explore what happens after the transaction, from protecting the local brand and retaining employees to helping founders choose the role they want in the company's next chapter.Episode Chapters: 05:22 - Why Monarch Collective was created and the opportunity it saw in the market 08:07 - Preserving local brands, teams, and community relationships 11:12 - Anchor acquisitions versus tuck-in acquisitions 11:51 - The qualities Monarch looks for in an established business 13:57 - When owners should begin preparing for a potential sale 16:14 - Creating a transition plan around the founder's goals 22:16 - The performance indicators buyers consider 25:03 - Financial readiness, valuation, and common seller blind spots 28:04 - Building a shared data layer across different technology platforms 33:43 - How Monarch is approaching AI across operations and marketing 38:13 - What an acquisition can mean for employees and local leadership 46:48 - How owners can get feedback before they are ready to sellConnect with Igor:Email: isimkin@gomonarch.comLinkedIn: https://www.linkedin.com/in/igor-simkin-4902993/ Connect with Monarch Collective:Website: https://gomonarch.com/Thinking about the next chapter for your vacation rental business?Connect with Monarch Collective to explore what your options could look like and how to prepare before the time comes.

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, where sellers are often unprepared, and why the conversation should begin long before an owner is ready to step away.They also explore what happens after the transaction, from protecting the local brand and retaining employees to helping founders choose the role they want in the company's next chapter.Episode Chapters: 05:22 - Why Monarch Collective was created and the opportunity it saw in the market 08:07 - Preserving local brands, teams, and community relationships 11:12 - Anchor acquisitions versus tuck-in acquisitions 11:51 - The qualities Monarch looks for in an established business 13:57 - When owners should begin preparing for a potential sale 16:14 - Creating a transition plan around the founder's goals 22:16 - The performance indicators buyers consider 25:03 - Financial readiness, valuation, and common seller blind spots 28:04 - Building a shared data layer across different technology platforms 33:43 - How Monarch is approaching AI across operations and marketing 38:13 - What an acquisition can mean for employees and local leadership 46:48 - How owners can get feedback before they are ready to sellConnect with Igor:Email: isimkin@gomonarch.comLinkedIn: https://www.linkedin.com/in/igor-simkin-4902993/ Connect with Monarch Collective:Website: https://gomonarch.com/Thinking about the next chapter for your vacation rental business?Connect with Monarch Collective to explore what your options could look like and how to prepare before the time comes.

In this episode, Bob Milne discusses the lessons learned from scaling one of the industry's largest vacation rental companies, why niche hospitality brands are on the rise, building First Chair Destinations, balancing technology with exceptional guest experiences, sustainable growth, ski vacation rentals, and a lot MORE!Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellBob MilneFirst Chair Destinations

Connect with Tim: https://www.linkedin.com/in/tim-rosolio-434b2a98/ Connect with Zach: https://www.linkedin.com/in/zacharybusekrus/ Apply to join the Journey Alliance: http://journey.com/alliance/ — Vrbo just did three things most operators haven't connected yet: it purged 100,000 homes, surveyed 2,000 guests across seven countries, and started rolling out sponsored listings. Put them together and you get the clearest signal yet on where vacation rentals are headed. Tim Rosolio is VP of Vacation Rental Partnerships at Expedia Group, where he leads the supply and host side of Vrbo. He's also a Vrbo host himself. In his return to Behind the Stays, Tim and Zach get into what that survey actually revealed — and it wasn't what the industry has been selling. Quality isn't luxury. It isn't the private chef or the infinity pool. It's accurate photos, verified reviews, a fully stocked shelf, and linens and silverware worth touching. 81% of guests said they'd pay more for a stay they can trust to be consistent. Then there are the sponsored listings landing this summer — a pay-only-if-you-book model that lets hosts buy visibility without gaming the algorithm. Tim explains how it works, why bad operators won't be allowed in, and where it goes across Expedia next. The conversation also covers the "coach up or coach out" program behind the purge, why the future of discovery is personalization instead of a star-rating system nobody trusts, expanded distribution across Expedia's 70,000-business B2B network, and the one fear keeping every VRM up at night: owner retention in a market where 2022 numbers aren't coming back. Reach out to Tim on LinkedIn — he's an open book. —   Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world's top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more.   Your host is Zach Busekrus, Head of Growth at Journey. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we'd love for you to apply to join our Alliance at journey.com/alliance.

In this episode, Bill Murphy shares his journey in real estate investing, focusing on short-term and mid-term rentals, market opportunities, and lessons learned along the way. Discover practical strategies and insights to elevate your real estate business.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

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 same thinking applies in vacation rentals. OTAs may help bring guests in, but operators still need a way to understand who those guests are, stay connected, and create reasons for them to book again.Orlie and Patti also share the mentorship behind that journey, including what it means to take a chance on someone, recognize when a role is no longer the right fit, and support a person as they move toward something bigger.We discuss:00:51 - Meet Patti Ziegler and learn how she worked with Orlie02:04 - Building a direct-to-consumer brand from zero to one03:19 - How established brands create new pathways to the customer08:39 - What retail distribution can teach operators about OTAs and direct bookings11:50 - How direct-to-consumer thinking shaped Lasoh13:36 - The mentorship behind Orlie's move into entrepreneurship21:46 - How a career pivot brought Orlie closer to her purpose28:33 - What vacation rental operators can learn from full-funnel marketing30:46 - Why awareness, conversion, and guest loyalty all need attention36:23 - Building a business in a way that still supports people40:22 - Why the guest experience is central to Orlie's work in vacation rentalsLearn more about Lasoh:Website: https://tinyurl.com/52nvyw8tLinkedIn: https://www.linkedin.com/company/lasoh/ Facebook: https://www.facebook.com/people/Lasohio/61575721958679/ Instagram: https://www.instagram.com/lasoh.ioConnect with Orlie:LinkedIn: https://www.linkedin.com/in/orliebenjamin/ Facebook: https://www.facebook.com/profile.php?id=61585160391720 Instagram: https://www.instagram.com/orlie.benjamin/ Connect with Patti:LinkedIn: https://www.linkedin.com/in/patti-ziegler-4649173/ ✨ Exclusive Offer to Alex & Annie Listeners: Turn every guest interaction into more revenue with Lasoh.Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through September 30, 2026.

In this episode, we interview Christian to discuss the future of AI in hospitality, the evolution of property management systems, why operators should rethink their AI strategy, custom AI models, hotel vs. vacation rental innovation, and so much MORE!Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellChristian H.

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 behavior, higher homeowner expectations, and an increasingly complex distribution landscape. Rick and Brandon share why long-term success requires a willingness to evolve, strong systems, careful attention to detail, and people who can grow with the organization. They also discuss Elliott Realty's approach to homeowner relationships, property standards, direct bookings, OTA distribution, brand development, and local tourism advocacy. Episode Chapters:06:42 - How Elliott Realty Has Evolved Since 195907:15 - Why Strong People and Systems Matter More Than Technology Alone12:20 - Hiring Intentionally and Promoting Future Leaders From Within15:59 - Understanding Individual Homeowner Goals and Expectations19:05 - Maintaining Property Quality Across a Large Portfolio27:52 - Balancing Direct Bookings With OTA Distribution35:56 - The Importance of Local Advocacy and Community Involvement48:00 - Why Investing in Your Brand Creates Long-Term Value48:47 - How Founders Can Step Back and Empower Their Leadership Team For vacation rental leaders thinking about the future of their business, this episode offers practical lessons on building a company that can adapt, develop new leaders, and remain strong for generations. Connect with Rick:LinkedIn: https://www.linkedin.com/in/rick-elliott-192aba11/ Connect with Brandon:LinkedIn: https://www.linkedin.com/in/brandon-cox-87930a56/ Connect with Elliott Realty:Website: https://www.elliottbeachrentals.com/ Facebook: https://www.facebook.com/elliottrealty Instagram: https://www.instagram.com/elliottbeachrentals?igshid=YmMyMTA2M2Y%3D LinkedIn: https://www.linkedin.com/company/elliott-beach-rentals/about/ ✨ Exclusive Offer to Alex & Annie Listeners: List your professionally managed properties on VacationFinder.com with no listing fees or booking commissions.Join through the link below for a chance at featured launch placement and a $250 Amazon Gift Card. Drawing August 15, 2026.

In this episode, we interview Annie Holcombe to talk all things OTAs, platforms, vacation rental management, podcasting as a growth platform, being independent and a lot MORE! Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellAnnie HolcombeAlex & Annie PodcastAnnie & Co.

One California city has been quietly collecting $5,000-per-incident fines from short-term vacation rental owners. And if the regime is struck down, the city may owe half a million dollars back.Former constitutional law attorney David Koslow joins Tim Kowal and Jeff Lewis to break down two Appellate Division challenges that expose a structural flaw in how cities administer and collect STVR fines, and why SEC v. Jarkesy may be the tool that finally pries these cases open.Key points:The $1,000 cap hiding in plain sight: Government Code §36901 sets a default $1,000 ceiling on city fines—but Cathedral City and several other Coachella Valley municipalities have been imposing $5,000 first-offense STVR penalties for years.Forfeiture swallowed the first case whole: In Montanaro v. City of Cathedral City, the pro per defendant said the fine was "draconian"—but never said "excessive fines clause." The Court of Appeal dismissed on forfeiture. “Draconian,” says the court, is not the same as “excessive.”

In this episode, Misti and Troy Petrie share their journey into short-term rentals, focusing on cabins and guest ranches across Colorado, Florida, and Alaska. They discuss acquisition strategies, marketing, operations, and their vision for creating memorable guest experiences.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

In this episode, we interview James Cornwell and his excellent accent to talk all things growth, profit, luxury, choosing the right properties to manage and a LOT more... Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellJames CornwellCurated Property

Joining us in this episode of Living Off Rentals is Yiwei Cheng, a short-term rental investor and the founder of Pink Cash Cow Property Management. Through plenty of trial and error, she built a portfolio and a successful property management company while proving that strong cash flow doesn't have to come from expensive vacation markets. Listen as Yiwei talks about finding profitable deals in the Midwest, managing short-term rentals, avoiding common investing mistakes, and why she believes the best opportunities are still ahead.  Enjoy the show! Key Takeaways: [00:00] Introducing Yiwei Cheng and her background [03:35] What more do people actually make money on real estate? [06:04] The first property she purchased [09:02] Her real estate experience during COVID [12:23] Replacing her corporate income through short-term rentals in 2022 [16:38] Choosing profitable properties over popular vacation destinations [23:50] What makes a perfect deal for Yiwei [32:04] How Yiwei finances her rental properties [35:24] DSCR loans explained [38:40] Yiwei on managing her team [46:10] Quality matters more than growing a large management company [51:19] Building systems to manage rental properties efficiently [55:20] Connect with Yiwei Cheng [56:16] Outro Guest Links: Website: https://www.pinkcashcow.com/  Instagram: https://www.instagram.com/yiweicheng1/  YouTube: https://www.youtube.com/@YiweiCheng1  Show Links: Living Off Rentals YouTube Channel – youtube.com/c/LivingOffRentals  Living Off Rentals YouTube Podcast Channel - youtube.com/c/LivingOffRentalsPodcast  Living Off Rentals Facebook Group – facebook.com/groups/livingoffrentals  Living Off Rentals Website – https://www.livingoffrentals.com/  Living Off Rentals Instagram – instagram.com/livingoffrentals  Living Off Rentals TikTok – tiktok.com/@livingoffrentals  Want to start investing in short-term rentals? Book a call to see if my STR Blueprint program is a good fit for you: livingoffrentals.com/call   

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 marketplace for professional property managers. The conversation gets into why lower fees alone are not enough to change booking behavior, how OTAs have shaped traveler expectations, and why direct booking needs a better discovery path if it is going to scale.Episode Chapters:06:21 - How professional property managers can build stronger guest relationships06:53 - Why repeat business starts with owning guest data07:56 - Why direct booking has struggled to reach the consumer09:04 - How traveler behavior has been shaped by OTAs18:16 - Why property managers still need OTAs while building a stronger direct strategy20:55 - How destination content can support discovery and conversion27:05 - Why property managers cannot rely on direct booking websites alone33:28 - How trust, reviews, verification, and clear pricing influence conversion34:18 - Why saving money is not always enough to win the booking42:00 - What AI and structured data could mean for the future of travel searchIf you are a vacation rental operator trying to reduce OTA dependency, build more repeat business, or understand how travelers are discovering and booking stays today, this episode is for you.Connect with EricLinkedIn: https://www.linkedin.com/in/ericgoldreyer/ Connect with Savvy:Website: https://www.savvy.com/LinkedIn: https://www.linkedin.com/company/stay-savvy/Instagram: https://www.instagram.com/savvy_stayFacebook: https://www.facebook.com/savvystays ✨ Exclusive Offer to Alex & Annie Listeners: Reach more direct-booking travelers with Savvy.List your professionally managed properties for free.

In this episode, we interview Cristiana Carpini from her Italian home to talk all things Europe, regulations, where we're headed, a long-term view, AI disruption and a LOT more.  Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellCristiana CarpiniTara Home Consulting

**Think passive real estate investing only means buying rental properties? Think again.** In this episode, G. Brian Davis and Denise break down **8 high-yield passive investment opportunities** that can help you build wealth, diversify your portfolio, and generate income—without becoming a full-time landlord. Whether you're an experienced investor or just getting started, you'll learn how to evaluate different passive strategies, understand their risks, and decide which investments may fit your financial goals. ### **

In this episode, we interview Ashley Ching (again!) with Inhaven to talk all things scale, AI, human vs AI, brand standards, why Vacation Rental brands keep failing to grow and a LOT more...Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellAshley ChingInhaven

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 recognizable names in the industry.Now, with First Chair Destinations, Bob is returning to a more focused, locally grounded model of vacation rental management.Throughout the conversation, Bob shares what he has learned from building and scaling vacation rental companies, what the industry can take away from the Vacasa to Casago transition, and why the future of vacation rental management still depends on strong local teams, trusted owner relationships, and consistent guest hospitality.He also discusses the role of technology, AI, distribution, OTAs, private equity, and consolidation in shaping what comes next for the industry.Episode Chapters:03:22 - Bob's path through Steamboat, Wyndham, Vacasa, Casago, and First Chair06:26 - What the Vacasa to Casago transition revealed about the industry10:25 - How First Chair is approaching its next chapter15:29 - What rapid growth has taught the vacation rental industry16:18 - Why local teams still matter in a scaled industry17:05 - How hospitality can get lost as companies grow23:56 - What operators can learn from the Vacasa to Casago transition27:51 - What consolidation could mean for the industry30:06 - Where AI can support vacation rental operations33:16 - Building a hospitality-first culture across local teams40:47 - Why OTAs still play a major role in distribution46:56 - How owner expectations around channel visibility are changing49:34 - Why the future of vacation rentals is still local51:57 - How guest expectations are changingConnect with Bob:LinkedIn: https://www.linkedin.com/in/robertemilne/ Website: https://www.firstchair.com/ ✨ Exclusive Offers to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

We're joined this week by Jamey King, industry veteran to talk all things data, finding new sources of data and research to improve your marketing, ROAS improvements, vendors shifting sands in 2026 and a LOT more...Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jamey KingWiland

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 and 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 vacation rental marketing, website strategy, and guest acquisition.Richard argues that AI will reshape websites, search, and distribution in ways the industry has not fully prepared for yet. Mark makes the case that strong website infrastructure, brand strategy, PMS connectivity, and niche positioning still matter, especially for operators who want to grow direct bookings.Together, they explore whether AI search will create new opportunities for independent vacation rental companies or make it even harder to compete with OTAs.Episode Chapters:05:29 - How AI is changing the future of vacation rental websites07:10 - The debate between WordPress websites and AI-built websites10:00 - Why website design alone is not enough to drive direct bookings28:25 - How Airbnb, Vrbo, Booking.com, and Expedia continue to shape guest behavior36:29 - Why broad search terms are becoming harder for local operators to compete for18:00 - How AI search could make niche positioning more important21:53 - The growing role of TikTok, creators, and social media in travel discovery46:03 - Why brand trust still matters in an AI-driven search environment48:22 - How PMS data, integrations, and distribution may evolve53:22 - What vacation rental operators should be thinking about now as search changesAs guest behavior shifts, vacation rental operators are being pushed to think more carefully about how people find them, what makes their brand memorable, and how they can stay visible beyond the major booking platforms. Connect with Richard:LinkedIn: https://www.linkedin.com/in/richardvaughton/ Website: https://yes.consulting/ Connect with Mark:LinkedIn: https://www.linkedin.com/in/mrmarksimpson/ Website: https://boostly.co.uk/ ✨ Exclusive Offers to Alex & Annie Listeners: Thinking about the next chapter for your vacation rental business? Connect with Monarch Collective to explore what growth could look like with the right platform behind you.

We're joined this week by Ivan Nikolov of Repull & FantasticStay to talk all things AI, building with agents, workflows, "levels" to AI in the vacation rental industry, pitfalls of current AI tooling and a LOT more... you do not want to miss this one. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell RepullIvan Nikolov

We're joined this week by Frank Bosi from Hostfully to talk all things AI, PMS platforms, building tech today vs several years ago, growth, winning with software and ops and a LOT more...Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Frank BosiSave $500 On Onboarding By Signing Up Via This Link

We're joined this week by Luca De Giglio and Richard Vaughton to talk all things SaaS, the growth of agents, building your own PMS platform, coding platforms growth, how Vacation Rental managers should use AI and a lot more... Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell LinkedIn PostLuca De GiglioRichard Vaughton

Research published by MarketerMedia in March 2026 confirmed that 91% of property managers believe timely communications directly impact their guest review scores. Learn how ResortCleaning can help. ResortCleaning City: Orange Beach Address: PO Box 1155 Website: https://www.resortcleaning.com/

We're joined this week by Jan Sahagun of Trellis (backed by YC) to talk all things agents, the future of STR/Vacation Rentals tech, running with lean teams, 150 properties with 1 person and a lot more. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jan SahagunTrellis

We're solo this week to explore a fun thought experiment: what if we had to open our own vacation rental company? How would we operate it? Fund it? Grow it? What types of inventory are we targeting and why? Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell 

We're joined by an all-star cast from all over the US to talk AI, practical use-cases and growth in tooling that is going to move the needle. JJ King, Jack Zoppa and Jacob Mueller join us to each give one example of how they're using AI in their business spanning hiring, reviews, brand rep and a LOT more. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jamie LaneAirDNA

Today, on the 224th episode of the As The Raven Dreams podcast, we have 13 True Chilling stories. These stories come from the shadowy corners of reality, where everyday life takes an eerie twist & ordinary people experience the extraordinary. Today we will be diving into The Terrors of vacation rentals (like Air BNB), scary things in the middle of nowhere, and other scary stories from listeners! Hey There! Would you like to participate in the postcard exchange? It comes with a free ATRD Sticker! Just Send a post card to the following... Lucas PO BOX 8198 Rochester, MN 55903 If you enjoyed this episode, be sure to like or rate the podcast, and leave me a comment with your thoughts if the platform your on supports it! I upload episodes every 3 days, so there are 2 days between new uploads. The podcast consists of new scary story collections, Glitch in the matrix collections, and also what I call the "Dark Dreams" collections (which are older stories, remastered and layered with rain sounds). If you have a story to submit, would like to find where to listen to the podcast, or want to find me on social media platforms, all of that info can be found at https://www.astheravendreams.com You can also send stories into my subreddit (r/theravensdream) or email them to me at AsTheRavenDreams@gmail.com Want to check out some ATRD Podcast Merch? ➤ https://teechip.com/stores/astheravendreams Or for signed merch ➤ https://ko-fi.com/AsTheRavenDreams I wrote a novel, "The Insomniac's Experiment" by Raven Adams! Check it out on amazon (Or you can email me for a signed copy!) Join Patreon to get early access and support the Podcast! ➤ https://www.patreon.com/AsTheRavenDreams Check out my gaming channel with my pal Ghost_Ink ➤ @superNefariousBros On YouTube Thank you to all of the authors that have stories in todays episode... SonOfaBeach, JudyAndPaul, TeacherTeachingTeachers, GarrettWithAMountainView, Stephen, Just another small town girl, Wade, Rabbit Rabbit , Kisu, Ray Ray, louise, Jane F, Tricia M As Well As Any Author That Has Requested Anonymity. TimeStamps… Ad breaks after Story 1 & Story 5 1 ➤ 1:07 2 ➤ 9:49 3 ➤ 19:54 4 ➤ 28:39 5 ➤ 35:06 6 ➤ 43:56 7 ➤ 46:07 8 ➤ 55:22 9 ➤ 58:18 10 ➤ 1:02:30 11 ➤ 1:14:57 12 ➤ 1:18:13 13 ➤ 1:24:47 ----- Disclaimer ➤ Episodes include a content warning for language and sensitive/disturbing content. Listener discretion is always advised. ALL Audio and visuals on this podcast are copyright of AS THE RAVEN DREAMS / RAVEN ADAMS and may not be duplicated, in any format. Bless This Mess. None of my audio is AI Generated, I am a real person reading real stories into a real microphone. Note: The podcast nor the host endorses any advertisements played during the podcast, ads are not chosen by ATRD or Raven Adams, they are chosen automatically by the advertisement systems by the platforms that host the podcast. I do not endorse, support, or promote any opinions or statements made in any adverts played during the show. #ScaryStories #UnexplainedMysteries #GlitchInTheMatrix Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Ryan Moyer shares his expertise in short-term rental investments and property management, focusing on operational excellence, high-end experiential rentals, and strategic growth. Learn how to stay competitive, optimize revenue, and build a strong network in the vacation rental industry.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

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 create value beyond the initial sale or stay.Alex, Annie, and Mike also explore what short-term rental operators can learn from Marriott Vacations Worldwide, especially when it comes to consistency, brand standards, guest experience, and creating reasons for people to stay connected over time.Episode Chapters:02:32 - Why Mike returned to the industry and joined Marriott Vacations Worldwide10:06 - How Marriott Vacations Worldwide thinks about loyalty11:02 - The role of Marriott Bonvoy in brand affinity and direct bookings18:53 - What vacation rental operators can learn from timeshare19:30 - How brand standards help build guest trust28:20 - Why lifetime value matters in the customer journey29:00 - Viewing vacation ownership as a subscription business31:09 - Using experiences to strengthen loyalty and engagement40:11 - How Marriott Vacations Worldwide is using AI in sales training41:41 - How AI is changing digital search and hospitality marketing47:52 - Why prepaid vacations create resilience51:43 - What is ahead for Marriott Vacations WorldwideConnect with Mike:LinkedIn: https://www.linkedin.com/in/mike-flaskey-13496094 Instagram: https://www.instagram.com/thevacationdr/reels/ Connect with Marriott Vacations Worldwide:Marriott Vacation Club: https://www.instagram.com/marriottvacationclub/ Westin Vacation Club: https://www.instagram.com/westinvacationclub/ Sheraton Vacation Club: https://www.instagram.com/sheratonvacationclub/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.

We're joined by a favorite guest, Jamie Lane of Airdna to talk all things q1 2026 wrap up, World Cup demand, reading data the right way, how AI is impacting the AirDNA product, future-looking tips for vacation rental managers and a LOT more. Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Jamie LaneAirDNA

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 supporting communication, operations, channel management, direct bookings, payments, and more.The conversation also explores why many hosts and operators still hesitate to adopt property management software, how Hospitable is working to make software more accessible, and what AI could mean for guest communication, support, direct bookings, and the future of vacation rental distribution.In this episode, we discuss:02:27 - How Pierre-Camille's experience as an Airbnb host led to the creation of Hospitable04:22 - Why guest messaging became the starting point for a larger software platform09:45 - How Hospitable evolved from Smartbnb into a broader property management system20:16 -  Why software adoption remains low across parts of the short-term rental industry21:55 - The challenges that keep smaller hosts and operators from adopting software23:44 - Hospitable's approach to making property management software more accessible17:47 - How self-managers can grow into co-hosts or professional property managers41:47 - The role of AI in guest messaging, customer support, and software usability44:07 - Why AI should make tools easier to use, not simply add more complexity53:07 - What AI agents could mean for OTAs, direct bookings, and property discovery53:07 - Why strong owner service, guest experience, and operational consistency still matter as technology evolvesConnect with Pierre-Camille:LinkedIn: https://www.linkedin.com/in/pchamana/ Connect with Hospitable:Website: https://hospitable.com/partners/alex-annie LinkedIn: https://www.linkedin.com/company/hospitable/ Instagram: https://www.instagram.com/hospitable_com/ Facebook: https://www.facebook.com/hospitable/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable.Start a 14-day free trial and get 25% off your bill for the first 6 months.

We're pumped to welcome Michael Friedman, Chief Executive Officer of Simple Life Rentals onto the show to talk all things AI, growth, team, profitability, smart homeowner marketing that works, where we're headed into 2026 and a LOT more.Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Michael FriedmanSimple Life Rentals

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 how Vrbo selects winners from millions of properties across its global network, using a mix of performance data, guest reviews, local market insight, and hospitality storytelling to identify homes that deliver standout guest experiences.The conversation then shifts to David Rose, owner of Lakefront Escape, who shares how he transformed a dated lake house into an award-winning retreat designed with intention, warmth, and usability in mind.From intuitive in-home tech and thoughtful labels to tailored recommendations and architectural details, this episode highlights how exceptional hospitality is built through the details.In this episode, we cover:03:50 - Why Vrbo created the Vacation Rentals of the Year program04:39 - How Vrbo selects its Vacation Rentals of the Year08:04 - What makes a vacation rental experience feel personal and memorable13:35 - Meet David Rose and the story behind Lakefront Escape16:42 - Why intuitive technology matters more than flashy features23:00 - How David Rose designed Lakefront Escape for connection, comfort, and discovery25:20 - Why David chose self-management and how Vrbo supports pricing and promotion26:43 - How personalized recommendations can elevate the guest stay30:34 - How labels, notes, and in-home guidance reduce guest friction32:21 - The Japanese design influence behind the home's guest experience35:27 - How design, layout, and local insight help create repeat guestsThis episode captures both the criteria behind Vrbo's recognition and the real-world hospitality choices that help a property earn it.Connect with:David Rose / Lakefront Escapehttps://www.squamlakehouse.com/ Tim Rosolio / Vrbohttps://www.linkedin.com/in/tim-rosolio-434b2a98/ ✨ Exclusive Offer to Alex & Annie Listeners:Automate your short-term rental operations with Hospitable. Start a 14-day free trial and get 25% off your bill for the first 6 months.

We're thrilled to be joined today by Neely Khan and Rachel Alday to talk all things storytelling, marketing to luxury, being chosen vs being found, AI / LLM discoverability, and a LOT more.Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell Neely KhanRachel AldaykahaniAbode Luxury Rentals

Join Scott Bursey as he interviews Kevin Anderson, a real estate expert specializing in luxury villas and ghostwriting. Discover insights on high-end property management, market opportunities, and the value of passion-driven investments.   Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind:  Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply   Investor Machine Marketing Partnership:  Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true 'white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com   Coaching with Mike Hambright:  Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike   Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a "mini-mastermind" with Mike and his private clients on an upcoming "Retreat", either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas "Big H Ranch"? Learn more here: http://www.investorfuel.com/retreat   Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform!  Register here: https://myinvestorinsurance.com/   New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club   —--------------------

​Comedian Tony P joins the show to discuss why he's accidentally "swinger bait" in Florida and the absolute nightmare of his latest vacation. We also deep dive into the 2026 World Cup price gouging at MetLife Stadium—from $150 train rides to the $255 parking "deals."​Highlights:​World Cup Chaos: Why FIFA told Chuck Schumer to kick rocks while fans face $10,000 tickets.​Albert the Alligator: After 34 years, Tony Cavallaro officially loses his 750lb "best friend."​The Backyard Guests: A hot air balloon emergency lands in a California yard and the passengers act like it's a social call.​Politics vs. Religion: Why are people trading their faith for politicians?​Tony P's Vacation: Rental car rage and why Florida swingers were eyeing him at the bar.​Keywords: NYC Comedy, Tony P, MetLife Stadium World Cup, Albert the Alligator Buffalo, Tony Cavallaro, Podcast Comedy NYC, Swinger Stories, Hot Air Balloon Landing.

Short-term rentals have matured fast. But many operators are still stuck paying rising distribution costs while losing control of the guest relationship. In this episode, Eric Goldreyer, hospitality entrepreneur and founder of BedandBreakfast.com, former co-founder of TurnKey Vacation Rentals, and creator of Savvy, joins Brian to unpack what's happening behind the scenes in vacation rental distribution. Eric has built, scaled, and sold companies in the space. He also owns and operates a 20-key boutique hotel outside Austin, giving him both strategic and ground-level insight into hospitality operations. This conversation focuses on one core issue: Who owns the guest relationship — and what does that cost you? What We Cover: Why vacation rental distribution costs have increased while hotel distribution costs have decreased The "Airbnb tax" and how it affects long-term profitability Why hosts don't truly own their customer data on major OTAs The difference between transaction fees and customer acquisition costs Why professional property management is separating from gig-economy hosting How book-direct marketplaces are changing the economics of short-term rentals What it takes to scale a property management company nationally Leveraging tech stacks, automation, and AI in modern vacation rental operations How Eric approaches hiring high-performance teams Why hospitality — not just technology — is the real differentiator Eric also shares how his company Savvy is building a book-direct marketplace designed to reduce fees for travelers while giving property managers ownership of their customer relationships. Key Themes Short-term rental profitability OTA dependency risk Distribution strategy Hospitality vs platform control Direct booking models AI in vacation rental tech stacks Resources Mentioned Savvy: https://savvy.com Eric Goldreyer on LinkedIn Sage Hill Inn (Boutique Hotel outside Austin) Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and medicare benefits. https://www.rcbassociatesllc.com

This week started with the news that the Myanmar military junta held elections, plus an Italian art heist. Also an F-15 crew ejects over Iran, Gucci Mane kidnapping plot, Australia cop killer shot and killed, Indonesia social media ban for minors update, and a CA vacation rental owner is not only accused of secretly recording his guests having sex, buy having a bound-up child sex doll in his closet. Music: Gucci Mane/"Stick 'em Up"

What you'll learn in this episode: ● The difference between short-term and long-term rental markets ● Why vacation-driven markets with limited hotels are the best investment ● How to choose markets that maximize cash flow ● The #1 mistake investors make when buying their first Airbnb ● Why Avery avoids “emerging markets” everyone is hyping online ● How to scale a short-term rental business efficiently (even with a full-time job) ● How to out-host the competition and treat rentals like a real business ● How regulations impact profitability—and how to choose markets that protect you ● Avery's journey from one rental to a 250+ property empire To find out more about Dan Rochon and the CPI Community, you can check these links:Website: No Broke MonthsPodcast: No Broke Months for Salespeople PodcastInstagram: @donrochonxFacebook Page: https://www.facebook.com/NoBrokeMonths/Facebook: Dan RochonLinkedIn: Dan RochonTeach to Sell Preorder: Teach to Sell: Why Top Performers Never Sell – And What They Do Instead

In this bonus episode, we are joined by the hosts of the new HGTV series “Wild Vacation Rentals”, Sherry Cola and D'Arcy Carden! You may recognize them from hits like The Good Place and Joy Ride, but for today, they are two besties who take us along as they travel around the US and stay at some of the most unique places. "Wild Vacation Rentals" premieres on Monday, March 2nd at 10:00pm on HGTV!You can find us:Podcast: ACast, iTunes, Spotify, wherever you listen!Instagram & Threads: @twojudgeygirlsTikTok: @twojudgeygirls // @marytwojudgeygirls // @courtneytjgFacebook: www.facebook.com/twojudgeygirlsMerch: www.etsy.com/shop/twojudgeygirlsPatreon: www.patreon.com/twojudgeygirls LTK: @marytwojudgeygirls // @courtneytjg Hosted on Acast. See acast.com/privacy for more information.