Podcasts about vacation rentals

Brought to you by Up! The Bank That's Got Young Aussies' Backs... Hawaiian, Mark Healy, is considered one of the greatest tube riders, big wave surfers and all round watermen of his generation. He grew up in a violent and contested period of North Shore, Oahu surfing history and made a name for himself charging maxing Pipeline, Cloudbreak, Waimea, Mavericks and elsewhere. He has won Wave of the Winter, come 3rd at the 2023, Eddie Aikau Invitational, and won a Spearfishing World Cup in Mexico in 2008. See omnystudio.com/listener for privacy information.

What happens when a vacation rental executive who has experienced the industry at virtually every level decides to go back to the basics? In this episode of The STR Data Lab, Jamie Lane sits down with Bob Milne, COO and President of First Chair Destinations, to unpack decades of lessons from building, scaling, and reshaping vacation rental management businesses. From running thousands of homes in Steamboat to navigating Wyndham and Vacasa, Bob shares why he believes vacation rentals are ultimately a hospitality and relationship business—not simply a technology business.The conversation explores the tradeoffs between scale and local operations, what can—and can't—be centralized, the challenges of proprietary technology, and what Bob learned from Vacasa's rapid growth and transition to a more localized model. He also dives into why ski destinations offer opportunities beyond the traditional winter season, how events and summer demand can reshape seasonality, the role professional managers can play in local regulation, and why First Chair is pursuing moderate, deliberate growth rather than growth for growth's sake.You don't want to miss this episode!Key TakeawaysWhy vacation rental management is fundamentally a people and hospitality business, and where technology can—and can't—replace local expertise.Which parts of a vacation rental business actually benefit from scale, from technology and marketing to operations and owner communications.What the transition from Vacasa's national model to more localized operations reveals about the importance of boots-on-the-ground teams.How ski destinations can reduce seasonality by tapping into summer travel, weddings, events, outdoor recreation, and improved air access.Why sustainable growth may require a different approach than rapid expansion, particularly when balancing owner retention, local relationships, and operational quality.Sign up for AirDNA for FREE

In this episode, we interview Tanya Rooney to talk about all things AI in vacation rentals, outsourcing and specialization, automation vs. AI, using technology to save time and make more money, maintaining the human side of hospitality, knowing what to automate and what to hold onto, AI creep, and a lot MORE! Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellTanya Rooney WebsiteTanya Rooney LinkedInTanya Rooney - "Tribe Builders" Podcast

Booking a beachfront Perdido Key condo through the wrong site could add 15-20% in fees. With demand rising, discover what a week-long stay may cost and how direct booking can save hundreds. Learn more at https://www.emeraldcoastbyowner.com/florida/perdido-key Emerald Coast By Owner City: Destin Address: Destin Website: https://www.emeraldcoastbyowner.com

In this episode, we interview Jenn to talk about all things destination marketing, the relationship between DMOs and vacation rental managers, tourism vs. hospitality, industry standards, changing traveler perceptions, creating better guest experiences, driving more demand to local markets, and a lot MORE! Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellJenn BarbeeDestination InnovateHosts and Home Teams

https://www.emeraldcoastbyowner.com/florida/panama-city-beachBooking a Florida beach getaway? Over half of Miami rental listings analyzed showed scam warning signs, and one silent response to a simple request exposed a fraudster instantly. Here's how to protect yourself before you pay. Emerald Coast By Owner City: Destin Address: Destin Website: https://www.emeraldcoastbyowner.com

How do you design cleaning operations software that hosts and cleaners actually use when they're not at a desk?Gabi Celemin from Turno joins Turnover Tactics to share how customer support informs product development, what customers asked for versus what was actually built, and how to design for everyone from new hosts to managers with hundreds of doors. Plus: product localisation and the impact of AI on Turno and the future of turnovers.Turnover Tactics is powered by Host Planet and Turno – helping you build a smarter, more sustainable hosting business.In this episode:2:12 The Turno user experience4:15 Customer support informs product development5:55 Designing a solution for people who are not at a desk9:05 How to help hosts and cleaners11:55 Surprising elements which have changed the product13:50 What customers asked for versus what was built16:24 Product localisation18:53 Trying to please new hosts and people managing hundreds of doors20:43 The impact of AI on TurnoConnect with Gabi Celemin: https://www.linkedin.com/in/gabrielcelemin/Contact: gabriel@turno.comPowered by Turno: https://turno.com/?utm_source=youtube&utm_medium=podcast&utm_campaign=host_planet#ShortTermRentals #AirbnbCleaning #VacationRental #PropertyManagement #HostPlanet #TurnoverTactics #AI

Panama City Beach short-term rentals are booming, but platform fees can quietly add hundreds to a booking. Going direct on a four-thousand-dollar stay could save travelers up to six hundred dollars. To learn more, visit https://www.emeraldcoastbyowner.com/florida/panama-city-beach Emerald Coast By Owner City: Destin Address: Destin Website: https://www.emeraldcoastbyowner.com

In this episode, Alex & Annie sit down with Vinny Dicarlo, CEO of Ciirus, and Josh Parry, Chief Product Officer, for a conversation about the philosophy that has shaped the company over nearly two decades.Founded as a family business, Ciirus has taken a deliberately measured approach to growth. Rather than building around outside investment or pressure to scale at all costs, Vinny and Josh explain how the company has focused on long-term customer relationships, continued investment in its technology, and human support that keeps the team closely connected to the property managers it serves.That approach opens up a broader conversation about what operators should expect from a technology partner today. Vinny and Josh share why they believe there are limits to how much vacation rental operations can be automated, where AI can genuinely help, and why human involvement still matters in an industry where every property, owner, guest, and stay can look different.Episode Chapters:11:14 - Building customer relationships designed to last17:15 - Why Ciirus has chosen measured growth over growth at all costs18:28 - How independent ownership shapes investment in customers and technology22:38 - Why vacation rental operations cannot automate everything27:39 - Building a global team around specialized talent32:49 - Helping property managers get more from their technology38:14 - Why customer and employee satisfaction matter together39:55 - Ciirus' new mobile app, owner tools, and Booking.com integration46:03 - How LoveRentals helps property managers expand their capabilities54:59 - Finding vacation rental demand beyond the major OTAs57:55 - Reaching guests through travel agents, wholesalers, and international markets1:02:24 - What is next for the Ciirus platformIf you are evaluating your tech stack, thinking about sustainable growth, or looking for new ways to reach guests, this episode offers a closer look at what a strong technology partnership can bring to your business.Connect with Josh & VinnyJosh Parry: https://www.linkedin.com/in/josh-parry-47165997/ Vinny Dicarlo: https://www.linkedin.com/in/vincenzo-dicarlo/ Connect with CiirusWebsite: https://ciirus.com/✨ Exclusive Offers to Alex & Annie Listeners:Alex & Annie listeners can receive their first three months of Ciirus subscription fees waived when joining the platform.Visit https://ciirus.com/ and let the team know you heard about Ciirus through the Alex & Annie Podcast.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.

In this episode, Conrad and Adam talk about all things local vacation rental marketing: building an authentic brand, creating content that actually connects with guests and homeowners, using local knowledge as a competitive advantage, staying consistent, building an audience, and a lot MORE! Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'Connell

Simon Baker and Harvey Hancock are joined by Christian Schwarz Lausten, founder and CEO at Landfolk, for a peek behind the curtain of an increasingly AI-first vacation rentals marketplace that has expanded from its native Nordics into Europe, including a proprietary AI intelligence layer called PAX...00:00 intros00:54 What is Landfolk?07:25 Context, Business model and monetisation13:31 Awareness, engagement, and bookings for the properties?20:20 AI at Landfolk, and introducing PAX24:42 AI goosebumps and AI Trustability34:18 Christian's question for Simon

In this episode, we interview Rick, CTO of Hostaway, to talk all things vacation rental technology, the evolution of property management systems, AI co-hosts, automation, point solutions vs. all-in-one platforms, building smarter operations, the future of AI in the industry, and a lot MORE! Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellRick van der PlasHostaway

This is a slightly different episode of the Hospitable Hosts podcast, where we delved into a very important topic: short-term rental advocacy. Our guests are representatives from the Right to Rent Collaborative, Florida Alliance for Vacation Rentals, and Colorado Short-Term Rental Association.We explore the often overlooked, yet vital role of advocacy organizations in shaping the future of short-term rentals across the US, the efforts of various state associations, their challenges, and the importance of community and professionalization in the short-term rental industry.For more information, visit:https://r2rcollaborative.org/https://floridaavr.org/https://coloradostra.org/Timestamps:0:00 - Introduction3:55 - Right to Rent Collaborative9:50 - STR advocacy in Florida13:32 - STR advocacy in Colorado16:00 - The importance of advocacy21:05 - How Right to Rent Collaborative's grants work24:45 - How the grants are used in Colorado26:23 - How hosts can contribute to the Right to Rent Collaborative and local associations32:00 - How the $1/stay contributions help FAVR33:40 - How the $1/stay contributions help COSTRA36:00 - Future trends in STR advocacy

Annie Holcombe has spent her career refusing to pick a side in the hotel versus vacation rental debate, working her way through property management, Expedia during the HomeAway and Vrbo years, channel management, and business development for Marriott Homes and Villas. She is now founder of Annie & Co, coaching independent vacation rental operators on distribution and growth, while also serving as a brand ambassador and US market consultant for Booking.com, sitting on the VRMA board, and co-hosting the podcast Alex and Annie: The Real Women of Vacation Rentals. Susan and Annie talk about convergence, consistency, and commissions. What You'll Learn - Why the early job Annie's most grateful for wasn't the one you'd guess - What it took to finally convince Annie to bet on her own business instead of someone else's - What happened to the company Annie and her husband ran together before this one - How Annie decides what gets her time between consulting, board seats, a podcast, and her own company - Why hotels and vacation rentals used to feel like separate worlds, and what's pulling them together now - What a converted roadside motel reveals about where hospitality is headed - How the OTA relationship changes depending on which side of the lodging industry you're standing on - Why rate parity gets complicated the moment you're not a thousand-room hotel chain - Why the vacation rental industry can't seem to agree on standards, and whether that could ever change - What conventional wisdom Annie wants new rental operators to ignore, and what she'd tell them instead - Where Annie predicts the hotel versus vacation rental rivalry actually lands Key takeaway:  The hotel and vacation rental worlds are converging, whether the industry likes it or not, and the winners will be the ones who stop fighting over turf and start listening to what guests actually want. Our sponsor, Lodgify [https://www.lodgify.com/], has a special Labor Day promo from August 25th to September 8th. Using code TOPFLOOR60, our audience will get 60% off their Professional and Ultimate plans (one- or two-year plans). This is a huge deal, so jump on it quickly! Annie Holcombe on LinkedIn https://www.linkedin.com/in/annie-holcombe-vrgal/ Annie & Co. https://anniecosolutions.com/ Join the Top Floor Mail Club https://www.topfloorpodcast.com/mail-club

Welcome to Episode 300 of the Alex & Annie Podcast!

In this episode, we interview Cole Rubin, co-founder and CEO of Conduit, to talk all things AI agents, guest communication, automation, hospitality tech, and what the future of vacation rental operations could look like.We dive into balancing AI with the human side of hospitality, what it really takes to automate guest messaging, why context matters, the future of the vacation rental tech stack, AI pricing and security, and a lot MORE!Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellCole RubinConduit AI

We sit down with Matt Sanderson, founder of STRIQ, to break down how data finds profitable short-term rental properties in seconds instead of weeks. We cover the below key aspects: Why a single AirDNA number can hide $100,000 a year in missed revenue. The exact filters that clean up comp data so a 5-mile radius stops lying to you How one bedroom conversion turned a $150,000 property into a $210,000 property The 4 questions to ask yourself before you ever open a single listing Why chasing the "top 10 markets" everyone talks about might be costing you money If you are ready to stop guessing and start finding properties backed by real data, this episode gives you the exact framework to use. Subscribe to the STR Riches Podcast so you catch every new episode. 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/  

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. 

In this episode, we interview Rachel Alday of Abode Luxury Rentals to talk all things luxury vacation rentals, scaling with standards, hospitality and leadership, private equity and industry consolidation, building authentic connections with guests and homeowners, her upcoming book Please Do Disturb, and a lot MORE!Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellRachel AldayAbode Luxury RentalsRachel's Book: Please Do Disturb | Penguin Random HouseRachel's Book: Please Do Disturb | Amazon

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

​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.