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Send a textEveryone keeps yelling “Airbnb is dead,” but the real truth is harsher: the easy wins are gone. If you learned STRs during the 2–4% rate era, you weren't a genius… you were playing on easy mode. Now it's a sophistication game: better deals, better hospitality, and way better execution.Learn how to invest in real estate with the Cashflow 2.0 System! Your business in a box with 1:1 coaching, motivated seller leads, & softwares. https://www.wealthyinvestor.com/Want to work 1:1 with Ryan Pineda? Apply at ryanpineda.comJoin our FREE community, weekly calls, and bible studies for Christian entrepreneurs and business people. https://tentmakers.us/Want to grow your business and network with elite entrepreneurs on world-class golf courses? Apply now to join Mastermind19 – Ryan Pineda's private golf mastermind for high-level founders and dealmakers. www.mastermind19.com--- About Ryan Pineda: Ryan Pineda has been in the real estate industry since 2010 and has invested in over $100,000,000 of real estate. He has completed over 700 flips and wholesales, and he owns over 650 rental units. As an entrepreneur, he has founded seven different businesses that have generated 7-8 figures of revenue. Ryan has amassed over 2 million followers on social media and has generated over 1 billion views online. Starting as a minor league baseball player making less than $2,000 a month, Ryan is now worth over $100 million. He shares his experiences in building wealth and believes that anyone can change their life with real estate investing. ...
In this episode of the STR Investing Podcast, co-host Mark Lumpkin sits down with Jack Roberts from STR Cribs to talk sales, design, and what it really takes to build high-performing short-term rentals today.Jack breaks down why “being real” wins in sales, how to build trust fast, and why the best salespeople don't hide behind scripts or corporate talk. From there, we get into STR design strategy, how guest expectations keep evolving, and why you can't out-design a bad property.We cover:Why Jack says “I am the sales pitch”How to break down walls and get clients to open upThe difference between designing for homeowners vs. designing for guestsWhat refreshes actually move revenue (and what's just wasted spend)Why STRs can pivot faster than hotelsJack's favorite travel inspiration spots, plus rapid-fire favoritesConnect with Jack:Linkedin: @jackroberts00Book a call: STRCribs.com__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
The short-term rental industry is evolving fast—and the strategies that worked five years ago may not cut it today. In this episode, Natalie Palmer shares how she scaled from co-hosting in a single condo complex to raising capital for luxury destination properties. If you're wondering where STR investing is headed next, this conversation might change your approach. How Natalie scaled to 10 co-hosted units in one condo complex—and why that model simplified operations Why housekeepers are your most valuable asset (and how to structure your team for success) The pricing strategy shift that's working in today's more competitive STR market How luxury upstate New York properties are generating $150K–$200K annually at a fraction of major-market purchase prices Why the "middle-tier" STR may disappear—and how to position your property to survive and thrive The STR landscape is shifting—but opportunity is everywhere if you know where to look. Whether you're refining operations, upgrading amenities, or exploring passive investing, this episode is packed with actionable insights. Be sure to subscribe, share with a fellow investor, and explore the resources below to level up your portfolio. 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, Lady Landlords founder, Becky Nova…sits with Jessie from Blue Caribbean Properties and shares what it really takes to buy rental property abroad, focusing on the Dominican Republic and Mexico. She opens up about moving overseas, breaking down key challenges, and why working with licensed, knowledgeable agents is critical.Connect with Lady Landlords here to learn more about how we can help scale your portfolio: https://lady-landlords.com/pd-chat-with-becky===
In this episode of the VRMA Arrival Podcast, Pierre Camille Hamana, CEO and founder of Hospitable, joins us to unpack key findings from Hospitable's newly released 2026 STR Industry Report and what they signal for hosts and professional property managers.Hamana explains why 2025 was a revealing year for the industry, marked by “stacked pressures” that included rising operating costs, softening demand, staffing challenges, and economic uncertainty. Rather than facing isolated problems, many operators experienced multiple constraints at once, forcing a renewed focus on discipline, efficiency, and day-to-day execution.Despite those headwinds, confidence remains intact. Nearly 60% of surveyed hosts and property managers plan to expand their portfolios in 2026, reflecting long-term belief in short-term rentals as a durable asset class. The challenge, Hamana says, isn't demand for the product itself, but whether operators have the systems in place to deliver consistent performance and reliable financial returns.A major theme of the conversation is the evolving role of technology. Property management software is no longer just about channel distribution; it's becoming an operating system for housing—centralizing pricing, guest communication, team coordination, device control, and owner reporting. Automation, AI, dynamic pricing, and smart devices are now core infrastructure, not optional add-ons.Hamana also shares practical advice for mid-size property managers planning for the year ahead, emphasizing operational efficiency over growth at all costs. Without strong systems, he warns, expansion only amplifies existing weaknesses. The operators best positioned for 2026 will be those who reduce variable costs, automate aggressively, maintain service quality at scale, and make their value to owners visible through clear reporting and performance metrics.
In this episode of the STR Investing Podcast, co-host Mark Lumpkin sits down with Lance Morgan, founder of College Funding Secrets, to break down a different way to think about short-term rentals—using them to help pay for college and reduce taxes.Lance explains how high-income families can reposition college savings, lower “financial aid income” on paper, and use STR tax benefits (bonus depreciation) as what he calls “tax scholarships.” The goal: stop writing big checks for tuition and instead buy an asset that can help cover college costs while continuing to generate long-term wealth.We also talk about:Why the “secret cost of college” can be over $1M when you factor in opportunity costHow STR cash flow can cover student loan payments after graduationWhy income matters more than assets when qualifying for aidCreative alternatives like “box houses” and other tax strategy rabbit holesLance's STR portfolio growth and what he's building next: Scholarship Houses + Scholarship VacationsConnect with Lance:CollegeFundingSecrets.comScholarshipHouse.com (and ScholarshipVacations.com coming soon)__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Beacon cites lack of resources to compel compliance Nearly six years after Beacon legalized short-term rentals, most Airbnb listings are not registered with the city. According to Inside Airbnb, a data collection project based in Newburgh, 133 units in Beacon were listed on the booking site in July 2025. But files obtained by The Current under the Freedom of Information Law show only 33 are registered with the city, as the law requires. STR laws typically allow municipalities to limit the number of housing units being rented to visitors and ensure that rentals have safety features such as smoke detectors and don't disrupt neighborhoods. The 2020 Beacon law allows homeowners and tenants to rent or sublet their homes or apartments for up to 30 days at a time, for a maximum of 100 days per year. Rental spaces must be the host's primary residence, and accessory dwelling units cannot be rented. According to Inside Airbnb, which pulls its data from information posted by the platform, the hosts of 14 Beacon listings live in New York City and six live out of state. The 133 listings are more than triple the number (40) on the site a decade ago, but nearly the same as in June 2020 (126), when the council amended the zoning code. City Administrator Chris White said this week that Beacon does not have the staff to adequately enforce its STR regulations. Since Building Inspector Bryan Murphy was hired in March, the department has prioritized health and safety issues, including overdue fire inspections and enforcing sidewalk snow removal. White said enforcement of STRs has been mostly in response to complaints about noise or parking. New York State authorized Beacon to collect a 2 percent occupancy tax on hotel stays and STR rentals as of Jan. 1, 2025. The Roundhouse, Mirbeau Inn & Spa and other hotels are expected to generate the bulk of the $200,000 in tax revenue in 2026, White said. Airbnb will begin collecting the Beacon tax on its platform starting March 1. The City Council is likely to revisit its STR regulations this year. During a discussion of agenda priorities on Tuesday (Feb. 17), Mayor Lee Kyriacou noted that enforcing limits on short-term rentals could have the quickest impact on the "acute" need for housing. "The fundamental issue is rental costs are really high because there's not enough supply," he said. "Restricting short-term rentals would force them into the long-term rental stock immediately." According to the most recent U.S. Census Bureau data, 41 percent of Beacon households are renter-occupied, and 185 units are listed as vacant, meaning they do not have long-term renters. "If some of those Airbnb units were returned to the market, it would make it easier to find housing," said Murray Cox, who founded the data project. A New York City law adopted in 2023 is stricter than Beacon's: It also requires hosts to register with the city before accepting rentals of 30 days or less. Property owners must reside (and remain) in the unit; bookings are limited to two guests; and booking platforms cannot process transactions for unregistered listings. The law had an immediate effect, with 50,000 listings falling off the services between 2019 and 2023. There are now about 5,000, Cox said. In 2024, Gov. Kathy Hochul signed legislation authorizing counties to establish STR registries. Dutchess County officials have discussed creating a list; there has been no discussion in Putnam, a representative said. In Cold Spring, the Village Board enacted a law in 2021 to regulate STRs but began to review the measure three years later, saying the regulations were too cumbersome to enforce. Mayor Kathleen Foley says updating the STR code is a priority for 2026. The Philipstown Town Board this week discussed revisions to regulations it drafted in October that would require annual permits and inspections and ban parties. Critics say STRs need to be limited because they remove long-term housing from the market, drive up rents and negatively aff...
Kenny Bedwell explains why short-term rentals are harder today—and how data, design, and discipline still create outsized returns.In this episode of RealDealChat, Kenny Bedwell—short-term rental investor, former Citibank data analyst, and founder of STR Insights—breaks down what has actually changed in the Airbnb market over the last eight years.Kenny shares his journey from house hacking a duplex in Buffalo to owning short-term rentals across multiple states and even operating a hotel. We dive into why the “throw it on Airbnb and print money” era is over, how competition and regulation reshaped the landscape, and why data—not hype—must drive every STR decision today.This conversation covers how Kenny uses nationwide data to identify high-ROI markets most investors overlook, why regulated markets can still outperform, how to self-manage STRs without burning out, and what amenities and design choices actually move the revenue needle. Kenny also shares his most expensive mistakes, why parking and neighbors matter more than Instagram aesthetics, and how to think about guest avatars instead of generic “travelers.”If you're considering short-term rentals—or already in the game and feeling squeezed—this episode will reset your expectations and sharpen your strategy.
On this episode of Good Morning Hospitality, A Skift Podcast, Wil Slickers, Jamie Lane, Brandreth Canaley, and Michael Goldin dive into the latest shifts across short-term rentals and online travel. They start with Brian Chesky dismissing rivals' chatbots and arguing that Airbnb's AI advantage is rooted in its marketplace and community data, then unpack Airbnb's new report positioning STRs as a critical pressure valve for lodging demand during peak travel periods. The conversation then turns to Expedia Group's Q4 2025 earnings, where stronger B2B results helped offset softer consumer trends, before closing on leadership tension at Casago as franchisees react to shifting power dynamics. The episode wraps with a broader look at AI strategy, consolidation, and who really controls distribution in today's STR ecosystem. Connect with Skift LinkedIn: https://www.linkedin.com/company/skift/ WhatsApp: https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/ Facebook: https://facebook.com/skiftnews Instagram: https://www.instagram.com/skiftnews/ Threads: https://www.threads.net/@skiftnews Bluesky: https://bsky.app/profile/skiftnews.bsky.social X: https://twitter.com/skift Subscribe to @SkiftNews and never miss an update from the travel industry.
On this episode of Good Morning Hospitality, A Skift Podcast, Wil Slickers, Jamie Lane, Brandreth Canaley, and Michael Goldin dive into the latest shifts across short-term rentals and online travel. They start with Brian Chesky dismissing rivals' chatbots and arguing that Airbnb's AI advantage is rooted in its marketplace and community data, then unpack Airbnb's new report positioning STRs as a critical pressure valve for lodging demand during peak travel periods. The conversation then turns to Expedia Group's Q4 2025 earnings, where stronger B2B results helped offset softer consumer trends, before closing on leadership tension at Casago as franchisees react to shifting power dynamics. The episode wraps with a broader look at AI strategy, consolidation, and who really controls distribution in today's STR ecosystem. Connect with Skift LinkedIn: https://www.linkedin.com/company/skift/ WhatsApp: https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/ Facebook: https://facebook.com/skiftnews Instagram: https://www.instagram.com/skiftnews/ Threads: https://www.threads.net/@skiftnews Bluesky: https://bsky.app/profile/skiftnews.bsky.social X: https://twitter.com/skift Subscribe to @SkiftNews and never miss an update from the travel industry.
How do you scale a short-term rental business in one of France's most competitive coastal markets?In this episode of the Host Planet Playbook – powered by Hospitable – Oihan Campandegui from Destination Côte Basque shares his journey from hotel receptionist to managing 55 short-term rental listings on the Basque coast, including Biarritz. We dive into standardised systems, delivering standout guest experiences, and the biggest lessons learned when scaling a property management business.Topics include:• Scaling with systems and procedures• Competing in Biarritz's premium market• Standing out as a local operator• The mindset shift every host needs• Rapid-fire questions to finish1:37 Managing 55 listings on the Basque coast in France2:35 From hotel receptionist to short-term rental owner and manager5:01 Scaling with standardised procedures 8:23 How to deliver an outstanding guest experience 12:54 Challenges and opportunities in Biarritz21:14 How Oihan stands out among the competition 24:05 Biggest lesson learned: don't take it personally25:48 Quickfire questions Download a free copy of the Host Planet Playbook: https://www.hostplanet.club/host-planet-playbookThe Host Planet Playbook was created in collaboration with property management software, Hospitable. Interested in using a PMS which will help you manage your rentals on autopilot? Get 25% off Hospitable for the first three months: https://hospitable.com/partners/hostplanetDestination Côte Basque: https://destinationcotebasque.com/The Host Planet Playbook series is presented by James Varley, Founder and CEO of Host Planet. Connect with James on LinkedIn: https://www.linkedin.com/in/jdsvarley/Host Planet: https://www.hostplanet.club/The Host Planet Podcast is where Airbnb hosts, Booking.com hosts, Vrbo hosts, and short-term rental operators come to learn what actually works. Each episode features expert insights from people actively building, managing, and scaling short-term rentals, covering everything from Airbnb hosting fundamentals to advanced rental strategies. Whether you're focused on guest satisfaction, rental management, or smarter automation tips, the show delivers practical advice you can apply immediately to improve performance and increase Airbnb bookings.Across the series, we explore Airbnb host tips, listing optimization, price optimization, and Airbnb listing optimization – alongside real-world investing insights and behind-the-scenes Airbnb secrets you won't hear elsewhere. From hosted conversations with industry leaders and Airbnb ambassadors to actionable guidance on bookings and short-term rental growth, Host Planet helps hosts navigate short term rentals with confidence and clarity.The show is presented by James Varley, a holiday let investor and property manager who is also the Founder of Host Planet. Before founding Host Planet, James spent 20 years in the media, including a decade leading corporate communications for the FIFA World Cup Qatar 2022.Contact the show: info@hostplanet.club#DirectBookings #VacationRental #HostTips #ShortTermRental #GuestExperience #PropertyManagement #HostPlanetPlaybook #HostPlanet #Hospitable #PMS #PropertyManagementSoftware #CoteBasque #France #Biarritz
WEBINAR LINK:https://shawnmoore.clickfunnels.com/optiniyvvg89sWant to learn more about Vodyssey or start your STR journey. Book a call here:https://meetings.hubspot.com/vodysseystrategysession/booknow?utm_source=vodysseycom&uuid=80fb7859-b8f4-40d1-a31d-15a5caa687b7PROPERTY:https://www.airbnb.com/rooms/1580750884841571778?viralityEntryPoint=1&s=76FOLLOW US:https://www.facebook.com/share/g/16XJMvMbVo/https://www.instagram.com/vodysseyshawnmoorehttps://www.facebook.com/vodysseyshawnmoore/https://www.linkedin.com/company/str-financial-freedomhttps://www.tiktok.com/@vodysseyshawnmooreCONTACT US:support@vodyssey.comChapters00:00:00 Intro00:01:09 Jesse's Journey into Hospitality and Real Estate00:03:05 Transitioning to Short-Term Rentals00:07:15 The Importance of Experience in Rentals00:10:11 Finding the Right Property00:12:06 Budgeting for Immersive Experiences00:13:06 Navigating Challenges in Property Acquisition00:19:38 Overview of the New Hampshire Market00:20:57 Launching the Property00:23:04 Creating a Unique Experience00:25:05 Target Audience and Marketing Strategy00:28:35 Design and Immersive Experience Plans00:31:06 Community Engagement and Support00:34:51 Lessons Learned and Future Plans
⭐ This is a featured encore of one of our most downloaded STR Investing episodes. Originally released on June 6th 2024, this episode continues to inspire investors to think bigger and execute smarter.In this episode of the STR Investing Podcast, co-host Taylor Jones welcomes Tyann Marcink, the "Queen of Guest Experience," to share how she transformed a $55,000 drug house into a $1.5 million short-term rental success story.Tyann walks through: • How she identified hidden potential others overlooked • The renovation strategy that unlocked massive value • The guest experience upgrades that drive revenue • Lessons learned from turning a distressed property into a high-performing assetThis episode proves that creative vision, execution, and guest-focused design can completely change the trajectory of a deal.If you're serious about scaling your short-term rental portfolio, this is one to study.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Joining us on this episode of Living Off Rentals is someone who built confidence, systems, and time freedom by learning real estate from the ground up. Stephanie Bacue is a U.S. Air Force veteran, short-term rental investor, and founder of Simply Welcome Stays. After transitioning from military service to corporate consulting, she began learning real estate as a complete beginner and went on to build a remote portfolio of short-term rental duplexes in Greenville, South Carolina. Listen as she shares how she bought her first duplex remotely, why she chose Greenville as her market, and how military discipline helped her create systems, remove emotion from decisions, and manage STRs with confidence from afar. She also talks candidly about leaning into community, building the right team on the ground, and what it really takes to move from W-2 work toward more control over your time through real estate. Enjoy the show! Key Takeaways: [00:00] Stephanie Bacue and her background [03:03] Getting into real estate investing and wanting to own time [05:44] Setting a simple first goal: buying one property within six months [06:45] Closing on her first duplex and evaluating long-term vs. short-term rentals [08:10] How military training helped Stephanie in her real estate investing journey [11:10] Buying and managing short-term rentals remotely for the first time [15:02] Choosing Greenville based on population growth, jobs, and fundamentals [17:10] Biggest lessons after purchasing short-term rental properties [19:53] Running conservative numbers and preparing for worst-case scenarios [23:48] Visiting the property and deciding to self-manage instead of paying 25% fees [25:00] Interviewing cleaners and handymen in person to build a reliable bench [28:45] Lessons learned from owning property with a partner [29:48] Why joint ventures can be simpler than LLC partnerships [32:42] How coaching and community reduced costly mistakes [35:42] Stephanie's advice: surround yourself with active investors and take action [39:26] Connect with Stephanie Bacue [39:57] Outro Guest Link: Website: https://www.simplywelcomestays.com/ 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
WEBINAR LINK:https://shawnmoore.clickfunnels.com/optiniyvvg89sWant to learn more about Vodyssey or start your STR journey. Book a call here:https://meetings.hubspot.com/vodysseystrategysession/booknow?utm_source=vodysseycom&uuid=80fb7859-b8f4-40d1-a31d-15a5caa687b7FOLLOW US:https://www.facebook.com/share/g/16XJMvMbVo/https://www.instagram.com/vodysseyshawnmoorehttps://www.facebook.com/vodysseyshawnmoore/https://www.linkedin.com/company/str-financial-freedomhttps://www.tiktok.com/@vodysseyshawnmooreCONTACT US:support@vodyssey.comChapters00:00:00 Intro00:02:44 Debating the Value of Short-Term Rentals00:07:09 Housing Costs and Market Dynamics00:09:00 Interest Rates and Investment Decisions00:12:39 Risk vs. Reward in Real Estate00:19:42 Saturation in the Market00:25:40 Time Investment for Returns00:30:59 Effort Required in Short-Term Rentals00:35:50 Understanding Costs in Real Estate00:41:59 The Impact of One Property00:45:32 Choosing the Right Coach
Are you sick of recycled guru advice and worried about making the wrong move in today's wild STR market?Kenny Bedwell cuts through the noise with brutal honesty and stark data, giving you the freedom to say no to hype and yes to cash-flow-positive deals.In this punchy solo episode, he dives into the real state of the industry for 2026: how incentives twist advice you hear, why copycat “hotspots” will cost you big, and the practical innovations it takes to own your future profits. From dissecting shady vendor deals to revealing why being different is safer than ever, Kenny Bedwell arms you with rare, actionable insights.Don't get taken for a ride. Listen now to dodge avoidable disasters and seize proven, data-driven strategies you won't find in the TikTok echo chamber. This is your unfair advantage, before the market leaves you behind.Timestamped Highlights[00:00] — The explosive problem with industry advice everyone ignores[00:01:06] — Why “I just want to help” usually hides a dollar sign[00:04:13] — The hidden motives that can quietly sink your next deal[00:05:50] — Who's selling short-term rental hope… and who's selling hype?[00:07:16] — The low-rate loan trap: what most investors miss before it's too late[00:10:04] — Realtor myths exposed: why those “best markets” rarely are[00:11:01] — Overhyped markets vs. overlooked goldmines: what really works in 2026[00:17:02] — The real shortcut to stand-out STR success (hint: it's not more decor)Mentioned ResourcesDSCR loans / second home loansAirdna (indirect mention: short-term rental data providers)STR Scale SummitSTR Wealth ConChatGPT (tool for creative brainstorming)Wayfair (STR furnishing and amenity sourcing, referenced in context)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwell
Most STR hosts misunderstand influencer marketing — and it's costing them bookings.In this episode, Madison Rifkin breaks down what actually works when partnering with content creators, why follower count is a useless metric, and how STR operators should think about social media as a long-term control channel — not a quick ROI play.We also go deeper into founder identity, building brands that can be sold, and the mistakes operators make when they tie everything to themselves.If you want more direct bookings, stronger brand trust, and a business that isn't dependent on Airbnb alone, this episode is required listening.Inside the episode: • Why follower count doesn't matter anymore• How to vet influencers the right way• The real way to think about ROI from content creators• Why social media is your only true control channel• Content ideas that work even without a “viral” property• Founder identity mistakes that kill exits• How to build a brand that survives without youTimestamps:00:00 – Why Influencer Marketing Is Broken for Most STR Hosts03:20 – Madison's Journey Building Mount and Entering STRs06:40 – Why Follower Count Is a Terrible Metric10:10 – How to Vet Influencers Based on Brand Alignment13:30 – The Truth About ROI in Influencer Marketing17:10 – Why Social Media Is a Control Channel, Not an Ad20:00 – Content That Works Without a “Viral” Property23:10 – Founder Identity and Why It Hurts Exits26:30 – Building a Brand That Isn't Tied to You30:45 – Lessons From Selling a Company and Starting the Next ChapterGuest Bio:Madison Rifkin is the Founder and CEO of Mount where she finds the world's best hidden gems. She connects STR hosts and local businesses to local influencers and travel content creators so travelers can discover these hidden gems. She's rooted in the Short Term Rental Industry where she's won the Rising Star Award in 2022 and 2023.Guest links:https://www.linkedin.com/in/madison-rifkin-23037712a/Get FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
In this episode of The Academy Presents: Real Estate Investing Rocks, Angel breaks down how real estate investors at every stage can level up by understanding cost segregation, especially within the short-term rental space. Joined by cost segregation expert Mark Gross of CSSI, the conversation dives deep into depreciation strategies, bonus depreciation timelines, STR classifications, CAPEX considerations, and why doing cost seg the right way can mean massive tax savings and peace of mind.Topics CoveredWhy 90% of millionaires invest in real estateWho the Real Estate Investing Rocks podcast is for, from beginners to seasoned investorsWhat cost segregation really is and who it benefitsHow short-term rentals are classified differently for depreciationThe difference between 27.5-year and 39-year depreciation timelinesBonus depreciation and what happens as it phases outWhy owning (not arbitraging) is required for cost segregationHow land value impacts depreciation calculationsWhy turnkey STRs can unlock additional depreciation opportunitiesHow furniture, fixtures, and furnishings factor into cost segCAPEX expenditures and when additional studies make senseHolding period considerations and recapture riskWhy site visits matter and the dangers of shortcut cost seg firmsIRS audits, documentation, and defending a studyHow cost segregation fits into a long-term buy-and-hold STR strategyQuotes“Insurance follows the property, and depreciation follows the details.”“Even when bonus depreciation goes away, cost segregation still creates real value.”“Short-term rentals are treated like hotels, and that changes everything.”“Don't skip the site visit. That's where the real depreciation is found.”Connect with Angel: https://www.linkedin.com/in/angel-williams-re/Connect with Mark: https://www.linkedin.com/in/jmarkgross/
Check out Rental Property Pro: https://rentalproppro.com/booking?am_id=reign 290 - Scaling Real Estate Investments with Chandra Adduri Jen Josey kicks off this REIGN "Past Project" episode with a Badassery Bestowment on turning family and friends into private money lenders—without wrecking relationships. She walks through how to lead with education, focus on safety and clarity, keep terms simple, use professional paperwork (title company/attorney), and communicate like a CEO so lenders feel protected and respected. Jen then welcomes first-time podcast guest Chandra Adduri, a New Jersey-based tech professional and long-time investor with an 18-property, multi-state portfolio. Chandra shares how his upbringing in India shaped his "invest in land/assets" mindset, why mentorship matters (shoutout to Rental Property Pro and John Blackburn), and how buying out of state helped him avoid the "DIY trap" that kills scalability. The featured project is Chandra's newest acquisition: a 3 bed/2 bath beach condo in a Myrtle Beach resort community, purchased to expand into short-term rentals (STRs) and leverage STR tax advantages. He breaks down why he likes HOA amenities for competitiveness and convenience, how he financed with a specialized "condotel" loan, what he changed to stand out (colorful furniture + crisp white linens), and what it really takes to self-manage STRs—systems, fast responses, and a reliable local team. The episode wraps with Jen's BADASS acronym segment, covering Chandra's favorite book, advice, goals (including acquiring a home services business), and his definition of success: buying back time. 00:00 Introduction to REIGN and Today's Episode 00:58 Badassery Bestowment: Turning Family and Friends into Private Money Lenders 03:44 Meet Today's Guest: Chandra Adduri 04:59 Chandra's Real Estate Journey and Background 09:56 Exploring Short-Term Rentals and HOA Benefits 15:19 Financing and Furnishing a Short-Term Rental 18:30 Coffee Maker Tips and Initial Advice 18:44 Breaking Down the Numbers 19:04 Cash Flow and Tax Benefits 20:38 Long-Term vs Short-Term Rentals 21:48 Managing Short-Term Rentals 22:48 Building a Reliable Team 25:40 Future Plans and Goals 27:49 BADASS Acronym Breakdown 34:32 Final Thoughts and Success 5 key takeaways Private money works best when you educate first, not pitch first—and you protect relationships with clarity, structure, and consistent communication. Out-of-state investing can be a "self-control strategy" if you're tempted to DIY every repair; distance forces you to build a team and scale. Resort/HOA STRs can be a competitive advantage because amenities (pools, lazy river, hot tubs) help you stand out without personally managing them. STRs are hospitality, not landlording—expect constant questions, fast messaging, local-area knowledge, and SOPs for cleaners/handymen. Chandra's Myrtle Beach deal shows how STRs can be bought for cash flow and tax strategy (cost segregation + bonus depreciation), especially for high W-2 earners. Chandra Adduri Chandra Adduri is a New Jersey-based tech professional on the engineering side of the industry who has spent the last decade building a data-driven real estate portfolio. He owns 18 properties across multiple states, including New Jersey, North Carolina, South Carolina, Louisiana, Tennessee, Mississippi, and Florida. Known for his systems-first approach and strong local "dream teams," Chandra is now expanding into short-term rentals to explore growth potential and tax advantages while continuing to scale with disciplined operations.
Most STR hosts misunderstand influencer marketing — and it's costing them bookings.In this episode, Madison Rifkin breaks down what actually works when partnering with content creators, why follower count is a useless metric, and how STR operators should think about social media as a long-term control channel — not a quick ROI play.We also go deeper into founder identity, building brands that can be sold, and the mistakes operators make when they tie everything to themselves.If you want more direct bookings, stronger brand trust, and a business that isn't dependent on Airbnb alone, this episode is required listening.Inside the episode: • Why follower count doesn't matter anymore• How to vet influencers the right way• The real way to think about ROI from content creators• Why social media is your only true control channel• Content ideas that work even without a “viral” property• Founder identity mistakes that kill exits• How to build a brand that survives without youTimestamps:00:00 – Why Influencer Marketing Is Broken for Most STR Hosts03:20 – Madison's Journey Building Mount and Entering STRs06:40 – Why Follower Count Is a Terrible Metric10:10 – How to Vet Influencers Based on Brand Alignment13:30 – The Truth About ROI in Influencer Marketing17:10 – Why Social Media Is a Control Channel, Not an Ad20:00 – Content That Works Without a “Viral” Property23:10 – Founder Identity and Why It Hurts Exits26:30 – Building a Brand That Isn't Tied to You30:45 – Lessons From Selling a Company and Starting the Next ChapterGuest Bio:Madison Rifkin is the Founder and CEO of Mount where she finds the world's best hidden gems. She connects STR hosts and local businesses to local influencers and travel content creators so travelers can discover these hidden gems. She's rooted in the Short Term Rental Industry where she's won the Rising Star Award in 2022 and 2023.Guest links:https://www.linkedin.com/in/madison-rifkin-23037712a/Get FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
AI is reshaping short-term rentals fast. In this episode, Mark sits down with Shahar, founder of Boom, to break down how operators can use AI + automation to scale without adding chaos.Shahar shares how he went from broker/investor to building a tech-enabled property management company (managing roughly $150M of property)—then spinning the technology out into Boom as a standalone platform built for operators running at scale.What you'll learn:How Shahar validated his first Airbnb using staged “virtual design” photos before furnishingWhy “market fit” matters more than building a great product—and how his first tech product struggled to monetizeThe real operational pain that forces software creation: owner statements, task management, approvals, vendor payments, reconciliationWhy scaling STRs breaks from operations, not demand—and how “one system” reduces errors and laborThe shift from SaaS tools everywhere to one operating system + AI agents (guest messaging, reporting, workflows)How AI can reduce guest-message volume so teams can focus on real problems and higher-touch hospitalityWhere the industry is heading: AI travel planning, agent-driven bookings, direct booking disruption, and even the long-term impact of roboticsWhy companies that don't adopt AI won't survive—and how top operators will scale from 100 doors to 500–1,000 with the same team__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Send us a message!Destination marketing is in a pressure test.Short-term rentals have become a major part of how people travel, yet many DMOs still struggle with how (or whether) to include them. At the same time, AI is speeding up the research-to-booking journey and forcing destinations to rethink what “relevance” even means.In this episode, Alex and Annie sit down with Stuart Butler (President of Visit Myrtle Beach) and Adam Stoker (President of Brand Revolt) to unpack what's getting in the way, what alignment can look like, and why the next version of destination marketing is going to require better coordination across the whole destination economy.You'll hear practical takes on funding dynamics, stakeholder value, the “illusion of relevance” in reporting, and why the future may turn DMO websites into something closer to infrastructure than a traditional marketing channel.Episode Chapters:00:54 – Stuart's background and how he landed in destination work02:27 – Adam's background and how he sees the DMO landscape05:37 – The “illusion of relevance,” metrics, and why DMOs feel behind07:44 – The Indianapolis example, why some DMOs leave STRs out09:28 – Can DMOs stay relevant without vacation rentals11:53 – Why STRs need a seat at the table and what it takes to get one14:34 – What STR operators can do in markets without big PM groups19:16 – Funding reality, stakeholder influence, and how STRs earn attention22:27 – Why getting involved with a DMO teaches you more than you expect23:51 – The bigger DMO question, purpose, scope, and identity30:31 – How performance reporting shaped destination websites30:54 – Why the booking engine path can be a strategic dead end36:49 – Stewardship, community trust, and what destinations are accountable for50:06 – AI as a watershed moment for travel discovery and decision-making57:59 – What destination content needs to look like in an AI-first world1:02:21 – Closing thoughts on websites, infrastructure, and the road aheadConnect with Stuart:LinkedIn: https://www.linkedin.com/in/stuart-butler-50aaa45/ Website: http://www.visitmyrtlebeach.com/ Connect with Adam:LinkedIn: https://www.linkedin.com/in/adamstoker/ Website: https://thebrandrevolt.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Streamline your short-term rental operations with Hostfully.Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).
The moment a guest opens your door, you're no longer just a real estate investor, you're running a hospitality business. In this episode, I'm sitting down with my friend Katie to talk about something a lot of hosts say they care about, but don't always know how to execute: true hospitality. Katie spent years in global PR and communications for brands like W Hotels, Ritz-Carlton, Le Méridien, and more, and now owns and operates three short-term rentals while co-hosting a fourth. She's lived on both sides of the industry, and she has a very grounded perspective on what it really means to move from "real estate investor" to "host." We talk about the moment you open your doors and how, from that point on, you are running a hospitality business, not just holding an asset. Katie shares a hotel study that found the first ten minutes of a guest's arrival sets the tone for their entire stay, and we unpack what that looks like inside an STR: clear directions, lights that actually come on, intentional amenities, and those small, thoughtful touches that make guests feel seen instead of nickel-and-dimed. We also get into bachelorette groups, kids and pets, and why welcoming every member of the family changes how people experience your space and how they talk about it later. Katie walks us through her own portfolio in Lake George, Saratoga Springs, and the Finger Lakes, and how staying in a destination as a guest shaped what she looked for as an owner. We talk about design gaps, experience gaps, and why she's now exploring boutique motels and hotels with the same heart for hospitality she brings to her STRs. If you've ever felt the tension between automation, profit, and genuinely caring for the people in your homes, this conversation will feel like a reset and a reminder of why this work matters. Connect with Steph: @theweberco Theweberco.com Connect with Katie: @bykatiecline
WEBINAR LINK:https://shawnmoore.clickfunnels.com/optiniyvvg89sWant to learn more about Vodyssey or start your STR journey. Book a call here:https://meetings.hubspot.com/vodysseystrategysession/booknow?utm_source=vodysseycom&uuid=80fb7859-b8f4-40d1-a31d-15a5caa687b7FOLLOW US:https://www.facebook.com/share/g/16XJMvMbVo/https://www.instagram.com/vodysseyshawnmoorehttps://www.facebook.com/vodysseyshawnmoore/https://www.linkedin.com/company/str-financial-freedomhttps://www.tiktok.com/@vodysseyshawnmooreCONTACT US:support@vodyssey.comKATHERINE'S PROPERTY: https://www.airbnb.com/rooms/1308042637927871289?viralityEntryPoint=1&s=76Chapters00:00:00 Intro00:01:57 Katherine's Journey into Real Estate00:06:01 Choosing the Right Market for Investment00:12:02 The Importance of a Good Real Estate Agent00:17:54 Navigating Property Features and Market Demands00:19:39 Navigating Natural Disasters and Homeownership Challenges00:22:03 Overcoming Initial Setbacks in Property Management00:26:23 Building a Strong Team for Successful Management00:30:35 Adapting to Market Changes and Guest Needs00:32:58 Innovative Solutions for Unique Guest Experiences00:36:32 Lessons Learned and Future Aspirations
Short-term rental guest expectations are rising fast — and “manual everything” breaks the moment you try to scale.This week, Mark is joined by Frank from Hostfully to talk systems, PMS strategy, and what it really takes to run a professional operation as you grow from 1–2 properties to 10+.Frank shares how his luxury hotel background (Ritz, W, Westin) shaped his view of STR operations — and why structure, branding, and professionalism are now non-negotiable if you want to win your market.We cover:The biggest differences between luxury hotels and mom-and-pop short-term rentalsWhy guest expectations keep moving toward “hotel-level” standards (and won't go back)When it becomes impossible to manage without a PMSHow a PMS helps reduce operational friction and scale without chaosWhy “growth at all costs” is dead — and sustainable growth is the new edgeWhat to look for when choosing a PMS (and why there's no one-size-fits-all)If you're serious about scaling your STR portfolio, this episode is a must-listen.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
The STR market isn't crashing — it's recalibrating.In this episode, we break down AirDNA's 2026 outlook and translate the data into real, tactical decisions for hosts and property managers. Demand is softening, supply is shifting, and average properties are losing ground — but operators who adapt will win.This is a data-backed walkthrough of what's changing, why it matters, and exactly what to do next.If you want the Training on how you should look at increasing your pricing so that you are not making 15 to 18% less than you were a year over year just click the link and DM "FEE".https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T035&utm_content=FEEInside this episode:• What AirDNA's 2026 data actually says about demand and supply• Why average properties will lose occupancy and revenue• The markets and property types positioned to outperform• How to talk homeowners into smart upgrades (with ROI)• Why property managers are pulling ahead of solo hosts• Using AI and systems to protect reviews and prevent burnout00:00 – What the 2026 STR Outlook Means for Hosts & Property Managers03:30 – Why STR Supply Has Flattened (And Why That Matters)06:10 – Demand Is Softening: The Economic Reality Hosts Must Accept09:15 – Average Properties Will Lose Occupancy in 202612:00 – Why Larger, Luxury Properties Are Winning Again15:00 – Shedding Low-Performing Properties to Refocus Growth18:20 – Coastal & Urban Markets: Where Smart Money Is Moving21:00 – How to Sell Homeowners on Strategic Property Upgrades24:30 – Property Managers vs Solo Hosts: The Performance Gap27:40 – AI, Systems, and the Only Way to Scale Without Burning OutGet FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
The STR market isn't crashing — it's recalibrating.In this episode, we break down AirDNA's 2026 outlook and translate the data into real, tactical decisions for hosts and property managers. Demand is softening, supply is shifting, and average properties are losing ground — but operators who adapt will win.This is a data-backed walkthrough of what's changing, why it matters, and exactly what to do next.If you want the Training on how you should look at increasing your pricing so that you are not making 15 to 18% less than you were a year over year just click the link and DM "FEE".https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T035&utm_content=FEEInside this episode:• What AirDNA's 2026 data actually says about demand and supply• Why average properties will lose occupancy and revenue• The markets and property types positioned to outperform• How to talk homeowners into smart upgrades (with ROI)• Why property managers are pulling ahead of solo hosts• Using AI and systems to protect reviews and prevent burnout00:00 – What the 2026 STR Outlook Means for Hosts & Property Managers03:30 – Why STR Supply Has Flattened (And Why That Matters)06:10 – Demand Is Softening: The Economic Reality Hosts Must Accept09:15 – Average Properties Will Lose Occupancy in 202612:00 – Why Larger, Luxury Properties Are Winning Again15:00 – Shedding Low-Performing Properties to Refocus Growth18:20 – Coastal & Urban Markets: Where Smart Money Is Moving21:00 – How to Sell Homeowners on Strategic Property Upgrades24:30 – Property Managers vs Solo Hosts: The Performance Gap27:40 – AI, Systems, and the Only Way to Scale Without Burning OutGet FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
Send us a message!In this episode, we are joined by Deepak Mehrotra, founder and CEO of California Design Den, for a practical discussion on how linen decisions affect short-term rental operations over time.Drawing from more than 20 years in textile manufacturing, Deepak shares how California Design Den evolved from supplying major retailers to working directly with short-term rental operators. The conversation focuses on how linen choices shift as portfolios grow, and why decisions that seem straightforward early on can become more complex at scale.Rather than treating linens as a one-time purchase, this episode explores them as an operational system that touches guest experience, laundry workflows, replacement cycles, inventory planning, and cost control.Episode Chapters:01:07 – Deepak's background in textile manufacturing and direct-to-consumer bedding04:55 – How and why STR operators became a core customer segment16:45 – Cotton performance and durability in high-turnover environments17:45 – Common reasons linens need replacement in STR operations13:33 – Renting versus owning linens and how operators assess the tradeoffs14:43 – Laundry considerations for in-house and outsourced models25:31 – Inventory availability, fulfillment speed, and consistency at scale31:56 – How linen strategy evolves as portfolios grow28:09 – Operational simplicity when managing linens across multiple propertiesConnect with Deepak:LinkedIn: https://www.linkedin.com/in/deepak-mehrotra-9752682/ Connect with California Design Den:Website: https://www.californiadesignden.com/ ✨ Exclusive Offer to Alex & Annie Listeners:Upgrade your guest sleep experience with California Design Den.Get 10% off with code AlexAnnie10OFF.Apply for California Design Den's Linen VIP Club to access preferred pricing and dedicated hospitality support.
In this episode of the Tax Smart REI Podcast, Thomas Castelli breaks down how high-income earners can legally build tax-advantaged, tax-free income through real estate - even without REPS or short-term rentals. You'll get a practical crash course on how the U.S. tax system actually works, why real estate is treated so favorably by the IRS, and how savvy investors use depreciation, refinancing, and smart exit strategies to increase cash flow while lowering their effective tax rate. This episode is for high-income W-2 earners, business owners, and real estate investors who want to zoom out, understand the bigger picture, and stop chasing one-off tax hacks. If you're looking to build long-term, tax-efficient wealth through real estate -- this is your roadmap. To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.
Are you hustling for cash flow but secretly terrified of buying the wrong property? What if you're obsessing over the wrong number… and it's killing your returns?In this punchy, numbers-driven solo, Kenny Bedwell (founder, STR Insights) reveals the overlooked metric that separates the real STR winners from the wannabes: ARV (After Repair Value). He breaks down why focusing only on cash flow or gross revenue is the most common — and expensive — mistake investors make, especially as the market shifts in 2026 and beyond. Learn how the savviest investors lock in instant equity, create options, and bulletproof their portfolios… while everyone else chases hype.Don't wait. Listen now to avoid the pain of a dud deal and embrace an approach that gives you more freedom, flexibility, and long-term wealth. There's no fluff here, just the data-driven truth no one else will say out loud.Timestamped Highlights[00:00] The #1 investor mistake that's rarely talked about—are you making it?[00:02:18] Why cash flow worship could backfire: brutal deal math exposed[00:03:45] The California trap: when betting on appreciation costs you real money[00:06:30] The $450k blunder: how over-improving can destroy your exit options[00:10:17] The illusion of “winning”—when high gross revenue is secretly a loss[00:14:21] Why 2026 will punish investors who ignore forced appreciation[00:17:01] Case study: how to engineer instant equity and triple your exits[00:24:47] Scouting for gold: how to spot ARV spreads in crowded markets[00:29:47] The real goal: buying so well, operations become nearly stress-freeMentioned ResourcesPriceLabsAirbnb (smart pricing)Hunter, New York (market example)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
In this Monday Market Data Report, co-host Mark Lumpkin breaks down the short-term rental numbers for Park City, one of the most in-demand ski towns in the country.This episode reveals some of the largest performance gaps we've seen in any market — where top-performing properties earn more than double what average listings make in the same bedroom category.Inside the data, you'll learn:What 3-bedroom homes earn at average vs. top-tier performance levelsWhy performance matters more than bedroom count in Park CityHow 4- and 5-bedroom homes can push well into six figures annuallyWhy 6+ bedroom properties are producing $300K+ per yearHow nightly rates and occupancy combine to create massive revenue swingsThe takeaway is clear: in Park City, average properties get crushed, while well-designed, well-executed homes dominate the market.If you're investing in ski towns, underwriting luxury STRs, or deciding whether Park City is worth the premium buy-in, this episode gives you the real numbers behind the hype.Have a market you want us to break down next? DM Mark and we'll bring the data.
The short-term rental market has changed fast. The old “furnish it cheap and it still books” playbook is fading—and Merritt Harris breaks down what actually wins now.Merritt shares how he went from long-term rentals in New York to building a property management company during the COVID peak, then adapting as competition intensified and guest expectations rose.In this episode, we cover:Why “corporate” posting and insider jargon doesn't convert—and what to post insteadThe shift from selling a bed to selling an experience-driven stayAmenities vs. design: what matters most and how to decideWhy larger properties are outperforming smaller ones in many marketsHow to find value-add opportunities (basements, egress, bonus rooms) to increase revenueThe systems-first approach to management: automation, cleaners, and scaling without burnoutA practical tech stack for operators and property managers (PMS, pricing tools, cleaning ops, comms)If you're trying to compete in today's market—whether you own one property or manage dozens—this episode will help you rethink what “good enough” looks like in 2026.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Send us a textIn this episode of Weiss Advice, host Yonah Weiss sits down with real estate investor and broker Christina Kovacs to unpack her full journey through residential flips, short-term rentals, multifamily ownership, and asset management at scale.Christina shares how getting her hands dirty early in her career shaped her as an operator, why she ultimately pivoted away from single-asset investing, and the lessons she learned the hard way about property management, partner selection, and staying focused in one lane.They also dive into tenant management, underwriting realities in Class C assets, the power of LinkedIn as a business tool, and why Christina is now doubling down on multifamily and commercial brokerage heading into 2026.This is a must-listen for investors who want real, operator-level insight into what actually drives performance in multifamily deals.⏱️ Episode Timestamps00:01:30 – Christina's early real estate journey and live-in flips 03:30 – Pivoting from single-family and STRs into multifamily 06:45 – Joint ventures vs syndications and building confidence as an operator 07:50 – Why property management can destroy a great deal 09:00 – The 42-question property manager vetting process 11:00 – Auditing ledgers, hidden expense creep, and CapEx tracking 16:15 – Tenant horror stories and inherited problems after acquisition 18:45 – Managing delinquency and underwriting reality in Class C assets 20:00 – How LinkedIn became a powerful networking and deal-making tool 22:20 – The “Final Four” questions: books, skills, failure, and success 26:30 – Transitioning into commercial real estate brokerage 28:15 – What success truly means to Christina today
Paul Campbell went from long-term rentals and house flips to launching a booming vacation rental business. In this episode, he reveals how one costly mistake turned into a profitable pivot—and why luxury STRs might just be the smartest move in real estate today. Get Interviewed on the Show! - ================================== Are you a real estate investor with some 'tales from the trenches' you'd like to share with our audience? Want to get great exposure and be seen as a bonafide real estate pro by your friends? Would you like to inspire other people to take action with real estate investing? Then we'd love to interview you! Find out more and pick the date here: http://daveinterviewsyou.com/ #realestateinvesting #vacationrentals #shorttermrentals #luxurySTR #propertyprofits
What actually makes one short-term rental crush it… while another barely books?Today we sit down with Kenny Bedwell, a former data analyst turned short-term rental expert, to unpack what truly separates top-performing properties from the rest. We talk about why blending in is the fastest way to lose (and why your rental needs its own “Impossible Whopper”-style edge), how Kenny's investment strategy has evolved over time, and what most hosts still misunderstand about ROI and aligning with real client goals.Whether you're buying your very first property or scaling a growing portfolio, this conversation is packed with real-world, data-backed insights to help you stand out, book more, and build smarter in today's ultra-competitive short-term rental market.Things we discussed in this episode:Kenny Bedwell's “Impossible Whopper” analogy for making short-term rental properties unique.The importance of being in the top 10% of rental markets to achieve success.Kenny's transition from data analyst to real estate investor and consultant.How Kenny helps clients find, analyze, and acquire short-term rental properties using data.The need to align investments with clients' budgets, ROI goals, and personal preferences.Setting realistic expectations for short-term rental returns and correcting misconceptions.The significance of data-driven market analysis and adapting to changing market conditions.Consulting for current property owners, focusing on guest avatar and unique amenities.Kenny's personal portfolio management strategies, use of teams, and focus on scaling up.Advice for new investors, including the importance of starting research early and leveraging expert resources (like STR Insights' annual report).Get in touch with Kenny :Facebook - https://www.facebook.com/ShortTermRentalInsightsWebsite - https://www.strinsights.com/Instagram - https://www.instagram.com/strinsights/Youtube - https://www.youtube.com/@strinsights7414#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #STRInsights #VacationRentals #DataDriven #ROI#UniqueStays #PropertyManagement #InvestSmart#RentalIncomeFollow Us!Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.SmartStay Show Website and on Instagram and YouTubePrideaway Stays Website and on Facebook and LinkedInStraightforward Short-Term Rentals Website and on InstagramAttorney Rory Gill on LinkedInJason Muth on LinkedIn
In this Monday Market Data Report, Mark Lumpkin breaks down Gatlinburg, Tennessee, one of the most talked-about short-term rental markets in the country. Using real performance data, Mark walks through how revenue, occupancy, and nightly rates change as you move from three-bedroom cabins to six-plus bedroom luxury properties.In this episode, you'll learn:How three-bedroom STRs in Gatlinburg earn between $55K and $95K annuallyWhy four-bedroom properties can generate $20K–$45K more per year than three-bedroomsHow five-bedroom cabins separate average performers from true top-tier experiencesWhy six-plus bedroom properties show the largest revenue jump Mark has seen in any marketHow ADR and occupancy work together to drive outsized returns in GatlinburgWhat the data reveals about guest expectations for larger, experience-driven homesIf you're considering investing in Gatlinburg or already own in the Smokies, this episode breaks down exactly what size property performs best and why.Tune in every Monday for market data reports and every Friday for expert guest interviews on the STR Investing Podcast.
Are you scared of losing tens of thousands to the IRS on your next property sale? Wondering if a 1031 exchange is really the secret weapon for building unstoppable cash flow… or just a headache waiting to happen?This episode, Kenny Bedwell, no-fluff educator and the data-driven mind behind STR Insights, breaks down exactly how to prepare for a 1031 exchange the right way—using numbers, timelines, and real investor mistakes. From crushing the fear of tax bills to unlocking hidden strategies for short-term rental success, Kenny's frank approach is full of hard truths and simple steps.Listen now to sidestep costly errors, dodge timeline traps, and discover insider tactics you won't hear anywhere else. Miss this episode, and you risk making one of the most expensive mistakes in real estate. Tune in while the stakes are high and every dollar counts!Timestamped Highlights[00:00] The hidden 1031 pitfalls that even experienced investors miss[00:01:14] Why “waiting until closing” could wreck your 1031 dreams[00:02:12] The shocking impact of capital gains—the numbers that matter now[00:03:16] How to use the IRS rules to your advantage (and avoid a nightmare)[00:05:13] The #1 reason most investors lose money on STR furnishings[00:07:37] The uncommon truth about 1031 down payments and boot traps[00:11:03] Kenny's proven equity audit method: Should you sell or wait?[00:14:04] Mapping your cash flow and equity for a powerful portfolio move[00:16:50] When you should start hunting for your next market (spoiler: it's not what you think)[00:20:46] The 60-day strategy no one is teaching for stress-free 1031 shopping[00:22:03] The risky world of reverse 1031 exchanges—what you must knowMentioned ResourcesSTR Scale Summit (event)STR Insights softwareIRS Section 1031 (1031 exchange rules)QI / 1031 Intermediary servicesReturn on Equity (ROE) auditImportant LinksWant us to find the deals for you? https://strinsights.comGet Top Markers for STRs (2025) - https://rebrand.ly/28b1dfInstagram – @kenny_bedwellYouTube – Cash Flow...
Is the short-term rental industry struggling — or simply growing up? In this episode of The STR Data Lab, AirDNA Chief Economist Jamie Lane sits down with Simon Lehmann to unpack what “normalization” really means for STR operators, investors, and property managers heading into 2026. After years of explosive growth, the industry is entering a new phase — one defined less by expansion and more by execution.Simon shares why demand hasn't collapsed the way headlines suggest, why strong operators are still thriving, and why the biggest shift happening right now is in expectations. Growth rates, margins, and valuations are resetting — but that doesn't spell trouble. Instead, it's forcing a long-overdue focus on discipline, systems, and unit-level profitability. As competition intensifies and margins compress, professionalism is no longer optional.The conversation also dives into technology and AI, exploring why the future isn't about more tools, but fewer — and better — ones. From fragmented tech stacks and data silos to the elusive “source of truth,” Jamie and Simon explain why operators who master their data will be best positioned to survive (and win) in the next chapter of STRs.You don't want to miss this episode if you're planning for 2026 and beyond.Key Takeaways from This EpisodeNormalization ≠ downturn: The STR industry isn't collapsing — growth expectations and return profiles are simply resetting.Execution now beats expansion: We've moved from a growth story to a selection story, where strong operators pull ahead.Professionalization means discipline: Systems, process rigor, and unit-level economics matter more than portfolio size.Margins are under pressure: Rising costs and regulation make revenue management and cost control essential skills.Tech stacks must simplify: The next wave of STR tech will focus on integration, AI-driven insights, and a single source of truth — not more point solutions.Sign up for AirDNA for FREE
AI is changing short-term rental marketing—but not always for the better.In this episode of the STR Investing Podcast, Taylor sits down with Conrad, founder of BuildUp Bookings, to break down what actually drives bookings in today's crowded STR market.They discuss how overused AI messaging can turn guests away, where automation still adds real value, and why authentic communication is becoming a competitive advantage for Airbnb hosts and property managers. Conrad shares practical insights from nearly a decade in STR marketing, helping operators rethink how they attract, convert, and retain guests.Key topics covered:AI vs human messaging in STR marketingHow to improve bookings without sounding automatedGuest psychology and conversion fundamentalsMarketing mistakes hurting Airbnb performanceIf you want more bookings without relying on spammy AI tactics, this episode delivers clear, actionable insight.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Ever scroll past a vacation rental photo and feel like you had to stay there—like, yesterday? That's not an accident. That's story-driven strategy at work.In this episode, I'm joined by the incredible Nicole Alexander—a woman who's mastered the art of making STRs look so inviting, guests can't help but click “Book Now.”We talk about:How Nicole went from wedding photography to capturing the soul of spacesHer three-month adventure across Europe, camera in hand, documenting dreamy cabinsWhy cozy corners, golden light, and personal touches matter more than you thinkBut this isn't just about pretty pictures. It's about creating an emotional connection.Nicole walks us through her process—how she uncovers what makes a property special and translates it into visuals that spark curiosity, desire, and trust. You'll hear why professional photography isn't just a “nice to have.” It's a brand builder. A booking booster. A guest experience enhancer.If you've ever wondered whether great photos really move the needle in your STR business... this conversation will open your eyes.Get ready to rethink how you show up online—and how guests see your property through the lens of story.HIGHLIGHTS AND KEY POINTS:[01:03] A short introduction about our guest Nicole Alexander, and how she got started in the short-term rental industry[03:01] Nicole's shift from wedding photography to cabin photography, and her approach to translating storytelling and vision into impactful property photography[07:46] Why it's so important for hosts to invest in high quality story driven images, instead of just hiring a real estate photographer, or snapping their own pictures with their iPhone[12:22] Nicole's emphasis on atmospheric moments as the emotional bridge that turns a property into an experience guests can already feel themselves living[14:51] Nicole's commitment to honest, accurate photography as a trust-building tool rather than a marketing illusion[18:15] What are some of the biggest mistakes that Nicole sees when hosts rely on subpar or non-experiential photography[20:34] Nicole emphasizes that while professional photography is essential for listings, candid and non-professional shots play a crucial role in storytelling, particularly on social media[22:42] Nicole talks about the common styling mistakes and preparing a property for photography[25:32] Nicole's advice on finding a creative photographer beyond traditional real estate specialists[28:06] Nicole's insights on vetting photographers to ensure they can deliver on your vision [29:56] Nicole breaks down realistic photography investment ranges and what hosts should expect in return[35:18] How investing in professional, story-driven photography directly drives stronger cash flow, higher nightly rates, and better guest alignment[37:39] Nicole's guidance on prioritizing hero images that quickly communicate space, amenities, and setting to drive booking decisions[39:18] The lightning round Golden Nuggets:
The STR game has changed—and most operators haven't caught up.In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets.This isn't theory. It's what's working right now.Inside this episode:- Why “good enough” STRs are getting crushed- The amenity arms race (and how to win without wasting money)- What guests notice that most hosts completely miss- How ops and hospitality matter more than design long-term- Why disciplined systems protect profit—even in down years- The leadership mindset required to scale without chaosIf you want longevity in this industry, this episode is required listening.00:06:15 – Becoming “The Guy” in a Hyper-Competitive STR Market07:45 – Why Copying Competitors Is a Losing Strategy09:15 – The New Minimum Standard for STR Design & Amenities11:40 – Why Half-Upgraded Properties Always Underperform18:50 – The Amenity Arms Race: What Actually Moves Revenue20:00 – When Design Stops Mattering and Ops Take Over26:10 – Building Teams and Systems That Don't Break Under Stress30:45 – Leadership Lessons from Military and STR Operations34:05 – How Efficiency Protects Profit in Down Revenue Years39:35 – The Long-Term STR Play: Scale, Discipline, and LongevityGuest Bio:Shane O'Connor is the CEO & Founder of Alchemy Real Estate & Alchemy Hosting. Alchemy is based in Tampa, FL, building a portfolio of Short-Term Rental assets primarily focused in Central Florida. By delivering vertically integrated, top-tier service from beginning to end in the investment process, Alchemy has grown from a single property (and single employee) to 11 properties & a team of four in less than a year. In that same time, Alchemy will have also delivered more than $3M in closed real estate deals for its clients.By the end of 2022, it is Shane's goal to have a blended Direct Ownership & Co Hosting portfolio of 30 properties centered in Florida, to then begin expanding to other markets. Shane is a graduate of the United States Naval Academy and served as an Officer in the U.S. Navy for 9 years. He received an M.S. Degree in Real Estate from the University of Florida. He runs the company with his brother, Captain Devin O'Connor, who is an active duty Marine Corps helicopter pilot in addition to being the Director of Operations for Alchemy.Guest Link:https://www.instagram.com/oc_dreams19/Get FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
The STR game has changed—and most operators haven't caught up.In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets.This isn't theory. It's what's working right now.Inside this episode:- Why “good enough” STRs are getting crushed- The amenity arms race (and how to win without wasting money)- What guests notice that most hosts completely miss- How ops and hospitality matter more than design long-term- Why disciplined systems protect profit—even in down years- The leadership mindset required to scale without chaosIf you want longevity in this industry, this episode is required listening.00:06:15 – Becoming “The Guy” in a Hyper-Competitive STR Market07:45 – Why Copying Competitors Is a Losing Strategy09:15 – The New Minimum Standard for STR Design & Amenities11:40 – Why Half-Upgraded Properties Always Underperform18:50 – The Amenity Arms Race: What Actually Moves Revenue20:00 – When Design Stops Mattering and Ops Take Over26:10 – Building Teams and Systems That Don't Break Under Stress30:45 – Leadership Lessons from Military and STR Operations34:05 – How Efficiency Protects Profit in Down Revenue Years39:35 – The Long-Term STR Play: Scale, Discipline, and LongevityGuest Bio:Shane O'Connor is the CEO & Founder of Alchemy Real Estate & Alchemy Hosting. Alchemy is based in Tampa, FL, building a portfolio of Short-Term Rental assets primarily focused in Central Florida. By delivering vertically integrated, top-tier service from beginning to end in the investment process, Alchemy has grown from a single property (and single employee) to 11 properties & a team of four in less than a year. In that same time, Alchemy will have also delivered more than $3M in closed real estate deals for its clients.By the end of 2022, it is Shane's goal to have a blended Direct Ownership & Co Hosting portfolio of 30 properties centered in Florida, to then begin expanding to other markets. Shane is a graduate of the United States Naval Academy and served as an Officer in the U.S. Navy for 9 years. He received an M.S. Degree in Real Estate from the University of Florida. He runs the company with his brother, Captain Devin O'Connor, who is an active duty Marine Corps helicopter pilot in addition to being the Director of Operations for Alchemy.Guest Link:https://www.instagram.com/oc_dreams19/Get FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
Cleaning issues, last-minute cancellations, and unreliable contractors are some of the biggest threats to STR performance. Chris Rule, VP of Customer Experience at Turno, joins the show to explain how top operators are solving these problems—and what's coming next for the industry.Chris shares how Turno is helping hosts and property managers eliminate turnover chaos by connecting guest cleanliness reviews directly to cleaners, automating scheduling, and creating real accountability at scale. The conversation dives deep into why turnovers are one of the most stressful (and most overlooked) parts of short-term rental operations, and how better systems lead to better reviews, happier guests, and fewer late-night emergencies.We also explore Turno's rapidly expanding ecosystem, including global contractor coverage, cleaner guarantees, faster payouts, tax compliance, and what's next beyond cleaning—including maintenance and handyman services designed specifically for STR operators.Whether you're managing one property or hundreds, this episode breaks down how professional operators are building reliable, scalable systems that protect performance and peace of mind.Topics covered:Why turnovers make or break guest experienceHow guest cleanliness reviews create real cleaner accountabilityPreventing last-minute no-shows and operational emergenciesScaling cleaning and maintenance without growing headachesTurno's expansion into maintenance and contractor servicesWhat STR operators should expect in 2026 and beyondIf you're serious about running a high-performing short-term rental, this is a must-listen episode.Get in touch with Chris:LinkedIn: Chris Rule Sign up at Turno here today!__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
In this episode of Living Off Rentals, host Kirby Atwell sits down with Stephen Arnaud, an engineer, W-2 employee, and father of three, who's intentionally building his path out of the 9-to-5 through short-term rentals. Stephen shares why, even though he enjoys his career, the demands of a W-2 job started to conflict with family life and long-term freedom. Like many high-performing professionals, he realized that traditional investing alone wasn't going to give him the flexibility he wanted anytime soon. That realization led him to short-term rentals. If you are still working a 9-to-5 but thinking seriously about building income outside of it and a pathway to financial independence, this episode offers a realistic roadmap. Listen and enjoy! Key Takeaways: [00:00] Introducing Stephen Arnaud and his background [02:21] Getting into the real estate through short-term rental [06:33] The moment he realized short-term rentals could replace earned income [09:45] How Stephen picked his market [11:59] Deciding on the properties that he purchased [13:43] Details on Stephen's first two STR properties and why he targeted larger homes [16:25] Financing with conventional loans as a W-2 investor [17:18] Using IRA funds strategically for down payments and furnishings [18:12] Stephen's perspective on retirement accounts vs. building income today [21:08] Building a reliable cleaning and support team [23:36] The biggest challenge on the flip side: Neighbors [25:30] Screening guests and avoiding party issues [28:15] Balancing a W-2 job with managing STRs during the early stages [31:38] How virtual assistants can outperform owner-operators with the right systems [34:24] Stephen's advice for people wanting to exit their 9-5 and get into short-term rentals [37:55] A real mistake with scheduling cleaners and how communication saved the situation [39:52] Outro Guest Links: Website: https://www.airbnb.com/rooms/1389202306719070032 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
Are you terrified of sinking your cash into a dying market or worse, following the herd off a financial cliff? In this masterclass episode, Kenny Bedwell rips the lid off his 2026 Top STR Markets Report, arming you with the real numbers, raw pitfalls, and hidden opportunities no one else will dare mention. You'll hear the unbiased, hard-hitting truth: where data says to buy, where strict regulations ruin even the prettiest towns, and razor-sharp strategies to squeeze maximum ROI in a landscape rocked by new rules and unpredictability. Kenny reveals not only the top 10 investable markets, but exactly why they're worth your attention (and why some previous darlings are falling off).Do not wait. Miss this, and you're risking real money, real time, and watching your freedom slip away, while others secure the deals that change their financial destiny. This episode gives you numbers, biases called out, and actionable steps you won't get anywhere else.Timestamped Highlights[00:01] – Why most “top STR market” lists are wrong (and what everyone's missing)[00:10] – The wild, thrilling impact of new regulations and market shakeups—this year's biggest surprises revealed[00:23] – Kenny's ultra-candid red light, green light analysis: Where you really should be scared (and where to pounce)[00:46] – The shocking climb of Mohican State Park and the overlooked cash cows in rural regions[01:13] – Dirty little secrets behind high-grossing mountain and lake towns (and why access and permits matter more than hype)[01:38] – Are you sitting on cash? Kenny reveals the uncommon ways budget transforms your deal-finding lens (with 4 ROI-driven categories)[01:57] – How to beat city restrictions with region plays and advanced location hunting—no more bureaucratic land mines[02:15] – The final, blunt warning: What happens if you listen to influencers over the data... and why you can't skip this downloadMentioned ResourcesSTR Scale Summit (event)Airdna (STR market data)BiggerPocketsInterview reference: "Part 2: How to make over $500k on one STR with Jeff Usner” episode, August/September 2024Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow Positive
If I were starting over in short-term rentals today, I wouldn't rush into the first deal just to say I owned one — and I definitely wouldn't invest where everyone else is telling you to. In this episode, I'm walking you through our real journey: buying our first STR, building a six-figure co-hosting business, and realizing pretty quickly what wasn't the right long-term play for us. We talk about market selection, cash flow vs. equity, why I'd avoid certain oversaturated markets now, and what I wish I had understood sooner about renovations, contracts, and boundaries. If you're in the "should we buy?" or "what's our next move?" phase — or you're thinking bigger than single-family STRs — this episode will help you slow down and make smarter, more intentional decisions. We cover: The investing choices I'd change if I started over Why market selection matters more than ever Cash flow vs. long-term equity (and how I think about it now) What co-hosting actually looks like behind the scenes Why we're focused on micro resorts and boutique hotels moving forward Connect with me:
From corporate hustle to hospitality powerhouse, Janel's story is the kind every host needs to hear.In this episode, I sit down with the inspiring Janel Gallucci, who walked away from a high-pressure San Francisco career to build a short-term rental business on her own terms. What began with a single Lake Tahoe cabin quickly evolved into a thoughtfully scaled portfolio — each property designed with intention, creativity, and an unwavering commitment to delivering a true 5-star guest experience.You'll hear how Janel shifted from “one-property owner” to savvy portfolio builder, the systems and mindset she used to scale sustainably, and the decisions that helped her create guest-loved stays while protecting her time and energy. This conversation is a powerful reminder that a purpose-driven business can grow without sacrificing the life you're building it for.Janel shares:The pivot point: How a moment of burnout prompted her and her husband to leave the corporate grind and dive head-first into STRs.Taking control: Why early missteps with property managers forced her to self-manage—and how applying her corporate skills dramatically boosted her returns and created unforgettable stays.Guest-Magnet Strategies: The exact systems she uses to turn listings into best-in-class properties, from leveraging market data and building local partnerships to offering dog-friendly welcome baskets and locally sourced amenities.The Blueprint for Growth: Why defining your ideal guest and implementing robust systems is essential for managing properties confidently, whether they're nearby or across the country.Janel's story is a powerful blueprint for building a richer, more flexible life through short-term rentals. It's packed with actionable tips, mindset shifts, and the courage required to build an intentionally successful business. Tune in now to unlock the strategies for your own STR success!HIGHLIGHTS AND KEY POINTS:[01:15] A short introduction about our guest Janel Gallucci, and how she got into the short-term rental industry[04:24] Janel reveals how miscommunication and poor property care pushed her to replace her property manager with direct self-management[08:04] Janel's approach to shifting into self-management to enhance confidence and control in her short-term rental[11:02] How Janel handles tough guest situations to enhance satisfaction and protect reviews[14:23] I share my experience at Airbnb headquarters and unpack why hosts have seen a dramatic shift in Airbnb's willingness, and ability to remove unfair reviews [17:12] Janel's thoughts about the challenges of subjective guest ratings to highlight the flaws in Airbnb's value and accuracy metrics[20:12] Janel outlines her strategy for breaking past her revenue ceiling by elevating her property into the luxury tier[22:06] How small luxury touches elevate the guest experience and reinforce premium positioning[23:27] Janel outlines the intentional upgrades and guest-avatar strategy that fueled her jump from average earnings to six-figure revenue[27:20] How low-cost, locally sourced, and thoughtfully branded welcome baskets enhance the guest experience while
Are you one tough market away from making or breaking your STR dreams? In this eye-opening solo episode, Kenny Bedwell delivers his no-BS, data-driven breakdown of 2025's market shakeups and lays out urgent, can't-miss predictions for 2026.With competition at a boiling point and Airbnb's pricing bombshell still sending shockwaves, Kenny Bedwell exposes where investors keep getting crushed, and who's quietly winning big. From wild price slashes to the “big fish or die” investor mentality, this episode is packed with the kind of ruthless honesty and hard metrics you won't get from any hype-driven guru.Tune in now or risk fumbling the next 12 months. Discover the exclusive moves smart investors will make next, before the rest of the market catches on, and before average operators are left behind for good.Timestamped Highlights[00:00] – Why “average” properties are getting destroyed while 90th percentile performers quietly flourish[00:03:51] – The mindset shift every STR buyer must make now to avoid draining cash flow[00:06:26] – Markets you'd written off are making a shocking comeback—here's why[00:08:17] – Explosive legal shakeups: Are STRs still real estate or something else?[00:10:33] – The Airbnb fee switch: How hosts are sabotaging themselves and tanking in search rankings[00:13:10] – The real reason your smart price hikes backfired—and how to break the algorithm instead[00:18:46] – The “turnkey trap”: Why offloading STRs is about to flood the market (and what smart buyers must do now)[00:24:33] – Surprise winners & fallen stars: The brutally honest 2026 top markets preview[00:26:31] – Kenny's wild 2026 prediction: The coming Airbnb “pay to play” eraMentioned ResourcesSTR Scale Summit (event)Top Markets Report (via STR Insights)Airbnb LuxeAirdna (STR market data)Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df Instagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.
2026 is not the year to play it safe — and it's definitely not the year to keep relying on Airbnb alone. In this episode of Branded and Booked, I break down what I see coming next for short-term rentals, boutique hotels, micro-resorts, and the investors behind them — and why branding, direct strategy, and personal visibility are no longer optional. From platform changes and rising fees to the growing gap between checkbox amenities and truly curated guest experiences, this conversation is a wake-up call for hosts who want longevity, leverage, and real brand value. In this episode, we cover: Why more investors are shifting away from single-family STRs and toward boutique hotels, micro-resorts, and larger experiential projects The real cost of relying solely on Airbnb — and why 2026 is the year direct booking strategies become essential Why design alone isn't enough (and what real brand strategy actually includes) How brand clarity directly impacts the guests you attract — and the problems you avoid The rise of personal branding for hosts, operators, and real estate investors with bigger visions What it actually looks like to leverage your personal brand to attract partners, clients, and opportunities Why the guest experience gap is widening — and how curated rituals, storytelling, and intentional touchpoints win The evolution of influencer marketing (no more random trades, ever) Why hospitality brands are becoming media brands — and how content now drives demand How strong branding and marketing directly increase the exit value of your properties Connect with me:
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