Podcasts about strs

In this episode, Micah Johnson interviews Heather Loduca and Erin Knight of Pink Wall Designs, experts in hospitality interior design for short-term rentals (STRs) and boutique hotels. They share insights on how thoughtful design directly impacts guest experience, increases revenue, and strengthens branding for rental properties.   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 of the STR Investing Podcast, co-host Mark Lumpkin sits down with  Tyann Marcink - Hammond, owner of Tyann Hospitality and one of the newest VRMA board members, to talk about what actually drives five star stays: hospitality.Tyann shares why communication is the foundation of every great guest experience, how small moments can shape an entire stay, and why hosts who ignore hospitality are leaving money and reviews on the table. They also recap the Poconos STR conference, discuss Tyann's new book Hospitable Host: The STR Sisterhood Edition, and dig into what she is helping lead inside VRMA.They also cover:Why five star reviews do not always mean true hospitalityThe simple communication shift that can separate you from most hostsHow to train your team to create better guest experiencesWhy investors need to think beyond spreadsheets and ROIWhat Diane sees next for hospitality in the STR industryThis episode is a reminder that short-term rentals are not just a real estate business. They are a hospitality business first.__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

Ever wonder why some real estate investors explode their portfolios while others fumble with endless spreadsheets? Today, Kenny Bedwell pulls back the curtain on the STR Scale Summit and shares proven strategies, uncommon lessons, and hard truths from inside the event. If you crave more than generic advice, Kenny's frank, numbers-driven breakdowns of scaling, partnerships, and real-world deal structures will give you exactly what you need.This episode hits everything from micro resorts, boutique hotels, and creative financing, to why relationships—not just deal math—make or break your business. It's the shortcut to avoid expensive mistakes, get access to exclusive insider tactics, and finally feel confident about scaling your STR game.Listen now, because next year's opportunities won't wait, and this episode delivers practical, actionable takeaways you won't get anywhere else.Timestamped Highlights[00:00] – STR Scale Summit recap: Will you be a victim of FOMO or grab your victory?[00:01:24] – Why micro resorts are revolutionizing the cash flow game—economies of scale revealed[00:03:15] – Inside boutique hotel investing: Real costs, real risks, and a live tour that shocked the crowd[00:04:13] – The “whoopsie budget”—the surprising truth that blows up perfect spreadsheets[00:05:47] – The 3 C's of STR investing: Cute, Comfortable, Clean… and not over-amenitizing[00:06:47] – Kenny's “secret formula” for $100K+ cash flow properties—do you really know what to look for?[00:07:25] – Raising capital, partnerships, and how not to get screwed—unfiltered deal structure lessons[00:12:02] – Trust but verify: The hard rules for protecting yourself in partnerships[00:13:08] – Why commercial lenders care about relationships more than your spreadsheets[00:16:15] – The game-changing logistics every big investor now needs from Wayfair[00:19:18] – Relationship ROI: Why “having a guy” beats hiring the big box company every timeMentioned ResourcesSTR Scale SummitBoutique hotel investingWayfair Professional account managerBRRRR strategyCommercial lending – Mark Sacco506(c) and 506(b) syndication structuresImportant 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 episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., answer listener questions on a wide range of real estate and tax topics. They cover tax benefits available for raw land purchases, including property tax deductions under SALT and investment interest expense on Schedule A. They explain the IRS tax code reference for short-term rentals — IRC Section 469 and Treasury Regulation 1.469-1T — and address special considerations for Airbnb-type rentals in foreign countries, including the mandatory alternative depreciation system (MADS) and foreign tax credits. Amanda and Eliot discuss minimum purchase prices for cost segregation studies and highlight property types like RV parks, car washes, and convenience stores that offer strong bonus depreciation benefits. They tackle the vacation home standard deduction question, clarifying how Schedule E rental properties interact with itemized deductions. The episode dives deep into multiple 1031 exchange questions, including timelines for entering a second 1031, California's clawback provisions on out-of-state replacement properties, and the drop-and-swap strategy for LLC partnerships. They also explain how to navigate delayed IRS refunds using the Taxpayer Advocate Service, and break down the time limits and rules for changing LLC tax status, including Form 8832 and the five-year rule. Tune in for expert advice on these topics and more! Submit your tax question to taxtuesday@andersonadvisors.com Highlights/Topics: 00:00 — Intro 07:06 — "We recently made a large land purchase. Are there any tax benefits we can claim against our income?" — Deduct property taxes under SALT and investment interest expense on Schedule A. 14:27 — "Is there an IRS tax code reference I can look at for short-term rentals?" — Yes: IRC Section 469 and Treasury Regulation 1.469-1T define short-term rental rules. 18:20 — "Any special considerations for short-term Airbnb-type rentals in foreign countries?" — Use mandatory ADS depreciation; claim foreign tax credits to avoid double taxation. 22:55 — "Is there a minimum purchase price you recommend for STRs? Also, what type of property is ideal?" — A building value of $150,000–$300,000 is an ideal cost segregation starting point. 28:21 — "With today's Individual Standard Income Tax Deduction now so high, how can a Schedule E Vacation Home still be a tax advantage when write-offs no longer exceed the Standard Deduction?" — Schedule E rental deductions are entirely separate from your standard deduction benefit. 35:46 — "I sold one investment property and bought two under a §1031 exchange. When can I sell the two §1031 exchange replacement properties and enter a new §1031 exchange without a tax penalty?" — Hold replacement properties at least two years and thoroughly document your rental intent. 41:15 — "If a property is sold in California in a §1031 exchange and the replacement property in Tennessee is later sold through a second §1031, does California have capital gains taxes that need to be paid?" — Yes; California tracks deferred gains annually on Form 3840 until the tax is due. 44:34 — "If you have an LLC partnership with 3 members that recognized a sale, can each member make their own election with respect to a 1031 exchange? Or must the entire entity participate in the replacement property?" — Use the drop-and-swap strategy carefully; the IRS watches closely for step transactions. 49:15 — "In June of last year, the IRS asked me to submit my previous taxes before receiving my current tax refund. I did so. When I check the IRS website periodically, it says my refund is delayed. I have attempted to call, but no answer from the IRS. How do I expedite receiving my tax refund? Thank you in advance." — Contact the Taxpayer Advocate Service and review your IRS tax transcripts online. 53:18 — "What's the time limit on changing LLC tax status?" — File Form 8832 with an election date up to 75 days back or 12 months forward. Resources: Tax and Asset Protection Events https://andersonadvisors.com/real-estate-asset-protection-workshop-training/?utm_source=how-to-sell-1031-replacement-properties-without-tax-penalties&utm_medium=podcast Schedule Your FREE Consultation https://andersonadvisors.com/strategy-session/?utm_source=how-to-sell-1031-replacement-properties-without-tax-penalties&utm_medium=podcast Anderson Advisors https://andersonadvisors.com/ Toby Mathis YouTube https://www.youtube.com/@TobyMathis Toby Mathis TikTok https://www.tiktok.com/@tobymathisesq Clint Coons YouTube https://www.youtube.com/@ClintCoons

Have you ever considered that one misunderstood clause in your insurance policy could cost you tens of thousands of dollars? Most hosts view insurance as a "set it and forget it" expense, but in the world of short-term rentals, what you don't know can absolutely bankrupt your business.In this episode, I'm joined by Darren Nix, the founder of Steadily Insurance. Darren is a real estate investor and former software developer for the world's largest carriers who realized the industry was broken—so he built a better way for landlords to protect their assets.We talk about:Why treating insurance as a tool for major disasters, not minor claims, is the secret to lowering your premiumsWhy your standard homeowners policy is a ticking time bomb and how a true STR policy differs in the eyes of an adjusterThe dangerous mistake of insuring for "purchase price" instead of "rebuild cost," and how to estimate your true riskDarren's personal story from a Chicago rental and the one simple email every host should send their agent to avoid a denied claimWhy $300,000 in coverage might only cover your legal fees, and how to match your limits to your actual wealthThis isn't just about fine print and premiums, it's about strategic risk management. Darren pulls back the curtain on the "unsexy" side of scaling, from how past claims influence your future growth to the difference between homeowner- and landlord-focused carriers.You'll hear practical tips on content coverage for furnished rentals and why a higher deductible paired with a solid reserve fund is the ultimate wealth-protection move.If you've ever felt uneasy about whether you're actually covered, this conversation is your reality check. Get ready to stop crossing your fingers and start protecting your rental business with total confidence.HIGHLIGHTS AND KEY POINTS:[00:59] A short introduction about our guest Darren Nix, and shares how personal frustration with rental property insurance led to founding Steadily[04:53] Darren outlines the biggest misconceptions investors have about insurance before filing a claim, and explains why insurance should protect against catastrophe, not cover every minor issue[08:49] Darren talks about Steadily's national coverage and the rare exceptions to insurability[10:11] Darren outlines the key differences between short-term rental policies and standard homeowner or landlord insurance[13:47] Darren highlights common insurance gaps, especially underinsuring property replacement costs and emphasizes when insurance policies should be reviewed[19:20] Darren explains insurance considerations when shifting from short-term to midterm rentals, including vacancy risks[22:30] How to maintain insurance coverage during property renovations and extended vacancies[24:35] Darren confirms it's possible to insure his own properties and shares that Steadily's very first policy was written on his own rental property in Indianapolis[25:19] Darren emphasizes that the single most effective way to lower insurance costs is simply to avoid filing claims for minor incidents[28:12] The importance of sufficient liability coverage for short-term rental hosts[31:18] Darren advises key areas to review in an insurance policy and emphasizes that being proactive and informed can prevent surprises when a claim arises[32:36] Darren explains insurance and safety considerations for house-hacking and STRs[35:42] Darren advises new property investors to start locally and build the right support system[48:11] The lightning roundGolden Nuggets:“What you paid for the house doesn't typically have that much of a relationship with what it costs to rebuild the house.”“The single best thing you can do to reduce your cost of insurance is to not file a claim.”“I like to carry roughly the amount of my net worth in liability coverage, because the juicier target someone is the more aggressively a plaintiff's attorney is going to go after them to get a payday.”“Buy a property in a city that you know very well, that you can keep close eyes on until you've built the reps of knowing the ins and outs, because there are so many surprises of things that will happen.”“It's so important to surround yourself with people who push you and also are smarter than you.”Connect with our guest:Website: https://strsisterhood.steadilypartner.com/Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

Can a firefighter and paramedic build a profitable midterm rental business while working demanding W2 jobs? In this episode, you will learn how monthly rentals on Furnished Finder can create consistent income, significantly fewer turnovers than Airbnb, and a scalable real estate side hustle without quitting your job.  Mike and Celine Gonzalez share how they transitioned from accidental insurance bookings to a thriving monthly rental portfolio that now includes STRs, MTRs, partnerships, and a coaching business.  After discovering Furnished Finder through this very podcast, they listed their property before it was even finished and received multiple 3 to 4 month booking requests within days.You will learn:The difference between short term vs midterm renter psychologyHow couples can divide roles without damaging their relationshipThe exact Furnished Finder tools they rely on for tenant screening, leases, rent collection, and messaging templatesWhy responding fast to leads can make or break your occupancyHow midterm rentals align with full time or service based careers like fire and EMSIf you are a real estate investor, W2 employee, or couple looking for a scalable rental side hustle with less turnover and more stability than Airbnb, this episode breaks down a proven path.List Your Property on Furnished Finder:https://www.furnishedfinder.com/list-your-property Use code LLD10 for $10 off new listings ⏱ Episode Timestamps0:00 Introduction to Landlord Diaries and Monthly Rental Investing2:05 Who introduced the idea of furnished and midterm rentals first4:30 Scaling beyond the first 9 month insurance booking6:20 Short term vs midterm renter mindset and guest behavior differences7:30 Current STR and MTR portfolio breakdown and partnership properties10:55 How a firefighter and paramedic manage a midterm rental side hustle15:25 Advice from experienced hosts on working with your spouse18:20 Creating boundaries between marriage, W2 careers, and rental business20:00 Staying in your lane and focusing on growth instead of busy tasks21:45 Essential systems and tools for running a successful midterm rental24:50 Why Furnished Finder leads drive consistent monthly bookings25:55 Using message templates to respond quickly and win bookings27:35 Leveraging the Furnished Finder dashboard for screening, leases, and payments28:40 Defining your mission and long term goals before scaling30:45 Why service first hosting leads to long term profitability32:55 Receiving booking requests before the property is fully furnished35:05 Rapid fire questions: The one rental task you would hand off to your partner Explore Midterm Rental Resources:https://www.furnishedfinder.com/Resources/PMResources  View Mike and Celine's Furnished Finder Listings:https://www.furnishedfinder.com/members/profile?u=Mike_G   The Landlord Diaries is brought to you by Furnished Finder, where you can list your property for one low price and pay zero booking fees.

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene interviews Dan Rivers, co-founder of SynergyStays and founder of Rivers Capital Group. Dan shares how he built a diverse real estate background spanning property management, sales, flipping, private lending, and short-term rentals before narrowing his focus to revenue management for STR operators. He explains why trying to do everything at once held him back and how focusing on his strengths allowed him to grow more intentionally. Dan discusses the evolution of the short-term rental market, from the post-pandemic gold rush to today's more competitive, professionalized environment. He breaks down why many operators struggle when they treat STRs passively, and why success now requires attention to revenue management, guest experience, and consistent optimization. The conversation also explores house hacking, mindset shifts, and the power of showing up consistently in investor meetups to accelerate growth. If you're feeling scattered in your investing journey or unsure where to start, this episode offers clarity: focus on your superpower, surround yourself with the right people, and treat real estate like the business it is. In this episode, you will hear: Why focusing on one strength can unlock faster growth How the short-term rental landscape has shifted since 2020 The importance of revenue management in maximizing STR performance Why guest experience and reviews directly impact profitability How house hacking can accelerate wealth building The power of consistent networking and investor meetups Follow and Review "If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth." Supporting Resources Connect with Dan: Website: http://www.synergystayslocal.com/  Youtube: SynergyStays  Facebook: Dan Rivers Instagram: @danrivers_RCG  Special Link for Zen guests: https://bit.ly/synergyzen Connect with Jonathan: Website - www.streamlined.properties  YouTube - www.youtube.com/c/JonathanGreeneRE/videos  Instagram - www.instagram.com/trustgreene  Instagram - www.instagram.com/streamlinedproperties    Zillow - www.zillow.com/profile/streamlinen​j Bigger Pockets -  www.biggerpockets.com/users/jonathangreene Facebook - www.facebook.com/streamlinedproperties  Email - info@streamlined.properties   This episode was produced by Outlier Audio.

Ever worry that one bad cleaning review could shatter your STR returns or even threaten your bookings? Imagine systematically boosting your ratings, delighting guests, and generating reliable cash flow, all simply by revolutionizing your approach to quality and teams.This episode, host Kenny Bedwell sits down with short-term rental powerhouse Stacey St. John, whose unique playbook has catapulted her from long-term investor to founder of a wildly impactful community and management empire. Together, they destroy myths about “minimum viable cleaning,” break down why most owners are still losing thousands, and share the real leverage hidden in systems, mindset, and (yes) the legendary “toilet test.”If you're serious about staying competitive, maximizing income, and avoiding industry shakeout, you need these exclusive upgrades now, not next season. Listen in for data-backed strategies that no other podcast is telling you about.Timestamped Highlights[00:00] – A wild Ohio-to-beach vacation trend exposes a hidden rental goldmine[00:02:13] – COVID, eviction bans, and the shocking trigger for a rental pivot[00:03:33] – Why oceanfront for under $100k changed everything (and you missed it…)[00:05:08] – Accidentally creating a 66,000-member community and why it matters[00:11:46] – The real numbers: How “clean team” upgrades spiked ratings and revenue[00:15:34] – Cattle call cleaners, uncomfortable truths, and busting industry norms[00:29:40] – The “toilet test” and secrets of inspection culture that make or break your reviews[00:41:56] – Building a true team: How to transform cleaners into your STR profit weaponMentioned ResourcesFemale Short-Term Rental Investors Facebook GroupCozy GetawaysBook: Live Big by Stacey St. JohnAirbnbVRBOAbout the GuestStacey St. John is a data-driven short-term rental investor, educator, and founder of Female Short-Term Rental Investors, the largest women's STR community with over 66,000 members. Based in Cincinnati and operating properties across Myrtle Beach and Ohio, Stacey is also CEO of Cozy Getaways, where her focus on quality, systems, and empowering women has set new industry benchmarks for guest experience and financial performance.

Send a textNational parks can be unbeatable demand engines… but hype also creates overpriced disasters. Then comes the deeper punch: people buying STRs that don't cash flow just to chase depreciation and getting hit again with recapture later. If you've ever justified a bad deal with “tax benefits,” this is your wake-up call.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. ...

WSJM Afternoon News for 03-04-26See omnystudio.com/listener for privacy information.

WSJM Afternoon News for 03-04-26See omnystudio.com/listener for privacy information.

In this episode, we take a trip down memory lane and reflect on how Airbnb has evolved over the past decade. From the early days of personal connections with hosts to the modern streamlined check-in experience, things have changed dramatically. What we'll cover: 10 years ago on Airbnb vs today's culture Why this shift happened. What has changed and what's important to stay ahead today. Investing in STRs in 2026: Short-term rentals are still a great investment if done right. Our counterintuitive takeaway While the Airbnb landscape has changed, the opportunities are still strong. Hosts who embrace technology, dynamic pricing, and high guest expectations will succeed in this evolving industry. 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/

Are your short-term rental photos quietly costing you thousands in lost revenue? Most hosts lock in their listing photos and hope for the best, but what if a single, data-backed tweak could drive a double-digit leap in bookings? In this eye-opening solo episode, Kenny Bedwell pulls back the curtain on a simple yet game-changing hack designed to bump your STR revenue by 15% (or more). Forget the tired advice about marketing and pricing. Kenny gets razor-specific about leveraging seasonality, booking lead time, and the psychology of Airbnb's search algorithm so you can outshine saturated competition and start ranking higher, faster.Don't miss this episode if you're done losing bookings to “average” listings or fighting the algorithm blind. Tune in now or risk staying buried while others claim the cash flow you deserve. This is an exclusive, numbers-driven tactic you won't find in the usual STR playbooks!Timestamped Highlights[00:00] The #1 mistake hosts make that kills their revenue potential[00:00:45] Why seasonality crushes static listing photos every time[00:01:34] Booking lead time: the underrated, live metric that changes everything[00:02:41] Natural disasters, “anomaly events,” and their surprising aftermath in STR bookings[00:06:07] Want more bookings? Here's how your photos can attract the right demand, fast[00:07:49] The wrong photo at the wrong time: Are your snow pics scaring off summer travelers?[00:11:01] What amenities to spotlight for instant desire in every season[00:12:56] Christmas magic on Airbnb: the tiny photo tweak most hosts overlook[00:14:56] How the Airbnb algorithm picks winners (and why early bookings are your lifeline)[00:17:17] Are you overthinking seasonal photos? Kenny's zero-fluff take on what “enough” really meansMentioned ResourcesAirbnb search algorithm strategies (in-episode explanation)Watkins Glen property case studyBooking lead time analysisImportant 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.

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. ...


From Maui Firefighter to Real Estate Freedom: Mike Neubauer on STRs, Mindset, and Building a Life You Don't Retire From James Short hosts Leading and Growing Your Real Estate Business with guest Mike Neubauer, a former Maui firefighter, master photographer, and real estate investor behind Our Family Invests. Mike shares how he moved from creative work into firefighting for stability, then learned short-term rentals from a mentor, studied relentlessly, and replaced his fire department income within about two and a half years, retiring after 10 years to secure pension benefits.

 He explains his “scale of passivity,” starting with STRs for strong returns and transitioning toward more passive investing to protect family time, emphasizing “solve for Tuesday morning” and overcoming analysis paralysis by focusing on what could go right. He discusses joining mastermind rooms earlier, common success traits of taking action, and upcoming projects including a luxury glamping resort near Zion and building a home in Coeur d'Alene. Subscribe to Coach James Short's channel for more insights! 00:00 Solve for Tuesday 00:26 Show Introduction 01:08 Meet Mike Neubauer 03:00 From Art to Firefighting 06:11 Real Estate Spark 08:30 Scale of Passivity 10:23 Mastermind Advantage 12:37 Action Over Analysis 14:53 Lifestyle Projects Ahead 16:01 Rapid Fire Quiz 18:17 Wrap Up and Links

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

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.

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...

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/