Thanks For Visiting

Airbnb Superhosts Annette Grant & Sarah Karakaian
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Jun 26, 2025 • 26min

475. Content Shoots at Your Airbnb: What to Ask, What to Charge, What to Avoid

A local photographer wants to use your Airbnb for a shoot. Should you say yes?In this episode, we’re walking through the exact questions we ask when we get these requests—and all the lessons we’ve learned the hard way. From influencer swaps to full-on commercial productions, we’ve seen it all. And we’re here to help you protect your property, price it properly, and make smart decisions about the kind of content being created in your space.Whether you’re already hosting photoshoots or a guest just asked to “pop in for a quick brand shoot,” this episode will help you set better boundaries, ask the right questions, and explore new income opportunities in a smart and sustainable way.In this episode, we cover:The different types of content shoots you might be approached aboutWhy it’s critical to ask what kind of content is being createdHow to protect yourself legally with a COI (Certificate of Insurance)What to charge (and why it’s not just your nightly rate!)How to manage timing, cleaning, and neighborhood impactReal stories from our own experiences—both great and not-so-greatRed flags to watch out for before you say yesResources📺 Subscribe to our YouTube channel | 6 Ways to Use ChatGPT in Your Airbnb Business📸 Check out Peerspace – a platform for listing your space for hourly rentals, perfect for photoshoots and production: peerspace.comMentioned in this episode:StayFi | Go to www.stayfi.com and enter TFV to get 50% off your first three months.Hostfully | Go to https://www.hostfully.com/tfv and use TFV500 to get $500 off your subscription.
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Jun 24, 2025 • 13min

474. Hosting Hotline: Should You Trade Free Stays for Influencer Content?

This week on the Hosting Hotline, listener Julia calls in with a timely question: should you host influencers in exchange for a free or discounted stay—especially when your property is new and you’re trying to build buzz?Julia runs a fully immersive Star Wars-themed short-term rental in Kissimmee, Florida, and recently experimented with a creator collaboration through the platform Stayamo. While she didn’t see immediate bookings, the exposure raised awareness and boosted her Instagram following. But is that worth the cleaning fee—or more?In this episode, we dig into:– How to evaluate whether an influencer is truly a good fit– What red flags to watch for when receiving creator collaboration requests– How to define success from influencer content– Smart ways to protect your time, energy, and budget– Why a holistic influencer marketing plan beats saying yes ad hoc– And how to communicate “no” without burning bridgesWe also share our favorite tips for setting expectations, building contracts, and using influencer content intentionally—so you’re not left wondering if the trade was worth it.Resources:– YouTube: The Right Way to Use Influencers to Promote Your Airbnb– Stayamo (influencer collaboration platform)
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Jun 19, 2025 • 59min

473. Hosting Through a Crisis with Catherine Morris of Edenwood NC

When a once-in-a-generation storm hit the mountains of Western North Carolina, Superhost Catherine Morris found herself not only without power—but with stranded guests, canceled reservations, and major cleanup ahead. In this episode, we talk with Catherine of Edenwood NC about her transition from corporate life to full-time hosting, the realities of managing two unique properties (yes, she still does the cleaning herself!), and the lessons she learned when Hurricane Helene shut everything down.From insurance battles to wood-fired hot tubs, this episode covers the gritty details of what it really looks like to be a hands-on host through disaster and recovery. Whether you're new to short-term rentals or a seasoned pro, Catherine’s insights on preparedness, communication, and guest care will leave you inspired—and better equipped for anything that comes your way. RESOURCESCatherine’s Rentals: https://edenwoodnc.comFollow on Instagram: @edenwoodncAirbnb Business Loss Coverage Info: https://www.airbnb.com/help/article/1320/extenuating-circumstances-policyMentioned in this episode:Minoan | Visit MinoanExperience.com and tell them TFV sent you!
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Jun 17, 2025 • 10min

472. Hosting Hotline: Can You Ask Guests to Book Direct After Their Stay?

In this Hosting Hotline episode, listener Colby from Humble Abode in Australia calls in with a question many hosts are asking: Can you still nudge guests toward booking direct after their stay—even with Airbnb’s updated policies?Colby has been sending post-stay messages encouraging repeat visits and direct bookings. But with Airbnb tightening its rules, is that strategy still allowed?We break down:Why post-stay messages via Airbnb’s platform are now a hard noWhat is still okay when it comes to asking for reviewsHow to compliantly shift communication off-platformWhy your in-home marketing game matters more than everSimple tools and strategies (like StayFi) that keep you compliant and effectiveThe real reason you shouldn’t try to outsmart Airbnb's AIPlus, we share smart alternatives to keep your marketing efforts alive—without breaking the rules.🔗 Mentioned in this episode:StayFi: A platform for collecting guest emails with consent, post-bookingThanks for Visiting Bootcamp: Get on the waitlist for our next deep-dive session
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Jun 12, 2025 • 1h 14min

471. Is Airbnb Just the Beginning? A Conversation with Phil Kennard of FutureStay

This week on Hosting Hotline, we’re joined by Phil Kennard, founder of FutureStay—a platform built specifically for rental-preneurs. Whether you're managing one short-term rental or a growing handful, Phil is here to help you take back control of your business and stop relying solely on platforms like Airbnb.We dig into:What it means to be a “rental-preneur”The truth about Airbnb's off-platform policyWhy direct bookings aren’t as scary (or risky) as you thinkHow to use the “billboard effect” to drive bookingsCommon listing mistakes that quietly hurt your rankingThe direct booking loop and how to build guest trustWhy even 10% direct bookings can change your bottom lineWhether you’re brand new or deep in your hosting journey, this episode will inspire you to think like a business owner—and start setting yourself up for long-term success.RESOURCES:FutureStay | Direct booking platform for rental-preneurs (exclusive offer for TFE listeners)Google Vacation Rentals | Where 70%+ of travel searches beginAirbnb’s Off-Platform Policy | New rules effective May 2025Proper Insurance | STR insurance designed for hostsThe Hosting Handbook | Your beginner’s guide to starting strongMentioned in this episode:Quiz | Take our quiz to reveal your hosting personality style!StayFi | Go to www.stayfi.com and enter TFV to get 50% off your first three months.Host Checklist | Grab our Airbnb Essentials Checklist and make stocking your Airbnb a breeze – we've got all your hosting needs covered!
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Jun 10, 2025 • 20min

470. Hosting Hotline: Are You Leaving Money on the Table by Not Offering Gap Nights?

This week on Hosting Hotline, we’re answering a question from Joanna—a host in Central Virginia—who’s working to increase bookings by upselling gap nights before or after a guest’s stay.Also known as adjacent nights or half-day stays, these nights are often overlooked revenue opportunities. But the truth is, guests are more willing than you think to arrive early or stay late—if you offer it the right way and at the right time.In this episode, we cover:– What “gap nights” really are (and why guests say yes)– The 3 best times to offer a gap night– Why “half-day stay” might sell better than “early check-in”– The importance of testing and tracking guest responses– How to automate these offers without sacrificing conversions– A reminder that your core upsell is your core product: the stay!Whether you’re managing a single unit or scaling a portfolio, don’t miss this conversation about one of the easiest ways to boost your revenue without increasing your workload.Want to get your questions answered on the show? Visiting HostingHotline.com. RESOURCES: – Hostfully | PMS with automated messaging tools– Breezeway | Smart guest messaging & turnover management– Get the Hosting Handbook | New host? Start here
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Jun 5, 2025 • 1h 1min

469. Unlocking the STR Tax Loophole with Amanda Han, CPA

You’ve heard whispers of a short-term rental tax loophole that can save hosts big money—but is it real? And more importantly, does it apply to you?In this episode, we're joined by Amanda Han, CPA and tax strategist, who breaks down exactly how short-term rental owners can legally reduce their tax burden without qualifying as a real estate professional. Amanda walks us through the difference between material participation and real estate professional status, how to track your hours, and how to avoid some of the most common mistakes hosts (and even CPAs!) make when trying to claim this benefit.We also talk about:How short-term rentals create tax losses even when they cash flowWhat actually counts toward your material participation hoursWhether midterm rentals qualify (spoiler: not usually)Common write-offs hosts overlook—and how to structure your finances to make the most of themWhen a cost segregation study makes sense (and when it doesn’t)How to find the right tax professional for your STR businessThis episode is a must-listen if you own, co-host, or are considering investing in a short-term rental and want to keep more of the money you’re making.Resources:Amanda’s Website: Keystone CPAAmanda on InstagramAmanda’s YouTube ChannelSTR Host Tax Advantage Cheat SheetShould You Fire Your Property Manager? (Or Are Your Expectations Misaligned?) | Subscribe to our YouTube channelMentioned in this episode:Hostfully | Go to https://www.hostfully.com/tfv and use TFV500 to get $500 off your subscription.Minoan | Visit MinoanExperience.com and tell them TFV sent you!
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Jun 3, 2025 • 9min

468. Hosting Hotline: Should You Add a Security Camera to Your STR?

If you're a new host wondering whether a Ring camera is worth the investment—or how to manage your smart locks like a pro—you’re not alone.On this Hosting Hotline episode, Sarah and Annette answer listener Winn’s questions about securing her very first short-term rental. They cover everything from guest privacy concerns to how often you should change your keypad code.You’ll learn:What your insurance provider needs to know about outdoor camerasHow to decide whether security devices are right for your listingBest practices for guest communicationManual vs. automated keypad code systemsHow to use SimplySafe or similar services for an extra layer of protectionWhether you’re managing one property or building a short-term rental portfolio, this episode will help you feel more confident about keeping your space—and your guests—safe.Want to get your question answered on the show? Visit HostingHotline.comRESOURCES:Hosting Handbook: Our on-demand course for new STR hostsSimplySafe: Affordable and easy-to-install home security systemsSchlage Keypad Electronic DeadboltYale Assure Wi-Fi Connected Smart Lock
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May 29, 2025 • 1h 14min

467: Hosting Across the Pond: Global Lessons from the UK Retreat

This week’s episode is a special one—we’re taking you behind the scenes of an exclusive short-term rental retreat held in the UK at the stunning, historic Knowsley Hall. Alongside 17 founders, CEOs, and global leaders in the STR space, we got to talk shop, exchange ideas, and ask bold questions about where our industry is headed.In this episode, you’ll hear:How Knowsley Hall (est. 1385!) is blending historic preservation with modern hospitalityLessons from tech leaders who got their start as hosts—and the problems they built businesses to solveCandid insights on profitability, pricing, direct bookings, AI risk, and OTA algorithmsInterviews with Ella (Autohost), Bart (Autorank), Phil (Futurestay), and Marc (Boostly)—all with actionable takeaways for your businessWe asked them:What separates thriving hosts from those struggling right now?Is there hope for direct bookings—and how do we make it work?What tech is worth investing in (and what can you ditch)?What’s one trend in hosting that needs to die already?If you’ve ever wanted an inside look at the STR industry from a global perspective, this episode is packed with high-level insight, practical advice, and some spicy opinions on what needs to change.RESOURCES:Hostfully | Use Code TFV500 for $500 off!Stayfi | Provide an exceptional WiFi experience for your vacation rental guestsAutohost.ai – Smart Screening for HostsAutorank.io – Optimize Your Airbnb RankingFuturestay – Simplified Property ManagementBoostly – Build Your Direct Booking BrandShort Stay SummitKnowsley Hall on InstagramSubscribe to our YouTube Channel | Top 10 Amazon Cleaning Must-Haves for Your AirbnbMentioned in this episode:StayFi | Go to www.stayfi.com and enter TFV to get 50% off your first three months.Hostfully | Go to https://www.hostfully.com/tfv and use TFV500 to get $500 off your subscription.
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May 27, 2025 • 15min

466. Hosting Hotline: Should You Try Midterm Rentals? Here’s What to Know Before You List

In this week’s Hosting Hotline, we’re answering a question we hear all the time: Should I consider midterm rentals (30+ day stays)? If you’re wondering whether it’s the right move for your property, this episode will help you break it down.We cover the pros, cons, and what it really looks like to add midterm rentals into your hosting strategy—including Sarah’s firsthand experience with listing on Furnished Finder during the off-season.We break down:What counts as a midterm rental—and how it’s different from STRs and LTRsThe pros: lower turnover, longer stays, consistent income, and guest qualityThe cons: more hands-on screening process, less automationWhy midterm guests are not just short-term guests staying longerHow to test the waters using platforms like Furnished FinderWhat amenities, furniture, and stocking levels midterm guests expectHow to check demand in your market before jumping inA $30-off listing code to get started risk-free on Furnished FinderWe’re also joined by Tanya Shin, Chief Growth Officer at Furnished Finder, who shares trends they’re seeing (hint: it’s not just nurses anymore) and the best way to see if your city is midterm-ready.

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