Short Term Rental Riches

Tim Hubbard
  • 4.9 (135)
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  • UPDATED WEEKLY

Tim Hubbard, successful investor and CEO of a seven-figure short term rental management company shares it all. The insider tips you need to know to acquiring, operating and scaling a successful short term rental business.

  1. 313. Hospitable CEO: How we Manage $5B in Annual Reservations

    5D AGO

    313. Hospitable CEO: How we Manage $5B in Annual Reservations

    In this episode of the Short-Term Rental Riches podcast, Tim sits down with Pierre, the CEO of Hospitable, a leading property management software that powers hundreds of thousands of properties across the globe. Pierre shares the story behind Hospitable's founding, its incredible growth over the last nine years, and the unique challenges they've overcome to help property managers automate and streamline their operations. Origin Story of Hospitable From 0 to over $5B in reservation revenue AI vs. Human Touch in Hospitality Impact of Dynamic Pricing and Automation The Future of Property Management Software *]:pointer-events-auto [content-visibility:auto] supports-[content-visibility:auto]:[contain-intrinsic-size:auto_100lvh] scroll-mt-[calc(var(--header-height)+min(200px,max(70px,20svh)))]" dir="auto" tabindex="-1" data-turn-id= "447bff70-3d3f-47ed-9ddd-9a4e7801510c" data-testid= "conversation-turn-4" data-scroll-anchor="false" data-turn= "assistant"> Tune in for an insightful conversation on the evolution of short-term rental management and the innovative solutions that are changing the game for hosts worldwide! Resource Links: 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/

    41 min
  2. 312. 7 Winter Safety Checks Every Airbnb Hosts Needs

    NOV 4

    312. 7 Winter Safety Checks Every Airbnb Hosts Needs

    Winter is here—and so are the risks and expectations that come with cold-weather hosting. From fireplaces to frozen sidewalks, the season can be a liability minefield for short-term rental owners. In this episode, we walk through your essential winter checklist to keep guests cozy and your property protected. Stay tuned—it's more than just turning up the heat. - Why swapping out your traditional fireplace might save you a major insurance headache - How your kitchen setup could be silently tanking your reviews—and what to do about it - The real risk of winter slips and falls (and the easy fixes most hosts ignore) - Why lighting and insulation matter more than ever for winter guest satisfaction - The critical safety items that boost your Airbnb visibility and protect your property This winter-ready checklist isn't just about staying warm—it's about staying protected, profitable, and five-star rated. Tune in, prep smart, and give your guests a season to remember (for the right reasons). Don't forget to subscribe and share with a fellow host who needs a winter refresh. Resource Links: 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/

    18 min
  3. 311. How Smart Hosts Use Promos (Airbnb Vs. Booking.com Vs. VRBO)

    OCT 28

    311. How Smart Hosts Use Promos (Airbnb Vs. Booking.com Vs. VRBO)

    Platform promotions are everywhere right now, but are they actually helping your short-term rental business, or just draining your profits? In this episode, we dig into the truth behind Airbnb, VRBO, and Booking.com discounts, uncovering how they work and how you can use them strategically without sacrificing revenue. Learn how to stand out in search results without slashing your nightly rate. What You'll Learn in This Episode: • How Airbnb's early bird, last-minute, and length-of-stay discounts really impact visibility • The "new listing" discount every OTA is pushing—and whether you should use it • Why dynamic pricing tools miss these promotions and how to avoid double discounts • Booking.com's loyalty Genius Program and how it compares to Airbnb or VRBO • A pro hack using PMS channel markups to gain visibility without lowering your prices If you've been unsure about whether OTA discounts are worth it, this episode brings clarity and strategy. Learn how to work the system—without letting it work you. Don't forget to subscribe, share, and check the links below for free tools to help you scale your rental income the smart way. Resource Links: 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/

    14 min
  4. 310. Airbnb's 15.5% Commission: What Hosts Need to Do Now

    OCT 21

    310. Airbnb's 15.5% Commission: What Hosts Need to Do Now

    If you've ever wondered how Airbnb's commission changes will impact your short-term rental business, this episode is for you. We break down what you need to know about the new guest service fee changes, and how to adjust your pricing to protect your profits. Get ready to make sure your property stays competitive, no matter the changes. • Discover why Airbnb is shifting the guest service fee to hosts and what this means for your bottom line. • How to mark up your prices by the right percentage to ensure you earn the same amount you do now. • Why hosts with PMS connections need to adjust their prices differently than those not using one (and what this means for competition). • The impact of Airbnb's changes on guests and how California's new law is keeping your pricing transparent. • Pro tips on how to adjust your cleaning fees, stay competitive, and keep your rental attractive for guests. If you're serious about staying ahead of the game on Airbnb and other platforms, this episode is a must-listen.  Resource Links: Download the Growth Handbook: https://strriches.com/growth-blueprint/  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/

    10 min
  5. 309. Furnished Finder CEO: The Future of STR Is Mid-Term

    OCT 14

    309. Furnished Finder CEO: The Future of STR Is Mid-Term

    If you've ever wondered how to profit from real estate without jumping through short-term rental hoops, this episode is for you. CEO of Furnish Finder, Jeff Hurst, shares how midterm rentals are solving affordability and regulatory issues—and why they're becoming one of the hottest trends in housing. Get ready to rethink your rental strategy. • Discover how Furnish Finder is quietly dominating the 30+ day rental space—more listings than Airbnb for monthly stays! • Why midterm rentals are booming—and what tenant types are driving demand in 2025. • Jeff Hurst's insider take on why Airbnb-style platforms miss the mark on midterm stays. • How to scale profitably with less turnover, more stability, and fewer regulations. • Pro tips to price and manage midterm rentals like a pro (and avoid costly gaps). If you're serious about sustainable rental income in today's economy, this episode is a must-listen. Jeff brings deep insight from years at Expedia and VRBO, now focused on the booming midterm rental space. Share this episode, leave a review, and stay tuned for more expert strategies. 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/

    40 min
  6. 308. Use these 9 Red Flags to Avoid Problem Guests

    OCT 7

    308. Use these 9 Red Flags to Avoid Problem Guests

    Are you spotting red flag guests before they check in? Managing guest bookings effectively is key to running a smooth short-term rental business. In this episode, we reveal 9 red flags to look out for when screening guests — and how to avoid problematic stays before they happen. Discover the 9 red flags that could indicate a difficult guest. Learn why incomplete profiles and lack of communication are immediate red flags. Understand why last-minute bookings could signal trouble for your property. Hear how pushing boundaries on your house rules could lead to bigger issues. Get tips on handling local guests to avoid potential problems. Don't let bad guests disrupt your short-term rental success. Stay ahead of these red flags and protect your property with effective guest screening strategies. Stay proactive in your rental management — ensure your guests are a good fit before they arrive. If today's episode helped, make sure to subscribe, share, and check out our free tools and expert resources to run a smoother operation. Resource Links: 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/

    12 min
  7. 307. The Ultimate Stripe Guide for Vacation Rental Hosts

    SEP 30

    307. The Ultimate Stripe Guide for Vacation Rental Hosts

    Are hidden Stripe fees eating into your profits? Most short-term rental hosts don't realize they're losing up to 1% on every transaction — and it's totally avoidable. In this episode, we uncover the overlooked costs tied to Stripe integrations and reveal the simple steps to keep more of your earnings. Discover how most hosts are unknowingly paying 30% more in transaction fees Learn the biggest mistake hosts make when setting up Stripe (and how to fix it!) Understand the sneaky "application fee" your PMS might be charging you Get the inside scoop on ChargeAutomation and other gateway alternatives Hear battle-tested tips for winning chargeback disputes and staying protected Get ready to rethink how you collect payments and unlock real savings on every booking. Still using Stripe the default way? This episode could save you thousands. Don't let Stripe fees quietly drain your short-term rental profits. With the right setup and tools, you can save big while keeping full control over your payments. If today's episode helped, be sure to subscribe, share, and explore our free tools and expert management services to scale smarter. Resource Links: 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/

    15 min
  8. 306. Airbnb Discount Requests: How Hosts Should Handle Them

    SEP 23

    306. Airbnb Discount Requests: How Hosts Should Handle Them

    Discount requests from guests are inevitable, even when your pricing is perfectly optimized. But how you handle them can make or break your rental's profitability. In this episode, we're diving into the psychology behind discount requests, how to respond with confidence, and when—if ever—you should say yes. 5 Key Takeaways: Why guests really ask for discounts and how cultural norms may influence their behavior. The one scenario where offering a discount might make sense (and when it doesn't). 5 crucial considerations before you ever offer a discounted rate—including a warning on guest quality. Alternatives to discounts that can still delight guests (without slashing your profits). How to professionally respond to discount requests using pre-set rules, empathy, and AI tools like ChatGPT. Discounts don't have to be the norm—and they shouldn't be. With a clear strategy, professional responses, and a little confidence, you can keep your pricing intact while still giving guests a great experience. Don't forget to subscribe and share if this helped clarify your approach! Resource Links: Download the Growth Handbook: https://strriches.com/growth-blueprint/  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/

    13 min
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4.9
out of 5
135 Ratings

About

Tim Hubbard, successful investor and CEO of a seven-figure short term rental management company shares it all. The insider tips you need to know to acquiring, operating and scaling a successful short term rental business.

Information

  • Creator
    Tim Hubbard
  • Years Active
    2019 - 2025
  • Episodes
    313
  • Rating
    Clean
  • Copyright
    © Tim Hubbard
  • Show Website
    Short Term Rental Riches

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