Short Term Rental Riches

Tim Hubbard
  • 4.9 (150)
  • Investing
  • 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. 6d ago

    348. From 1 Property to 100+: Inside the PMS Powering 62,000 Rentals

    Running more than one short-term rental often means answering the same guest questions, jumping between platforms, and hoping nothing slips through the cracks. In this episode, we sit down with Frank Bosi from Hostfully. We break down what a property management system automates, who it is built for, and one mistake that slows new users down before it pays off. The one automation that gives hosts back two or more hours every single day Why syncing every booking channel might matter more than any single guest message The setup mistake almost every new PMS user makes in week one What actually happens to guest satisfaction scores once messaging goes automatic How many properties one person can realistically run once the busywork disappears That is how the right system turns short-term rental management from a full-time scramble into something that actually scales. If this episode helped, subscribe so you do not miss the next one, and leave a review. It helps more hosts find the show and build operations that run without them. 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/

  2. Jul 7

    347. Should You Leave a Bad Review for a Bad Airbnb Guest?

    Every host eventually faces a difficult guest. When they check out, the question hits: should we leave a bad review? More hosts get this wrong than you might expect. In this episode, we break down Airbnb's blind review system, make the case on both sides, and share a practical framework for writing a negative review the right way. How Airbnb's blind review system works and why it changes everything about the risk of leaving a critical review The strongest argument for leaving an honest review and why the host community depends on it The underrated downside most hosts never consider before hitting submit The exact approach for writing a negative review that reads as professional and credible A simple framework for deciding when to write a review and when to let it go Handling difficult guests is part of this business. What defines you as a host is how you respond, right down to the review you leave after they check out. If this episode helped you, please subscribe and share it with a fellow host who needs it. We will see you next week on Short Term Rental Riches. Download the Host's Communication Checklist here: https://corzly.com/str-communication-checklist/ 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/

  3. Jun 30

    346. Before You Invest in Airbnb Amenities, Use This Framework!

    Not every amenity pays for itself, and the ones that look great on a competitor's listing might do nothing for yours. This isn't about trends or gut instinct. It's about data and real ROI. In this episode, we share the exact framework he uses to evaluate any amenity before spending a dollar, so you can stop guessing. How to use AirDNA to compare listings with and without a feature: the data reveals your actual revenue opportunity before any money changes hands. Why a 25% revenue lift from a pool might still be the wrong move. Not every amenity shows up cleanly in the numbers, but photo value is real. What Orlando teaches every STR investor about market saturation. The five-tier amenity framework. The right amenity in the right market can transform your numbers, the wrong one ties up capital for years. Tim gives you the framework to tell the difference. If this episode helped, subscribe and leave a review. It takes thirty seconds and helps more hosts find the show. Download the Amenity Evaluation Checklist here: https://corzly.com/short-term-rental-amenity-checklist/  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/

    346. Before You Invest in Airbnb Amenities, Use This Framework!

  4. Jun 23

    345. 5 Things Your STR Software Should Be Doing (But Probably Isn't)

    Most STR hosts have a pricing tool, a cleaning checklist, and a messaging app. The gaps between those systems are where money quietly disappears. Today I'm walking through five things we've built at Corzly that most STR software doesn't do — from routing guest notes to your housekeeper to automatically adjusting your base price. Use Corzly or not, these gaps matter. Why your dynamic pricing tool might be working off a base price set months ago, and why that single error compounds into every daily rate adjustment you make How routing guest messages, private feedback, and review mentions to your housekeeper automatically closes the loop on recurring cleaning issues The reason your review score needs to be factored into your pricing strategy, and why a 4.6 and a 4.9 property should never be competing at the same rate Why most STR software, even good tools, still doesn't make turnover confirmation fail-proof, and what a proper AI-backed system actually looks like A preview of what's coming in Part Two: the AI features that let housekeepers confirm turnovers and submit notes via SMS or voice, automatically logged into Breezeway These five things aren't complicated — but most STR software doesn't do them, and most hosts don't know they're missing them until something goes wrong. Start with the ones that fit your operation. Subscribe and leave a review, it helps us reach more hosts who need this. Part Two is coming. Download the Short-Term Rental Software Audit here. 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/

    345. 5 Things Your STR Software Should Be Doing (But Probably Isn't)

  5. Jun 16

    344. They Have 87 STR Deals Under Contract: Here's What They're Seeing

    Download the STR Acquisitions Checklist here. Most STR investors spend months researching markets, then hire the first agent they find. That gap between your research and your representation is costing more than you think. Tyler from Savvy STR Agents works across 25 markets and sees the same investor mistakes repeatedly. What he shares today could change how you buy your next short-term rental property. Why the agent you hire for your STR purchase might be your biggest blind spot, and what to look for in someone who actually understands the business The permit research, zoning checks, and revenue projections most generalist agents never think to run before you make an offer How to evaluate any market for STR potential and what a property walkthrough with STR-specific eyes looks like in practice What has shifted in the STR buyer's market over the last 12 to 18 months, and where the real opportunities are sitting right now The single most underrated property feature serious STR investors look for, and the one thing first-time buyers consistently do wrong Tyler, thanks for pulling back the curtain on this. To everyone listening, the agent across the table from you at your next closing matters more than most investors realize. Find someone who speaks the language. Subscribe, leave a review, and share this with an investor who needs to hear it. 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/

    344. They Have 87 STR Deals Under Contract: Here's What They're Seeing

  6. Jun 9

    343. 10 Ways to Collect Airbnb Guest Contact Info (Without Getting Flagged)

    Download the Guest Contact Info Capture Checklist Your Airbnb account can change overnight. Algorithm shifts, fee increases, a sudden suspension, and if your entire guest relationship lives inside the platform, you have nothing. In this episode, Tim walks through 10 platform-compliant ways to collect your guests' real contact info, legally, automatically, and without sending a single message that could put your listing at risk. The in-property QR code strategy that converts at the highest-intent moment of any guest stay — and why the offer matters more than the placement How WiFi login tools like Stayfi turn a giveaway you're already offering into an automatic email capture that runs in the background 24/7 Why your Stripe dashboard may already hold dozens of real guest emails you've never used — and how to start putting them to work The exact post-stay message approach that stays compliant with OTA terms while sending guests directly to your own contact form How listing on Google Vacation Rentals and VRBO direct changes the contact info equation entirely — every booking comes with real data by default If this episode helped you see your guest list differently, subscribe so you never miss what's next. Share it with a host who's still relying entirely on platform traffic — it could be the most important thing they hear this year. See you in the next one. 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/

    343. 10 Ways to Collect Airbnb Guest Contact Info (Without Getting Flagged)

  7. Jun 2

    342. Airbnb's AirCover: What It Actually Covers (And What It Doesn't)

    If you're an Airbnb host, you've heard the pitch: three million dollars in AirCover protection. Sounds bulletproof. But after managing over 50,000 guests, Tim has seen why the gap between the promise and the payout catches so many hosts off guard. The claims process is more specific than Airbnb lets on, and knowing it before something goes wrong changes everything. How AirCover actually works: it is a goodwill program, not contractual insurance, and that distinction matters the moment you file a claim The 14-day filing window most hosts have never heard of, and why the old "60 days" advice is dangerously outdated The exact order of steps to follow in the Resolution Center, and why skipping any one of them can get your claim denied before Airbnb ever reviews it A real-world win: how Tim's team documented a $6,727 HVAC damage claim and recovered it in full from both AirCover and their insurance carrier Why AirCover only covers Airbnb bookings, what dedicated STR policies cover that it never will, and the one coverage gap that can easily exceed your repair costs AirCover is a valuable safety net, but it's not a substitute for real STR insurance. File claims within 14 days, document everything, and carry a dedicated policy underneath. If this episode helped save you money on a future claim, share it with a fellow host who needs to hear it. Download the AirCover Claims Checklist: https://corzly.com/aircover-claims-checklist/  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/

    342. Airbnb's AirCover: What It Actually Covers (And What It Doesn't)

  8. May 26

    341. 4 Best Security Cameras for Your Airbnb (Plus the One I Actually Use)

    Most hosts put up a security camera and call it done. But the right setup does far more than watch the front door. In this episode, Tim breaks down the three features every STR camera needs, compares four popular options, and reveals how cameras can verify guest counts, catch unauthorized pets, and support your housekeeping team — all while keeping your listing fully compliant. Discover the three non-negotiable features any STR security camera needs before you spend a dollar — and the one common feature that actually does not matter Get a side-by-side comparison of Ring, Google Nest, Arlo, and Reolink, including the one Tim puts on every new property right now Learn how cameras go beyond security to help you charge for extra guests, unauthorized pets, and other policy violations through Airbnb's resolution center Find out the exact disclosure requirements every host must follow to stay compliant on Airbnb and protect their listing from being taken down Understand how to use cameras operationally to confirm check-ins remotely, support your housekeeping team, and protect guests during their stay Security cameras are one of the highest-ROI tools an STR host can add. Whether you have one property or fifty, the right setup protects your revenue, your guests, and your listing. Subscribe so you never miss an episode, and share this with a host who needs to hear it. Download the camera checklist: https://corzly.com/camera-checklist/  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/

    341. 4 Best Security Cameras for Your Airbnb (Plus the One I Actually Use)
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4.9
out of 5
150 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 - 2026
  • Episodes
    348
  • Rating
    Clean
  • Copyright
    © Tim Hubbard
  • Show Website
    Short Term Rental Riches

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