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. 4d ago

    350. Security Deposits vs Damage Waivers: Which Protects Your Short-Term Rental Better?

    Security deposits come up in almost every hosting conversation, but a lot of what hosts believe about them is wrong. We break down the difference between a deposit and an authorization hold, and why refunding deposits drains money from every stay. We cover damage waivers, when to charge a guest for damage, and how to build one full protection strategy. How a security deposit and an authorization hold are actually different Why hotels never really "hold" your cash, and what they do instead The nine-day window a lot of hosts don't know they're racing against How to decide between an authorization hold and a damage waiver What to document before you ever charge a guest for damage Thanks so much for hanging out with us today. We know this one got a little technical, but understanding how the money side of damage protection actually works will save you real headaches down the road. If this helped, subscribe and leave us a quick review, it means a lot. 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/

    350. Security Deposits vs Damage Waivers: Which Protects Your Short-Term Rental Better?

  2. Jul 21

    349. How to Build a Hotel-Quality Bed Setup for Under $1,000

    Mattresses seem like a small decision, but they shape almost every guest review a short-term rental gets, and getting it wrong is the kind of mistake guests always mention. In this episode, we share the exact mattress and bed frame we use, why the premium option rarely earns its price tag, and how to prioritize spending when budget is tight. The exact mattress our team buys for every rental Why a $5,000 mattress didn't make the cut The bed frame mistake that ruins a great mattress The right way to respond to a mattress complaint Where to spend first when the budget is tight Mattresses are one of those details you set once, and guests either love it or barely notice, but get it wrong and they will mention it in the review. Choose wisely, don't overspend, and don't skip the bed frame. Subscribe today if you haven't already, we'll see you next time. Bed Frame Link - https://www.wayfair.com/furniture/pdp/alwyn-home-16-premium-heavy-metal-platform-bed-frame-with-metal-supports-for-maximum-durability-in-black-w110994947.html?piid=1025917393 Mattress Link - https://www.amazon.com/dp/B0CKYYHD47?_encoding=UTF8&psc=1&ref=cm_sw_r_cp_ud_dp_BJKBNQC9JA460HJD1K8P_1&ref_=cm_sw_r_cp_ud_dp_BJKBNQC9JA460HJD1K8P_1&social_share=cm_sw_r_cp_ud_dp_BJKBNQC9JA460HJD1K8P_1 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. Jul 14

    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/

  4. 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/

  5. 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!

  6. 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)

  7. 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

  8. 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)
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4.9
out of 5
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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
    350
  • Rating
    Clean
  • Copyright
    © Tim Hubbard
  • Show Website
    Short Term Rental Riches

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