Short Term Rental Riches

Tim Hubbard
  • 4.9 (151)
  • 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. Aug 17

    353. BiggerPockets's Investment Strategy for Building High-Performing Vacation Rentals

    Most hosts pick their next STR on a gut feeling, a beachfront view or a cozy cabin. Garrett Brown from BiggerPockets took a different approach… He built a data comparison today across 5 property archetypes, scoring cash flow, appreciation, and long-term risk. In this episode, we break down which property type won, and why management matters more than location: The property type most investors overlook actually scored highest on cash flow. Why lakefront properties deliver strong appreciation but almost no day-1 cash flow? The 1 management decision worth $18,000 a year on the same property. Why the highest-ceiling property type also carries the widest range of outcomes. The property type that scored lowest despite the strongest nightly rates. If this episode helped, subscribe, leave a review, and share it with someone weighing their next short-term rental purchase. We'll catch you again real soon. 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. Aug 11

    352. Damage Waivers Explained: What They Cover (And What They Don't)

    Damage waivers sound like free protection. But the wrong setup can shrink bookings instead of protecting a property. In this episode, we break down how damage waivers work, what they cover, and 1 alternative we recommend for properties with a lower nightly rate. How a damage waiver actually works, from claim to payout. The dollar range most damage waiver programs actually cover. What a damage waiver almost never covers, even with good documentation? Why a flat waiver fee can quietly price out a short stay? The alternative we recommend once ADR drops below a certain point. Thanks for spending this time with us today. If this helped clarify a booking policy question, subscribing and leaving a review genuinely helps this show reach more hosts working through the same decision. 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. Aug 4

    351. What a Direct-Booking Website Builder Wishes Every Host Knew

    We sit down with Gil Chan, founder of CraftedStays, about what it takes to build a direct booking website for a STR. We cover the gap between a generic template and an expensive agency build, the new AI tool Aria, and why owning a few direct bookings changes a host's leverage across platforms: What a direct booking site actually replaces for an Airbnb-only host? The 2 options hosts face for a website, and why neither worked? How Aria reads a portfolio and reviews before writing a single word? What OTA fees really add up to over a year of bookings? Why this isn't about leaving Airbnb, and what it's really about? Gil's story is a good reminder that owning your guest relationship matters as much as owning your listing. Subscribe to the show, leave a review, and share it with another host who is tired of renting shelf space on someone's platform. 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 28

    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?

  5. 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/

  6. 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/

  7. 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/

  8. 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!
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4.9
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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
    353
  • Rating
    Clean
  • Copyright
    © Tim Hubbard
  • Show Website
    Short Term Rental Riches

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