Short Term Rental Riches

Tim Hubbard
  • 4.9 (149)
  • 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. 345. 5 Things Your STR Software Should Be Doing (But Probably Isn't)

    5d ago

    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/

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

    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/

    39 min
  3. 343. 10 Ways to Collect Airbnb Guest Contact Info (Without Getting Flagged)

    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/

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

    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/

    12 min
  5. 341. 4 Best Security Cameras for Your Airbnb (Plus the One I Actually Use)

    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/

    10 min
  6. 340. Airbnb Cheap vs. Expensive Furniture: Where to Splurge and Where to Save

    May 19

    340. Airbnb Cheap vs. Expensive Furniture: Where to Splurge and Where to Save

    Download the Furniture Checklist 👉 https://corzly.com/furniture-checklist/ Most hosts guess their furniture budget and hope for the best. In this episode, Tim shares his full real Orlando property breakdown — $40,983 in costs, by category — plus the framework he uses on every new property. From knowing where to always splurge to building your annual refresh cycle, this is the furniture episode every STR host needs. Find out why more expensive furniture does not always mean better returns — and what the difference actually comes down to when you look at the numbers Discover the $10-20 per square foot formula Tim uses to estimate any property's furniture budget before he spends a dollar Learn exactly where to always splurge (the items tied directly to your review scores) and where you can safely save without guests ever noticing Get Tim's full real Orlando property cost breakdown — $40,983 in total startup costs, category by category, including the numbers most hosts never talk about Understand how to plan your annual refresh cycle so you are never caught off guard by replacements, and how to use AI to track costs for tax purposes Smart furnishing is one of the highest-ROI decisions any STR host can make. Budget well, prioritize the right items, and your review scores and revenue will follow. Subscribe so you never miss an episode of Short-Term Rental Richest, and pass this one along to a host who needs 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/

    22 min
  7. 339. From Owner to Exit: How to 10X Your STR Value

    May 12

    339. From Owner to Exit: How to 10X Your STR Value

    Short-term rental management companies are becoming some of the most sought-after businesses in hospitality — but what actually makes one valuable? In this episode, Tim sits down with Jacobie from C2G Advisors, who has helped close over $750 million in STR business transactions. From EBITDA and profit margins to AI efficiencies and buyer demand, this conversation breaks down what operators need to know to grow smarter and potentially position their company for a future exit. Why clean financials and accurate reporting dramatically increase business value The EBITDA ranges and valuation multiples buyers are paying right now How operational systems and team structure impact profitability and sale price What buyers look for during acquisitions — and why retention matters How AI, automation, and operational efficiencies could reshape STR management margins Whether you're managing 20 properties or scaling toward hundreds, this episode offers a behind-the-scenes look at how the biggest players in the short-term rental industry think about growth, profitability, and acquisitions. If you want to build a more valuable company and stay ahead of where the industry is heading, this is an episode you won't want to miss. 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/

    46 min
  8. 338. I Manage 230+ Airbnb's: Here's My Housekeeping System

    May 5

    338. I Manage 230+ Airbnb's: Here's My Housekeeping System

    Your short-term rental might look perfect online, but behind the scenes, your housekeeping system could be quietly hurting your reviews and revenue. In today's episode, we break down why cleanliness is the #1 driver of guest satisfaction and how small operational changes can create massive financial results. If you want better reviews and higher income, this is an episode you can't afford to miss… Why cleanliness, not design or location, is the biggest driver of revenue The hidden risks of hiring large cleaning companies vs. smaller teams Simple systems to organize turnovers and prevent negative reviews Key questions to ask before hiring your next housekeeper How to turn guest feedback into better cleaning performance Your housekeeping team isn't just cleaning, they're protecting your reputation and driving your revenue. Dial in your systems, set clear expectations, and build the right relationships to unlock higher reviews and stronger profits. If you found this helpful, be sure to subscribe and share it with another host looking to level up. Download the Housekeeping Questionnaire: https://corzly.com/housekeeping-questionnaire/  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
See All (345)

4.9
out of 5
149 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
    345
  • Rating
    Clean
  • Copyright
    © Tim Hubbard
  • Show Website
    Short Term Rental Riches

You Might Also Like