Short Term Rental Riches

Tim Hubbard
  • 4.9 (145)
  • 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. 333. VRBO's Big 2026 Update Every STR Host Must Know

    5D AGO

    333. VRBO's Big 2026 Update Every STR Host Must Know

    If your VRBO bookings have slowed, the problem might not be your property—it could be a major platform shift. VRBO's 2026 update is quietly reshaping how listings get visibility, and most hosts haven't caught on yet. In this episode, we unpack what changed, why it matters, and how to adapt before your competitors do. VRBO's move from portfolio-based to listing-specific Premier Host status—and why it changes everything The 5 exact requirements you must hit to unlock higher visibility and better placement Hidden "visibility tiers" most hosts don't even realize exist (including the top 1%) Why a single bad listing no longer drags down your entire portfolio—and how to leverage that A smart (and slightly unconventional) strategy to rebalance bookings across Airbnb and VRBO This update isn't just a tweak—it's a shift in how visibility, trust, and bookings are earned on VRBO. If you want to stay competitive (and profitable), this is one episode you can't afford 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/

    12 min
  2. 332. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 2)

    MAR 24

    332. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 2)

    The short-term rental game is evolving fast—and staying ahead means asking better questions. In this live Q&A, we dive into real challenges operators are facing right now—from AI tools and hiring to market shifts and scaling pains. If you're growing (or thinking about it), this episode uncovers what's working today… and what could be holding you back. Key Takeaways: How AI is transforming guest communication, inspections, and operational efficiency The fastest way to find reliable local cleaners and maintenance teams (hint: it's easier than you think) What actually changes when scaling from 5 to 15 properties—and where most people fail Why 1–2 bedroom properties may no longer be the "easy win" in today's market The pricing mistakes (like cleaning fees & damage waivers) that quietly kill your bookings Whether you're just starting or scaling fast, this episode is packed with real-world insights you can apply immediately. Don't fall behind as the market shifts—stay informed, stay optimized, and stay competitive. Be sure to subscribe, share with a fellow host, and explore the resources below to level up your STR game. 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/

    27 min
  3. 331. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 1)

    MAR 17

    331. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 1)

    The short-term rental landscape is evolving fast—and if you're not adapting, you're falling behind. In this live Q&A, Tim Hubbard breaks down the realities of dynamic pricing, AI-powered guest communication, and the systems top operators use to stay competitive. From pricing pitfalls to automation myths, this episode uncovers what's really working right now… Key Takeaways: Why relying solely on dynamic pricing tools could be costing you thousands—and how to fix it The hidden flaw in "base pricing" that most hosts completely overlook How review scores and listing performance should directly impact your pricing strategy The truth about AI in guest communication (and why 95% automation is misleading) What separates top-performing operators from everyone else when it comes to systems and tech Success in short-term rentals comes down to smarter systems, better data, and constant adaptation. This episode gives you the edge to stay competitive in a rapidly changing market. If you're serious about scaling and maximizing revenue, don't miss these insights—then take action on what you've learned today. 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
  4. 330. How to Allow Pets Without Risking Your Short Term Rental Property

    MAR 10

    330. How to Allow Pets Without Risking Your Short Term Rental Property

    Short-term rental hosts are divided on one big question: should you allow pets in your property? While some hosts see massive boosts in visibility and bookings, others worry about damage, cleaning headaches, and insurance issues. In this episode, we break down the real pros, cons, and strategies behind pet-friendly listings—and what every host should consider before flipping that pet-friendly switch. Why allowing pets can instantly increase your listing visibility and reduce competition in many markets The smartest ways to structure pet fees on Airbnb, VRBO, and Booking.com without hurting bookings Essential pet rules every host should include in their house rules or rental agreement Damage protection strategies, deposits, and insurance considerations when hosting pets The critical difference between service animals and emotional support animals—and what hosts can legally ask Allowing pets can be a powerful strategy to boost occupancy and stand out in crowded markets—but only if it's done the right way. From setting smart policies to protecting your property, this episode walks you through everything you need to decide if pet-friendly hosting is the right move for your rental business. 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
  5. 329. The Airbnb Rules That Have Completely Changed in 10 Years

    MAR 3

    329. The Airbnb Rules That Have Completely Changed in 10 Years

    In this episode, we take a trip down memory lane and reflect on how Airbnb has evolved over the past decade. From the early days of personal connections with hosts to the modern streamlined check-in experience, things have changed dramatically. What we'll cover: 10 years ago on Airbnb vs today's culture Why this shift happened. What has changed and what's important to stay ahead today. Investing in STRs in 2026: Short-term rentals are still a great investment if done right. Our counterintuitive takeaway While the Airbnb landscape has changed, the opportunities are still strong. Hosts who embrace technology, dynamic pricing, and high guest expectations will succeed in this evolving industry. 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
  6. 328. These STRs Earn $150K/Year and cost ONLY $300K property

    FEB 24

    328. These STRs Earn $150K/Year and cost ONLY $300K property

    The short-term rental industry is evolving fast—and the strategies that worked five years ago may not cut it today. In this episode, Natalie Palmer shares how she scaled from co-hosting in a single condo complex to raising capital for luxury destination properties. If you're wondering where STR investing is headed next, this conversation might change your approach. How Natalie scaled to 10 co-hosted units in one condo complex—and why that model simplified operations Why housekeepers are your most valuable asset (and how to structure your team for success) The pricing strategy shift that's working in today's more competitive STR market How luxury upstate New York properties are generating $150K–$200K annually at a fraction of major-market purchase prices Why the "middle-tier" STR may disappear—and how to position your property to survive and thrive The STR landscape is shifting—but opportunity is everywhere if you know where to look. Whether you're refining operations, upgrading amenities, or exploring passive investing, this episode is packed with actionable insights. Be sure to subscribe, share with a fellow investor, and explore the resources below to level up your portfolio. 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
  7. 327. 25 Conferences Later: My Best STR Insights

    FEB 17

    327. 25 Conferences Later: My Best STR Insights

    The short-term rental industry is shifting fast — and if you're not paying attention, you'll get left behind. In this episode, I'm breaking down the six biggest takeaways from the IMN Conference, where top operators managing hundreds of properties reveal what's really happening behind the scenes. From venture capital moves to AI breakthroughs, here's what you need to know before 2026. 5 Key Takeaways: Venture capital is quietly buying 100–200 unit property managers and reshaping the industry. Luxury rentals are outperforming commodity listings as investors chase higher returns. 80% of guest experience depends on processes — and poor systems lead to bad reviews. AI is transforming guest communication and operations — but no single tool does it all. Design matters more than ever: invest in your top 5 photos, prioritize comfort, and create visual impact. The STR market is evolving quickly — and the operators who adapt will win. Whether it's refining your processes, leveraging AI, or repositioning toward luxury, now is the time to level up. If you found value in this episode, subscribe, share it with another operator, and keep building smarter. 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/

    23 min
  8. 326. 8 Airbnb Mistakes You Need To STOP Today

    FEB 10

    326. 8 Airbnb Mistakes You Need To STOP Today

    Most short-term rental hosts focus on what they should be doing, but what about the things quietly hurting your business? In this episode, we flip the script and break down eight common mistakes holding hosts and property managers back. From guest screening to tech overload, these missteps could be costing you bookings, reviews, and peace of mind, and you may not even realize it yet. • Why poor guest screening can lead to damage, bad reviews, and long-term platform risk • The hidden danger of relying too heavily on a single booking channel • Where cheap furniture costs you more in the long run, and where it doesn't matter • How shiny new tech and AI tools can quietly hurt your operations if chosen wrong • The mindset shift growing hosts must make to scale without burning out Avoiding mistakes is just as powerful as taking the right actions. These eight reminders can help you protect your properties, improve guest experiences, and build a more resilient rental business. If this episode sparked a few "aha" moments, be sure to subscribe, share it with another host, and keep learning. 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
See All (333)

4.9
out of 5
145 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
    333
  • Rating
    Clean
  • Copyright
    © Tim Hubbard
  • Show Website
    Short Term Rental Riches

You Might Also Like