Tune in for an insightful conversation on the evolution of short-term rental management and the innovative solutions that are changing the game for hosts worldwide!
313. Hospitable CEO: How we Manage $5B in Annual Reservations
Release Date: 11/11/2025
340. Airbnb Cheap vs. Expensive Furniture: Where to Splurge and Where to Save
Short Term Rental Riches
Download the 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...
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339. From Owner to Exit: How to 10X Your STR Value
Short Term Rental Riches
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...
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338. I Manage 230+ Airbnb's: Here's My Housekeeping System
Short Term Rental Riches
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...
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337. What Most Successful STR Investors Are Focussed on Today: From a 300+ Investor Meetup
Short Term Rental Riches
Fresh off a high-level STR summit in Phoenix, this episode unpacks what top-performing operators are doing differently right now. With rising competition and shifting guest expectations, standing out is no longer optional. Discover the strategies driving massive revenue gaps—and the one theme everyone keeps coming back to… • Why some short-term rentals outperform others by up to 300% in the same market • The 5-step framework to confidently choose your next (or first) STR investment • Practical design tips that actually increase bookings—not just aesthetics • How top hosts use...
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336. Is Your STR Actually Profitable? Use This Financial Setup
Short Term Rental Riches
Short-term rentals can generate incredible income—but are you actually keeping any of it? In today’s episode, we sit down with David Richter, author of Profit First for Real Estate Investing, to uncover why so many investors feel broke despite growing portfolios. If you’ve ever wondered where your money is going, this conversation will open your eyes… Why doing more deals doesn’t guarantee more profit—and how investors get stuck The “black hole bank account” problem silently draining your cash flow A simple system to start paying yourself consistently (even with tight margins)...
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335. Turning Raw Land into $865K/Year Colombia Resort
Short Term Rental Riches
After three years of building a boutique hotel resort in Colombia, it’s finally time to pull back the curtain. This episode dives into the real opportunities, and unexpected challenges, of international real estate development. If you’ve ever considered building or investing abroad, this behind-the-scenes breakdown reveals what most investors never see… and what you must prepare for. Key Takeaways: Why Colombia’s tourism boom created a compelling (but competitive) investment opportunity The hidden risks of international construction projects—including permits and delays How exchange...
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334. How to Make More Per Booking Without Raising Your Rate
Short Term Rental Riches
In today’s competitive short-term rental market, efficiency and automation aren’t optional—they’re essential. This episode dives into how top operators are eliminating fraud, increasing revenue, and creating seamless guest experiences through smart tech. If you’re still relying on manual processes or missing out on hidden income streams, you may be leaving serious money on the table… Key Takeaways: How one operator scaled to 200 properties—and eliminated chargebacks entirely Why preventing fraud upfront is far more effective than fighting disputes later The real revenue...
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333. VRBO's Big 2026 Update Every STR Host Must Know
Short Term Rental Riches
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...
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332. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 2)
Short Term Rental Riches
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...
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331. STR/Airbnb Q&A: AI Tools, Tasks & Revenue in 2026 (Part 1)
Short Term Rental Riches
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...
info_outlineIn this episode of the Short-Term Rental Riches podcast, Tim sits down with Pierre, the CEO of Hospitable, a leading property management software that powers hundreds of thousands of properties across the globe. Pierre shares the story behind Hospitable’s founding, its incredible growth over the last nine years, and the unique challenges they’ve overcome to help property managers automate and streamline their operations.
- Origin Story of Hospitable
- From 0 to over $5B in reservation revenue
- AI vs. Human Touch in Hospitality
- Impact of Dynamic Pricing and Automation
- The Future of Property Management Software
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