337. What Most Successful STR Investors Are Focussed on Today: From a 300+ Investor Meetup
Release Date: 04/28/2026
Short Term Rental Riches
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...
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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...
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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...
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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...
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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...
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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...
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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...
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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...
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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...
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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...
info_outlineFresh 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 revenue pacing and data tools to stay ahead of the market
• The real strategy behind direct bookings—and why social media drives demand
The STR game is evolving fast, but the opportunity is still massive for those who adapt. From smarter design to stronger branding and better data use, this episode shows what’s working now. If you’re serious about increasing revenue and staying competitive, this is one you don’t want to miss.
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