STR Investing, The Podcast

STR Lessons From Surviving a Million Dollar COVID Loss

34 min · 22. touko 2026
jakson STR Lessons From Surviving a Million Dollar COVID Loss kansikuva

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What happens when a short-term rental operator loses over $1,000,000 during COVID? In this episode of the STR Investing Podcast, Mark Lumpkin sits down with Jason Baxter to talk about the highs, lows, and future of the short-term rental industry. Jason shares how he accidentally got started in Airbnb over 10 years ago, scaled to a portfolio of 50 lofts in Montreal, and then watched everything collapse during the COVID shutdowns in Canada. Facing bankruptcy, Jason rebuilt from the ground up by leaning into technology, automation, hospitality, and smarter booking strategies. In this episode, they dive into: * The early days of Airbnb automation * Surviving a million-dollar loss during COVID * The biggest mistakes STR hosts make with tech * Why hospitality still matters more than AI * How Airbnb algorithms really work * Pricing strategy and booking optimization * The future of direct bookings and alternative platforms * Why “short-term rentals are a long-term game” Jason also explains how the right positioning and strategy helped one property grow from $65,000/year to over $210,000/year in bookings. If you’re an STR investor, property manager, or host trying to scale smarter, this is an episode you don’t want to miss. __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

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126 jaksot

jakson 28 Years in the Hospitality Industry kansikuva

28 Years in the Hospitality Industry

What does it take to stay relevant in the short-term rental industry for nearly three decades? In this episode, Mark Lumpkin sits down with Michael St. Pierre, a hospitality veteran with 28 years of experience spanning vacation rentals, luxury resorts, revenue management, owner acquisition, and some of the industry's most recognized brands. Michael shares how he got started in the business, the lessons he learned from working in Hawaii and with Hyatt-affiliated properties, and why hospitality is still the foundation of long-term success in a rapidly changing industry. They also discuss: • What investors can learn from luxury hotel brands • Why relationships are one of the most valuable assets in business • The evolution of revenue management and dynamic pricing • How AI is changing the vacation rental landscape • The importance of building systems, standards, and memorable guest experiences • What the next generation of STR operators needs to focus on Whether you manage one property or hundreds, this conversation is packed with practical insights on hospitality, growth, and building a sustainable business in the vacation rental industry. Connect with Michael St. Pierre on LinkedIn to learn more about revenue management, owner acquisition, and the future of short-term rentals. 🎧 Listen now and be sure to subscribe for more STR Investing Podcast episodes. __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

19. kesä 202635 min
jakson Monday Market Data: Breakdown of Sevierville, TN Amenities Market kansikuva

Monday Market Data: Breakdown of Sevierville, TN Amenities Market

In this week's Monday Market Data Report, Mark Lumpkin breaks down one of the most competitive short-term rental markets in America: Sevierville. With more than 15 million annual visitors to the Great Smoky Mountains and over 13,000 active short-term rentals in the surrounding market, Sevierville has become the perfect example of the "Amenities Arms Race" that has transformed the STR industry. The data is eye-opening: • Hot Tubs → 94.8% of listings • Game Rooms → 77.8% • Fire Pits → 52% • Pools → 45% • Pool Tables → 50% These aren't luxury amenities anymore. They're the baseline. In this episode, Mark breaks down what amenities you need just to compete and which upgrades can still help you stand out from thousands of competing cabins. If you're investing in the Smokies, this episode is a masterclass in understanding what it takes to win in a mature STR market. Tune in for new Market Data Reports every Monday and expert guest interviews every Friday.

15. kesä 20267 min
jakson STR Tax Loophole with Ryan Carriere kansikuva

STR Tax Loophole with Ryan Carriere

Tax season just got a lot more interesting. In this episode, Mark Lumpkin sits down with CPA and real estate tax strategist Ryan Carriere to break down one of the most powerful tax strategies available to short-term rental investors today. Ryan explains how the return of 100% bonus depreciation under the One Big Beautiful Bill impacts investors, why the Short-Term Rental Tax Loophole remains a game changer for high-income earners, and the specific rules you must follow to qualify. They cover: • The return of 100% bonus depreciation and what it means for investors • How the Short-Term Rental Tax Loophole actually works • The 7-day average stay rule explained • Material participation requirements and common mistakes • How to track hours correctly for audit protection • Personal use rules that can destroy your tax benefits • Why most investors need a tax strategist, not just a tax preparer • Real-world examples of how investors can potentially save six figures in taxes If you're buying short-term rentals for cash flow, appreciation, and tax savings, this episode is essential listening. Connect with Ryan Carrier: Website: CarrierTaxConsulting.com [https://carrieretaxconsulting.com/] LinkedIn: Ryan Carrier, CPA [https://www.linkedin.com/in/ryancarriere/] YouTube: Ryan Carrier, CPA [https://www.youtube.com/@ryancarrierecpa] __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

12. kesä 202650 min
jakson Monday Market Data: Breakdown of Seattle, WA Market kansikuva

Monday Market Data: Breakdown of Seattle, WA Market

In this week’s Monday Market Data Report, Mark Lumpkin heads to the Pacific Northwest to break down the short-term rental market in Seattle, Washington. With more than 5,000 active listings, nearly 40 million annual visitors, and inventory growth exceeding 50% over the past few years, Seattle has become an increasingly competitive market for STR investors. But despite the growing competition, the data reveals something surprising: Seattle may be one of the least amenitized STR markets we've analyzed. In this episode, Mark covers: * Seattle's tourism demand and seasonality * The impact of corporate and mid-term rental travelers * Current STR regulations and licensing requirements * Why occupancy and revenue vary so dramatically across the market * The amenities that can instantly separate your property from the competition The takeaway? Unlike many markets where amenities have become standard, Seattle still offers tremendous opportunity for investors willing to create something unique. A simple hot tub and gym combination immediately puts you ahead of most of the competition, while a true "super property" would have virtually no competition at all. If you're considering investing in Seattle, this episode provides a roadmap for how to stand out in one of the country's fastest-growing STR markets. Subscribe for new Market Data Reports every Monday and expert guest interviews every Friday.

8. kesä 20267 min
jakson Dream Cleaning with the Dream Team kansikuva

Dream Cleaning with the Dream Team

A dirty property can ruin a guest experience before the vacation even begins. In this episode, Mark sits down with Logan, founder of Dream Clean Team, one of the largest vacation rental cleaning companies on Florida's Emerald Coast. Starting as a side hustle with his wife cleaning properties during summer break, Logan has grown the business into a full-service operation serving hundreds of short-term rentals across Northwest Florida. The conversation dives into one of the most overlooked parts of STR success: cleaning systems, guest readiness, and operational consistency. You'll learn: • The difference between a clean property and a guest-ready property  • Why laundry is often the biggest bottleneck in vacation rentals  • How professional operators scale cleaning across hundreds of properties  • The systems and SOPs that transformed a small side hustle into a major operation  • How cleaning impacts reviews, rankings, and repeat bookings  • Real stories of the wildest guest damage and turnover situations they've encountered  • How AI is helping streamline operations without replacing people If you're an STR owner, host, property manager, or investor, this episode will change the way you think about cleaning, guest experience, and operational excellence. __ Episode Sponsored By: STR Search STR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com [http://strsearch.com/]

5. kesä 202637 min