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.

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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