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Latest / SmartStay Show - Short Term Rental Counsel | Airbnb Hosting Tips

How a Tech Sales Guy Built an Airbnb Business on Cape Cod (Unfiltered) | Matt Cutler

Ever wondered what it really takes to leave your 9–5 and build a successful short-term rental business on Cape Cod? 🌊🏡

In this episode, we sit down with Matt Cutler, who made the bold leap from a traditional W2 career to creating a thriving STR operation in one of New England’s most iconic vacation destinations. Matt pulls back the curtain on the emotional and financial realities of leaving corporate life, what it’s like to manage properties in a seasonal market, and why guest experience is everything. He also shares how he builds strong relationships with property owners, attracts repeat…

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