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Art of Business: Q&A with Jennifer Grimes of Red Cottage 

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Before there was AirBnB, before the region started racking up "coolest town" awards, Jennifer Grimes was brokering brief stays in magazine-worthy Catskills properties to eager visitors; 11 years later, Architectural Digest drools over her portfolio ("5 Reasons Why We Want To Try Red Cottage," April 2016.) We asked her for the story.

In 2005, you were a self-admitted real estate novice who barely knew a hamlet from a town; two years later, you were founding Red Cottage. What inspired you?

Red Cottage is more lodging than real estate, but frankly I knew nothing about either when I took a stab at renting my weekend pad (a little red cottage!) on Craigslist in 2007. I had some luck, guests were having a ball, so my neighbors started asking me to rent their houses too. When I was canned from Wall Street, I was available to turn this into a proper business. As the financial markets tanked, more people started traveling locally, while homeowners started panicking about carrying two mortgages and were asking us to set up their wonderful Upstate homes as rentals. So the recession is really responsible for Red Cottage's success.

How do you locate the properties?

We've never solicited homeowners, they've all approached us, often through word of mouth from other homeowners, which is wonderfully validating. We on-board about 10 percent of the properties and you can always tell when photos of a winner land in the inbox, because we all gather round the computer and ooh and aah over them. That's what you want in a vacation, right? Something out of your routine that makes your heart race a little. Perhaps that's something sleek with modern furnishings, or a rural farmhouse with a bright kitchen and big dining table. The portfolio originated in Claryville and fanned out through Sullivan and Ulster Counties. Now we have some dreamy listings over the river in Hudson, a town I'll use any excuse to visit. The other part of our secret sauce is that I have a real estate brokerage, Country House Realty, and we can advise buyers which houses are particularly rentable.

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