727 SE Locust St, Dundee, OR from Ruum Media on Vimeo.

The Cloud Wine Cottage

Last summer Michelle and I bought a home in Oregon to use as a short-term rental. After a leaseback with the owners, a few months to set it up, and a few more months working through licensing with the city, we’ve now officially begun to rent it.

The Cloud Wine Cottage is officially a thing.

It has four bedrooms and two and a half bathrooms. We’ve always been surprised how many rental homes have queen-sized beds. Not this one. We’ve got a California king in the main bedroom, king beds in bedrooms two and three, and two bunk beds in the fourth room. This allows us to comfortably stay there with our family of seven (which is not an easy thing to find) as well as host ten people at a time.

It’s in the heart of Oregon wine country, one of my absolute favorite places ever. Not only does this area showcase the beauty of the PNW, but it also wows you with more than 600+ wineries within a short driving distance. Not to mention that a handful of wineries are in WALKING distance from our home.

It’s become a really fun project for Michelle and me to do together. I really enjoy the software and automation involved in setting all the systems up and getting the details dialed in. She is amazing at creating a killer vibe for the house and helping to think like a concierge for our guests.

We’ve decided to manage it ourselves as this is something we want to pursue more of in the future. That’s why we’ve also created an umbrella entity called JStays (click here to check out our Instagram). The learning curve is steep but I’m thoroughly enjoying it. As I near my 40s the idea of creating passive income to leverage my time for the things that matter most to me is increasingly appealing.

In my head, I primarily imagined groups of people eager to enjoy Oregon wine (which is second in the US only to California). We’ve had a few of those bookings, but we’ve also booked a group coming for a family funeral, another group celebrating a kid’s graduation from George Fox University, and we’re currently booked for a ten-day business trip for a team of guys. And we’ve only been doing this for a couple of weeks. Basically, we get to help facilitate important life events for others.

It’s been a fun reminder that we don’t have to follow any script in life. We can keep growing and trying new things and reinventing ourselves. Curiosity is a heck of a driver.

If you’re interested, you can book the home through us directly (rather than using a rental platform) and avoid the fees involved. Click here to check it out and we’d love for you to pass it on to someone who may be interested.

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Jeremy Jernigan

Speaker | Author | Founder of Communion Wine Co. https://linktr.ee/JeremyJernigan