About Us
We’re not just names on a website, meet the Joes, the faces behind the stays, and the people you just might bump into at a launch party, winery, or your next favorite café.
Origin Story
The Joes didn’t begin as a business idea. It began as two neighbors, both named Joe, meeting by chance and discovering they saw the world in remarkably similar ways.
Joe R had recently purchased a former bed-and-breakfast down the road from the Farmhouse Inn. It was a property Joe B had admired for years but could never quite figure out how to make it work, so he reached out to meet the new owner. What he found was someone with a fresh perspective and a clever approach to transforming outdated B&Bs into thoughtful, design-forward, high-performing vacation rentals. They clicked immediately, two people who valued beautiful spaces, intentional travel, living well, and smart ideas that break the mold.
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Their friendship grew quickly. Through long talks, Joe R shared the bigger idea behind his midterm rental vision. After years spent traveling full-time, he wanted to build a portfolio of second homes that made extended stays easier and more comfortable for people like him. The concept was strong, but it wasn’t yet imagined as a lifestyle brand or a community.​
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That’s where Joe B saw the missing piece. With his background in luxury hospitality, he immediately recognized the audience this concept could serve and how to speak to them. He brought the brand vision, the guest perspective, and the idea that The Joes could be something more than a portfolio, it could be a curated, personality-rich experience rooted in belonging, connection, and living deeply in a place.
​​From that shared understanding, The Joes was born, a platform built on friendship, complementary strengths, and a desire to help people live, work, and travel a little better. And we named it The Joes because, in a world full of noise, we wanted something real. We’re just two Joes who value what you value and we built this for people who want something genuine.
Joe B.
Joe B has spent more than two decades shaping what meaningful hospitality feels like. With a degree in engineering and an early career in the industry, he developed a love of architecture and problem-solving long before he ever welcomed a guest. In his twenties, he took a gamble on a rundown collection of cottages in Sonoma County and, despite being told repeatedly that his ideas were too unconventional, transformed it into the Farmhouse Inn, one of the most celebrated boutique hotels in the country. His out-of-the-box thinking didn’t just work, it helped redefine what luxury in wine country could be.
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Over 20+ years of working with luxury travelers, Joe developed an instinct for what people want before they can articulate it themselves. Tens of thousands of guest interactions sharpened his ability to anticipate needs, create connection, and understand the subtle difference between a good stay and an unforgettable one. He also watched the market shift. Long before it became obvious, he saw that true luxury was moving beyond amenities toward authenticity, community, and experiences that felt personal. The idea of longer, more intentional stays resonated deeply with what he had been seeing for years.
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Joe is also a serial entrepreneur, having co-founded a successful wine brand, worked on multiple development projects throughout Sonoma County, and continued to co-operate his family’s vineyard, land his family has stewarded for five generations. Deeply connected to Sonoma, he’s often described as the unofficial mayor of the place, a natural connector who brings people together and uplifts the communities he cares about.
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Today, as CXO of The Joes, Joe brings a rare combination of hospitality expertise, creative vision, engineering-minded problem-solving, and an intuitive sense for human connection. He ensures that every home - every stay - carries the same warmth, authenticity, and thoughtful detail that have defined his entire career.
Joe R.
Joe R has spent much of his adult life in motion. As a young tech entrepreneur based in Washington, D.C., his work had him traveling constantly, and when he wasn’t traveling for business, he was exploring new places for pleasure. Between the two, he spent more nights away than at home. Somewhere in all those check-ins and late-night arrivals, he became a true student of travel, learning the subtle difference between a bed for the night and a place that makes you feel something.
As his company grew and success gave him the ability to work remotely, Joe set out on a thoughtful, sometimes meandering search for his forever home. He wanted a more connected, intentional lifestyle, one rooted in community and beauty, which ultimately led him to Healdsburg California. But along the way, he kept running into the same problem, finding beautiful, comfortably furnished homes for extended stays was far harder than it should have been. There was no real marketplace, no easy way to browse midterm homes, and no single place where great options lived. Instead, he found himself DM’ing hosts, messaging realtors, chasing Zillow listings, and piecing together month-long stays one awkward conversation at a time. He never anticipated how difficult it would be to find a place that simply felt good to live in for a few months. So, in classic Joe R fashion, he set out to solve the problem himself.
Joe brings a rare blend of curiosity, analytical clarity, and out-of-the-box thinking to The Joes, a technologist with the lived experience of someone who understands deeply what makes a home feel right for a month or more. Equal parts business-minded strategist and traveler fueled by genuine wanderlust, he’s uniquely wired to help lead a company built around living well, exploring thoughtfully, and making extended stays feel effortless.
Together, we’re building more than a platform, we’re creating a trusted community of travelers, hosts, and friends, and we can’t wait to welcome you into The Joes family!
