Today we’d like to introduce you to JW Ray.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
JOLO Winery & Vineyards owner and winemaker JW Ray has built one of the most acclaimed winery destinations in the Southeast. Just last year, Tripadvisor recognized JOLO as one of the top seven wineries in the United States outside of California.
Prior to founding JOLO with his wife Kristen and their two sons, Joey and Logan — the namesake behind “JOLO” — JW spent decades building businesses across finance, technology, hospitality, and entrepreneurship. Twelve years ago, after the acquisition of Learn.com, the cloud-based human capital management company he co-founded in 2000 in Sunrise, Florida, JW and his family embraced the opportunity to reset and pursue a very different dream. Having long been captivated by the romance and legacy of multi-generational European wine families — stewards of both the land and their family reputation for generations, with every bottle and celebratory sip carrying the family name — they jumped at the chance to build something enduring of their own beneath the shadow of Pilot Mountain.
Before entering the wine industry, JW served as Founder and Managing Director of Backlog Capital, a venture debt fund focused on cloud-based software companies. Earlier in his career, he spent ten years with Merrill Lynch, Morgan Stanley, and in the mortgage banking industry. His entrepreneurial roots, however, trace back even further to hospitality, where he worked in hotels in Florida and Massachusetts and owned his own restaurant. JW also proudly served in the United States Army.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
As smooth as can be expected. We have a multi pronged business, farmers first, then a wine manufacturing business, then a tasting room/hospitality destination and a full scale restaurant. Each present their own challenges but that is what keeps it engaging, exciting and constantly challenging. This business is not for the faint of heart.
Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
At JOLO Winery & Vineyards, we’ve always believed wine should tell a story — not just of grapes and winemaking, but of place, family, hospitality, and time itself. What began as a dream for our family has grown into one of the most recognized winery destinations in the Southeast, yet at our core we still view ourselves as stewards of the land and caretakers of every guest experience.
We specialize in producing luxury, terroir-driven wines from the Yadkin Valley of North Carolina, with a focus on estate-grown fruit, minimal intervention winemaking, and creating wines that can stand proudly alongside respected producers anywhere in the country. Our portfolio ranges from elegant Bordeaux-style reds and sparkling wines to distinctive varietals such as Norton, which has become one of our signature expressions. Many of our wines have earned national recognition, including Double Golds, Best of Class awards, and high-90s scores in major competitions across the United States.
What truly sets us apart, however, is that JOLO is not simply a winery — it is an immersive hospitality experience. Long before I entered the wine business, I worked in restaurants, hotels, and hospitality, and that foundation shaped everything we built. From the moment guests drive onto the property beneath the backdrop of Pilot Mountain, every detail is intentionally designed to create a sense of escape, romance, and connection. Whether someone joins us for an elevated wine tasting, an alfresco lunch overlooking the vineyards, or one of our curated food and wine pairing experiences, we want them to feel transported.
Another thing that differentiates us is our sense of place. We are the only vineyard and winery located directly at the northern base of Pilot Mountain, and we lean heavily into the geological and historical uniqueness of the region. The soils, mineral composition, elevation, and ancient geological formations all contribute to wines that are unmistakably tied to this landscape. We are deeply passionate about expressing that terroir authentically in the bottle.
Brand-wise, what I am most proud of is that JOLO has remained family-centered and purpose-driven as we’ve grown. The winery itself is named after our two sons, Joey and Logan, and every bottle that leaves our cellar carries our family name and reputation with it. We were inspired early on by the great multi-generational wine families of Europe — families who spent decades and centuries building something meaningful for future generations — and we approached JOLO with that same philosophy from day one.
Ultimately, I want readers to know that we are incredibly serious about quality, but equally passionate about hospitality and creating memories. Wine is one of the oldest and most celebratory beverages in human history. It brings people together around tables, milestones, conversations, and experiences. We never lose sight of the privilege of being part of those moments for our guests.
What do you like best about our city? What do you like least?
One of the things I love most about the Pilot Mountain area is the incredible balance it offers between natural beauty, history, and accessibility. There is something truly special about waking up each morning beneath the shadow of Pilot Mountain and being surrounded by rolling vineyards, farmland, forests, and some of the most beautiful scenery in North Carolina. The area has a peaceful, bucolic quality that immediately slows people down and allows them to reconnect with nature, conversation, and one another.
I’m also deeply fascinated by the history and geology of the region. Pilot Mountain has served as a landmark for centuries — from Native American tribes to early settlers and travelers — and there is an incredible sense of permanence and story embedded in the landscape. As someone in the wine business, I’m naturally drawn to places where the land itself has identity and character, and this region certainly has that.
At the same time, what makes the area even more attractive is its proximity to larger cultural and business centers like Winston-Salem. Within a relatively short drive, you have access to an incredible arts scene, restaurants, music, innovation, healthcare, and business infrastructure, while still being able to return home to the quiet beauty and charm of wine country. I think that combination is rare and incredibly valuable.
If there is one challenge for the region, it is that many people outside of North Carolina still do not fully realize what exists here. The quality of the wineries, restaurants, hospitality experiences, outdoor recreation, and overall lifestyle in this area often surprises first-time visitors. In many ways, I think the region is still one of the Southeast’s best-kept secrets — although that is changing quickly.
Contact Info:
- Website: https://www.jolovineyards.com
