Jessica and Chris Zazo are Partners in Wine

The newlyweds' award-winning winemaking effort feeds their passion for the culinary arts and desire to serve the community

Jessica and Chris Zazo. Shot on location at Burn by Rocky Patel, Naples. Photography by Michael Caronchi
Shot on location at Burn by Rocky Patel, Naples. Photography by Michael Caronchi

For Naples residents and Napa Valley vintners Jessica and Chris Zazo, everything’s just wine and dandy. The newly minted Mr. and Mrs. tied the knot in November at a Napa Valley vineyard, capping off a year that saw their Hailstone Vineyards Proprietor’s Reserve Cabernet Sauvignon capture gold at the prestigious Texsom International Wine Awards in Dallas. 

The honor is just one of many earned by Hailstone during the past decade; however, one prize in particular stands out. In 2019, the winery’s 32 Degrees Sauvignon Blanc won best of show at the Rodeo Uncorked! International Wine Competition in Houston. Because the annual contest takes place in a state where everything is big, the award isn’t the customary gold medal. “It’s a giant belt buckle like the ones rodeo champions win,” Chris explains. 

Chris Zazo. Photography by Michael Caronchi
Chris Zazo

The unconventional trophy is perhaps a metaphor for the unconventional journey this passionate oenophile has traveled. Along the way, Chris made a fortuitous stop for a drink at The Continental one evening in the fall of 2018. There, he had a chance meeting with Jessica Stoots, a Naples Realtor. The couple soon became inseparable, and Chris proposed two years later during a vacation in Nantucket. They married late last year on the heels of their greatest success to date as winemakers. 

That either of the Zazos are in the wine business was an unexpected next step in their journey. He grew up on a 100-acre topsoil farm in Akron, Ohio. She’s a native of Cincinnati, Ohio, and an accomplished equestrian and horse trainer—and has been licensed for more than a decade by the United States Equestrian Federation as a judge for competitive show jumping. Though neither grew up aspiring to be in the wine business, their pastoral beginnings did hint at their proclivity for this kind of venture. 

“Being raised on a farm, I got a real good helping with hard work and learned the value of a dollar,” Chris says. His upbringing also inspired an entrepreneurial spirit, giving him the confidence to strike out on his own and take calculated risks. 

Jessica, Hailstone’s operations director, saw the limitations with her equestrian career. “I figured at some point I’m not going to be able to ride anymore, and I don’t want to get hurt,” she says. “This is the perfect back-up plan.” 

Chris and Jessica Zazo. Photography by Michael Caronchi

Chris attended The Ohio State University and sold insurance for a few years before seeking employment outside of his home state. He worked as a sales rep for a building-materials supplier in Dallas until a coworker convinced him to go to Florida to chase hailstorms and hurricanes. Chris jumped at the opportunity, bought a 45-foot “rock star” bus, and for two years traversed the storm belt drumming up restoration work for a roofing company, soon becoming its top salesman. 

The aftermath of Hurricane Katrina in 2005 opened his eyes to the unfortunate dark side of the storm restoration industry, ending his road career. “I saw a lot of scams being perpetrated by unscrupulous roofing contractors against people who had lost everything,” he says. 

Chris realized he could do things better and with greater integrity, so he returned to Dallas to start Aspenmark Roofing and Solar. The company experienced rapid expansion, and Inc. magazine named it one of the fastest-growing businesses in the United States for two years running in its Inc. 500 ranking. It was recently acquired by a nationwide network of restoration contractors, freeing up Chris’s time for other pursuits that spoke to his passions, as well as his desire to support the communities he lives in. 

Chris has had a lifelong interest in the culinary arts. He learned to cook from his grandmother and that experience grew an appreciation for wine, which led to a curiosity about winemaking. He founded Hailstone Vineyards in 2013 and immersed himself in the complexities of the business. “It was a massive leap of faith,” he says, recollecting the naysayers who told him he was out of his mind. “I was known as the crazy roofer who started a winery.”

Hailstone wines. Photography by Michael Caronchi

From Interest to Intention

Hailstone owns no vineyards, which allows the Zazos to source choice grape boutique vineyards—producing a small annual yield of just under 1,000 cases among its five hand-crafted varietals. Visitors to the Napa Valley can sample Hailstone wines at the Vintner’s Collective, a tasting room featuring vintages from some 20 local boutique wineries. The wines also are served at restaurants and country clubs in select markets in Florida, Texas, Colorado, and California.

Among Chris’s most memorable experiences in his new business was participating in culinary excursions with Darren McGrady—longtime personal chef to Queen Elizabeth II, Princess Diana, and other royals—pairing Hailstone wines with dishes served at Buckingham Palace. Another was showcasing his wines on a Rolls Royce–sponsored tour of private homes. “There I was, this farm boy from Akron, able to hold my own and talk about our wines,” he recalls. “I’d come a long way from people telling me I couldn’t do it.”

In Naples, the couple enjoys visiting some of their favorite local eateries, many of which pour Hailstone—including The Continental, Nosh on Naples Bay, Campiello Ristorante & Bar, Sea Salt, Bha! Bha! Persian Bistro, The French, Ocean Prime, Ruth’s Chris Steak House, Andre’s Steakhouse, Bleu Provence, Seventh South Craft Food + Drink, Del Mar, Cosmos Ristorante and Pizzeria,  Aqua Seafood & Steaks, and others. 

Jessica and Chris Zazo. Photography by Michael Caronchi

“Chris is extremely passionate about wine, and theirs is absolutely spectacular—one of the best around for a boutique winery,” says Gordon Stojkoski, owner of Aqua Seafood & Steaks, which carries all Hailstone varietals. 

The couple frequently travels between their homes in Naples and Yountville (a town of 3,500 in Napa Valley), promoting the Hailstone brand and supporting charitable causes important to them. “We have no children between us, so we’re able to be footloose and fancy free,” says Chris. Jessica adds, “Our dogs ground us.” 

These Neapolitans share their Lake Park home with rescue Ainsley, an 8-year-old female pit bull/chocolate Labrador mix, and a 1-year-old male Australian labradoodle, Dutton, named after the family on the hit television drama Yellowstone.

The devotion the Zazos have for their dogs has fostered their involvement with Humane Society Naples and inspired the development of Hailstone Hounds, a charity they plan to soon launch to promote the adoption of senior dogs. Additionally, Chris remains involved in a nonprofit he founded called Roof Angels, which provides roof repair and replacement assistance to low-income and uninsured homeowners in the Dallas-Fort Worth Metroplex. 

Through Hailstone Vineyards, the Zazos also support several other charities and events in Collier County as well as in Napa. Says Chris, “Our wine provides a means to lift ourselves and others and leave a legacy.”

Jessica and Chris Zazo own Hailstone Vineyards in Napa Valley. Their award-winning boutique wines are served at numerous establishments in Naples. Photography by Michael Caronchi
Jessica and Chris Zazo own Hailstone Vineyards in Napa Valley. Their award-winning boutique wines are served at numerous establishments in Naples.

Heard it Through the Grapevine

What’s in a name? Hailstone Vineyards founder Chris Zazo’s fascination with hailstorms, coupled with a desire to pay homage to what helped him achieve success in the roof-restoration industry, inspired the winery’s name.

All hail! Hailstone’s first wine, Impact Cabernet Sauvignon, is so named as it connotes the effect of hail on whatever it strikes. The Chardonnay is called Restoration, which is often needed after a hailstorm. Its Sauvignon Blanc is known as 32 Degrees, the temperature at which hail forms. The latest variety, a dry French-style rosé, is named Weather Dancer. 

Talk about the weather. In its 10 years, Hailstone’s harvest has been impacted by a hurricane and two wildfires. Fire is a particular bane for vintners—smoke clings to the skin of the grapes, tainting the fruit and rendering it unsuitable for winemaking.

Unexpected advantage. Drought years often produce the best vintages. Even though the grapes are starving for moisture and the yield is less, the flavor of the wine is more intense.

Perfect picking. The grapes used in Hailstone wines are harvested at sunrise when they are still cold and 20 percent plumper due to the increased moisture content.

Tempted to taste? Hailstone wines can be purchased here and select local restaurants. 

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