Last year (on December 19, 2022), The Berkshire Edge celebrated the beginning of the “baton pass” from founders Matt and Chris Masiero to the next generation (their children Luke, Nick, and Anna), as well as the re-opening of their beloved and greatly enhanced Great Barrington marketplace.
Almost exactly a year later, we again honor the two legendary entrepreneurs, who are crossing the finish line at the end of the year and officially beginning their well-earned retirement. With flags waving high, we join the crowd of local customers giving thanks for the bounty they’ve created and the years they’ve dedicated to serving the Berkshire community.
We also salute the next generation, who are perfectly poised to carry on their legacy. “Don’t worry shoppers, you will still see Chris and Matt’s faces in the stores!” Anna promises. “If something comes up, they said they will be a phone call away.”
While next week marks a turning point, the training process began long before. “[For} the past three years, our dads have lifted their workloads and put more responsibility on us kids,” Anna acknowledges. She adds, “We understand that Guido’s is their ‘baby’ and we haven’t taken this transition lightly. We are ready for this transition and are proud and grateful to keep Guido’s in the family.”
Here, reprinted from last December and offered with our gratitude to Matt and Chris, is their story:
Like the long-running Star Trek series, the Guido’s enterprise is introducing a new crew—its next generation—along with a new frontier of expanded space, design, and features in its Great Barrington location.
The homegrown grocery celebrated 40 years in business in 2019 and has been growing ever since (despite the pandemic and inflation). Suffice to say founders and owner/operators Matt and Chris Masiero have enjoyed an exceptionally long shelf life, with two flagship stores (Pittsfield and Great Barrington) and a name and reputation that have become synonymous with high quality, good value, deep passion, and strong community involvement. They are now training their children, Luke, Anna, and Nick, to guide the enterprise into the future.
From roadside stand to traditional marketplace
Guido’s is known, among other things, for its fresh produce—a nod to the Italian abbodanza concept upon which it is built and also how the brothers got their start.
The brothers Masiero and their five siblings were raised in Manchester by the Sea by their father, Guido (a gym teacher from New Jersey), and mother, Rena (from Lee), and made regular trips to the Berkshires to visit their mother’s side of the family and ski at Bousquet Mountain.
Drawing on a background in culinary arts and produce retail along with some construction experience, they started their own roadside produce stand on Route 7 in Pittsfield in 1979. They borrowed $2,500 to buy a truck and relied on their own passion and hard work (including 2 a.m. drives to Boston and back) to make it a success.
In 1983 they opened Guido’s Fresh Marketplace in Pittsfield, their first year-round store; the second store in Great Barrington opened in 1995. From the very beginning, the Masieros shared a deep commitment to making a difference in other people’s lives—those who shop at Guido’s and those who manage the departments and work the aisles. They credit their father with teaching them, ”The way you treat your staff is the way your customers will be treated.” They also led by example, considering no job beneath them and every task done with care. As Chris notes, “Your staff’s passion for your business is always directly related to yours.”
Guido’s prides itself on being an old-world marketplace that has developed organically through partnerships with local vendors. Bella Flora (owned by sister Annie and her husband Chris Whalen) and Mazzeo’s Meat and Seafood (owned by Mike, Mark, and Rudy Mazzeo) are longstanding tenants, while the Chef Shop is a more recent tenant, relocating here after Rob Navariono closed his store at the top of Railroad Street.
“Our tenants are great partners who bring in new customers for us just as we do for them,” Anna Masiero notes. With a host of departments—ranging from the expected (bakery, kitchen, produce, meat and seafood, cheese, grocery, and wine/beer/spirits) to the unexpected (pizza, cookbooks, gift baskets, wellness, bulk, and specialty items)—it may be easier to list what Guido’s doesn’t offer than what it doesn’t.
Young branches on the family tree
Some family history helps to understand the next generation. Matt and Tammy Masiero currently have two sons involved in the business. Luke, the older, began bagging groceries when he was 12, moving to produce in his high school years while also working summers at Baba Louie’s, owned by his uncle, Paul. “When I was younger, I didn’t really think I would go into the family business,” he admits. He fell in love with Colorado during his college years at Colorado University at Boulder and had no plans to come back.
After graduating with a communications degree, however, he tore his ACL, putting a pause on outdoor pursuits. It was while rehabbing at home post-knee surgery that he started doing accounting work for Guido’s. “Working with all these people I’ve always known, it hit me how special a place Guido’s was and how many people it impacted,” he recalls. “I saw the potential opportunity and how it could be meaningful work.” He began working for the family business full-time in 2012.
Anna, daughter of Chris and Dawn Masiero, took a similarly roundabout path into the family business. “I was a dance major at the Hartt School for Dance (University of Hartford) until my hips crashed,” she says, an outcome that prompted a transfer to UMass where she earned a sociology degree. She then spent a year in Los Angeles exploring holistic wellness and healing and had planned to return to L.A. in 2020 when COVID hit.
Spending the pandemic back in the Berkshires, she began coordinating the “curbside shopping” option Guido’s offered to customers who weren’t comfortable coming inside the store. “We had 75 orders a day, which required a lot of time on the phone with customers. It was wild,” she sighs, thinking back on the mask patrols and CDC mandates. Being short-staffed also meant family members pulled many 80- to 90-hour work weeks. The importance of the services they were providing to the community at such a critical time drew her in, however. “Before I knew it, we were starting the renovation.”
Luke’s younger brother Nick also began bagging groceries while he was at Monument Mountain High School. Having siblings and cousins working in the store made it a lot of fun, but he, too, left for college (attending Skidmore in Saratoga Springs) with no plans of ever returning to the family business. “I was an exercise science major,” he explains, “with every intention of becoming a physician’s assistant.” Following graduation he spent a year at a vineyard in Sonoma and then moved to Colorado, working in a restaurant in Frisco and as a snowboard instructor at Breckenridge Ski Resort.
When he moved back home temporarily, he was enticed by the opportunity to work with Luke and Anna, training as “the pizza guy” to work with Dane Luhmann (Guido’s pizza chef). “Being 23 at the time, and knowing I could go anywhere, it was a tough decision in terms of the social aspect, but I’m very happy I made the decision to stay,” he says.
All three emphasize that they would not be expected to join the family business. While their fathers expressed interest in seeing their legacy continue, they (wisely) let it happen organically rather than steering the process. There was deeply embedded inspiration for getting involved, however. “Our dads were sculpted at a young age to have strong values, including working hard, putting family first, helping others, and being humble. We were also raised with those values and taught to see ourselves as part of the team,” Anna states. To all who know them, it’s obvious Anna, Luke, and Nick are continuing the legacy, carrying those traits into their training as second-generation operators. “We’ve needed to learn everything we could from the ground up in each department before moving on to the next to develop that owner’s eye and full understanding of what is involved in running the store,” she explains.
COVID craziness and renovation delays
Between COVID angst, heavy drilling and excavating for the renovation, and inconveniences like closed restrooms, 2020 was a challenging time for Guido’s employees. Luckily, everyone stayed on. Guido’s never closed during the pandemic, apart from on Sundays, when they gave their workers much-needed time off and sanitized the entire store.
In fact, they were busier than ever with all of the newcomers (both people moving here from the city and second homeowners staying here for longer stints to isolate). They launched their “Guido’s to Go” service on March 16 of 2019, but as Anna quickly points out, “It took a year to get fully online with an efficient IT form and site.” Other challenges included supply chain issues that caused food shipments to get stuck in ports for months. “Things are starting to get back to normal in that regard,” Nick says with relief.
Plans for expanding the Great Barrington store were developing early on, but the renovations were delayed (like everything during the pandemic) and did not begin until November 2020. Adding 25,000 square feet of space, including lower-level offices and storage, and all of the restructuring that goes with it was no small feat. The work eventually got underway and proceeded as smoothly as possible in the new state of “open” timeframes with the help of Plan B Retail Designs Project Management, general contractor Betnr Engineering, and Construction Corp. of Pittsfield along with other local partners like Climate Heating and Cooling, Henry’s Electric, and Paul Murphy Plumbing. The first year involved a lot of work behind the scenes, mostly moving storage to rented refrigerator trailers, but now that the holidays are approaching, it’s beginning to look a lot like… time to celebrate.
Old traditions in a new footprint
“We are approaching 300 employees (34 new hires just since the renovation). We’re nothing without them,” Anna says, adding, “It’s important to our dads to try to know everyone’s name and something about them, which is incredibly helpful when an employee needs a little leeway to deal with something personal.”
Ultimately, the secret to Guido’s incredibly loyal employee base (see their Instagram account for daily spotlights on individual and group efforts) is that the Masiero family works hard alongside their employees, pays them well, and treats them like family. With 250 local farmers and food crafters as partners within a 150-mile radius, Guido’s dedication to supporting the surrounding community is also a top priority.
“It’s been a pretty hectic last two to three years,” Anna, Luke, and Nick all agree, involving sweat equity, wearing multiple hats, and engrossing themselves in the different departments throughout the renovations. Their dads have been heavily involved in big decisions related to the renovation, allowing the three to be more focused on day-to-day management. Although they’re working on a succession plan, a transition date has yet to be set. “We still have so much to learn from them,” Anna admits, “and they still love coming in every day. I don’t think any family member will ever pull away completely.”
With its characteristic handwritten chalkboard signs, welcoming atmosphere, and open-market feel, Guido’s continues to distinguish itself from big box chains. Chris, who loves woodworking, makes many store fixtures himself (including wine racks, bookshelves, and conference tables) while Matt scouts new ideas. “They’re both Renaissance men in their own ways,” Anna says. “When they have their mind set on something, they’re determined to do it the best way.”
What truly sets Guido’s apart in the region, however, is its ability to import specialty foods. Luke’s and Nick’s faces light up when asked about their recent trip to Italy to introduce them to Guido’s European business partners. Tom Burger oversees the importing program and has longstanding relationships with their partners in Italy, but it was time for the next generation to establish their own ties. So the Masiero youngers toured the aging cave at Busti Cheese Company; visited Pasta Cuomo (now doing private labeling for Guido’s) to see how wind is collected off the mountains; and met with second-generation operators of the D’acunzi Brothers, whose La Carmela brand is known worldwide.
Those close encounters inform La Grotta, Guido’s cheese shop, which features an expanded selection of directly imported European cheeses and their own freshly made mozzarella, as well as Guido’s specialty foods shop—meaning even unseasoned cooks can prepare a delicioso meal come in Italia.
Other enhancements include a demo kitchen (with samples!), an expanded wellness department (with a consultant), and an even greater selection of prepared foods.
A promising future
What excites the next generation most about the renovation project? For Anna, a highlight has been designing Café Rena, named after their grandmother. “The goal is for customers to get a beautiful meal and feel inspired and welcome, taking the Guido’s experience to the next level with a cozy fireplace and vibe.”
For Nick, it might be the hot bar, pizza bar, or burrito bar—each featuring well-known creations by executive chef Bob Turner.
And for Luke? “It’s got to be the bakery department and the homemade croissants, macarons, and baguettes.”
They all acknowledge that the broader aisles and additional parking spaces of the more-than-doubled store footprint will make shopping much easier. That said, they admit it may take a few visits for the “loyal locals” to get used to the new layout.
For employees like Natural Foods Manager Cam Pease, the renovations mean their daily role takes on more breadth. Previously counting 21 department managers, the restructuring will consolidate those departments and place them under the supervision of eight category buyers. It will also increase consistency between the Pittsfield and Great Barrington stores. “We’ve asked a lot from our staff over the past two years—moving departments more than once, resetting the shelves in the late hours, dealing with drilling and construction,” Anna acknowledges gratefully. “They’ve always stepped up to the plate.”
