Chris and Matt Masiero, founders and operators of Guido’s Fresh Marketplace with locations in Pittsfield and Great Barrington, were celebrated Wednesday evening, September 12, at the Norman Rockwell Museum as the 2018 Business Persons of the Year by the Southern Berkshire Chamber of Commerce. When I sat down with them before the ceremony and told them that I shopped regularly at Guido’s, they immediately asked me, “Why? What is it about Guido’s that makes you want to come into the store and shop?”
As the festivities proceeded and speakers explored the secrets of the Masiero brothers’ success, I understood why they asked me those questions. “These guys never stop”, said Nate Winstanley, a lifelong friend of the brothers and a featured speaker at the event. “They focus on customer service and the customer experience. They are unflagging in the pursuit of excellence.”

And they are not about to slow down. As 2019 brings them to their 40th year in business, they announced two new projects:
- After Marguerite Gulick died in 2013, they bought her large and gracious home at 770 South Main Street, just south of the Guido’s Great Barrington store. Now they intend to renovate it. Still not clear is what they will do with it, but the fact that the house has a big, beautiful ballroom is certainly intriguing. Is Great Barrington about to have its first public dance hall? Stay tuned.
- And in March 2020, a complete renovation and expansion of the Great Barrington store will begin. “We will expand the store on the south end, toward where the solar panels are now, and the solar panels will provide all the electricity for the Guido’s operations there. We’re working with Chuck Bomely of Plan B Design in Connecticut, and we have great ideas and great plans,” the brothers told me.

These projects will be very expensive. “We will be spending a lot of money,” said Matt. The Masieros are consciously investing in their community. “What we are doing is important.” They are well aware that Guido’s has become a major player — and a major magnet — in the Southern Berkshires business community, and they feel strongly that their investment will make a difference to the local economy and to the quality of life here.
Nor should this concern for the community come as a surprise to anyone who knows the Masieros. With tears welling up in her eyes, Anna Masiero, daughter of Chris and his wife Dawn, talked about the principles that guide the two brothers: “Work hard. Family first. Help others. Be humble. And, eat really good food.”
And, as Anna described it, they really did work hard. The Masieros grew up in Manchester-by-the-Sea, on the northern coast of Massachusetts, where their father Guido taught school. But their mother Rena was from Lee, and the family came on weekends to visit with their Lee relatives while Guido worked as a ski instructor at Bousquet. In 1979, they had the idea to open a fruit stand on Route 7 south of Pittsfield where Berkshire Flower Co. now stands. They borrowed $2000 from their father to buy a truck. In 1981, they decided to open a year-round store. In 1982 they bought the land in Pittsfield, right next to the Price Chopper, and in 1984 they opened the Pittsfield Guido’s. And they looked around and recruited the best other people to join them. (“We don’t do this alone,” said Chris and Matt. “It’s great to work with partners like Mazzeo’s and the Marketplace Kitchen. These are high quality, owner-operated businesses. And we have built a family of people who work in the store and share our dedication to quality and customer service.”)

Anna described the long, grueling hours that Matt and Chris worked. Matt would start at midnight, drive to the Boston produce market, negotiate his way through the system of purveyors to acquire the best produce available at a price he could afford, load the heavy boxes of produce onto the truck himself and drive back to Pittsfield. Meanwhile, Chris started work at 4am to set up the displays so he could open the store in the morning. They worked 18-hour days, every day. And then, in 1995, as if the proximity to the Price Chopper wasn’t challenging enough, they bought land right next to the Big Y, and opened the Great Barrington store. (“These guys are risk-takers”, said Nate Winstanley.)
At some point in this process, Matt complained to his father, ”Dad, I don’t know if I can do this anymore.” “Don’t give up,” replied Guido. “It will get easier.” “Well, it did get easier,” said Matt in his acceptance remarks, “…30 years later, when it was no longer I who had to drive the truck to Boston.”
Anna talked also about how the brothers, despite the long hours, managed to find time to be loving members of an equally loving extended family. And their brother Paul Masiero, who owns and operates Baba Louie’s Pizza restaurants in Great Barrington and Hudson, N.Y., talked about the strength of that family’s bond, held together largely by their mother Rena, now well into her nineties but clearly adored by her children.

The festivities continued with the conferring of proclamations by both State Representative William “Smitty” Pignatelli and State Senator Adam Hinds, and with the presentation of the plaque by Emily Zelenovic, granddaughter of Mary White of Barnbrook Realty, the 2017 Business Person of the Year.
Finally, the brothers took the podium and effectively demonstrated one of the principles described by Anna: Be humble. They thanked their families, their employees, their friends and their community. They drew attention to the fact that the next generation of Masieros was already in place to run the business. And Chris concluded with the message that showed why they really got to the point of recognition as Business People of the Year: “Genuine success begins in small details executed in excellence.”