This is one outlet's own report from Business Insider — the article as it was filed.
AIPROPX ReportBusiness Insider · 55m ago
How one cult grocery chain is navigating the great boomer business handover
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Stew Leonard Jr. is greeted like a celebrity as he makes his way through his family's business. Known as Connecticut's " Disneyland of grocery stores ," Leonard's locations come complete with animatronics, petting zoos, and costumed mascots. Every few feet, a customer does a double-take and rushes over. Mostly, they want to say hello or ask for a selfie. A few have constructive criticism to share.
Over by the Stew Leonard's Farm Fresh Five, a band of singing milk cartons, a mom with two young kids approaches him. She has an idea to make the restrooms more family-friendly, showing a picture of a rest stop bathroom with child-sized toilets and superior design. Stew Jr. tells her to forward the picture to his team.
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Stew Jr. has been president of the small-but-mighty grocery empire since 1982, for 44 of the company's 57 years. He moves with the ease of a graduating senior walking their high school halls: He knows where everyone and everything is, and they know him. But Stew Jr. won't be the face of Stew's for much longer.
Walking with Stew Jr., but going mostly unrecognized, are his successors. His daughter, Blake Leonard, 41, will step in as president, and his nephew, Jake Tavello, 38, will take over as CEO. Blake is more likely to hop into photos with her father, while Jake — outfitted in a store uniform — more quietly hovers behind the lens.
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Stew Jr. has been the heart and soul of Stew Leonard's for decades — not only its president and CEO, but the literal continuation of its namesake and the person loyal customers know and trust. Blake and Jake will not only be taking over a quirky, beloved chain. They're hoping to become a case study in how family businesses can remain successful — and stay in the family — as they're passed down through generations .
It's a challenge familiar to millions of Americans. More than half of US business owners are over the age of 55, at a time when America is about to undergo a Silver Tsunami — a once-in-a-generation transfer of wealth . For family businesses, it's even more fraught, since the third generation is seen as the inflection point for a family business, with one famed research paper finding that 30% of firms make it to the second generation, 13% make it to the third, and just 3% to the fourth.
For Stew Leonard's, the transition is a delicate process, and the family has planned a meticulous handover spanning four years.
"I have devoted my life to this. I grew up here, literally, as a little kid," Stew Jr. said. "I would be devastated if the next generation didn't carry the torch."
Stew Leonard's is a Connecticut institution . A decade ago, this very publication proclaimed it the best grocery store in America, and its lore has only grown since. It's become a go-to destination for TikTokers. In 2024, it was featured on "The Bachelorette," when contestant Jeremy Simon tried to woo Jenn Tran , the titular bachelorette, by bringing her to the store during their visit to his hometown.
"I think there were probably a few people who thought it was kind of weird, like, 'Why would he take you to a grocery store?" Simon tells me when I reach him by phone. But fans responded that "this looks like the coolest grocery store ever — and they love the date," he says.
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Today, the chain has eight locations in Connecticut, New York, and New Jersey, and employs over 2,500 people. All stores are built around the same design concept, first dreamed up by Stew Leonard Sr.: a single, one-way aisle ( think: Ikea ) with the star of the show, the dairy section, arriving halfway through.
Disneyland was an inspiration when Stew Leonard Sr. founded the company, and there are still numerous references to be found. Workers dress up as Clover the Cow and Stewie the Duck (When I visited the flagship location in Norwalk, the store advertised character meet-and-greets with its own characters, as well as Paw Patrol and Disney favorites.) A life-size rendering of Stew Sr. in a dairy truck waves at shoppers as they enter the store, much like the iconic statue of Walt Disney and Mickey Mouse that greets visitors to the Magic Kingdom.
Roy de la Cruz for BI
But while Disney started as a family-run company under Walt and his brother Roy, it went public early in its history, and leadership moved beyond the family after the second generation. Stew Leonard's, which is privately owned and employs six third-generation family members — including three recent third-generation promotions — hopes to remain in the family's hands.
The first time Stew Leonard's was passed down, back in 1982, Stew Jr. wasn't given much of a choice. He remembers his father taking him out to the store's famed rock , etched with the company's ideals: "Rule 1: the customer is always right! Rule 2: If the customer is ever wrong, read rule 1." There, Stew Sr. had informed him that he was being named president of the family business.
Roy de la Cruz for BI
Never mind that Stew Jr., who was 27 and fresh out of business school at UCLA, had gone to California to get away. He was still considering a pivot to something like Microsoft or Apple. His father had decided on a different path. "Oh, by the way, congratulations," is how Stew Sr. framed the promotion that would rewrite the path of his son's life.
"I was like, 'Whoa, what? Wow, thanks," Stew Jr. tells me. "It wasn't like, 'Sit down, let's talk about your new compensation package. Or, here's your new duties that you're supposed to do.'"
Still, Stew Jr. took up the mantle and never looked back. He further professionalized the company's "chaotic and unorganized" culture and created the governance structure that undergirds the coming transition, mandating that Leonard family members aren't allowed to work for the company for at least two years after graduating from college.
Then, in 1991, Stew Sr. was arrested and later imprisoned for tax fraud in 1993. Stew Jr. told Westch...
RoyCruzBI Stew Leonard JrKnownConnecticut'sDisneylandLeonard'sEveryMostlyOverStew Leonard's Farm Fresh FiveStew's
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