How one cult grocery chain is navigating the great boomer business handover

Stew Leonard Jr. is greeted for illustration a personage arsenic he makes his measurement done his family's business. Known arsenic Connecticut's "Disneyland of market stores," Leonard's locations travel complete pinch animatronics, petting zoos, and costumed mascots. Every fewer feet, a customer does a double-take and rushes over. Mostly, they want to opportunity hullo aliases inquire for a selfie. A fewer person constructive disapproval to share.

Over by the Stew Leonard's Farm Fresh Five, a set of singing beverage cartons, a mom pinch 2 young kids approaches him. She has an thought to make the restrooms much family-friendly, showing a image of a remainder extremity bath pinch child-sized toilets and superior design. Stew Jr. tells her to guardant the image to his team.

Stew Jr. has been president of the small-but-mighty market empire since 1982, for 44 of the company's 57 years. He moves pinch the easiness of a graduating elder stepping their precocious schoolhouse halls: He knows wherever everyone and everything is, and they cognize him. But Stew Jr. won't beryllium the look of Stew's for overmuch longer.

Walking pinch Stew Jr., but going mostly unrecognized, are his successors. His daughter, Blake Leonard, 41, will measurement successful arsenic president, and his nephew, Jake Tavello, 38, will return complete arsenic CEO. Blake is much apt to hop into photos pinch her father, while Jake — outfitted successful a shop azygous — much softly hovers down the lens.

Stew Jr. has been the bosom and psyche of Stew Leonard's for decades — not only its president and CEO, but the literal continuation of its namesake and the personification loyal customers cognize and trust. Blake and Jake will not only beryllium taking complete a quirky, beloved chain. They're hoping to go a lawsuit study successful really family businesses tin remain successful — and enactment successful the family — arsenic they're passed down done generations.

It's a situation acquainted to millions of Americans. More than half of US business owners are complete the property of 55, astatine a clip erstwhile America is astir to undergo a Silver Tsunami — a once-in-a-generation transfer of wealth. For family businesses, it's moreover much fraught, since the 3rd procreation is seen arsenic the inflection constituent for a family business, pinch 1 famed investigation insubstantial uncovering that 30% of firms make it to the 2nd generation, 13% make it to the third, and conscionable 3% to the fourth.

For Stew Leonard's, the transition is simply a delicate process, and the family has planned a meticulous handover spanning 4 years.

"I person devoted my life to this. I grew up here, literally, arsenic a small kid," Stew Jr. said. "I would beryllium devastated if the adjacent procreation didn't transportation the torch."

Stew Leonard's is a Connecticut institution. A decade ago, this very publication proclaimed it the champion market store successful America, and its lore has only grown since. It's go a go-to destination for TikTokers. In 2024, it was featured connected "The Bachelorette," erstwhile contestant Jeremy Simon tried to woo Jenn Tran, the titular bachelorette, by bringing her to the shop during their sojourn to his hometown.

"I deliberation location were astir apt a fewer group who thought it was benignant of weird, like, 'Why would he return you to a market store?" Simon tells maine erstwhile I scope him by phone. But fans responded that "this looks for illustration the coolest market shop ever — and they emotion the date," he says.

Today, the concatenation has 8 locations successful Connecticut, New York, and New Jersey, and employs complete 2,500 people. All stores are built astir the aforesaid creation concept, first dreamed up by Stew Leonard Sr.: a single, one-way aisle (think: Ikea) pinch the prima of the show, the dairy section, arriving halfway through.

Disneyland was an inspiration erstwhile Stew Leonard Sr. founded the company, and location are still galore references to beryllium found. Workers dress up arsenic Clover the Cow and Stewie the Duck (When I visited the flagship location successful Norwalk, the shop advertised characteristic meet-and-greets pinch its ain characters, arsenic good arsenic Paw Patrol and Disney favorites.) A life-size rendering of Stew Sr. successful a dairy motortruck waves astatine shoppers arsenic they participate the store, overmuch for illustration the iconic statue of Walt Disney and Mickey Mouse that greets visitors to the Magic Kingdom.

But while Disney started arsenic a family-run institution nether Walt and his relative Roy, it went nationalist early successful its history, and activity moved beyond the family aft the 2nd generation. Stew Leonard's, which is privately owned and employs six third-generation family members — including three caller third-generation promotions — hopes to stay successful the family's hands.

The first clip Stew Leonard's was passed down, backmost successful 1982, Stew Jr. wasn't fixed overmuch of a choice. He remembers his begetter taking him retired to the store's famed rock, etched pinch the company's ideals: "Rule 1: the customer is ever right! Rule 2: If the customer is ever wrong, publication norm 1." There, Stew Sr. had informed him that he was being named president of the family business.

Never mind that Stew Jr., who was 27 and caller retired of business schoolhouse astatine UCLA, had gone to California to get away. He was still considering a pivot to thing for illustration Microsoft aliases Apple. His begetter had decided connected a different path. "Oh, by the way, congratulations," is really Stew Sr. framed the promotion that would rewrite the way 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 astir your caller compensation package. Or, here's your caller duties that you're expected to do.'"

Still, Stew Jr. took up the mantle and ne'er looked back. He further professionalized the company's "chaotic and unorganized" civilization and created the governance building that undergirds the coming transition, mandating that Leonard family members aren't allowed to activity for the institution for astatine slightest 2 years aft graduating from college.

Then, successful 1991, Stew Sr. was arrested and later imprisoned for taxation fraud successful 1993. Stew Jr. told Westchester Magazine successful 2015 he remembered erstwhile he received the telephone that IRS agents had arrived astatine the Norwalk location, "it was for illustration erstwhile JFK was shot, you retrieve precisely what you were doing." With his begetter successful prison, Stew Jr. was thrust into the domiciled of CEO. Despite the upheaval, he's opened six caller locations, including immoderate successful (gasp) New Jersey. It's difficult to show precisely really overmuch the market empire has raked successful — Stew Leonard's isn't a publically traded institution — but the Hartford Business Journal reported that gross was $116 cardinal successful 1991. Per the store's PR, gross now sits astir $550 million. And, erstwhile it came clip for him to retire, Stew Jr. was wished to do better.

Alejandro Cárdenas Villa, a family-enterprise lawyer and the writer of "Legacy Traps: Why Family Businesses Fail And How To Protect Yours," said that family businesses person 5 circumstantial make-or-break risks to relationship for. They request to beryllium capable to constructively reside conflict, found governance structures and nonsubjective capacity measures, guarantee that family members are not limited connected the business, and that those who are really progressive are trained to understand the business. At slightest immoderate of those considerations look to beryllium apical of mind successful Stew Jr.'s slow stepping away.

"It's astir apt the hardest point to person your kids activity for you because connected 1 manus you want to enactment for illustration a dada to them, but connected the different hand, you person to beryllium a boss," Stew Jr. said. He says you ne'er want to unit your kid aliases family backmost into the family business. Ideally, you want to coming it arsenic location breathtaking for them to land.

His different difficulty: letting go.

"I conscionable really want to ne'er spell away," he says, "I don't deliberation I'll spell away, but I person to fto the leash out."

Blake, the oldest of Stew Jr.'s 4 daughters — Stew Leonard III, her brother, drowned arsenic a mini kid — was ne'er told outright that the stores would beryllium her future. Instead, they were omnipresent. Life arsenic a kid was shaped by visits to the shop and the stories her begetter would bring location from work.

Playdates pinch friends would see dressing up successful cattle aliases duck costumes. During sleepovers connected the level supra the store, Blake and her friends would beryllium awoken astatine 4:30 successful the greeting by the dulcet tunes of Cindy Celery and Larry Lettuce, animatronics perched complete the nutrient section. At the property of five, Blake was put to activity putting sprinkles on crystal pick cones.

If the business had been little tactile, Blake isn't judge she'd beryllium arsenic passionate. But the market stores were a special, beingness place. That didn't mean Stew's felt pre-ordained. As she sewage older, Blake's liking turned to wine.

After college, she spent a decade moving her measurement up successful the vino industry, becoming a certified sommelier and moving successful New York City and California. As her profession progressed, she didn't cognize whether she would extremity up backmost astatine the family business. And starting astatine the bottommost built confidence; successful her first vino role, she wheeled deliveries to clients, waking up astatine 4 a.m. to particulate disconnected bottles and coordinate deliveries. Nobody location knew what Stew Leonard's was. Blake lived successful Napa, moving for a winery, and went to New York City to waste vino and do a yearlong programme astatine the Culinary Institute of America. Toward the extremity of her clip successful wine, she knew she wanted to caput backmost home.

"I saw if I came backmost here, I wasn't going to leave," Blake says. "And truthful for me, location was conscionable that infinitesimal wherever I was like, 'Okay, I would emotion to — and I deliberation I'm ready.'"

Tavello first came to the shop successful utero erstwhile his mom was pregnant, and spent beautiful overmuch each summertime moving location arsenic a teen. After college, he spent two years moving astatine a rival chain, Wegman's, which is besides 1 of the largest and astir successful family-owned supermarket chains successful the US. (The Leonard family considers the Wegmans' friends, or, astatine the very least, comrades successful keeping the family market business live and robust.) He returned to Stew's successful 2015 to tally the Danbury store.

Tavello described it arsenic an workout successful trust: He felt for illustration he was stepping connected eggshells astatine first, managing workers who had been location for upward of 30 years (he was successful his 20s astatine the time).

"Over time, they sewage to spot that connected my thrust home, I wasn't calling Stew, and they could spot me," Tavello says. Throughout our clip successful the store, Tavello is the consummate polite salesperson — pointing retired trendier items for illustration pickle-everything and the butter-covered soft serve. His favourite conception of the shop was the fresh mozzarella.

Part of the caller generation's situation will beryllium maintaining and updating immoderate of the brand's campiness — thing that looms ample for some the parents bringing their kids successful for entertainment, and for the nostalgic TikTok generation.

"When I bring my kids done Stew's, the aforesaid nonstop things that I loved complete 30 years agone erstwhile I was a kid are the things my kids coming are loving," Blake says. She adds, "I deliberation that we'll support evolving, but we really want to support the bosom and psyche and what you get truthful excited astir pinch Stew Leonard's the same."

Tavello says that he was inspired by a sojourn to Sesame Place pinch his children, who eagerly watched a characteristic parade featuring Elmo. Now, Stew's has its ain characteristic parade.

Still, moving for your dada aliases uncle isn't each cocoa beverage and pome cider doughnut holes.

Blake Leonard's first capacity reappraisal pinch her dada didn't spell great. She sensed he was tired. He made immoderate adjacent points, but was much blunt than he needed to be.

"He walked in, and I could conscionable show that he was tired," Blake said. "Because I'm his daughter, he could astir apt little his benignant of barriers, not beryllium arsenic immoderate he wanted to beryllium to maine that day."

It was the type of acquisition that you whitethorn want to telephone your dada to kick astir — if they weren't the 1 giving you the reliable talk successful the first place. After taking immoderate clip to process it, Blake thanked him for the honorable feedback, though she said his points could person been delivered differently. Stew Jr. says he was a "little tough" connected her, but that his extremity was to amended connected the measurement his ain dada had handled specified moments. "I had him extremity doing it because he would springiness maine each 10s," Stew Jr. says. He had to say: "Dad, it's not helpful."

It goes some ways. He's asked Blake and Jake to reappraisal him… he's still waiting for their feedback.

Blake says this 2nd modulation is being handled overmuch much intentionally than the first. If her grandfather's procreation figured it retired arsenic they went, pinch her begetter astatine the helm, galore much guardrails person been put successful place. "I don't emotion to telephone them that, but it gave america a small spot of a model for our future," Blake says.

Part of that readying is splitting Stew Jr.'s occupation successful two.

The family says that the divided domiciled is playing to each of the dual heirs' respective strengths: Blake is much outgoing, while Jake is much operationally minded.

I asked Blake if she thought stopping for pictures and receiving the adoring public would autumn to her aft Stew Jr. phases out. She says she thinks so. It's portion of the tricky balancing enactment that the Leonard family has to toe. It's not conscionable a familial succession — it's an research successful incorporating a community, and almost cultlike following, into what's usually litigated successful boardrooms and family roundtables.

Jennifer Strom, an advisor astatine the Family Business Consulting Group who useful pinch the Leonards, says the institution is amended positioned than astir to upwind the transition. Stew Leonard's civilization is "pretty overmuch incomparable" to that of immoderate different family Strom has worked with, she says. Their adjacent procreation is engaged, the marque is strong, and their chair is deep. Even if they don't work together connected everything, they're consenting to travel to the table. Blake says that the full Leonard clan gets together astatine slightest erstwhile a twelvemonth to talk the business. As third-generation-ers — aliases G3, successful the business-school parlance — Blake and Jake's journeys bespeak an inflection constituent for Stew's.

By the clip a family business reaches its 3rd generation, it has to equilibrium some its original extremity of building a successful business and a much intentional attack toward the larger bequest that's accumulated complete time. It's the leap from haphazardly announcing to your kid that they're going to return complete to creating an soul governance system that tin equilibrium analyzable family dynamics.

"We are very intentional astir not ignoring the family dynamics and really calling them out," Strom says of the conversations she has pinch clients. "So immoderate past resentments that exist, we get retired connected the array and say, 'Okay, contempt that, what do we work together to? And what do we want to group up for the future?'"

That's portion of the particularly sticky quality of crafting a family succession plan. It's 1 point to occurrence a debased performer; it's different erstwhile that personification is related to you.

Strom says she's seen chairs knocked down, pens thrown, screaming, and declarations that family members will ne'er speak to 1 different again. Emotions aren't inherently bad — Strom is besides trained arsenic a therapist — they show erstwhile families are getting to the issues they really do request to activity retired astatine the table. And location are moments erstwhile families are fighting truthful much, and not happy, aliases consciousness stuck, that Strom will beryllium down pinch them and inquire if they really want to support the business going.

Sitting crossed from Stew Jr. successful his agency — Blake and Jake yet joining america astir the array — I was struck by really engaged he still is successful the business. For one, he's done his homework connected maine and moreover quotes from a fewer of my erstwhile articles. I announcement a printout connected his table pinch my headshot and a fewer paragraphs summarizing my work. It's the benignant of reception I expect from a Fortune 500 CEO.

Stew Jr. is besides heavy successful the weeds astir the day-to-day business, and astatine 1 constituent ticks disconnected really different products were faring connected TikTok. When I inquire him if he personally uses the app, he points maine to his heirs evident and a PR person. Both Blake and Jake person an online presence, truthful this is possibly an area wherever the younger procreation mightiness person a limb up.

Stew Jr. has a fewer much years near astatine the helm, and he intelligibly takes pridefulness successful knowing and greeting everyone we brushwood while moving connected the floor. He often stops to stock workers' life stories pinch me. He talked astir really the institution has brought successful a slew of immigrants (some of whom we met passim our stroll) and has fixed those workers training, pay, and beardown benefits. It's, arsenic Stew Jr. says, "really, the American dream" — difficult workers starting connected the crushed level and moving their measurement up.

The American dream, societal media dominance, and a family legacy: All of that is simply a lofty edict to spot upon the shoulders of Blake and Jake, who are preparing to balance the stewardship of a beloved marque pinch making their ain marks.

After our circuit wraps up, Stew Jr. has to tally to a CNN news deed to discuss really tariffs are affecting tomato prices. On the measurement retired of his office, Blake and Jake commencement meandering ahead, making their measurement backmost to the income floor. As I locomotion retired pinch Stew Jr., our photographer stops and asks to return a image of him nether his office's sign, which proclaims "Stew Leonard Jr. - President."

"I conjecture that's an aged sign, isn't it?" Stew Jr. says.

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