Stew Leonard’s succession plan is taking shape across four carefully choreographed years, as Stew Leonard Jr. prepares to hand the keys of Connecticut’s self-styled ‘Disneyland of grocery stores’ to his daughter Blake Leonard and his nephew Jake Tavello. The transition, still in progress, will split a job Stew Jr. has held since 1982 between two third-generation family members who grew up inside the brand before leaving it, and who have now come back to carry it forward.
Blake, 41, will become president; Jake, 38, will take the CEO role. The division is deliberate. The family describes Blake as more outward-facing and Jake as operationally minded, a structure designed to replace what one person has held for more than four decades.
A Chain Built on a Single Aisle and an Unusual Bet
Stew Leonard’s is a genuinely unusual business. Its eight locations across Connecticut, New York, and New Jersey are built around a single one-way aisle, inspired by Ikea, with the dairy section arriving halfway through rather than at the perimeter. The chain stocks only around 2,200 products, far fewer than a conventional supermarket, chosen specifically for freshness and value, as Business Insider noted when it named Stew Leonard’s the best grocery store in America in 2015. Animatronics, petting zoos, costumed mascots, and character meet-and-greets fill the space between the shelves.
The business employs more than 2,500 people. Annual revenue is reported at ‘more than $500 million’ on the company’s own website, though the store’s public-relations team has cited a figure closer to $550 million. The Hartford Business Journal reported revenue of $116 million back in 1991, the year Stew Jr. was thrust into the CEO role after his father’s arrest.
The chain’s record stretches further. According to data compiled by LeadIQ, Stew Leonard’s held a 1992 Guinness World Record for the greatest sales per unit area of any single food store in the United States, and spent ten years on Fortune magazine’s 100 Best Companies to Work For list.
The Tax Fraud That Reshaped Stew Leonard’s Succession Plan
The first handover, in 1982, was abrupt. Stew Jr., then 27 and fresh from business school at UCLA, was informed by his father at the store’s famed rock, etched with the company’s customer-service credo, that he was being named president. ‘Oh, by the way, congratulations,’ was how Stew Sr. put it.
The second shock came a decade later. In 1991, IRS agents arrived at the Norwalk store. Stew Leonard Sr. was arrested and, in a July 1993 plea bargain, pleaded guilty to one count of income tax fraud, agreeing to pay $15 million in taxes and penalties and a $650,000 fine, according to Supermarket News. The Hartford Courant, citing court records, reported that Stew Sr. had skimmed $17 million and was sentenced to 52 months in prison. The federal appellate court confirmed that sentence, followed by 36 months of supervised release, in a ruling available through Justia.
With his father imprisoned, Stew Jr. became CEO by necessity rather than design. He has since opened six new locations and professionalised what he describes as a once ‘chaotic and unorganised’ internal culture, including a rule that Leonard family members must work outside the company for at least two years after graduating from college before they can join.
That rule shaped both heirs. Blake spent a decade in the wine industry, becoming a certified sommelier and working in Napa and New York City before deciding to return. Jake spent time at Wegmans, one of the largest family-owned supermarket chains in the United States, before coming back to run the Stew Leonard’s Danbury store in 2015.
Why the Third Generation Is the Hard Part
The statistics on family-business longevity are not encouraging. Research by John Ward of Northwestern University’s Kellogg School of Management, published in 1987 and based on a study of 200 Illinois manufacturers, found that 30% of family firms survive to the second generation, 13% to the third, and just 3% to the fourth, according to the Family Business Consulting Group. Blake and Jake are the third generation at Stew Leonard’s.
Jennifer Strom, an adviser at the Family Business Consulting Group who works with the Leonards, says the company is better placed than most. Its next generation is engaged, the brand is strong, and the family bench runs deep. Even so, Strom describes the work as getting unresolved tensions onto the table: ‘We are very intentional about not ignoring the family dynamics and actually calling them out. So any past resentments that exist, we get out on the table and say, “Okay, despite that, what do we agree to? And what do we want to set up for the future?”‘
Blake’s first performance review with her father did not go smoothly. She felt he was tired and more blunt than the situation called for. ‘He walked in, and I could just tell that he was tired,’ she said. ‘Because I’m his daughter, he could probably lower his kind of barriers.’ She eventually thanked him for the feedback while telling him the delivery could have been better. Stew Jr. acknowledged he was ‘a little tough’ on her.
He has since asked both Blake and Jake to review him. He is still waiting for their feedback.
More than half of US business owners are now over 55, and a generational transfer of business ownership is under way across the country. For the Leonards, the question is whether the brand’s particular mixture of nostalgia, community identity, and operational discipline can be institutionalised without losing what makes it feel personal. Stew Jr. is due to remain at the helm for a few more years. When the sign outside his office is eventually changed, Blake and Jake will need to be the ones the selfie-seekers recognise.