Hartford Business Journal

10 HARTFORDBUSINESS.COM | DECEMBER 15, 2025 On The Record | Q&A Stew Leonard Jr., president and CEO of Stew Leonard's grocery stores, stands in one of the company's eight locations. Contributed Photo Family Transition Stew Leonard Jr. eyes CEO hand off after 34 years guiding regional grocery chain advises companies on succession. Andrews said the Leonard family's process — which includes outside work experience, education requirements and defined pathways into management — appears more structured than most. "I think they're very sophisticated in the sense that they're not going to put someone in as CEO that can't do the job," Andrews said, noting that he doesn't know the family personally. Speaking generally, Andrews said succession planning in family busi- nesses can be tricky. Keeping the CEO job in the family can offer continuity, he said, but it may also create friction among relatives who aren't chosen. Favoritism can also surface in closely held companies, particularly when a CEO's children are contenders. "Does it create a family dynamic that becomes frictional, that causes prob- lems down the road?" Andrews said. "It's a really complicated dynamic." Tariffs, prices and family ownership Beyond succession planning, Stew Leonard Jr. talked to Hartford Busi- ness Journal about several factors impacting his business and the broader grocery industry. Here's what else he had to say. The Q&A was edited for length and clarity. Q: How have tariffs affected your company? A: There are a couple of areas that have really affected us. India has a 50% tariff on shrimp, so we had to buy all our shrimp from Ecuador. We've had 15% tariffs on bananas from Costa Rica, but our importer said he is not going to pass them on to us until a later date. He'll eat them now because you don't want to raise the price of bananas. You want to keep your prices as low as you can. By Michael Juliano mjuliano@hartfordbusiness.com A fter 34 years at the helm of his family's grocery chain, Stew Leonard Jr. says he expects to hand off the CEO role "within the next couple years," setting the stage for a third generation to lead the Norwalk-based retailer. Leonard, 71, became CEO of Stew Leonard's in 1991, succeeding his father, company founder Stew Leonard Sr., after the elder Leonard's conviction on tax-evasion charges. Under his leadership, the brand known for its animatronic displays and "wow" factor has expanded to eight grocery stores across Connecticut, Long Island and New Jersey, plus five Wine & Spirits stores in Connecticut and New Jersey. Annual revenue has climbed from $116 million in 1991 to more than $500 million last year, and the company today employs over 2,500 people. Leonard said he still enjoys being deeply involved in daily operations, but recognizes it's time to transition. "I think I'm going to hand the baton over within the next couple years," he said. "I mean, how much energy am I going to have? It's fun to get involved in different projects, but I've got to make sure I let the next generation make decisions for the company, and I keep my fingers out of it." Leonard said the next CEO will come from within the family. Potential successors include: • Chase Leonard, his daughter and the company's senior photo and video producer, who holds a master's degree in digital photography. • Blake Leonard, his daughter and pres- ident of Stew Leonard's Wine & Spirits, who has a master's in marketing. • Brittany Tavello, his niece and manager of StewsGifts.com, who has an MBA. • Jake Tavello, his nephew and the company's chief operating officer, who also holds an MBA. • Andrew Hollis, his nephew and a store director. Stew Leonard Jr. emphasized that the company maintains a strict vetting process for family members seeking management roles, requiring pre-col- lege experience working in the stores, a college degree and at least three years working at another company. "We're not going to hire somebody just because they're part of the family," he said. "They have to be selected based on their capabilities." Managing family dynamics Leonard's timing mirrors a broader generational shift sweeping across American businesses. More than half of U.S. small-business owners are now over age 55, and just over half have a formal succession plan in place, according to a 2025 U.S. Bank small-business owner survey. That wave of pending retirements — often described as a "silver tsunami" — has placed new urgency on ownership and leadership transitions, particularly within closely held or family-run companies. That makes Stew Leonard's proac- tive planning noteworthy, said Drew Andrews, CEO and managing partner of Hartford-based accounting and consulting firm Whittlesey, which LEONARD'S OTHER MISSION — SAVING LIVES THROUGH SWIM SAFETY Outside the grocery aisles, Stew Leonard Jr. devotes much of his time to water-safety advocacy — a mission rooted in personal tragedy. He and his wife, Kim, founded the Stew Leonard III Water Safety Foundation in 1990, a year after their 21-month-old son drowned. Since then, the foundation has raised about $6 million for water-safety education and training, helping fund hundreds of lifeguard certifications and more than 10,000 free or low-cost swim lessons each year for children who otherwise wouldn't be able to afford them. The organization also runs Stewie the Duck Swim Schools, opening its first in Norwalk in 2023 and a second in Clifton, New Jersey, in November. Leonard said the schools collectively have already provided tens of thousands of free lessons through partner- ships with more than 50 community groups, and could surpass 100,000 total lessons with the addition of the Clifton site. Leonard said he hopes to eventually build a dozen swim schools as part of the foundation's growth. "Every time I think of the Water Safety Foundation and the swim schools, I smile," he said. — Michael Juliano STEW LEONARD JR. President & CEO Stew Leonard's Education: Bachelor's degree in accounting, Ithaca College; MBA, UCLA's Anderson School of Management Age: 71

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