After 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. His nephew, Jake Tavello, will become CEO, while his daughter, Blake Leonard, will assume the role of president. The leadership transition is expected to take place within the next several years.
Tavello currently serves as chief operating officer of Stew Leonard’s and holds an MBA. Blake Leonard is president of Stew Leonard’s Wine & Spirits and has a master’s degree in marketing. Leonard said the succession plan is intended to ensure continuity while allowing the next generation to lead the company.
Stew Leonard Jr. emphasized that the company maintains a strict vetting process for family members seeking management roles, requiring pre-college 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 proactive planning noteworthy, said Drew Andrews, CEO and managing partner of Hartford-based accounting and consulting firm Whittlesey, which 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 businesses 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 problems 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 Business 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.
The importer doesn’t win because their sales go down. And Stew Leonard’s doesn’t win because our sales go down.
You really want to avoid price increases at any cost. We’re eating a little bit of the tariff cost right now. It’s not a huge amount, but we’re having a good year so far. We haven’t really raised prices due to the tariffs.
Q: Would you consider grocery prices to be high?
A: It always depends on what you compare it to. If you look back, even with the inflation right now around 3%, it was higher in the past under the last administration.
I’ll put it this way: I’m seeing some effort to lower prices in the grocery industry. Trump just took the 15% tariff off all of our tropical fruit from Costa Rica. That’s going to lower the price of the mangoes, the pineapples and the bananas. He just rescinded the tariff on Colombia, which had to do with our coffee, so that’s going to be able to relieve some of the coffee price.
Egg prices are down substantially. That had maybe a little bit to do with inflation, but it was mainly that avian flu that caused a supply-and-demand issue.
Q: Where are prices the highest?
A: Prices are high on a couple things like meat. It’s the highest I’ve ever seen it in my whole life.
I talked to our ranchers out in Kansas, and they just say, ‘look, we’ve had some droughts, so there’s not as much grass out in the fields. It’s more expensive for me to buy and raise a head of cattle right now because we have to buy more feed.’
The ranchers are at a point where they’re just saying it’s not really a good investment for them to buy a baby calf and then spend two years feeding it and caring for it.
Q: How have high grocery prices impacted your bottom line?
A: The food business works on razor-thin margins, so you’ve got to keep your eye on the ball every single day. If we think the price is going down in the future, we’ll wait and we won’t raise any prices. We’ll just keep things the same and eat a little bit of the price increase right now, so that has put pressure on our bottom line.
Then you look at our labor rate. Our average labor rate is $23 an hour, and we’re just getting ready to raise that up again. Energy costs are up like 30% for our kilowatt hours. There are other things aside from the food business that affect our margins, which are labor and expenses.
You’ve got to keep an eye on all this.
Q: Are you actively scouting new locations, and what criteria do you look for when choosing a site?
A: We’re looking all over. We have stores in Connecticut, New York and New Jersey. They’ve all been very successful in those markets. A lot of it comes to where is real estate available? You need a store that’s about 80,000 square feet. It has to be available right now. There might be some good sites, but they’re just not available right now.
We have our feelers out in the real estate market. If something comes up that we feel would be in a successful community, we’ll go ahead and decide to open a new store there.
Q: How long do you hope Stew Leonard’s stays under family ownership?
A: We probably get an offer a month from someone willing to buy Stew Leonard’s. Some group looks at us and says, ‘oh, wow, we’d love to buy that company,’ but our family is not excited about selling.
Our family’s philosophy is we’re going to take grandma’s wedding ring and we’re going to shine it up and hand it off to the next generation. We’re not going to sell grandma’s wedding ring.
This business is a love and a passion, and it’s been a wonderful experience to participate in the growth and in the changes in the industry and the people that I’ve met. It’s just been phenomenal.
We don’t want to sell it.
Editor’s note: This story was updated after publication to reflect Stew Leonard Jr.’s announcement naming his successors.
