Wealth Management & Estate Planning: What happens when there’s no one to take over the family business?


In late November, 83-year-old Peter Gerasopoulos closed the doors of Cobbler Shoe Service on Milwaukee’s south side after 62 years of business.

Over the course of six decades – during which the business moved from Bay View to the Point Loomis shopping center and ultimately to a storefront on West Oklahoma Avenue – Peter won a loyal customer base, repairing shoes alongside his wife, Judy, who worked at the shop counter for more than 50 years.

“He took care of a lot of people, and a lot of good people came through our life,” Judy said. “A lot of those customers weren’t just customers; they became friends.”

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When the couple decided it was time to retire last year, there wasn’t a clear path for the future of the business.

Both of their children, now 51 and 48 years old, chose to pursue other career paths outside the family business. Meanwhile, none of the interested buyers had a sufficient understanding of the intricacies of shoe repair, according to Judy.

“We tried for eight months to sell the shop,” she said. “We had people coming in, but they had no knowledge of shoe repair. Their big question was how much goes into the register, but in order to get money in the register, you have to have skills to fix the shoes. We could find no one. So we just had to decide to close it up and walk away.”

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When it came time to retire, Peter and Judy faced a challenge common to small business owners: the absence of a family member successor.

According to the Family Business Alliance, about 30 percent of all family-owned businesses survive into the second generation; 12 percent are still viable into the third generation; and 3 percent operate in the fourth generation and beyond.


“There are two miracles that happen in any transition from one generation to the next in a family business: the miracle of ownership succession and miracle of leadership succession,” said Rob Sligh, a consultant with The Family Business Consulting Group. “On the leadership side, it has to do with owners or top leaders willing to let go and the next generation being willing or interested in grabbing on. Each kid in a family has their own interests that need to be nurtured and developed and expressed. Sometimes those match the family business. Sometimes they don’t.”

Tina Kambouris took over ownership of Mykonos, a Greek restaurant in Milwaukee’s Yankee Hill neighborhood, from her brother and his wife in 2003 following a career in banking. During certain seasons, most of the restaurant’s employees were family members, including her brother’s children and her daughter, who worked there throughout high school and college.

Although the restaurant enjoyed a loyal customer base – 90 percent of patrons, she estimated, were repeat customers – Kambouris decided to close the business when her lease expired at the end of 2018.

Family members were offered an opportunity to take on the business, but they wanted to pursue other careers. Her daughter, who studied fashion at Mount Mary University in Milwaukee, went on to work for Kohl’s Corp. in Menomonee Falls.

“They all saw how hard it was to run a restaurant,” Kambouris said. “The restaurant industry is very labor intensive and even though you’re very passionate about it, it’s difficult to never have downtime. You miss out on many family events. It demands that you are there in order to be successful.”

Mykonos, a Greek restaurant on Milwaukee’s East Side, recently closed after 24 years.

Sligh said it is a best practice for family business owners to let their children work at the business when they are kids and teenagers to get acquainted with the operation, but then encourage them to work outside of it when they are older.

“Having teenagers work at the business during summers and school vacations helps them get a feel for what it’s like in the business and it also helps the kids meet and make friends with people in the business,” Sligh said. “But after completing whatever their schooling is, it’s good to go somewhere else so they can earn their own promotions and gain their own credibility, gain confidence and perspective in their own abilities and interests. Then, if there is a match between interests and skills and demonstrated abilities, that’s a great time for the next generation to come into the business.”

Judy and Peter Gerasopoulos’ children grew up at their parents’ business.

“As soon as they came home from the hospital, I was back at work and they were there,” Judy said. “They used to sleep in the stroller and play in playpens in the front of the store. They worked in the store in grade school and high school, taking in shoes, doing shoe shines, counter work, any jobs that we could give them to do. Everybody knew them.”

Peter’s work paved the way for his children to attend college, during which they continued to work at the store, but both ended up diverging from the family business. Their son went on to move to Colorado, initially working for a steel company, while their daughter became a corporate event planner.

“When they saw their father leaving at 7 in the morning and getting home at 9 at night, five days a week, and a shorter day on Saturday, I don’t think they were interested in that. There had to be an easier way to make a living than that,” Judy said. “ … There are many businesses that can be passed on but I don’t think they are in labor as much. Being in shoe repair, it’s a lot of labor.”

Sligh said it’s wise for business owners to begin having conversations early on with their children about the family business, but the tone of those conversations also matters.

“A very early age is none too soon to be telling stories about the business and getting them involved experientially,” he said. “One of the things that business owners need to remind themselves of is to not go home and feel free to just complain about the stress of the business. If we’re, in essence, educating the next generation of what it’s like to be in a family business, we’ll want to have at least as many stories around the dining room table about the good things happening in business as we have about worrying about the problems.”

Chiappetta Shoes is in rare company among family businesses, now operated by its fourth generation. Founded in 1921 by Italian immigrant Pasquale Chiappetta, Chiappetta Shoes in Kenosha is now owned by the family’s third generation, Fred Chiappetta and his wife, Lori; and run by the family’s fourth generation, Tony (chief executive officer) and Nick (chief operating officer) Chiappetta.

From a very young age, Tony said he and his brother helped out around the shop, breaking down cardboard and setting up window displays.

He never felt forced to take on the business, but both Tony and Nick chose to officially join the company after graduating from the University of Wisconsin-Milwaukee in 2008 and 2010, respectively.

During college, Tony worked part time at a liquor store, in addition to the shoe store. By the time he graduated, he was excited about returning to the family business full time to modernize the back-of-store processes. Chiappetta has since launched an e-commerce website to encourage online sales. While competition is high amid online retail giants like Amazon and Zappos, Tony sees the longevity of his family’s business as an asset.

“I have a fantastic foundation to work off of,” he said. “It gives me a great opportunity to build on something.”

The father of two young boys, ages 1 and 3, Tony said he doesn’t plan to apply pressure on them to carry on the business.

“I’ll never push them into being a part of the business,” he said. “But it’s something I take great pride in; not many people can say they’re fifth generation. It’s something to be proud of and build on. My great-grandfather came here with nothing and started a business and I’ve always been proud of something that has had such a long run.” ν

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