In the restaurant industry, where long hours, high pressure and constant problem-solving are part of daily life, some operators choose to navigate it alongside their spouse. Behind several of southeastern Wisconsin’s most prominent independent restaurants are husband-and-wife ownership teams that are building and growing businesses together while also managing the complexities – and joy – that come with blending family, entrepreneurship and hospitality.

BizTimes spoke to three couples who shared insight on partnership, balance and what makes family-owned restaurants unique in today’s hospitality landscape.

Dane and Anna Baldwin

James Beard Award-winning chef Dane Baldwin and his wife, Anna Baldwin, own The Diplomat on Brady Street on Milwaukee’s East Side. The two met while working at a downtown Milwaukee restaurant where Dane was cutting his teeth as the chef de cuisine and Anna was bartending while going back to school for a degree in fine arts.

The night they met, Dane told Anna about his long-term plan to open a restaurant of his own by the time he was 35. About 10 years later, that’s exactly what he did.

“That kind of set the tone and the stage,” said Anna. “I didn’t know … you meet this guy and he’s like, ‘Yeah, I’m chefing now, and I’m gonna open a restaurant when I’m 35.’ Well, then I started to get to know him, and we dated and got married, and I was like, ‘Oh, yeah, this guy does what he says he’s going to do,’ and so, that was always the path.”

Opening the restaurant was entirely “Dane’s goal, his drive, his vision,” said Anna, “and I got to be along for it.”

While working in a restaurant brought the couple together, it wasn’t the core of their relationship.

“It’s not like we’re both charting a path in hospitality necessarily,” said Dane. “(Working in a restaurant) was a sensible way for Anna to support the goal she had at the time and that’s how we were able to meet. It’s a pretty cool coincidence  that’s charted so much since.”

In the roughly 10 years between their brief overlap as co-workers and the launch of their restaurant, the Baldwins undertook several other “team projects” that defined their partnership.

“We had two kids, we had a dog, we bought a house,” said Anna.

When The Diplomat opened in August 2017, the Baldwins’ daughters were 3 and 7. With his years of restaurant experience, Dane was the one who put together the business plan and secured the necessary partnerships and resources to get the concept off the ground. In the early days when the business wasn’t making much money, Anna traded morning-time stay-at-home parent duties with Dane to take a part-time job baking and prepping.

“Our roles changed a little bit for a short period of time,” said Dane. “Anna was working to make sure we had some money coming in, so in a lot of ways our dynamic and what we needed to do to make this go started right then because that was the flexibility we needed to count on one another to make it happen.”

Now with nine years of operations and a prestigious award under their belts, the Baldwins’ team-oriented and flexible dynamic remains central to operations, culture and the overall dining experience at The Diplomat. Dane was awarded Best Chef Midwest by the James Beard Foundation in 2022, becoming one of only five Milwaukee chefs to earn what’s considered among the highest national recognitions of culinary talent.

As business partners, the Baldwins think of themselves as working with – not for – each other. And as owner-operators who work in the business as much as on it, they think about and interact with their team in much the same way.

During service, while Dane orchestrates the back-of-house, Anna fills in wherever needed.

“Whether it’s taking a position in front of the house helping out on a station in the kitchen when we need it, whatever it is, it’s pretty cool to work with someone who’s been able to wear that many hats,” said Dane.

Behind the scenes, the Baldwins’ separate responsibilities complement one another as he oversees the restaurant’s financial operations, while she manages the household finances and logistics.

Work life and family life have naturally blended together as the Baldwin kids have gotten older and more independent, now helping out at a restaurant they grew up around. But there are still boundaries for a healthy balance between work and home, such as designated times when any business-related talk is not allowed and keeping the restaurant closed on Sundays, which Dane said was an intentional, family-driven business decision.

As much as Anna leans on Dane’s day-to-day operational and culinary expertise, Dane relies on Anna’s perspective in decision-making and the sense of hospitality she’s infused into the business, allowing The Diplomat to evolve beyond its origins as a purely chef-driven concept to a neighborhood dining spot that regulars frequent.

“Anna is good at fostering those relationships, but it’s not by following a set of rules or a recipe or a standard operating procedure on how to get a repeat diner. It’s how she is,” said Dane.

Those personal relationships the Baldwins have developed with regular customers, as well as with a number of family-owned product vendors, is the essence of a restaurant being run and managed by the same people who own it, said Anna. It’s part of what gives mom-and-pop shops “that little bit of personality and soul” diners might not experience at chains or corporate-owned restaurants, said Dane.

“You can’t just write that on a piece of paper and sell it,” said Dane. “It’s gotta be there. You gotta be able to feel that, that beat. … There is some theater to a restaurant, and I think you can tell when it’s being manufactured, and I think you can tell when someone is really playing their song.”

Adam Siegel and Daria Aitken-Siegel

In business and at home, teamwork is the name of the game for the Siegels.

“I look at it just like when we are parenting our children, we work as a team,” said Adam. “We each have certain areas that we specialize in, but we both have a say, we both voice our opinions and work together to make decisions.”

“Our marriage has always been a true partnership,” said Daria. “We have always made decisions together and compromise when necessary. Neither of us ever gets our way all the time.”

They each bring unique yet complementary perspectives and expertise to the business – Adam from his long-running career in culinary arts and kitchen operations and Daria from her real estate and marketing experience – but having put the right leaders in place, the Siegels are now able to focus on high-level strategy, long-term growth and future concepts, like Il Ponte. Management is also involved in many of the decisions the Siegels make.

“We have a good reputation in the industry, and we think that is because we have a strong management team and we treat our staff with respect, gratitude and fairness. People know they will learn and grow in this industry by working with our team,” said Adam.

The realities of jointly owning and operating restaurants mean business discussions are often intertwined with daily life – something the Siegels have learned to navigate through communication, compromise and humor.

“When we do have ‘discussions’ at work, our staff will joke, ‘Mom and dad are fighting again,’ and we all laugh and move on,” Daria said. “You cannot be together for 26 years and not argue, but we are respectful and then make a joke and move on.”

Stefano and Whitney Viglietti 

Whitney Viglietti and Stefano Viglietti, a James Beard-nominated chef, have built their restaurant and retail enterprise over the past 32 years, garnering both a loyal local following and national acclaim. The couple owns four establishments – Trattoria Stefano, Il Ritrovo, Field to Fork and Stefano’s Slo Food Market – all clustered on one block along South Eighth Street and Pennsylvania Avenue in downtown Sheboygan.

The two met as undergrads at Knox College in Illinois, locking eyes across the salad bar in the cafeteria. Moving to Chicago after graduation, Stefano was working in real estate while Whitney was managing a dance company; a shared career in restaurant ownership was not yet part of their plan.

“But cooking was what I wanted to do every night, and I couldn’t wait to get home,” said Stefano.

After unsuccessfully searching out west for an opportunity to buy and operate a small bed-and-breakfast – and facing rejection while trying to break into the restaurant industry without experience – one door eventually opened in downtown Sheboygan, where Stefano decided to throw caution to the wind and start his first of what would be two Italian restaurants, Trattoria Stefano. While the building was under renovation, Stefano would spend Sunday through Tuesday working at a Chicago restaurant called Trattoria Roma, in an attempt to gain as much experience as possible.

The Vigliettis lived above Trattoria Stefano and when the restaurant opened in 1994 they would work together every day, morning to night, as Stefano continued to learn on the job from each chef that would come and go, while Whitney kept the books and helped out in the kitchen as needed.

“The biggest thing that was so important is I could completely focus on how little I knew about food and how much I had to learn because I knew that she had the other part on lockdown, that if we were low on money, if anything was going badly or we had a big tax payment coming up, she could tell me,” he said.

From those shaky beginnings, the Vigliettis built their business on local-sourcing practices, relationships with producers and slow-food principles. They’ve also invested in their people, offering benefits like health insurance, profit sharing and retirement plans at a time when almost no restaurants did so, as well as taking staff on educational trips to Italy. Today across their four businesses, the Vigliettis employ a team of 165 people, including several longtime employees who have worked for them for more than two decades.

“We’re always searching and really trying to keep our staff knowing that this can be their job, and that’s one of the biggest things that I think about in hospitality is people always think that this is a stepping stone, and for many it is,” said Stefano. “But if you get lucky and you work really hard, this can be what you do.”

These days – after years immersed in the daily grind of the restaurant business – the Vigliettis have been able to step back and give their leadership and management teams greater autonomy in day-to-day operations. This has allowed Stefano to focus primarily on product sourcing and Whitney on managing senior staff. It also means more time together as a couple and with their now-young adult kids.

“At first you’re like, ‘What do we talk about besides work?’” said Whitney. “But I think we’re starting to discover some other things to talk about and other things to do, and that’s a really exciting new chapter.”

Looking back, Stefano said, the business consumed more of his time than he realized in the moment, working 7 a.m. to 11 p.m. five to six days a week “for as long as I could,” and he acknowledged missing out on spending more time at home with family.

“It was tough, but at the same time we really enjoyed it,” he said. “I think if you love what you’re doing, and I’ve heard this said by other people, it’s almost not a work-life division but a circular thing where it’s all one. … There isn’t work and life. There just is life.”

Assembling a leadership team and putting the right managers in place is something the Vigliettis have prioritized in the past few years as they start planning for the future of their business. And it’s one of the greatest challenges they face, said Stefano, because it means weighing the desire to preserve something that’s made a significant impact on diners and the greater Sheboygan community, with the need to make space and decisions for their own lives outside of the business.

“ You need to take that first step of trusting that someone else can help, figure out what the next steps can be, whether it’s aesthetically fixing things or doing operational things or learning about sourcing,” said Stefano. “So you try to start to see that take form and hope that the right people can make it last, and it’s not a guarantee. Some things run their course, but our goal is to absolutely try to keep these (restaurants) flourishing in our community because we think they bring a lot to our community.”