After starting as a dishwasher 50 years ago, Gaylord Catering owner ready for retirement

Dave Chamberlain never left the company he started at part-time as a high schooler, but his impressive run comes to an end on Dec. 31.

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December 31 won’t just mark the end of another year, it’ll also be the end of an era for Madison-based Gaylord Catering and its longtime owner, Dave Chamberlain, who began working at the company in 1968 as a dishwasher while still in high school.

Chamberlain is retiring and hanging up his apron on New Year’s Eve in advance of a new owner taking over the venerable full-service catering business on Jan. 6.

Gaylord Catering has been operating since July 1963, catering wedding receptions, hors d’oeuvres parties, anniversaries, corporate breakfasts, lunches, and picnics. They also do contract catering for local senior communities and a clinical research company and will cater large-scale events as well as travel within a 50 mile radius of Madison or further. Gaylord Catering employs 10 full-time workers and 10 to 15 part-time employees, depending on the season, all of whom are expected to stay on and work for the new owner.

Chamberlain’s 50-plus years with Gaylord Catering began with that part-time dishwashing stint in high school and just never ended. He continued to work part time for the catering company while in school at (the since-closed) Madison Business College, where he earned a degree in accounting.

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“When I graduated, the guy who started the business, Gaylord Matti, offered me a job,” Chamberlain recalls. “He offered me more money than anybody else did, so I stayed.”

It also helped that Chamberlain wasn’t really enthusiastic about the prospect of sitting behind a desk for the rest of his career either. “I thought, ‘Well, I’ll give it a try.’ And I never left. I got into it and once I bought the business and started working for myself, I didn’t want to go back to working for someone else.”

Chamberlain began working full-time in 1974 as general manager of Gaylord Catering, and in 1977 Matti offered Chamberlain part ownership in the company, which Chamberlain believes was likely Matti’s way of securing his own retirement.

In 1983, Chamberlain and a partner, who also started at the company as a dishwasher, bought the business from Matti together. Chamberlain’s partner left the business in 1998, leaving Chamberlain to run Gaylord Catering solo until his wife, Pat, became more active with the business after her retirement from the Madison Metropolitan School District in 2008. Pat will be joining Dave in retirement in a couple weeks.

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Chamberlain notes the catering business has changed quite a bit in his 50 years in the industry, and he’s seen it progress with the times.

“When I first started working in my earlier years, we did a ton of stuff for farm dealers and farmers in general, like ag days,” notes Chamberlain. “We also did a lot of sports banquets within about a 50-mile radius of Madison. All the surrounding schools had athletic banquets and it was all meat and potatoes, and most of them, of course, were for the boys.

“Well, then Title IX shows up and girls began to get equal billing — which rightly so, they deserve it — but school budgets didn’t have money for banquets for the guys and banquets for the girls, so that kind of fell by the wayside,” Chamberlain continues. “And then it also started to evolve where people were getting away from just meat and potatoes and becoming more health conscious. With the talk of farm-to-table, locally grown produce, people have become very interested in that. They’re interested in whether we’re buying food that’s grown locally in Wisconsin and of course we try to. Now, you can’t buy watermelons in December that are grown in Wisconsin, but those are the obvious things.”

Chamberlain also says back in the 1980s, they were no food carts around Greater Madison, which give local, small food-business operators a chance to try something.

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One such individual is Gaylord Catering’s new owner, David Rodriguez of Wisconsin Food Cart Collective. Wisconsin Food Cart Collective will become the umbrella company for both Gaylord Catering and MadSweetPea LLC.

MadSweetPea consists of three different businesses. Melted is a food truck that offers many different varieties of grilled cheese sandwiches and smash burgers and also has a space at Grateful Shed Truckyard in Wisconsin Dells. Taco Local is their second food cart, which features tacos and homemade sides and also does catering. The last business is International Catering Co., which specializes in high-end catering for weddings, corporate food service, and assorted events.

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Chamberlain says after 50 years, the biggest thing he’ll miss is the people. “It’s about relationships. I’ve got relationships with a ton of my customers and I’ll miss some of that, there’s no doubt about it. We’ve done a lot of weddings over the years, just a lot of events, and once you go do one of these events, it’s successful, and the people are happy, that’s what brings you back to do the next one.

“But I’m 68 years old and it’s time to go to the next chapter,” Chamberlain continues. “I’ve been thinking about this for four, five, six years. I’ve never had the right opportunity to sell it. I have had a couple people interested that just didn’t pan out. My goal from about my mid-50s on was that I’d work until I was about 66, which is full retirement, and my wife is a year younger, so we wouldn’t have to worry about buying health insurance. And, of course, if the right offer comes along you’ll always take it, but it didn’t.”

That was until about a year and a half ago when Chamberlain learned through one of his employees that Rodriguez was looking to rent some kitchen space. “At the time we weren’t quite as busy, so I thought, maybe it’ll work out,” recalls Chamberlain. “So, we struck up a deal and he started renting kitchen space from me last October or November. After the first of the year, maybe in February or March, we were talking one day and he said, ‘If you retire at some point I’d like the opportunity to possibly buy this.’ And I said that I can make it happen sooner than later if you want. He didn’t think I was quite as old as I was, I guess.”

Chamberlain and Rodriguez talked back and forth and soon a deal was struck to change hands at the end of this year.

“I won’t miss the day-to-day grind,” admits Chamberlain. “By my own choice, my idea of owning my own business is that I’m here a lot, and maybe way too much. I work seven days a week by my choice, and that’s just the way it’s come. Is it necessary? Maybe not, but it’s just like one of your kids and so that’s what I do. But as time goes on, it becomes a little harder.”

Chamberlain says his retirement plans are fairly simple. He and Pat want to do some traveling — “Nothing big or extravagant like going to China.” — mostly around the United States.

“We have four grandkids — two here and two in Minneapolis — so we definitely want to spend more time with the grandkids,” explains Chamberlain. “I’m a golfer and I haven’t had much time to play golf, so I’m looking forward to more time for that. But mainly, I’m just looking forward to not having a schedule where I have to be someplace.

“Everybody I know says it’s going to be a hard adjustment, but I’m the oldest of four kids and all my siblings are already retired and they all say I won’t have a problem,” Chamberlain chuckles. “They tell me once I get a week in, I’ll enjoy it. My mom is 92 and still lives in Madison, and my family is here, so I think I’ll have plenty to do.”

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