Double Duty: Douglas Stewart’s Cheryl Rosen Weston doing it all

To say that Cheryl Rosen Weston is a busy woman would be a little like saying Albert Einstein was a pretty sharp dude. Or that Andre the Giant was a bit on the husky side.

As the CEO and principal shareholder of The Douglas Stewart Co., one of the largest woman-owned companies in the state of Wisconsin, Rosen Weston might be content to punch out each evening and quietly reflect on an honest day’s work, but that would be too easy.

“The flippant answer that I always give is that I don’t have much of a social life.” — Cheryl Rosen Weston on how she manages her busy schedule

No, she’s also a full-time instructor at the UW Law School, where she’s taught since the 1970s. And while those two professional commitments alone would be enough to make your typical worker bee swoon, she doesn’t stop there. Her community service has included membership on numerous boards, including the State of Wisconsin Economic Development Board, and she’s worked tirelessly on behalf of the Madison Public Library Foundation and A Fund for Women. Currently, she says, she’s on six boards, and her volunteer spirit shows no signs of flagging.

So what takes up most of her energy?

“I have two grandchildren in town,” said Rosen Weston. “That’s really the primary focus of my work life, I would say.”

To be sure, it’s a sentiment many grandparents could relate to, but perhaps it’s misleading to say those two boys, ages 4 and 12, drain her energy. Talk to her long enough and you’ll get the impression that Rosen Weston is a crackling ball of electricity unto herself, with no discernible off switch.

At IB’s March 12 Icons in Business presentation, Rosen Weston will share some of the secrets to her company’s success — and maybe attendees will get a little insight into how she manages a day that still clocks in at an unforgiving 24 hours, give or take a leap second here or there.

So how, exactly, does she do it?

“The flippant answer that I always give is that I don’t have much of a social life,” said Rosen Weston, laughing. “They really are both full-time jobs, so you can’t do them without putting in a lot of extra hours. And you make the sacrifices required. I don’t recommend it to everybody, but they are so different in terms of what’s expected, and you get different types of satisfaction from them, so I felt neither one was satisfactory without the other.”

Following law

While running a leading electronics, school supply, and computer products distributor with more than 100 full-time employees might seem like it would have to be anyone’s sole and primary focus, Rosen Weston’s first love is actually the law.

Before taking over as CEO of Douglas Stewart, Rosen Weston was a partner in the law firm of Cullen, Weston, Pines, and Bach, and she taught part time around her law commitments. Douglas Stewart was her ex-husband’s company, and she was the company’s lawyer. Eventually, her work with Douglas Stewart became more involved and complex, and she was forced to leave the law firm, which spurred her to teach more.

“Teaching became a little more important to me, and then when I was ultimately asked to take over the company and buy out the Stewart family, I thought the only way I could do that and still hang onto the career I really loved, which was the law, was to up my teaching.”

Rosen Weston eventually became Douglas Stewart’s principal shareholder in 1999, shortly after separating from her husband.

“My husband and I had just finished divorcing, and I had assumed, which seemed reasonable, that I would return to my law firm and he’d have his business,” said Rosen Weston. “To my surprise, he decided to relocate and said, ‘I’m burned out, I don’t want to do this anymore.’

“So it was new enough to me that it really did capture my interest and attention. But mostly the reason I stepped in wasn’t because I was looking to do this at all, but I thought, ‘Gee, what’s going to happen to all the people who work here if all of a sudden no one’s in charge?’ And as we grew in size and in success, a lot of the satisfaction came from thinking I’m helping to support a lot of families here in town, and that was meaningful to me.”

Uncharted waters

In recent years, the company has seen new challenges, and job cuts have resulted. As a distributor of technology products, many of Douglas Stewart’s partners are recent startups, which adds an element of instability from the get-go.

Meanwhile, disruptive business models are always a threat — particularly so to a venerable company that traces its roots back to 1950.

“The way people shop is so different … so I’ve seen a lot of customers hurt by the fact that their business has moved elsewhere,” said Rosen Weston, “and then a lot of the products we sell are suddenly less in demand. So the biggest part of my business has been computer software, and you know people are downloading apps for $2.99 instead of buying multiple hundreds of dollars of software programs.”



Of course, it’s the kind of problem a lot of established companies have faced, but Douglas Stewart has done everything in its power to respond.

“The big focus is to try to identify where there are new opportunities, so in our case, we’ve been putting much more effort and energy toward the kind of items that are purchased by institutions, like K-12 school districts, which have big technology spends these days, as opposed to higher ed students, who are making individual purchases from all kinds of retail,” said Rosen Weston. “That’s a pretty good example. We actually analyze our business differently now, so it’s not so much the product as who is likely to buy this product. … Value-added retailers who go out and deal with school districts are now more profitable than retailers who we’ve traditionally worked with.”

But while Douglas Stewart has been pressured by new technologies and business models, it retains an inherent flexibility that points to a bright future.

“At the end of the day, we’re a distributor, so I don’t have the problem of all of my capital being tied up making something that is no longer in demand, and I have that ability to be flexible about what I choose to offer to sell people,” said Rosen Weston. “So that means I can recover faster than other people who have to truly reinvent themselves.”

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