Ali shops. Ali edits. Ali influences. What doesn't Twin Cities media maven Allison Kaplan do?

On a recent visit to a North Loop boutique, Allison Kaplan picked a glimmering gown off the rack and explained all the boxes it checks. First, its cap sleeves offer a bit of all-important arm coverage. Second, ruching along the waist flatters the silhouette. And third, its length nods to the wearer's special role in a very special occasion.

"It's pretty slinky and fab, but there's definitely a mom that could pull this off," Kaplan said.

Kaplan, known as Ali, may be the first editor of Twin Cities Business to describe anything as slinky and fab, but Kaplan's not a typical business magazine editor. Nor is she dress-shopping for her day job.

While Kaplan regularly covers local entrepreneurs, she also has a startup of her own. In 2022, she co-founded Mother Of, a website that helps bride-or-groom moms find a knockout wedding outfit — a problem that's more logistically and emotionally fraught than most glass-clinking guests ever realized.

Before Kaplan took the reins of TCB, in 2018, she'd been covering the Twin Cities retail scene for nearly two decades. She supplemented high-profile roles as a Pioneer Press columnist and style editor of Mpls.St.Paul magazine with side gigs hosting a radio show and creating an innovative digital shopping guide.

As the Cities cultivated more style cred, Kaplan brought depth and context to the stereotypically frivolous subject of fashion, chronicling, for example, how the North Loop emerged from Sex World's seedy shadow to become the city's hottest shopping destination.

Kaplan earned shoppers' trust because her zest for style has always been grounded by practicality — she'll call a Kate Spade a spade, so to speak. She can appreciate the luxurious fabric of a butter-soft camisole, while noting the cognitive dissonance of six-figure underwear.

After bringing more substance to the shopping beat, Kaplan is now focused on making business coverage more relevant to a younger, diverse audience. "With business in general, there was kind of this good 'ol boys thing," she said. "It just needed a little refresh."

Retail roots

Kaplan's retail roots are oh-so-Minnesotan: Her parents met at Dayton's.

Her mother worked in special events and her father was a home trend director — a fifth-floor markdown, Mom likes to joke.

Growing up, Kaplan followed her mother as she emceed fashion events and produced style segments for local TV. She strutted the runway in cowboy boots and a Snoopy sweater and offered fashion commentary of her own as a 5-year-old. By the time she was a teenager, Kaplan, too, had a job at Dayton's, in the Southdale branch's boys department. "It was Zubaz and Bart Simpson T-shirts, so now you know exactly how old I am," she hinted. (For those who dodged that fashion fail, she's 51.)

Kaplan's first paid writing gig was as the high school correspondent for Edina's community newspaper, but she found her niche as a young reporter in Chicago, covering the intersection of business and lifestyle. Kaplan wrote about retail from a consumer perspective, but also gave shoppers a peek behind the racks. And she started her first side gig: writing a singles column for a Jewish newspaper, which she syndicated to similar papers around the country.

By 2000, Kaplan was back in Minnesota, as the shopping and style columnist for the Pioneer Press. She didn't breathlessly gush like the glossy fashion mags ("Time to shop the celestial hairpin!"). But unlike her newspaper peers, Kaplan was a bona fide mall rat. "I felt like most people who were covering retail from the business desk never actually went shopping," she said.

Kaplan assessed everything from buying a new car to trying a $300 hair-smoothing treatment. ("I will say this: It did do something to my hair. And that's saying a lot, because I find so many products make absolutely no difference.") She covered the rise of the "heritage" look, explaining why Minnesota-made workwear and outdoor gear — Red Wing boots, Duluth Pack bags — was showing up at Barneys.

Kaplan name-dropped designers as fluently as she dug into the economics and psychology underpinning a trend. Sure, she could advise readers on accessorizing a white T-shirt and black shorts ("ankle-strap sandals, a little denim jacket, and a pile of gold jewelry"). But she also warned them to be wary when buying pink products to help fight breast cancer. And wondered if a spa catering to preschoolers was "too much indulgence too soon?"

Soon Kaplan realized that her reporting on store openings could help readers long after the newspaper hit the recycling bin. So in 2006, she launched her own brand, Ali Shops — a blog, e-newsletter and a searchable directory of local shops — that was pioneering in the market.

Shortly thereafter, the female-focused talk-radio station FM 107 asked Kapan to co-host a show called "Shop Girls." Kaplan took on the second side-gig thinking it would help promote her first one, even though it meant working Saturdays (by now she was married and had a toddler).

A few years in, Kaplan's mom, Harmony, became her "Shop Girls" co-host, and their dynamic proved popular with listeners. "They liked us, you know, arguing about whether or not a woman of my age could wear shorts," Kaplan said with a laugh.

"Shop Girls"

More than a decade later, Harmony was doing what she usually does at quarter to 11 on a Saturday morning: waiting for Ali to arrive at the radio studio. The ever-chic grandmother had paired a heart sweater and heart earrings with hot pink lipstick the same shade as her eyeglasses. (She has more TikTok followers than her grandsons after going viral singing COVID-themed musical parody duets with her husband.)

Kaplan breezed in, wearing jeans, a leather jacket and silver boots that exuded a casual polish. Her phone pinged with her husband's play-by-play of their younger son's wrestling match, which sounded like a foreign language to both women. "It was a takedown to the left," Ali read aloud, in mock tough-guy voice. "Decisive victory."

"I hate wrestling," Harmony replied. "I don't need them hurting my grandson."

Over the next two hours, the duo interviewed a fashionista who organizes clothing swaps and discussed why retailers hate returns. Then Harmony revealed the musical artist she listened to most last year (Rihanna, as Ali correctly guessed) and shared a list of lame holiday gift recommendations she received from ChatGPT. "Those aren't the things I want," Kaplan complained of its suggested dog accessories and mock magazine cover featuring her family.

AI can't yet replace a style guru's good taste.

From MSP to TCB

By 2010, "Shop Girls" helped Ali Shops establish such a large following that Mpls.St.Paul Magazine saw Kaplan as competition. After much negotiation, she joined the magazine as its style editor and incorporated Ali Shops into its website.

Lifestyle influencers had just started coming online. Suddenly, anyone who could put together an outfit and snap a selfie was a self-styled fashion expert. While Kaplan had presciently developed an approachable personal brand, Ali Shops wasn't All About Ali. Instead of the self-focused, promotional personas cultivated by many of her up-and-coming counterparts, Kaplan stuck to her journalistic approach of reporting information and lending insight.

Kaplan's role at Mpls.St.Paul led to her current one leading Twin Cities Business (the two magazines are owned by the same company). She's the magazine's first female editor, covering a male-dominated community. (In Minnesota, roughly 20% of executive roles are held by women and about 10% of its large public companies are run by women.)

While some questioned what a style editor was doing running a business magazine, Kaplan focused on expanding readership beyond the 30-year-old publication's core demographic. She featured a more diverse array of businesspeople and stories about topics such as soft skills and work-life balance.

"You can talk about business in a way that's serious, but doesn't have to be stuffy," Kaplan said, explaining her vision. "I wanted to make sure we were bringing in younger readers and bringing in women. I think that it had a little bit of a reputation of being — like many things in business — very focused on Fortune 500 culture, which has tended to be very male and very white."

Kaplan's first "Shop Girls" co-host, Alexis Walsko, had started her own public-relations firm, Lola Red, more than two decades ago, at age 22. Though Walsko's status as a business owner placed her squarely within the demographic of business publications, she found most of them unrelatable. Coverage tended to emphasize large companies, with limited attention given to the other 99% of the country's businesses, which are, like hers, classified as small.

Walsko said that Kaplan's being so attuned to her audience helps her connect with the CEO of a household — and one listed on the NASDAQ. "She has a gift for figuring out and being interested in what helps her readers or listeners," Walsko said. "What is the information that they need to make their lives better or richer?"

While a quarterly earnings report is a business story, so, too, is a company founder's personal journey, Kaplan notes. To emphasize the people behind local companies, she started a TCB podcast, "By All Means," interviewing founders of well-known Minnesota brands, and annual magazine, StartMN, focused on startups.

As Kaplan put it on a recent podcast: "Big companies used to be small companies, and somewhere along the line, even if you have to go back 100 years, there was one person who had a really big idea."

Mother Of

Kaplan's latest big idea-slash-side-gig is just the sort of small, women-owned business that used to be overlooked by business publications. And it came from opening the phone lines to "Shop Girls" listeners and hearing from hundreds of moms fretting over what to wear to their children's weddings.

So she partnered with Betsey Kershaw, a friend who runs her own digital marketing agency, hoping to help solve a longstanding problem at an opportune time.

"There is a white space for women over 50," Kaplan said. "You're seeing so much more focus on talking about menopause, or watching 'The Golden Bachelor,' and there's a real shift in the idea that women aren't, you know, dead when they turn 50. They aren't matronly. They don't want to be perceived as old and over the hill. They're doing all kinds of cool things. A lot of them feel better than they ever have before, but the fashion and retail world don't see it that way. And it can be really discouraging."

Mother Of independently curates a wide selection of wedding-day dresses (they earn commissions from some brands) to solve dress-shoppers' logistical problems. ("I talked to a woman who ordered 70 dresses to find the one," Kaplan said.)

But the site also shares stories of real "mothers of" to buffer the emotional hazards of dress-shopping and to reassure moms that they don't have to fade into the background wearing beige. "I think women want validation. They want someone to say, 'Yes, you can wear that, you look great, that is not inappropriate.' "

Helping those "mothers of" motivates Kaplan to spend nights and weekends on her startup. Between her multiple jobs and family responsibilities, Kaplan juggles so much that some wonder if her clock somehow contains additional hours. "She has that extra gear that motivates and inspires people around her," Kershaw said. "She does not stop," Walsko said. "I'm just not that good at sitting around," Kaplan admitted.

The through line in both how Kaplan has covered business and the businesses she's launched is her interest in the people who make, sell and buy products and services. Which is to say, all of us. "We all shop, whether we like it or not," she says.