August 17, 2022

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Fashion entrepreneur wants Madison to stop shopping and start swapping | Business

At the 500-square-foot second-hand clothing shop at 836 E. Johnson St., there’s one question that owner Lindsay Leno and her employees hear a lot: “Where are the price tags?” 

When Leno opened Upshift Swap Shop in 2013, the basic premise was that nothing would be for sale. Instead, shoppers would bring a bag of gently used clothes to trade in, pay a $20 “swap fee” and then pick new items to fill the bag. 







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Secondhand shoes are displayed near the entrance of Upshift.




For Leno, who teaches fashion merchandising at Madison College, swapping is a way of life. This model, she believes, offers fresh style without all the waste that comes with the “fast fashion” industry. She knows that industry well, having spent seven years working for a Minnesota big box retailer before moving to Madison.

“I was going into work and … contributing to something that didn’t align with my personal values,” said Leno, a sustainability enthusiast who claims she hasn’t used a dryer in 20 years. Swapping, she said, not only keeps clothes out of the landfill, but it reduces the customer’s carbon footprint because clothes continue to circulate locally. 

With her upswept hair, colorful dress and cat eye glasses, Leno calls herself a “walking advertisement” for her swap shop, fashionable proof that swapping doesn’t mean sacrificing style. 

“Every single thing I wear is from here, and I pride myself in dressing nice,” Leno said. “I really do believe that if you have stuff sitting in your closet, it’s going to go to a good home within your community.”

Basement boutique to storefront success

When Leno came to Madison in 2009, she started hosting weekly clothing exchanges in her living room on the near east side, inviting friends to bring what they were ready to part with and take home new-to-them treasures. Before long, she’d turned her basement into a curated “boutique” of swap-ready apparel. 

She asked friends if they’d consider paying for the service, and they agreed that $20 seemed fair. She started taking donations.

Still, Leno figured hosting swaps was just a hobby until strangers started showing up to swap too.







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Outfit pairing suggestions are posted behind clothing racks at Upshift, a thrift shop located at 836 E. Johnson St. in Madison.




“I (figured) this absolutely could be a business, because people are just coming in off the streets and showing up with friends of friends,” Leno said.

As she and her husband were biking home from downtown one evening, Leno spotted an East Johnson Street storefront that had long stood empty. Before, she’d felt nervous about opening a retail location, but the place just felt right. She met with the landlord and negotiated a rent she could manage. If her business could make it through the upcoming major road construction, he told her, she’d be fine. She did.

In 2016, Upshift survived another blow when an SUV drove into the shop, shutting down business for nearly two months. Local artist Steph Hagens painted a mural across the store’s temporary wooden wall, emblazoned with the words “Change is good.” Today, it provides a backdrop for the shop’s fitting rooms.

Then came the pandemic, forcing the shop to adapt once again. Leno temporarily revived the store’s delivery model, which allowed customers to mail in a box of items to swap, pay a $49.99 fee to cover shipping and styling costs, and receive a box of clothing hand-picked by a shop stylist. That summer, instead of setting out bins of free clothes during its twice-yearly inventory purge, staff filled Ziploc bags with several items, sorted by size, to minimize the COVID risk.

Once again, the shop made it through the rough patch, as Leno expected. “There never was a moment … where I thought, ‘This is it. We’re gonna close,’” Leno said. “I just refused to believe that.”







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The plywood mural that was once used to secure the windows of Upshift after an SUV drove into the building now decorates the walls of the fitting rooms. The mural was painted by local artist Steph Hagens.




A revolutionary model?

Today, the shop is back to fully in-person operation. Open seven days a week, it’s busier than ever, Leno said. Where before the main clientele was moms looking for clothes to accommodate their changing bodies during and after pregnancy, the shop now sees lots of young adults looking for one-of-a-kind items.

Leno has also added the option to buy instead of swap. Those who don’t bring clothes to trade can buy most items for $5 each, or fill a bag for $30. Some particularly trendy items are $10 each, while a $2 sidewalk rack showcases discounts. 

She thinks it’s an ideal time for a swapping business, as many people emerged from their sweats-wearing pandemic isolation and found their closets lacking. 

“With that two year gap … fashion changed a lot,” Leno said. “All of our closets became very stale … so we actually have a huge influx of inventory right now.” 

Leno, who takes pride in keeping a well-curated shop, said she and her staff have been overhauling their offerings, making buying trips to other local thrift shops and donating jeans that don’t fit the looser style that clients now want. The shop mostly stocks sizes 4 to 12. 

What doesn’t sell at the store goes to Agrace Thrift Store or the local Goodwill. The shop also hosts free shopping sessions where residents of local halfway houses can take home the new outfits they need for their next steps after getting out of jail or rehab. 

Staffing the shop this summer are a handful of interns: fashion students from Madison College and high schoolers from La Follette. Interns earn credit instead of money, but Leno said most choose to stay on as paid employees once their internships end. 







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Upshift intern Emily Bender hangs clothing on a rack at the Johnson Street clothing shop. Bender is a fashion merchandising student at Madison College.




Though the shop didn’t turn a profit at first, Leno said it now makes enough to pay its few employees, though Leno still doesn’t pay herself. Instead, she works two jobs, at Madison College and Lake View Elementary, and puts profits back into the business to cover renovation costs and the like. 

To her, it’s worth it, because the business model is so important. “I truly believe that this swap system, if it became a mainstream way of retail, would completely change where consumerism is going,” Leno said. “You could still have a closet full of clothing, but without hurting the environment.” 

She’s got a storage unit filled with enough inventory to open two more stores. She’d like to open a second location for maternity and children’s clothing, and eventually expand into home goods, athletic gear or even unused cosmetics.

“The market is way beyond when I first opened,” Leno said. “I think, in the long term, it’s gonna continue to grow.”

For now, though, Leno’s just proud that the gospel of swapping has won so many converts.

“There was a year or two where I just had many, many nights of sitting here going, ‘People don’t get it.’ (Now) people finally get it. We’re lucky.”

The four questions 

What are the most important values driving your work?

I insist my staff approach all confrontation and interaction through kindness, which I know sounds cheesy, but that’s how I live my life. Also, communication is huge. I want people overly communicating with each other. And then, of course, there’s the sustainable piece. Reduce, reuse and recycle. That’s how my husband and I live our lives, and if I’m not doing that in my work life, then what’s the point?

How are you creating the kind of community that you want to live in?

People walk in and they’re like, “Oh, what a pretty store.” That’s great, but behind the scenes, I believe in working with the community to make it a better place. That’s why I have interns, because I truly believe in guiding them towards their future. Also, I just try to educate people on how you can live a life that’s more sustainable.

What advice do you have for other would-be entrepreneurs?

Jump in and do it. You can prepare and prepare, but unless you just decide to get that key and open a building, or get that URL … The other thing that I always tell my students is to read the book “The E Myth.” (Without it,) I absolutely would not have been able to open a business.

Are you hiring?

No. But that changes. I always tell people to come back at the end of the summer or when the semesters change over, because I’m based on my students.