Stephanie Sheldon Cleveland Flea Stephanie Sheldon Cleveland Flea
X Logo

An hour before showtime, Stephanie Sheldon glides through the clamor of what resembles a small city hastily rising. Artists, buskers and bakers are erecting tents, stocking shelves and firing up doughnut fryers for the season opener of the Cleveland Flea in a huge, semi-secluded parking lot in AsiaTown. 

A young-looking 38-year-old with a cellphone to her ear, she’s a hipster version of Martha Stewart. Her bright blond hair, stylish and short, contrasts with an all-black ensemble of jeans, hoodie and sneakers on this brisk April morning.

“Hi Steph!” a vendor calls. Another reaches for a high-five. Sheldon falls into a quick hug before her eyes stab a problem.

“Why is that truck there?” she shouts, marching toward a food truck crawling up East 36th Street. Her voice is calm but seems to cut through the din. People pause in their work and turn.

A man rolls down the passenger window and pops his head out of the Beachcomber. Painted in vibrant shades of blue with palm trees and Tiki masks, it resembles a rolling surf shack.

“You’re supposed to be over there,” Sheldon commands, pointing with her phone toward the far side of the scene. The engine roars, and the truck lurches toward its post. 

Order is briefly restored.

Watching from her booth a few dozen yards away, candlemaker Amy Maki laughs. “She’s always doing that,” Maki explains. “I know this looks insane, but they keep a nice flow. She’s definitely The Girl. You can spot her from a mile away.”

With the creative mind of an architect, the style of a wedding planner and the drive of an entrepreneur, Sheldon has become the maker of makers. By gathering a community of artisans, creatives and side hustlers, she’s built the Cleveland Flea from a pop-up arts-and-crafts fair into a model for economic development on the verge of becoming an export. But as the Flea enters its fifth season, can Sheldon keep the momentum as others look toward what she’s built and want a share of her magic?

Her influence has definitely spread beyond a monthly pop-up market. Economic planners are watching. Some of the 176 vendors here today have employees helping them set up. That’s because they now have a storefront, often in a neighborhood coming back to life, something unimaginable when they joined the Flea three or four years ago.

Through the Flea and her other ventures, such as holiday fairs and do-it-yourself classes, Sheldon has likely helped nurture more small businesses than any startup incubator in town. Her consulting firm, Indie Foundry, now gets calls from suit-and-tie executives for help energizing the mall or corporate offices. 

Fifty miles down the lakefront, Huron beckons. Word has spread about her success with the Flea, and city leaders have asked her to come and show them how to do something cool, even audacious. Sheldon has an idea — several, actually.

“I struggled, early on, to create a career or a job that brought me a lot of purpose,” she says. “This really does that for me. I feel like I can be full steam ahead.”


The Cleveland Flea unfolds behind a MidTown colossus. 

A former elevator factory, Tyler Village overwhelms East 36th Street between Superior and St. Clair avenues. Tucked between brick industrial buildings and elevated railroad tracks, the massive parking lot has transformed into a communal town square. 

Vendors, who started arriving at 5:30 a.m., work from beneath tents clumped together according to theme — handmade arts, street food, vintage finds and collectables. Food trucks semicircle a common like chuck wagons. Folk singers and DJs create the soundtrack that changes as one strolls.

The crowd is as diverse as what’s for sale. Artists and collectors, coffee-sipping couples, moms and dads with restless children, empty nesters who bought those vintage wares when they were new and a noticeable number of dogs walk the highly designed bazaar.

It’s the kind of market where you can leave with a handcrafted chair or a hammock, a porcelain tea set or a pair of Moscow mule-worthy copper mugs, quick stepping to a polka beat.

“It’s all types of people,” Sheldon says. “It’s a Cleveland thing. It just feels like a celebration of the city.”

Having arrived in Cleveland barely a decade ago, the small-town girl from Michigan has shown the region the untapped power in its army of artists and dreamers. Some call her the “Queen of the Flea,” but others see a catalyst for a new economy — a woman for her times.

They see a key addition to a city that possessed all the ingredients for an arts-driven renaissance — restless talent, empty buildings, online marketing tools — save the curator.  

“She’s created a new kind of culture that didn’t exist in Cleveland 10 years ago,” says Lillian Kuri, a vice president for the Cleveland Foundation. “We didn’t have a makers movement. We didn’t have a collective experience that’s authentic. That’s new.”

Kuri, an architect, is an expert in placemaking, a development strategy to revive urban spaces by creating quality experiences. 

“It’s the new wave of economic development,” Kuri says, adding that Sheldon puts Cleveland at the crest. “She’s on par with the best of the best.”

To that, Sheldon might say, I know. Her steady confidence could smack of conceitedness, if not for the happy smile that softens her go-go demeanor and ruthless work ethic. 

That she is doing something unprecedented, she has no doubt.

“We created all our own systems, all our own processes,” Sheldon points out. “I need to be the expert at this kind of business. There’s not a lot to draw from.”

It’s a point that irritates her a bit: While her success has drawn attention, the all-consuming work frequently gets overlooked.

Sheldon and the Flea’s two full-time staffers — Laura Drapac and Elizabeth Flanagan, both of whom have been with her less than a year — plot every detail from Flea headquarters on the third floor of Tyler Village’s Building 42. Their warren of offices display the tools of their uncommon trade: computers and whiteboards, coils of rope, a 300-foot tape measure, more than 100 extension cords, two tables saws, buckets of paint and a pallet of brightly painted tree stumps. 

Three days before the season opener, the forms and permits that could be demanded by a fire marshal, a health inspector or liquor control agent are neatly stacked beneath rocks on a tabletop. “Everybody thinks stuff like this just happens,” Sheldon says, snapping her fingers. “It’s hard. It’s risky. That’s why people don’t do it.” 

It’s not enough to stage a show that attracts thousands of people, many of them suburbanites, to an urban neighborhood off the beaten path. She needs them to come back next month. Thus the flourishes that appeal to people into art and whimsy.  

This day, colorful streamers flutter from scaffolding that forms a gateway on East 36th Street. Inside, diners nosh at ingeniously crafted portable picnic tables, the benches little more than boards bolted to Home Depot buckets. Cacti make sturdy centerpieces.

The mobile hand-washing station, near the portable toilets, resembles a homey bathroom with his-and-her sinks and mirrors. 

Sheldon designs, builds and positions almost every piece of infrastructure, following one golden rule: “It doesn’t need to be precious, but it has to be thoughtful,” she says.

You don’t just grab a beer at the Flea, you order a craft cocktail from the Happy Camper Bar Car — a silver, 1972 Airstream Safari converted into a mobile cocktail lounge. 

“Nothing is random,” observes Kuri. “She has a great design sensibility. You can’t understate how important that is. That’s why I keep going back.” 

Then there are the vendors, a select group of artists, jewelers and furniture crafters whom Sheldon fondly calls “creatives.” All of them have navigated an application process that looks for originality and passion. 

They greet one another like happy campers back for another summer. And why not? They’re doing what they like and love. They may earn many times the $325 vendor fee. Because of Sheldon, they can make the rent and maybe, one day, quit their day job.

“She’s driven by relevance,” says Drapac, the Flea’s vendor liaison. “She’s always interested in what people are looking for right now.”

Sheldon grew up a different drummer in Bad Axe, a city of 3,000 in the thumb region of Michigan two hours north of Detroit. 

Her older brother, Jim, smart and studious, became a mathematician. Her younger brother, Sean, a laid-back video gamer, is an electrician. Stephanie, the middle child, broke conventions and created new ones.

“I was always designing and building,” she says. “I was DIY from a very early age.”

By age 6 or 7, she had even taught herself to cook and began serving family dinners. 

“Our parents were working class, three kids,” says Jim. “Dinners were not special.” Then his little sister began presenting exotic platters, “veggies prepared in a way we didn’t know existed,” coaxing everyone to dig in.

By 12, she was an avid follower of creative maven Martha Stewart. Sheldon is especially proud of the apple pies she baked for her dad, 12-step creations that, in retrospect, required the same kind of passion her Flea vendors put into their food.

“It’s what makes your business special, that extra care,” she says.

As the middle child, she was always navigating between her brothers. Sheldon was always presenting a plan to someone, which only became enhanced by studying and practicing architecture.  

“She’s always been very assertive, headstrong, knowing what she wants and going and getting it,” Jim says. 

When time allows for introspection, Sheldon sees a handy personality trait. “I’m really good at convincing people to do what I want them to do,” she says. “That’s just my gift.”

Sheldon likely gleaned some entrepreneurial spirit from her father. He owned the J.C. Penney catalog store in Bad Axe, where neighbors picked up their mail orders. It was a hub of mercantilism in a small town without a mall in the pre-Internet age.

She also saw the emptiness her father felt after he sold the business. “It became clear to me that purposeful work is good for your mental health,” Sheldon says.

She earned bachelor’s and master’s degrees in architecture at the University of Michigan. Her thesis was prophetic: “Creative Engagement Through Pop-up Architectural Experiences.”

A design class introduced her to Midwest cities. She grew enchanted with Cleveland’s bridges, its Rust Belt burden and the “modest, self-deprecating people.” 

“I wanted to move to a place where I could make a difference,” she says. 

In 2007, she arrived with her newly minted degrees and a job with a small Ohio City architecture and design firm. After about six months of corporate design work, she left for a firm in Tremont that offered more direct contact with business owners. 

She liked the personal connection. “It taught me how to be the person who thinks from everyone’s perspective — the plumber, the electrician, the client,” she says. “To me, it was training to be the ringmaster.”

When the Great Recession stalled the building trade, her employer folded. She was 29, out of a job and facing stark decisions. 

Then Cleveland saved her, she says.

“I always had the desire to own my own thing, but I didn’t know what that would be,” Sheldon says. “If I was in a city like Chicago, I probably would have gone and gotten a boring job somewhere. Cleveland gave me the courage to do my own thing.”

She had some graphic design training and began planning weddings, initially for friends, then for the people who attended. The brides liked her creative touches such as how the flowers matched the table cards that matched the invitations.

“I began to brand their wedding,” she says. “I started doing that before I knew I was doing that.”

While working as a hostess at Luxe Kitchen & Lounge in the Gordon Square Arts District, she redesigned the menu, then the patio. She segued into her new role as a designer of other people’s dreams.

In 2011, she incorporated her consulting business, Indie Foundry. Her aim was to work with artisans and makers and help them make the jump from hobbyists to business owners. 

“A lot of people have ideas. They have no idea how to bring it to life,” she says. “They’re so close to it — they can’t figure it out on their own. That’s our specialty: understanding the processes of creating ideas.” 

It’s part grind, part passion. She calls the result “practical magic.”


Near the entrance to the Flea, 18-month-old Scout Wachter pushes his plastic lawn mower among the booths, trailed by his mother, Jackie, who greets the other vendors with smiles and hugs. They marvel at how big Scout has gotten since last year, when he was in her arms. 

Like Fount, the family business, Scout just might grow up at the Flea.

Four years ago, Jackie and her husband, Phillip, became a first-time vendor selling vintage finds. The next season they debuted leather handbags and wallets they designed, cut and stitched themselves. Last summer, the couple opened a 900-square-foot storefront on Detroit Avenue in the burgeoning Gordon Square Arts District. Fount shares space with Old City Libations, another business incubated at the Flea.

In March, the Wachters opened a second shop in Columbus’ trendy Short North neighborhood. Meanwhile, their workforce grows in the ArtCraft Building in Cleveland’s MidTown, where staff cuts the Italian leather and sews it into products. Suddenly, they have two stores, 36 employees and a precocious toddler to keep up with. 

“This was our school for learning a business,” says Phillip, an outgoing videographer. “We joke we graduated.”

“This let us know what would work, before we quit our day jobs,” says Jackie, who previously taught elementary school.

The Flea gave them a test market for bags that cost $100 to $1,400. It offered an income and an audience. Equally important, it gave them the confidence to keep going.

Both heap praise on Sheldon, whom they credit for relentlessly smiling, listening and pushing them beyond their comfort zones.

“She can make anything happen,” Phillip says, “anything she sets her mind to.”

Every startup needs a launchpad. 

For Sheldon, it was the Cleveland Hostel. A friend, Mark Raymond, had just opened the modest inn on West 25th Street, down from the West Side Market in Ohio City. He needed help with design and marketing.

Sheldon moved in with her dog and her cat, and spent a summer meeting travelers from around the world. “It was one of the best experiences I’ve had,” she says.

She also got to know “the West 25th Street crowd,” the fledgling brewers and jewelry makers, artisanal bakers and yoga instructors. In other words, she began meeting clients.

She soon realized that, more than a logo and a website, her clients needed customers. They needed an audience. So in 2012, she launched the forerunner to the Flea, a makers market, in Market Square Park.

The fair flopped, in Sheldon’s view, but it caught the attention of Michael Fleming, executive director of the St. Clair Superior Development Corp. Another visionary, Fleming set sheep to graze in a field off the Cleveland Memorial Shoreway, introducing free mowing to city folk, and brought the night market concept back from Hong Kong to AsiaTown.

Fleming was trying to fill vacant storefronts in the shopping district of the old
Slovenian neighborhood with a flurry of pop-up shops. He’d hoped to leverage the sidewalk flea markets that spilled out of some of the storefronts and needed someone who might take them to another level.

“It was sort of kismet,” he recalls. “She had the passion, the drive. We had the funding.”

With a $27,000 Retail Ready grant from Fleming, Sheldon launched the Cleveland Flea in 2013 from the Slovenian National Home (it rained) with about 30 vendors and 1,500 shoppers. 

“It was terrifying,” she recalls. “That whole first year of the Flea, I was terrified every single day. But it was also exhilarating.” 

But by the end of the season, the vendor ranks had grown to 65 and crowds surpassed 10,000. “We were hoping for a self-sustaining event,” Fleming says. “Obviously, we were blown away.”

Sheldon moved her market from the school parking lot of St. Martin de Porres High School to the roomier lot of Sterle’s Country House on East 55th Street. The Flea outgrew that space, too. In July 2014, it settled into Tyler Village. By the end of last season, the Flea was drawing between 20,000 and 30,000 shoppers, and its vendors had come to be seen as an economic force. 

“I was in the right place at the right time,” she says. “People in Cleveland wanted to shop local. They wanted to discover.”

Fleming concedes there was an element of timing — the city was on an upswing, shopping local was on a rebound and social media made grassroots marketing cost-effective and efficient. But Sheldon’s contribution can’t be downplayed, he says. “Stephanie is the master of the experience.”

For Sheldon, the Flea’s success was life changing. “By the last Flea that first year,” Sheldon recalls, “I literally said to myself, ‘If I can do this, I can do anything.’ ”

It focused all of her energies on a single event that demanded everything she knew about architecture, design, convening and convincing. “It became really clear that this is the avenue that really uses all of my skills,” she says. 


It can be tempting to exaggerate the impact of the Cleveland Flea, and thus of Sheldon. 

The Flea unfolds once a month for seven months. Indie Foundry’s workshops and special events — such as February’s wedding fair, Local Union — help to test new market avenues and keep the vendors engaged, but many will always be hobbyists. 

For every Fount, there’s an Itty Bitty Bakeshop, the new passion of Tiffany Dziak, who debuted at the April 22 Flea under a white tent.

Dziak, 28, sells artfully designed sugar cookies made from her mother’s recipe. She’s also a business strategist for Hyland, the Westlake-based tech firm. That job pays the bills and likely will for quite some time.

She envisions maybe selling her cookies from a tiny house on wheels, but she has no desire to report to a bakery every morning, should she ever start one.

Still, if the Flea is only a constellation of small businesses, their collective illumination is striking. About 15,000 shoppers streamed through the April Flea. Assuming an average vendor income of $2,500, which Sheldon says is conservative, the opening Flea generated $440,000 in sales. That’s $3 million across the season, a number Sheldon expects to grow as the weather warms and crowds swell.

There are other indicators of economic impact. Last year, Cleveland Hustles, the TV series taking startups to storefronts and co-created by LeBron James, debuted on CNBC featuring eight local entrepreneurs. More than half of the show’s contestants were graduates of the Cleveland Flea, including Fount, Old City Soda, Cleveland Bagel Co., Randy’s Pickles and Proper Pig Smokehouse.

Sheldon’s influence is spreading into the corporate community. As it readied its new world headquarters in Westlake, American Greetings Corp. called upon Sheldon to rebrand the company store, which to her resembled a card shop in a mall.

She added pop-up events and creative office supplies — the kind of stuff artists might use to make greeting cards — as she sought to create a hub.

More recently, a call came from Huron City Hall. Leaders of the city of 7,000, a popular spot for birding and boating, want to enliven their waterfront. They asked if Sheldon could create a happening. 

Plans are preliminary, but she’s proposing a market building filled with local artists and makers. She envisions oyster nights and Saturday farmers markets.

To get the creative juices flowing, Sheldon staged a tour of creative Cleveland. Huron business leaders, City Council members and city manager Andy White caravanned to Cleveland one day in early March. 

Sheldon guided them from coffee and bagels in Hingetown through the West Side Market and on to Flea-inspired businesses in Gordon Square. She called it her “Tour de CLE.” There will likely be more.

She sees herself as the designer and temporary operator of whatever arises in Huron. She thinks that’s an approach she could scale to other communities that have been calling, including one from out of state. 

“This is a really new model of development,” she says, growing excited. “Instead of bringing in Crate & Barrel, we’re actually starting all the businesses ourselves. Developers can’t do that, because they’re not operators. They don’t know how.”

There’s a window, an hour or two after the Flea opens, when the machine is firing on all its handmade cylinders. 

The tents are staked, the food trucks are slotted, the DJ is miced, there’s no more temporary fencing needing to be strung.

Sheldon melts into the throng. She’s racing the “treasure hunters” for the newly cool in the vintage world. She moves from booth to booth, soon burdened with a pair of copper mugs and a wicker stool. 

Her path takes her past Ode (Vintage)  and Articles, a treasure trove amassed by Nate and Erin Klees, who recently made the craft circuit a full-time pursuit, before coming to a hard stop at Great Lake Outfitters.

“Oh, you have a hammock,” she says to Kelly Pierce, the owner. Candy-striped, it hangs like summer between two poles. “OK, she’s 50 bucks,” Pierce says, “40 for you.”

“I’ll take it,” Sheldon says, offering a credit card. “I’m collecting them now.”

Then she spies it. Her eyes widen in wonder. Pierce helps to explain. It’s a 1950-era vibrating belt machine, also known as a jiggler, as it was supposed to slim a body by jiggling fatty thighs.

Sheldon is intrigued: “Does it work? Is it safe?” Finally, she asks what’s really on her mind, “Is this a thing?”


Her T-shirt reads DREAMER, and maybe her dreams could soar too high for one person to manage. 

On Sunday June 11, the Food Flea debuts at Tyler Village, the day after the Cleveland Flea. The brunch-themed fair of food trucks, food tent and drinks boosts the market’s expertise in cuisine. It replaces the monthly Sunday Market in Hingetown, which Sheldon says proved there was an audience for a bigger, food-focused event.

Cultural diversity at the Flea is a concern to Sheldon. She’d like to see more flavors from the region’s immigrant and minority communities. She sees a need for a mentoring program, where experienced vendors show newcomers the steps to success in the maker scene. The Food Flea could offer a new on-ramp.

Sheldon would also like to promote more love at the Flea. Many of the artisans are single and, well, art lovers would seem to be close by. Sheldon thinks some kind of message board — “Nice to meet you at the Flea” — could speed up destiny. 

She does not see a need to accelerate her own prospects. “I honestly haven’t been trying very hard,” she says. “I’m pretty into my work.”

And that’s only expanding. Sheldon has begun a book project, exploring public markets and their impact. She wants to find an indoor home for the Cleveland Flea, one that could serve as a year-round co-work, food hall and training center for creatives.

Her brother, Jim, isn’t concerned about his sister spreading herself too thin. Part of her success springs from her ability to learn on the fly. “We all have too many irons in the fire,” he says.

Sheldon acknowledges her workload is exhausting. But she’s no longer afraid. She’s sizing up opportunities. What’s more, she’s doing it from a position of strength. She’s been battle-tested, as have her strategies. 

“I get scared thinking about all the neat things we’re going to do, but the difference is I’m a lot better at managing fear,” she says. “It just fuels me now.”

As she’s pulled to offer her skills elsewhere in the world, Sheldon imagines pulling more of the world to Cleveland. She wants to export the city’s maker capabilities. She envisions creative conferences on par with conferences for health care and manufacturing. 

If people want to learn how artists and dreamers can change a place, let them come to Cleveland and see for themselves.

She’ll design the tour, every detail.

X Logo