The Cleveland Flea founder plans to recharge away from the Rust Belt—before returning with even bigger ideas. By Jillian Kramer
Photo: Heidi M. Rolf
The first time I met Stephanie Sheldon, in 2013, the Cleveland Flea founder had chopped her hair into an asymmetrical pixie cut, one side, blonde, just touching her cheekbone, the other, nearly buzzed and brown. Of all the questions I could have asked her, one bubbled out as I stared in awe: “What made you want to cut your hair like that?” I rudely asked.
Sheldon replied, “I woke up one day and decided to be a badass.” And she is. She really is.
Sheldon launched the Cleveland Flea in 2013 with some 30 vendors and 1,500 shoppers. In five years, the seasonal event has grown to welcome a whopping 10,000 visitors each date it’s open, with a diverse and sizeable team backing Sheldon as she has brought her visions of a business incubator that would revitalize the city and its residents to multi-colored life.
The event has a Cleveland Flea Bar and a groovin’ DJ, making it the place to be on any given Saturday from April ’til November. Plus, behind the scenes, Sheldon offers coaching for who she’s dubbed “female founders, creative startups, and millionaire makers” looking to elevate their big business ideas.
“The Cleveland Flea brought together a lot of people that felt passion and entrepreneurship and who wanted to do something different for Cleveland,” says Helen Qin, co-owner of Mason’s Creamery. “Having those vendors as a support system, and knowing there were people going through the same things you were going through,” was critical to its success.
This year, the Cleveland Flea was highlighted in a national Honda commercial; it opened Creative Clubhouse, a physical and online space for women to learn what it takes to run a business; and, due to high demand, it is running not one but two holiday shows this year.
Like I said: Sheldon is a badass.
But even badasses need a break, and that’s where Sheldon was when she posted a message in late August on her Instagram account that read, in part, “I think it’s time I take a bit of a breather from this beautiful city. … If I’m honest, building and running this business nearly killed me. It’s only because I love this city so much that it was even possible. I moved here 10 years ago with zero reservations. Where others saw decline, I saw possibility. And that’s still who I am today. I refuse to give up. But, god damn if it hasn’t taken its toll on my spirit.”
Sheldon confirmed to Modern CLE her plans to take as many as nine months away from Cleveland to rest, rejuvenate, and research—and come back inspired.
“It becomes the responsibility of anyone who runs a business to find a way to do what they love and what they need to do to support both their community and their livelihood, but to do it in a way that preserves them as humans,” Sheldon explains. But that last part, the part about finding a kind of work-life balance in business building, hasn’t always happened for Sheldon.
In fact, Sheldon has developed an emotional resilience test for entrepreneurs that she uses to gauge the demands placed on her clients, and their ability to meet them, emotionally and physically. It’s a test that if she self-administered, she would almost certainly fail.
“I was at the forefront of [Cleveland’s creative scene], so there was zero camaraderie, zero community, and zero commerce,” says Sheldon. “That’s why the Flea was created of course, but what you have to understand is that because none of that existed, I remained extremely unsupported for a very long time—and you can really only do that to yourself for so long.”
“The world expects perfection from female business owners.” — Stephanie Sheldon
She likens the experience to birthing and raising sextuplets as a single, working mother.
“That’s what it felt like,” she confesses, “because the world expects perfection from female business owners.” And that pressure, she says, has taken its toll over time.
“I spent a huge amount of time the first year or two—probably even more than that—just constantly over-explaining what I did to everybody,” Sheldon says. “It’s overwhelming, and the thing is, I’m not sharing that because I want anyone to feel bad for me, but it’s—I was a person doing everything that looked from the outside like a huge company was in control.”
She continues, “Every single day, we are committed to getting better—but the way to get better is that you’re constantly in the unknown. Bad stuff happens and then you just have to rebound from it. And so, to physically live through that—the emotional life of that thing is just really taxing and really overwhelming at times, and it became apparent to me that if I didn’t make my own creativity and the things that make me happy in the world a priority—if I didn’t make that super important and center stage—that I would close Cleveland Flea.”
Faced with those two choices, Sheldon has chosen to take a creative sabbatical. As Sheldon explained in an email to Modern CLE, “I’m choosing to prioritize my own self-care [and] creativity, and to refuel so that I can continue to be this committed to both my business and this city.” Her plans are in what she calls the “visionary” stages, but Sheldon imagines herself exploring three countries, immersing herself in their unique languages—a passion of hers—and their marketplaces, of course.
In her absence, one thing is crystal clear: the Cleveland Flea will continue, with its growing team running the show and Sheldon managing it from afar. ” The operations of market events won’t be my main job anymore,” she tells Modern CLE. “However, business development, market study, and growing us into markets beyond Cleveland will be.”
In the days before she departs, she’s been writing down all the behind-the-scenes knowledge the team will need next year.
“When I was doing it myself, I could just do the work. I didn’t have to direct anybody. I just internally, intuitively knew what to do, and how I make decisions,” Sheldon says. “But I’m learning my team doesn’t have that ability—or, it’s going to take them five years like it took me.” Luckily, helping others understand how things work is one of Sheldon’s specialties.
Sheldon will be back, she promises, because she isn’t done with Cleveland just yet.
But on the phone now, during the interview for this article, I pose another, much less rude question to Sheldon: Have you accomplished what you set out to accomplish in Cleveland?
“I don’t like doing things very small scale,” she reflects. “I knew that I wanted to be known here. I knew that I wanted to celebrate what’s so amazing about Cleveland, to teach people both to love themselves more and teach the people who doubt Cleveland to love Cleveland.”
She continues, “I also wanted creative business owners to stay in Cleveland, because the story I heard over and over is that Cleveland has a lot of boomerang-ers and a lot of people who decided they couldn’t make what they wanted to make in the city that they love, so they’re going to have to do it somewhere else. I kind of never bought that, and I decided, I’m going to turn Cleveland into a place that you can have a creative business. And look how many businesses we have helped build. There are literally hundreds of businesses now.”
I think that was a big, fat, yes.
“We all can relate to [my struggle], because we all have responsibilities, whether you’re a mother, a father, a grandmother, a teacher—anybody,” says Sheldon. “When you have responsibilities, life can be all about them. So, I think it’s a natural conclusion—or a natural phase—that I’m finding myself in and I’m really, really excited because I think what it means is that I’m not leaving Cleveland. I’m just taking time to nourish my own creativity so I can continue to remain a defender of Cleveland’s creativity. That’s what I’m here for.”