Steph Sheldon

July Superwoman: Stephanie Sheldon, Founder Of The Cleveland Flea

Cleveland: a city essentially built by the Rockefeller empire, but a city that fell victim to Rustbelt politics. It’s a city known for worshipping LeBron James and “inventing” stadium mustard; a place that loyally supports a chronically terrible football team and houses the Rock and Roll Hall of Fame. What Cleveland isn’t really known for is artistry, crafting and showcasing an entrepreneurial spirit. Enter the Cleveland Flea.

The Cleveland Flea is a massive gathering of creative people from the area who are pursuing their craft as entrepreneurial endeavor. Thousands of people attend, giving the vendors exposure and sales, while giving the shoppers unique pieces and inspiration to do something that fuels their artistic fire. Let’s not forget the food trucks, dogs and local flair galore. Stephanie Sheldon, founder/visionary of the Flea, is the reason that Cleveland is getting on the map for creative endeavors.


Steph has always been interested in helping entrepreneurs and visionaries succeed.

“I was kind of that person myself,” she said, adding that there was a point where she was unsure of what creative thing to pursue. Steph wanted to help others discover what their artistic future was. She had been working with “makers” and small business clients when the idea for the Cleveland Flea emerged; her clients wouldn’t take the plunge into full-blown business mindset.

“It didn’t make sense to me,” she recalled. Her clients were using Etsy to sell their craft, but they weren’t investing in themselves or their business. In other words, they didn’t want to spend money to make money. This realization led Steph to create a market on her own, helping to solve her clients’ core problem: the need for “commerce and comradery.” They needed to make money, but they also needed good conversation with people like them. Thus, the Flea.

It almost seems that the Flea was Steph’s destiny. She was “always a creative side-hustler,” whether it be shown through hunting for furniture at garage sales or constantly redoing her room. She went on to receive her Master’s degree in architecture and moved to Cleveland just as the recession started. The company she worked for started to crash, leaving her unemployed for months.

“With a stable job and everything going fine, that’s when people don’t take chances,” she said. Stephanie began designing wedding invitations on the side.

However, the Cleveland Flea is a huge undertaking for one person to handle, and that’s what Steph did at the beginning. She recalls one of the challenges she faced being “believing in [herself]” as well as the emotional toll that brings with it. Setting up the flea is like “moving house each day,” an intense physical process that goes virtually unseen.

Perhaps the most arduous challenge the Flea presents to Steph is that she doesn’t always receive the support of others. People seem to think putting the Flea on is easy, and it’s not seen as a small business. She receives quite a bit of criticism for the way she runs it, and she feel like she can be the “garbage can of people’s annoyances at times.” It’s actually super exhausting, said Steph, and that aspect has the capacity to take the joy out of the thing.

“I’m responsible for keeping 10,000 people safe,” she said. With that, it’s clear that the Flea is a new, unconventional type of business. However, she said that Cleveland is not a creative-centric city; the system is rigid and often hard to navigate, as the Flea requires permits and inspections for safety.

The Flea has had its share of successes as well.

“The fact that it still happens is amazing to me,” Steph said, referencing the fact that it has officially made it past year five. In fact, the Flea nearly closed last year because it was so difficult; there’s only “so much you can do to move a boulder up a hill.” Achieving the perceived success that the Flea has accrued is incredibly hard; it is fun, but a ton of work. Steph said if she didn’t have a compelling reason to do it, she wouldn’t be doing it.

What is her compelling reason? Her amazing team and her goal to really change the city in a way that creates opportunities for creatives.

“Running the flea was like having sextuplets; now they’re five years old. One was always crying,” she said of being the sole person behind the Flea, but her team has relieved some of the “crying” for her. People didn’t believe that she did it all on her own. This led her to get into life coaching because she wanted to facilitate those hard conversations with creatives about the reality of it all.

As far as changing the city, Stephanie believes that the Flea “operates as a constant pipeline” for creative people to have opportunities as well as allowing people to realize what creativity they want in their life. The Flea seeks to inspire people to love themselves and the city of Cleveland even more.

Even more so, she wants the Flea to instill a sense of creativity and joy within people who are part of it, whether they be vendors or shoppers. Steph was very specific about what joy was: it is something that is given to yourself intrinsically, and that’s something she believes is a motivating factor in what she does. It doesn’t really work within a capitalist framework, which caters to pleasure. Stephanie believes that the Flea could not be replicated anywhere else; it could only happen here because of the people who live here.

Steph has advice for other female entrepreneurs on their creative endeavors: “You are exactly where you need to be.” She believes that the process is vulnerable and long; a quick fix isn’t the answer, and that’s why most people give up. Digging deeper “only requires your commitment,” she said. With that, comparing yourself to other people and milestones you think you should be meeting is a toxic way to think.

“Whose milestones are they anyway?” she said, adding that you can’t really know the milestones before you start the journey. Each path is different, and they will change along the way.

As far as future plans for Steph, she said that she feels good about the forward vision for the Flea. She wants to teach her team to run the Flea so that she can become the creative director. This way, the Flea will become an even more creative and loving place, and maybe and even bigger one at that. Steph also just launched Creative Clubhouse Coaching, which help people become “dreamer-doers.” As the Flea is an exclusive Cleveland endeavor, she also mentioned a desire to consult with other cities about retail success in the small business economy. She said it would “help cities become more creative.”

Stephanie describes herself as someone who is inspired by visionaries who didn’t take the easy road and people who say things that get them in trouble. She feels like she is that kind of person. Her favorite quote is by Maya Angelou, which deftly sums up her Flea journey: “You can only become truly accomplished at something you love.”


Author: Sam Raudins
Email:  sraudins@harnessmagazine.com
Author Bio: Sam is a journalism major at Ohio State who lives for football and good iced chai lattes. She is an intern at Harness, Social Media Editor at The Lantern and Senior Editor at Her Campus Ohio State. In the past, Sam has created her own blog and developed a football column at Her Campus called “Femme Football.”
Link to social media or website:  http://theinternalmonologue.weebly.com | Instagram @sgr3| Twitter @sam_raudins


More From Culture

Black in America

by Jahmya Moody

Dear Parents:

by Jamie Henry

“You Don’t Look Old”

by Amanda Massey

Perseverance During Uncertainty

by Chelsea Leonard

Leave a Reply

Your email address will not be published. Required fields are marked *