What if the Cleveland Flea became a conference? It just did.

Cleveland Flea founder Stephanie Sheldon isn’t afraid to have the tough conversations around entrepreneurship—and that’s exactly why she’s dedicating an entire day to them with the upcoming Creative Conversations conference.

“It’s hard for me to have conversations with the [local small business] community because they’re not taking risks,” says Sheldon. “We’re hitting a wall helping creative business owners grow because they think it’s about business. Yes, numbers and spreadsheets are important, but it’s also about mindset.”


Cleveland Flea founder Stephanie Sheldon.Having run the Cleveland Flea for the last seven years, Sheldon has long had a place on the front lines—as she considers the Flea not just a market but also a business incubator. Though having a presence at the Flea has helped launch and grow businesses like Fount, Oceanne, and Brewnuts (all of which went on to open brick-and-mortar stores), Sheldon estimates that just 5% of the businesses and coaching clients she’s worked with have “truly gone on to build the business they love and want.”


Sheldon hopes to change that reality by empowering local entrepreneurs with the daylong Creative Conversations conference, scheduled for Saturday, Sept. 29, at the Fount Leather workshop (3615 Superior Avenue, Cleveland).

Panels and talks will center around four main themes of “courage, confidence, commitment, and creativity,” with speakers including Janae Bryson of Auden & Co., Jill Vedaa of Salt, and Giavonna Evans of GrooveRyde. The keynote will be given by
Brim Papery founder Jolie Akrom of Columbus.


“These are all people who’ve taken significant risks to do things that scared them, things that were financially terrifying,” says Sheldon. “There’s this really pervasive thought that small business should always feel fun and that you should never feel any discomfort, and that’s just not true. We want to share talks with these people and turn the light on for all these dreamers.”


Other highlights of the day will include a VIP breakfast and speaker meet-and-greet and a post-conference social hour and tour of the Fount workshop.


Overall, Sheldon says she hopes to harness the entrepreneurial energy of the Flea events and translate it to a wider group of women and would-be business owners in a fun conference setting.

“The energy is high at the Flea, and that’s directly related to the fact that everyone there is daring greatly,” says Sheldon. “This is for anyone who wants to change their lives, launch something, or create a higher purpose in the world.”

Read more articles by Jen Jones Donatelli.

As a Cleveland native and enthusiast, Jen Jones Donatelli is thrilled to take on the managing editor role at FreshWater. As a full-time freelance writer and editor for more than a decade, Jen has contributed to publications including Redbook, Budget Travel, GOOD, Playboy, Thrillist, Cleveland Magazine, Los Angeles Confidential, San Francisco, Ohio Today, and many more. She is also a contributing editor for Destination Cleveland and a proud graduate of Ohio University's E.W. Scripps School of Journalism.
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