Dave Roberson, Frederick Hutson, Nichelle McCall, Rodney Williams, Jason Caston, and Dawn Dickson, recounting her company's first big disaster Credit: Tatiana Walk-Morris

On Wednesday night, Chicago’s black tech community gathered at 1871 with one goal in mind: to share critical pointers for succeeding in their sector.

“We want to bridge that gap and help others get there. That’s what the founders’ series is all about,” said BlackInTech creator and CandidCup president Thomas K.R. Stovall

Panelists included Lisnr cofounder Rodney Williams, Pigeonly founder Frederick Hutson, Bold Guidance founder Nichelle McCall, Catson Digital founder Jason Caston, Flat Out of Heels founder Dawn Dickson, and Nexercise cofounder Gregory Coleman.

The speakers openly discussed their challenges and triumphs. Dickson, whose company sells rollable flats online and in vending machines, told the audience about her first machine, which set her back $10,000 and didn’t dispense shoes at all.

“I had to totally redo my business model,” Dickson said. “Never be too attached. I’ve launched Flat Out of Heels three times. We’ve had to continuously reinvent ourselves.”

The setback caused her to switch to an e-commerce model. Online orders now account for 80 percent of her business, she said.

During the Q&A session, attendees asked the panelists questions ranging from how to sustain their finances while starting a business to how to exude confidence when meeting potential investors.

“The reality is most investors aren’t technologists either,” said Williams. “Most of the time they understand that the technology may change.”

Additional key points:

  • Do extensive research. 
  • Figure out what your product, business model and consumers will be.
  • Beta test your product, testing it with a smaller consumer group before going full-scale.
  • Don’t get caught up in the mistakes you make along the way.
  • Though it may change, write a detailed business plan.
  • Make sure you own your product.

Christina Mighty, a 25-year-old “entrepreneur in the making,” said it was good to see women of color on the panel and to hear likeminded people that speak the same language in one room, adding that she’s glad the series will keep the conversation going.

“Panels like this are different from others, because this is focused on giving you tangible, real steps, and that’s what our community needs,” Mighty said. “We need a real game plan, real strategies, real lingo that’s out there that we don’t always know.”