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Cocoapreneur and Greenwood Plan Help Black-owned Businesses Succeed

When Khamil Bailey came to Pittsburgh from East Orange, NJ to study at the University of Pittsburgh in 2005, she was shocked at the climate for Black students in Oakland.

“I grew up in a very Black place; everyone was Black—our dentists, our service workers, our doctors. Here it was just people in the service industry with maybe just a few handfuls of Black professors. It just wasn’t a good feel,” she said.

Khamil Bailey

Bailey said she started to withdraw from the city, returning home nearly every weekend until she discovered Sankofa Circles. “I started attending meetings where people came from local Black communities, and I started connecting with them,” she said. “I finally felt like I fit in thanks to those communities.

According to Bailey, Sankofa is the philosophy that to make change in the future, we must look backwards to our history and the knowledge that we have gained. “We have to acknowledge what has happened in the past to learn and move forward,” she said.

After graduating from Pitt, Bailey stayed in Pittsburgh. “My formative adult years were spent here. I had good friends and connections, and you can’t beat the cost of living. I joke that I was trapped here,” she said.

Yet Bailey knew there were strides to be made in Pittsburgh for the Black community. In September 2015, she teamed up with the late Nazura Asaseyeduru to create the #BlackDollarsMatterPgh initiative.

“It was in the wake of the Trayvon Martin case and other high-profile murders of Black people where justice just wasn’t being served,” she said.

The year before, John Crawford, a Black man, had been shot in an Ohio Walmart as he looked at a BB gun. “We realized that large corporations were also not caring about what was going on, so we decided to look at how we could help people commit to Black-owned businesses in our area,” said Bailey.

While promoting Black-owned businesses, however, she realized that there was a problem. “In order to commit to Black-owned businesses, people had to be able to identify them,” she said.

That is when she created Cocoapreneur Pgh, LLC. “I used cocoa because it is rich and brown. We started as a social media campaign, and it organically grew from there,” Bailey explained.

People began reaching out through the Cocoapreneur social media outlets for recommendations, and Bailey knew they had to develop an online directory to be more effective. In 2017, she launched a crowdfunding effort and raised $3,600, which she used to launch an online directory in early 2018. “We started with about 200 businesses, and now we have about 350, but I know there are a ton more out there,” Bailey said. Cocoapreneur includes not only Black-owned, for-profit businesses, but Black-led nonprofits as well.

Bailey’s efforts to help Black-owned businesses succeed isn’t limited to Cocoapreneur. She is also the financial director and cofounder of The Greenwood Plan, a nonprofit dedicated to helping Black entrepreneurs succeed. The organization began as the Greenwood Week, a conference created in 2019 designed to help Black entrepreneurs learn how to grow their businesses.

Khamil Bailey, Samantha Black and Brandi Taylor

“The name is from Greenwood District in Tulsa, OK, where Black business owners were massacred in 1921. It was known as the ‘Black Wall Street,’” Bailey said, referring to the historic attack on the well-known Black business district. “We wanted to commemorate that time in history and that event.”

The weeklong conference expanded to become a nonprofit in February 2021 as a way to offer ongoing resources throughout the year. “It grew from the idea of creating a financial ecosystem for growth and prosperity for Black-owned businesses,” Bailey said.

Samantha Black is the organization’s director and co-founder, and in addition to hosting the one-week conference and offering ongoing resources and assistance, Greenwood has a coworking space, Emerald City Pittsburgh.

Both of the organizations that Bailey works with are dedicated to assisting Black-owned businesses to succeed, something that helps the region as a whole. More importantly, they recognize the importance of the Black population in the area.

“We can’t have the Pittsburgh region be one of the most livable places to live if it isn’t livable for Black people,” she said.

Others can assist these efforts by acknowledging history and having important conversations.

“We can’t ignore history. We have to acknowledge what has happened to Black and indigenous people in our history before we can talk about retribution,” Bailey said.

In addition to supporting Black-owned businesses, it is also important to support the community in other ways, she added. “Before we can solve a problem, we have to acknowledge there is a problem. We can discuss issues and from there, we can move forward.”

For more information about Cocoapreneur, visit Information and resources about The Greenwood Plan can be found at and Emerald City can be found at

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