Women & Business Profile: Khamil Bailey

“Everything I start, I am aiming to solve a problem that exists for many.”

Khamil Bailey’s entrepreneurial journey has never been about launching businesses for the sake of growth. Instead, each venture has emerged from a desire to address challenges facing Black and other marginalized business owners. What began as a single idea has evolved into a network of organizations working to expand opportunities for entrepreneurs across the Pittsburgh region.

Bailey is the founder and owner of Cocoapreneur Pgh, co-founder and executive director of The Greenwood Plan, and owner of Emerald City Pittsburgh. Across all three organizations, she serves as the primary decision-maker and has helped shape their missions from the ground up.

“My businesses can easily be considered social enterprises because of the mission and vision attached,” Bailey said. “I like to help people and I want my businesses to do that as well.”

Her work began with Cocoapreneur in 2015. After a successful fundraising campaign in 2017, she launched what became known as Pittsburgh’s Black business directory the following year. Partnerships with other women-owned businesses led to small-business classes for the community, which later inspired Greenwood Week, a business conference that became the foundation for The Greenwood Plan nonprofit in 2021. Later that year, Bailey launched Emerald City Pittsburgh to meet additional needs she had identified among Black business owners. Looking back, she sees each organization as a natural extension of the last.

“I would describe myself as a solution-oriented businesswoman,” Bailey said. “Everything I start, I am aiming to solve a problem that exists for many.”

Among the accomplishments she is most proud of are raising $100,000 during the COVID-19 pandemic to support Black business relief efforts through Cocoapreneur, helping The Greenwood Plan acquire The Pitt Building in Downtown Pittsburgh and serving more than 150 clients and members through Emerald City Pittsburgh. Her work has also earned recognition through honors including Pittsburgh Magazine’s 40 Under 40, the Pittsburgh Rotary Club’s Excellence in Ethics Award and the New Pittsburgh Courier’s Fab 40 Under 40.

As she looks ahead, Bailey hopes to deepen the impact of her organizations rather than broaden their reach. “I want them to keep developing to go deeper, not so much spreading wider,” she said. Her advice to other women in business is simple: trust that your perspective matters. “Your womanhood is not a hindrance on you,” Bailey said. “It is a gift.”