Khamil Bailey, founder and executive director of the Greenwood Plan, has built her career around advancing entrepreneurship for minorities in Pittsburgh. As a community curator, she leads the nonprofit organization in its mission to advance economic justice for Black communities.

The Greenwood Plan’s current direction, Bailey says, is rooted in the vision she, along with founder and board president, Samantha Black, established upon its founding in 2021: removing the fear of failure in entrepreneurship while encouraging business growth. “We wanted to make it so that people were not afraid of entrepreneurship and felt like they could approach entrepreneurship with a spirit of exploration,” she tells Pittsburgh City Paper.

“We wanted to make sure that Black entrepreneurs had the ability and the encouragement to go into entrepreneurship and pursue it at the highest level that they chose.”

In 2024, the Greenwood Plan continued to make strides in pushing Pittsburgh’s Black business sector forward.

Bailey says owning the Pitt Building on Smithfield St. has created the biggest impact this year. “That would be the biggest accomplishment of 2024, actualizing what we have planned with owning the building and putting Black-owned businesses and organizations in that building in downtown Pittsburgh,” she says.

The Pitt Building serves as a hub for Black-owned businesses and organizations, with two tenants already leasing space.

For Bailey, her work affirms a belief she has held for years: that Pittsburgh’s Black business community is filled with talent, but faces systemic barriers. “I’ve always felt that Pittsburgh’s Black business community did not get a fair shake, and I feel like there were a lot of barriers placed in front of Black entrepreneurs,” she continues. “I always felt like Pittsburgh had talent in its Black communities. Through this work, I’ve just been affirmed in that thought.” Bailey says she has seen many talented entrepreneurs, innovative ideas, and remarkable creativity within the city.

Stepping into 2025, Bailey is focused on growth — not just for the Greenwood Plan but for the businesses it supports. One of her primary goals is to attract more Black-owned businesses to downtown Pittsburgh, increasing foot traffic and visibility for the entrepreneurs the Greenwood Plan serves.

Internally, she is also prioritizing capacity-building within the organization by expanding their team. “In 2025, my goal is to bring on more staff to help build the capacity even more.” She continues, “It’s also to be a great leader for the staff that we have.”

Bailey’s passion for her work stems from a deep desire to see communities thrive. “With all the work that I do, the goal is to make sure that folks can take care of themselves and their neighbors,” she says.