In a city that continues to rank among the nation’s most challenging places for Black business ownership, one organization is working to change that narrative from the ground up.
The Greenwood Plan is a Pittsburgh-based nonprofit dedicated to advancing economic justice by strengthening Black-owned businesses, expanding entrepreneurial opportunities, and building pathways to generational wealth. Established in 2021, the organization has quickly become one of the region’s leading champions for Black entrepreneurship, offering year-round programming, networking opportunities, educational resources, and collaborative workspace for business owners across Western Pennsylvania.
Named for Black Wall Street
Named after the historic Greenwood District of Tulsa, Oklahoma — better known as “Black Wall Street” — the organization draws inspiration from one of America’s most successful Black business communities before it was destroyed during the 1921 Tulsa Race Massacre. The name serves as both a tribute to Black economic excellence and a reminder of the importance of rebuilding wealth and opportunity in Black communities today.
From Conference to Year-Round Resource
Founded by Khamil Bailey and Samantha Black, The Greenwood Plan grew out of the success of Greenwood Week, an annual conference launched in 2017 to connect Black entrepreneurs with mentors, investors, business resources, and one another. After five successful conferences, the founders recognized the need for year-round support, leading to the creation of The Greenwood Plan as a permanent resource for Pittsburgh’s Black business community.
Greenwood Smithfield: A Downtown Hub
Today, the organization operates Greenwood Smithfield, a downtown hub that serves as a co-working space, meeting venue, and business resource center. Entrepreneurs can access educational workshops, networking events, mentorship opportunities, pop-up markets, and programs designed to help businesses grow beyond the startup stage. The organization also hosts Radical Hour, community discussions focused on leadership and economic empowerment, and continues to expand Greenwood Week into one of the region’s premier Black business conferences.
Building an Ecosystem
The Greenwood Plan’s mission extends beyond helping individual companies succeed. Its broader vision is to create an ecosystem where Black entrepreneurs have greater access to capital, professional networks, partnerships, and opportunities that have historically been out of reach. By bringing together business owners, corporations, nonprofit organizations, philanthropic partners, and community leaders, the organization seeks to reduce barriers that have limited Black business growth for generations.
As Pittsburgh continues to grapple with one of the lowest rates of Black business ownership among major metropolitan areas, organizations like The Greenwood Plan are helping redefine what economic development can look like — one entrepreneur, one business, and one community investment at a time.
For Pittsburgh Urban Media, the story of The Greenwood Plan is also the story of what’s possible when Black businesses receive the support, visibility, and investment they need to thrive. It represents not only hope for individual entrepreneurs but also a blueprint for building stronger neighborhoods and a more inclusive regional economy.