Fertile Ground LIVE – Chicago Recap
RUNWAY Roots brought Fertile Ground LIVE to Chicago for the very first time—and it was a fruitful, sold-out gathering that brought together a vibrant ecosystem of Black entrepreneurs, dreamers, builders, and community leaders. After over a year of meeting virtually, being in person was powerful—to be able to laugh, share meals, throw cheeky side eyes from across the room, learn, problem-solve, and build power together. It was something we didn’t even realize we had been longing for until we got to collectively experience it. Together, we dug deep into the urgent question of how we build power, wealth, and legacy in a time of uncertainty and shifting landscapes.
The day began the way all powerful work should—with deep intention. Aya-Nikole Cook of Haji Healing Salon guided us through a wellness session that reminded us: we cannot talk about sustainability, legacy, or entrepreneurship without first centering and grounding ourselves. As Black entrepreneurs, tending to our minds, bodies, and spirits is itself a form of reclamation.
From there, the energy shifted into action. RUNWAY Roots’ own Tomme Faust, Naima McQueen, and Keena Pierre led an interactive workshop on Powerbuilding at the Local Level. This session struck a (power) chord. Through reflection and exercises like power mapping, participants explored different types of power—from social to financial to cultural—and how to wield them collectively. Many of us walked away not only with new tools, but also with a renewed sense of agency. The workshop echoed the spirit of our State of the People Power Tour: that power is not something to chase, it is something we already hold within us.
The afternoon then pushed us into future-oriented terrain with RUNWAY Roots entrepreneur-turned-board-member Bosko Kante, co-founder of Electrospit and founder of HiiiWAV. His session on Technology & AI for Black-Owned Businesses was bold, timely, and yes—a bit contentious. Many in the room voiced strong feelings about artificial intelligence, and rightfully so. Especially for artists and communities of color, AI raises layered questions:
Who is building these tools? Who benefits? Who owns the production? What happens when massive data centers harm communities of color through environmental degradation and economic instability? How do we reconcile innovation with environmental and social justice?
This is precisely why we need these conversations. Fertile Ground LIVE is not necessarily about presenting neat answers; it’s about holding complexity together. As Bosko reminded us, AI can be a tool for time-saving, creativity, and scaling Black businesses—but only if we approach it with discernment and a commitment to justice and equity.
We closed the program with a powerhouse panel moderated by our own Naima McQueen, featuring Andrea Yarbrough, co-founder of Cooperation Racine, who is pioneering cooperative business models that center collective ownership; Bernard Loyd, Founder and President of Urban Juncture, whose work builds infrastructure and community-based business ecosystems; and Tonika Johnson, Founder of Folded Map Project, who is transforming how Black-led organizations access resources and share power.
This conversation on Rewriting the Black Wealth Playbook rooted us back in legacy and community. Cooperative economics, real estate rooted in justice, and financial healing were named as critical paths forward. The panelists challenged us to expand our definition of wealth beyond dollars, and to see wealth as ownership, cultural continuity, shared infrastructure, and community care.
And finally, we brought the day to a close with what sustains us most: joy. Happy Hour and networking flowed with food from local Black-owned businesses, laughter, and new connections cemented the feeling of Fertile Ground as a convening of possibility.
Despite rollbacks, shrinking DEI commitments, and financial headwinds, our community continues to resist, innovate, and dream out loud. Fertile Ground LIVE is how we carry that forward—expanding city by city as a home for learning, connection, and collective reimagination. Because “we are the ones we’ve been waiting for.”
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