Every Disruption starts with Intention.
Every morning, as I reflect over my favorite tea, a simple question drives my day: how do we unlock resources for people and communities of color? This question led me to found Bold Ventures, a strategic advisory firm that has directed over $50 million to BIPOC-led and serving organizations—but funding is just the beginning.
My daily efforts focus on connecting disparate realms, creating pathways for economically divested communities to spearhead change, all while confronting systems that sustain inequality and concentrate power and wealth among a select few. When I partner with fellow waymakers, we're not just tweaking broken systems—we're creating regenerative ones that replenish communities rather than extracting from them.
Asking "Why Not?":
A Lesson in Leadership
For more than 15 years, I've been the voice asking "why not?"
I've forged my path questioning convention at every turn. My journey began in clinical research and reproductive health, focusing on enhancing the well-being of young people. From there, I moved to reducing gun violence through racial equity initiatives at the Joyce Foundation, then to advocating for BIPOC communities at Arabella Advisors. Leading Chicago's African Americans in Philanthropy revealed to me the significant impact of prioritizing excluded voices, which has since become my guiding principle.
Chicago is more than just my home; it is the soil where I have witnessed the impact of dedicated individuals coming together to sow seeds of justice to reduce inequalities.
Revolutionizing Philanthropy's Future
Each step in this journey has sharpened my strategic vision.
I don't settle for incremental improvements—I'm driven to develop restorative strategies that bring communities measurably closer to true collective prosperity.
The truth is, traditional philanthropic practices aren't working—they're yielding short-term gains while long-term systemic impact remains elusive. My values-aligned approach reshapes the economic landscape for future generations by putting decision-making power directly in the hands of those most impacted by inequalities. I center my work on trust, self-sufficiency, and community agency, creating fertile ground for a more fair and equitable capitalist society.
Featured In
Investing in Future Waymakers
I recognize that the future of equity hinges on those who are willing to reform economic inequalities. As a lecturer and adjunct professor at the University of Chicago, I advance fundraising, philanthropy, and the future of giving. I'm inspired when students connect historical challenges to future possibilities and then transmute that understanding into galvanizing action.
These are our future philanthropists, business leaders, and foundation executives who will shape how resources flow for decades to come.
"I feel inspired by Jessyca’s entrepreneurialism and leadership in our sector. I have experienced a lot of rejection in philanthropy and talking to Jessyca makes me feel seen and affirmed."
Finding Solitude in Uncertain Times
In my years of equity work, I've recognized an overlooked reality: substantive progress requires deliberate solitude. When I’m not reimagining wealth distribution, I'm kayaking Midwest waterways and navigating nature’s obstacles. In my garden, I find lessons in cultivation—whether growing people, ideas, or new ways forward. I believe everyone deserves these moments of clarity and renewal.