Jessyca Dudley

Founder & CEO | Bold Ventures

If you don’t yet know Learning Community member Jessyca Dudley, I’m excited to introduce you to her! Based in Chicago, Jessyca is advancing racial equity in the world of philanthropy. She is Founder and CEO of Bold Ventures, a strategic advisory firm that supports individuals, families, foundations, and donor communities who are committed to eliminating disparities through relationship, repair, and the redistribution of wealth.

Jessyca is hardly new to this work. She cut her teeth as the Executive Director of Chicago African Americans in Philanthropy and as a Director at Arabella Advisors where she developed new strategy approaches and advocated for investment in BIPOC communities. She also served as program officer for the Gun Violence Prevention program at the Joyce Foundation.

We first met Jessyca back in March of this year when she took the 21/64 virtual Approach Training. In just a few short months, we have been inspired and enriched from the relationship, working with her to organize next week’s 21/64 Chicago gathering at Impact House. Earlier this year, Jessyca and her team launched All Together Bold, an intimate learning community dedicated to building a more just and equitable world.

WHAT IS ONE VALUE THAT MOTIVATES YOU AND HOW HAVE YOU BROUGHT THIS INTO YOUR WORK? Born and raised in Chicago, I have seen firsthand how philanthropy has often excluded communities of color and their perspectives. I have been on both sides of the system – seeking funding and making grants – and have seen how the opaque practices of philanthropy are used to regulate access to funding for BIPOC communities. It’s critical that more people understand and engage with philanthropy if we are going to shift this system towards equity. Our work to disrupt traditional philanthropy and to support leaders in advancing racial equity was born out of our direct experiences and interaction with philanthropy, and a desire to see this sector work differently.

TELL US MORE ABOUT ALL TOGETHER BOLD. All Together Bold is an intimate community of people, dedicated to building a more just and equitable world. Employing a cohort learning model, our members dive deep into the tensions and challenges of advancing racial equity work, surrounded by a supportive network that understands the unique struggles we face.

WHAT IS SOMETHING ABOUT YOU THAT MIGHT SURPRISE PEOPLE? I find great joy in being outdoors and have a goal to visit every national park in the United States. Before my workday starts I am often kayaking, hiking, or just sitting outdoors enjoying time in nature as a way to ground myself before the chaos of the day begins.

WHAT IS THE BEST PART OF YOUR WORK? Leading a dynamic team that develops strong and trusting relationships with clients through facilitation and stakeholder engagement that enhances the impact of their efforts.