016: Are We Willing to Pay the Price for the Future We Want, with Keesha Gaskins-Nathan

How do we build a vital and inclusive democracy in a time of polarization, uncertainty, and systemic inequities? In this episode of Black Philanthropy: Our Stories, host Michelle Renee Jackson, MDiv, sits down with Keesha Gaskins-Nathan, Director of the Democratic Practice Program for the United States at the Rockefeller Brothers Fund, to explore her journey from law school and community organizing to leading philanthropic strategies that strengthen democratic systems and culture.

Keesha shares how her upbringing, her parents’ influence, and her early career in law and advocacy shaped her commitment to racial and gender justice. She discusses why voting is an expression of power, the ethical complexities of philanthropy, and why not all money is good money. This episode dives deep into future-oriented leadership, the grieving process of letting go of old paradigms, and the courage nonprofits need to say ‘no’ when funding misaligns with mission.

This conversation is a masterclass in strategic foresight, equity-driven philanthropy, and sustaining hope through intentional action.

Subscribe on Apple, YouTube, Spotify, or wherever you listen to podcasts.

Recorded on August 5, 2025

In this episode, you will hear:

·      Why voting rights and democratic engagement matter now more than ever

·      How the Future Bound project is reshaping leadership and systems for the next generation

·      Why nonprofits must learn to say ‘no’ and protect mission integrity

·      How grief and unlearning are essential for transformative leadership

Skills and Tips You’ll Learn:

·      How to embed futures and forecasting practices into your organization

·      Why relationship-building matters more than chasing dollars

·      How to evaluate funding opportunities and avoid mission drift

·      Strategies for sustaining hope and resilience in advocacy work

·      Why diversity—of thought, resources, and leadership—creates stronger systems

About the Host – Michelle Renee Jackson, MDiv:

Michelle Renee Jackson is an award-winning storyteller and leader in philanthropy, known for using film and visual storytelling to help organizations secure transformational gifts. She is the Founder and Principal Artist of Simuel + Murray, a production company with bases in New York and Los Angeles. Michelle’s work has redefined how nonprofits connect with donors through compelling narratives.

Connect on:
LinkedIn: https://www.linkedin.com/in/michellereneejackson/
Instagram: @michelle.renee.jackson

About Guest:

Keesha Gaskins-Nathan is a nationally recognized leader in democratic reform and racial justice. She directs the Democratic Practice–United States program at the Rockefeller Brothers Fund, advancing strategies to strengthen democratic systems and culture. Her career spans law, organizing, and policy advocacy, including roles as Senior Counsel at the Brennan Center for Justice and Executive Director of the League of Women Voters Minnesota. Keesha serves as Board Chair of The Workers’ Lab and holds advisory roles with national civic initiatives. A former adjunct professor at Columbia University, she is an Atlantic Fellow for Racial Equity and Aspen Ideas Scholar.

Connect on:
LinkedIn: https://www.linkedin.com/in/keeshagaskins/

Follow and Review:

We’d love for you to follow us if you haven’t yet. Click that purple ‘+’ in the top right corner of your Apple Podcasts app. Drop a review or 5-star rating—it only takes a second and helps spread the word about the podcast.

Produced by Simuel + Murray

Disclaimer

The views and opinions expressed in this episode are those of the host and guest and do not necessarily reflect the official policy or position of any organizations they are affiliated with or employed by. Listeners should consult their own attorney or financial advisor for guidance. This episode does not provide legal or financial advice.