Always Be Challenging with Rachel Pritzker

May 15, 2024

Episode 6 of “Break Fake Rules” calls on us to “always be challenging” norms

We have a new mantra on the show, and it’s all thanks to our latest guest, Rachel Pritzker, President and Founder of the Pritzker Innovation Fund. “A.B.C. Always be challenging.” So simple, so important, yet for many of us, hard to do. Tune into Rachel’s discussion with Glen to learn how we can challenge our assumptions, break out of our bubbles, and discover new solutions that lead to lasting progress. Her insights stretch beyond the fake rules of philanthropy to address how breaking the fake rules of politics and civil society can bring us closer together. As Rachel shares, I think it’s become very fashionable in philanthropy and civil society more broadly to take stands and draw lines. And the problem is, it just narrows our coalition and it often makes solving problems harder.”

Episode 6: “Always Be Challenging” with Rachel Pritzker

Listen to the full episode wherever you get your podcasts

In this episode, we’re lucky to hear from Rachel, a democracy and climate funder and coalition builder, who shares the healthy mental habits that can help us build new coalitions to solve generational problems. As Chair of the Democracy Funders Network, Chair of the Breakthrough Institute, Chair of Third Way, and Chair of the Energy for Growth Hub (check out their non-linear approach to measuring policy impact), Rachel wears many hats. Through her philanthropy, she has seen how polarization prevents progress and how entering into unlikely coalitions leads to more effective philanthropy and societal change. Learn more from Rachel about how leaning into disagreement instead of avoiding it can strengthen our relationships and enrich our society. 

This is a compelling episode. Watch the abbreviated version on YouTube or listen to the full discussion wherever you get your podcasts.

I hope you feel as inspired as we do by Rachel’s call to “Always be challenging” to break free of ideological barriers and expand our coalitions. Because it will take all of us to address the generational challenges we face today.

“Interacting with people we disagree with is actually one of the ways for us to become more effective. That’s how new ideas arise. We don’t come up with innovation and new ideas by just repeating the same stuff to each other.”

Rachel Pritzker

Up Next

It’s time to break the rules of our typical show format. Next month, we have a special edition of “Break Fake Rules” in the works—our first live show in front of an audience! Stay tuned for details on Stupski’s Instagram and LinkedIn

New episodes of “Break Fake Rules” drop monthly through October on your favorite podcast platform and Stupski Foundation’s YouTube channel.

We want to hear from you. Which fake rules do you want to see philanthropy break next? Share your thoughts with us on YouTube, and join the conversation with Glen on LinkedIn