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September 11, 2025 42 mins

In this episode, Kristine Michie sits down with Jess Tomlin for an inspiring conversation about reimagining what it takes to drive lasting change. She shares how play, imagination, and boldness drive, sustainable movements and organizations like hers, which has invested $100 MILLION to 1,500 human rights groups in over 100 countries. You’ll come away with a fresh perspective on resources, leadership, and the possibilities of building a more just world.


Key Takeaways:

  • Investment capital dwarfs philanthropic dollars, with $70 trillion circulating in markets compared to $70 billion in philanthropy, highlighting the need to influence where the real resources are.
  • Integrate gender-lens investing into your strategy by applying rigorous screens that lead to stronger company performance—such as parental leave policies, leadership development for women of color, and menopause policies.
  • Build play and imagination into leadership and team culture through intentional retreats or exercises that strengthen trust, collaboration, and innovation.
  • Prioritize relationship-building across silos—climate, philanthropy, racial justice, private sector—to unlock new opportunities for impact and collective power.
  • Support proximate leaders and grassroots organizations with long-term funding rather than short-term grants, recognizing that transformational change requires decades of investment.
  • In spite of operating on less than $20,000 annually, women-led grassroots organizations are the most powerful drivers of systemic, generational change.
  • People-powered movements demonstrate persistence through setbacks and continuity across generations to secure lasting progress.


"The social impact sector is just on a cliff. And so I definitely feel that sense of urgency, I would say, and I'm hungry for, like, the boldness that the moment requires." — Jess Tomlin


"Having the ability to be in a space of imagination is freeing, and it is joyful. And in this moment in time when there does not feel like a lot of freedom or a lot of joy, what a gift that is to be able to give ourselves permission to imagine." — Jess Tomlin


"I really believe that I want to master relationship-building as a tool and a strategy to help us bust the silos that we all find ourselves in right now." — Jess Tomlin


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