Jim Bildner
CEO, Draper Richards Kaplan Foundation
This episode premieres Thursday, October 8, 2026 at 7:00pm ET.
“The most effective leaders I know are vulnerable. If we don’t know the answer, we say we don’t know, but we have your back, and we’re going to work through this together.”
Summary
Hope is usually treated as a feeling, something we either have or lack. For Jim Bildner, it is closer to a discipline: rigorous, measurable, and rooted in a willingness to look at hard problems instead of walking away from them.
Jim is the CEO of the Draper Richards Kaplan Foundation, one of the world’s leading venture philanthropy firms. On this episode of Leadership Matters, he and I sat down to discuss what exactly ‘venture philanthropy’ means, along with his own professional journey. From his family’s grocery stores to a gourmet chain of his own that ended in bankruptcy, Jim learned early that mistakes need not define a career.
We discussed why DRK invests in each organization only once and asks every entrepreneur to share problems in real time, how the foundation traded elaborate impact metrics for a single question about lives served, and why improving existing systems has proven more powerful than disrupting them.
We also explored the ideas in his new book, A Matter of Hope, and why the barrier to making a difference is not ability but a decision to act.
In an era where leaders are expected to have every answer, Jim makes a compelling case that the most effective ones are vulnerable, present, and honest about what they don’t know.
Mentions & Resources in this Episode
Guest Bio
Jim Bildner is the CEO of the Draper Richards Kaplan Foundation, one of the world’s leading venture philanthropy firms. DRK brings the discipline of venture capital to social change, backing early-stage leaders with unrestricted, multi-year funding. Jim has invested in more than 250 social enterprises engaged in transformative work on everything from poverty and food insecurity to healthcare access and climate. He is also a lecturer and researcher at Harvard University’s Kennedy School, where he focuses on how private capital can be used to solve public problems. Jim earned his AB from Dartmouth College, his MPA from Harvard, his J.D. from Case Western Reserve School of Law, and an M.F.A. from Lesley University.