The Leaders’ Table

Darryl serves as President of the Charter School Growth Fund, where he leads investments supporting a national community of over 100 high-performing charter school networks. As the founder of the Emerging CMO Fund, he also supports and invests in charter school leaders of color.

 

In this episode, Darryl reflects on what failure taught him while leading a charter school in Chicago — and why growth comes from making mistakes rather than avoiding them. He shares why joy belongs in classrooms and boardrooms alike, and how his family shapes his leadership style and keeps him focused on what matters most.

 

A candid conversation on resilience, leadership, and finding purpose by leaning into unexpected career turns and nonlinear paths.

Michele Jawando, CEO of Omidyar Network, leads with both head and heart — grounded in analytical rigor, driven by collaboration, and deeply committed to people. A lawyer, former Hill staffer, and lifelong sci-fi fan, she brings curiosity and optimism into every space she leads — whether she’s thinking about the transformative power of technology or investing in the people and culture around her.

 

In this episode, Michele reflects on the mentors who shaped her career and the throughlines that connect her career across policy, advocacy, and philanthropy. She discusses technology’s potential to shape our future, emerging questions around AI, and how she applies lessons from public service — which she calls a sacred profession — to leading a major philanthropic organization.

 

A thoughtful conversation on creativity, values, connection, and what it means to be a builder of ideas, people, and place.

Andy Rotherham, Co-Founder and Senior Partner at Bellwether, has built a career in public service driven by a deep belief in expanding opportunity for those too often left behind. Growing up in Reston, Virginia, he saw how even communities that appear integrated can mask significant inequities — particularly in education, where disparities compound and shape outcomes over the course of a lifetime.

 

In this episode, Andy reflects on the importance of looking beyond ideology and asking a simple question: Is a policy good, or just partisan? He shares why leaders are stronger when they cultivate diverse circles, resist echo chambers, and stay curious: whether that means learning the banjo, serving as an EMT, or studying the double-edged impact of AI. 

 

A thoughtful conversation on leadership, lifelong learning, and unlocking the untapped potential in communities too often overlooked.

Carmita Semaan, the founder and CEO of Surge Institute, an organization that develops and elevates leaders of color, began her career as a chemical engineer before earning her MBA and stepping into corporate leadership. Across her career, she has kept social impact front and center — organizing colleagues, investing in local communities, and challenging systems to do better.

 

In this episode, Carmita recounts a pivotal moment early in her career when she spoke out against racism at her company, choosing integrity over silence and ultimately walking away from the organization. She shares how growing up in Birmingham, Alabama, and the influence of her resilient mother and uncle shaped her values and continues to inform the bold, fearless leadership she embodies today.

 

An honest, powerful conversation about courage, conviction, and what it means to lead decisively when the stakes are real.

Amanda Renteria leads Code for America as CEO, guided by a deep belief in public institutions and the promise of opportunity. She has led the organization in modernizing safety-net systems across states, launched innovative resources to combat child poverty, and streamlined services that impact millions of Americans. 

Raised in California’s Central Valley by her parents — including her father, who immigrated from Mexico —Amanda traces her drive to the teachers, coaches, and family members who opened doors she did not know existed. Her first role in public service was as a teacher — an experience that grounded her belief that the government should expand opportunity. As the first Latina chief of staff in Senate history, she sees civic leadership as a responsibility — one that demands authenticity, curiosity, and a commitment to bridging gaps between communities and government.

A conversation about public service, institutional trust, and how bringing a small-town lens to national leadership keeps you learning and open to new ideas.

Dr. Penny Lee Schwinn is currently a Senior Advisor at Emerson Collective, an organization that invests in entrepreneurs and innovators tackling complex challenges in education, immigration, the environment, and beyond.

Previously she served as Tennessee’s Commissioner of Education from 2019-2023 where she led the restructuring of the state’s $9 billion school funding system. Prior to this live taping, Penny was the recipient of the 2026 Courageous Leader Award from LEE for her intentional focus on changing outcomes for kids regardless of the political context.

In this episode, she discusses how she grounds all her decisions in the responsibility for her kids and the children of others. She also shares how she “dances it out” to prepare for tough meetings and recentering joy. Penny shares how many different people and groups have tried to define her, but she defines herself as a mom of three, educator, and someone who is always student and child focused. An inspiring conversation about leadership driven by a singular focus on providing every child what they deserve.