The Business of Giving

My guest today is one of Boston’s most respected civic leaders and a nationally recognized voice in youth development. Robert Lewis, Jr. is the President and CEO of the Boys & Girls Clubs of Boston, where he leads a vibrant network of eight clubs and community sites serving more than 12,000 young people annually. A Club kid himself, Robert has spent his life investing in youth, building opportunity, and challenging outdated narratives about talent and potential.He brings a deeply personal, place-based approach to leadership—one grounded in love, grit, and high expectations. From health equity to workforce readiness, from cultural pride to redefining return on community, Robert Lewis is helping reshape what it means to grow up strong in Boston—and what it means to lead with heart.

When ABC News anchor Bob Woodruff was catastrophically injured in Iraq in 2006, his family made a vow: if he survived, they’d use their platform to support others returning from war without the same safety net. Nearly 20 years later, that promise lives on through the Bob Woodruff Foundation.Its CEO, Anne Marie Dougherty, has scaled that vision into a national force for connection, dignity, and service—reaching 98.5% of all U.S. veterans through a powerful network of partners.She joins us now to share the Foundation’s remarkable journey—and the quiet acts of kindness that make it all work.

What does it mean to live—and lead—with clarity, restraint, and purpose? Robert Rosenkranz, a renowned investor, philanthropist, and author of The Stoic Capitalist, believes that ancient wisdom offers modern guidance—especially in how we respond to emotion. From founding a private equity firm by risking his entire net worth, to backing civil discourse through Open to Debate, to championing breakthroughs in healthspan science and immersive art, Robert offers a masterclass in rational decision-making and values-driven leadership. You’ll hear why he rejects the idea of “giving back,” how he navigates risk, and why—when it comes to building a life of impact—being busy is no substitute for being thoughtful.

Few issues more urgent—or more misunderstood—than poverty in America. And even fewer solutions as bold as simply giving people cash. Jeff Atwood, the tech entrepreneur behind Stack Overflow, and his partner Betsy Burton, a trained scientist with a deep commitment to equity, are working to change that. Together, they’ve launched a $50 million guaranteed minimum income initiative across some of the poorest rural counties in the country—places that mirror their own family roots. In this episode, Jeff and Betsy share a story that is as personal as it is political. From the hills of West Virginia to their home in Alameda, California, they speak candidly about wealth, dignity, hope, and the American Dream. We’ll explore how their own childhoods and their children have shaped their philanthropy, how storytelling is challenging tired myths about the poor, and why 2025 is the moment to rewrite the social contract in America. This is not your typical conversation about poverty—and it’s not your typical couple trying to solve it. Here is Jeff Atwood and Betsy Burton on The Business of Giving.

My guest today leads an organization with one of the simplest and most powerful models in philanthropy. It’s called 1% for the Planet, and the premise is this: businesses commit 1% of their annual revenue to environmental causes—and 1% for the Planet ensures those funds are directed with purpose and impact.With over 5,000 members in 60 countries and more than $750 million certified in giving, it’s a movement built on clarity, trust, and community. And Kate, who found her leadership voice on a snowy mountain pass at age 18, has carried that spirit of joy, grit, and teamwork into everything she does.She joins us now to talk about movement-building, climate leadership, and the power of collective action.

This week on The Business of Giving, the focus is on one of the most distressing — and solvable — crises in America today: medical debt.Each year, millions of families are forced to choose between paying their bills and getting the care they need. But what if there were a way to erase that debt — not just for a few, but for thousands at a time?That’s exactly what Undue Medical Debt does. Led by CEO Allison Sesso, the organization buys medical debt the way a for-profit company would — but instead of collecting it, they forgive it. The return on investment? For every $1 donated, $100 of medical debt is wiped away.Allison also shares how a nurse working during the pandemic found herself in medical debt at the very hospital where she worked — a stark example of how broken the system is, and why it must change.Here is my conversation with Allison Sesso, CEO of Undue Medical Debt.

My guest today believes that the greatest barrier to nonprofit fundraising success isn’t money—it’s clarity. Kevin L. Brown is the co-founder of Mighty Ally and the author of Fundable & Findable: The Brand-New Way to Fix Your Nonprofit Fundraising. In this conversation, Kevin explains why most organizations are stuck in a donor-chasing cycle and what it takes to become truly fundable and findable.If your organization has ever struggled to articulate why you exist or raise the resources you need, this episode may just shift your entire approach.

What if your supporters could step inside your story—feel it, not just hear it?In this episode of The Business of Giving, I speak with Chip Giller, co-founder of Agog, a groundbreaking philanthropic initiative helping nonprofits explore immersive storytelling through XR, or extended reality.  From Human Rights Watch to Harlem youth programs, Chip’s work is proving that the future of nonprofit communication isn’t just visual—it’s emotional, embodied, and unforgettable.If you’re rethinking how your organization moves hearts and drives action, this is a conversation you can’t miss.

This is The Business of Giving. I’m your host, Denver Frederick. Today, we’re joined by Jon Kane, President and CEO of CCS Fundraising, a global leader in strategic fundraising consulting. With a career spanning McKinsey, Goldman Sachs, and his own advisory firm, Jon has tripled CCS’s size since 2016, blending for-profit expertise with nonprofit impact. So let’s get started with Jon Kane.

Welcome to The Business of Giving, where we explore the leaders and ideas shaping the future of social impact.Today, I’m delighted  to welcome Jennifer Sirangelo, President and CEO of Points of Light, the world’s largest organization dedicated to volunteer service.Jennifer is leading a movement to double volunteerism in the United States by 2035. But her vision goes beyond numbers—it’s about helping people rediscover meaning, connection, and purpose. Here’s how she puts it:Get ready for a conversation about reimagining service as a cultural force that heals, unites, and transforms.