Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs

The nonprofit sector is entering a King Tide Era — a convergence of political, economic, and environmental pressures that won’t just strain the social sector, but fundamentally reconfigure it. Hillary explores uncomfortable questions: What if the nonprofit model isn’t the best vehicle for solving the problems we care about? What happens when philanthropy becomes volatile, identity-conflicted, and driven by instinct more than strategy? And what can we learn from mutual aid networks that are already operating without hierarchy, predictability, or formal structure?Hillary is joined by Dan Reed of Praxis, a longtime collaborator and mentor, for a conversation that moves from personal apprenticeship to the future of capital itself. You’ll hear them talk about:The Impact Returns Reversal for philanthropistsHow we ask what’s possible versus what’s feasible and the Overton WindowPhilanthropy’s identity crisisHow to identify leaders worth investing in within 5 minutesHow our obsession with impact might be making us dangerousAbout Dan: Dan Reed is a partner at Praxis Capital, an accelerator based in NYC supporting founders, funders, and innovators motivated by their faith to address the major issues of our time. Dan is animated by the power of generous, risk-forward capital to transform culture. At Praxis, he helps cultivate a community of funders committed to activating capital toward redemptive purposes. Previously, Dan served in leadership roles at National Right Work Committee, Denver Public Schools Foundation, and Morris Animal Foundation. In 2015, he founded Seed, a training and coaching company designed to help social entrepreneurs fundraise for scale. He loves the work of building new things and people that put their hands to the task.  Dan holds a BA in History and Philosophy from Geneva College. After many years in the mountain west, Dan lives in the small town of Beaver, PA.Research for this Episode: A new mindset changes donors' relationship with philanthropy. What's your endgame?The Innovator’s Tale of the Phoenix and Dragon.The T-Rex and the Snowshoe Hare: What’s Next for Philanthropy in the 2020s. The Black Panther Party: Challenging Police and Promoting Social Change. What can mutual aid do in a disaster? Megatrends: Five global shifts reshaping the world we live in. Six paradoxes of leadership. Big Bet Philanthropy and the Big Shift to Working With Government. Philanthropic leaders reflect on major trends – and tensions.Grappling With Systems Collapse: How Social Sector Leaders Can Respond. Coronavirus volunteering: how you can help through a mGet in touch

Frontline supervisors might be the key to our workplace culture. And they may need our attention. Supervisors are asked to do everything — schedule, train, manage quality, order supplies, write reports. And yet the one skill that might actually make their jobs easier is the one we almost never teach them: how to coach.Hillary thinks that the answer to your productivity challenges might not be more accountability, but more adult learning. She walks through the mechanics of in-the-moment reflection, a 30-second coaching practice that can dramatically shift a worker's motivation, and makes the case for internal certifications as a tool any organization can build, regardless of sector or budget.Then she hands the mic to her ex-wife, Steph Frances — founder of Prodigy Ventures and Little Square Studio— who has spent her career proving that the young adults most workplaces give up on are often the ones most hungry to grow.Some things you'll hear:How Prodigy reviewed footage of baristas working a rush, NFL-style, and why apprentices loved itWhat happened when a shift leader jumped over the espresso counter at a customer — and how that became a breakthrough coaching momentWhy one apprentice literally sprinted to work, and what that tells us about intrinsic motivationThe difference between a "blue ribbon for showing up" culture and one where people actually want to get betterHow to build an internal certification from scratch using questions you can ask your own supervisors this weekGuest: Steph Frances is the founder of Prodigy Ventures, a social enterprise and apprenticeship for young adults in northeast Denver. Over eight years as Executive Director, Steph led Prodigy’s enterprise to double-digit year-over-year sales growth, raised over $5M and built an apprenticeship model for disconnected youth with an 85% completion rate. Most recently, Steph served as the National Vice President of Programs and Training for Momentum Advisory Collective, the capacity-building organization for Cafe Momentum. In her role as a consultant over the past ten years, Steph has worked with social enterprises around the country, most closely with REDF ESEs in start-up, program development, certification, strategic planning and fundraising.Steph is also a proud 2020 Livingston Fellow, and a Denver Business Journal Outstanding Women in Business finalist. She was trained at Eagle Rock’s School of Professional Studies, has a Master’s in Nonprofit Management from Regis University and is an altMBA graduate. Steph also serves on the Board of Directors for BuCu West, a community-based economic development organization in Denver’s Westwood neighborhood; she is also a member of the Globeville, Elyria, Swansea Community Investment Fund at National Western Authority.Get in touch

Most of us in the nonprofit world were taught that real evaluation requires a research team, a grant, and a methodology section. So we measure what's easy to count — and quietly avoid the things that actually matter.This episode is about doing it differently.Hillary challenges the way program evaluation typically works: heavy on outputs, allergic to nuance, and overly deferential to "capital-R" Research. She makes the case for "small-r" research — using validated frameworks as a starting point, defining outcomes from lived organizational experience, and building measurement systems designed to help you learn, not just report.You'll hear from Christian Quijano, Director of Data & Analytics at the Downtown Women's Center in Los Angeles, on how his team took academic research on economic mobility and turned it into something their organization could actually use — an internal measure they called "earning power." (Spoiler: their first definition wasn't good enough, and that's exactly the point.)The episode closes with a case study from All Square, a social enterprise in Minneapolis working to shift public perception about incarceration. How do you measure something that lives in people's minds? Key informants, customer reviews, and existing research — it's more possible than you think.Mentioned: Acs, G., Conner, A. L., Lyons-Padilla, S., Markus, H. R., Patel, N. G., Tumolillo, M. A., & Eberhardt, J. L. (2018). Measuring mobility from poverty. Stanford SPARQ. https://sparqtools.org/wp-content/uploads/2018/06/measuring_mobility_paper.pdfGuest: Christian Quijano is a nonprofit data and strategy leader who helps organizations uncover the story their data is telling. He brings a continuous learning and improvement mindset to connect the dots between programs, operations, and outcomes. As Director of Data & Analytics at the Downtown Women’s Center in Los Angeles, he leads organization-wide data infrastructure, dashboards, and quality and compliance strategy to strengthen outcomes for women experiencing homelessness. With deep expertise in theory of change and monitoring and evaluation, he is known for answering big questions through clear, compelling visualizations, blending technical rigor with community-centered design—and is actively exploring how emerging tools like AI can support this work responsibly.Get in touch

Big bet philanthropists don’t fund “best practices.” They fund breakthroughs.In this episode, Hillary challenges the idea that multimillion-dollar philanthropy is unpredictable or out of reach. She argues that big bet funders behave less like traditional donors and more like venture investors—seeking leaders who are building for exponential impact, not linear growth.You’ll hear Hillary’s latest thinking on the difference between linear and exponential change, and how to spot the difference in your own work. Then, she’s joined by social impact entrepreneur Tomo Hamakawa, co-founder of Earth Company, to explore the Dragon and Phoenix leadership archetypes—and why Phoenix leaders, supported by strong Dragon systems, are uniquely attractive to big bet funders.Mentioned: Conrad, C. A. (2024, August 6). Lever for Change: How ‘big bet philanthropy’ is transforming the sector. Candid.Hamakawa, T., & Yamamoto, K. (2024). The innovator’s tale of the phoenix and dragon. Stanford Social Innovation Review. The Economist. (2023, February 9). How a tide of tech money is transforming charity. Smith, T. (2023, May 14). The greatest wealth transfer in history is here, with familiar (rich) winners. The New York Times. Starr, K. (2024). Big bet philanthropy: Scaling. Stanford Social Innovation Review. Guest: Tomo Hamakawa is a seasoned development professional having lived and worked in various corners of the world from the Tibetan plateau, Indian drylands, Indonesian tropics, to Japanese metropolises. He has held positions with international and local NGOs across Asia and Africa, including the World Bank, Kopernik, and the Children’s Investment Fund Foundation, and previously served as an Assistant Professor at the University of Tokyo’s Global Leadership Program.As the Co-founder and Chief Exploration Officer of Earth Company, Tomo helps visionary changemakers across Asia accelerate their impact through long-term tailored support. Earth Company also delivers innovative educational programs, offers strategic consulting, and manages Mana Earthly Paradise—the first B Corp–certified hotel in Southeast Asia.Tomo’s work bridges organizational development, personal transformation, and regenerative design. His widely read essay “The Innovator’s Tale of the Phoenix and Dragon” was published in the Stanford Social Innovation Review in multiple languages. He holds degrees from Harvard College and the Harvard Kennedy School, is a two-time East-West Center Fellow, and received the Dalai Lama’s Unsung Heroes of Compassion Award in 2014.Get in touch

Hillary breaks down why the next 5–8 years will require nonprofits to make sharper, more disciplined decisions about their revenue streams. We walk through the five major philanthropic strategies—major gifts, annual giving, grants, events, and corporate sponsorships—and learn how to assess whether your current approaches are scaling and operationalized enough to take on something new.She’s joined by Dan Ebert, Director of Development & Communications at City Kids Wilderness Project, who offers a thoughtful look at focus, capacity, return on investment, and why trying to do “everything” leaves money on the table. Together, they explore how high-performing organizations grow by choosing one or two revenue streams to master—rather than chasing every opportunity.Mentioned: Kelley, A., Isom, D., Seeman, B., Silverman, J., Cuevas-Ferreras, A., & Frei-Herrmann, K. (2024). How the biggest U.S. nonprofits are funded. Stanford Social Innovation Review.Guest: Dan Ebert is a seasoned fundraising and communications leader dedicated to expanding access, opportunity, and outdoor experiences for D.C. youth. He currently serves as the Director of Development and Communications at City Kids Wilderness Project, where he oversees fundraising strategy, donor engagement, organizational storytelling, and external communications.Dan joined City Kids in 2019 and has held progressive roles including Development Manager and Associate Director. Over his tenure, he has helped the organization strengthen its revenue systems, grow its donor community, and elevate its brand and impact narrative.Before transitioning into youth development, Dan spent several years in arts and culture fundraising, serving as a Major Gifts Officer, Membership Manager, and Membership Coordinator at the Shakespeare Theatre Company in Washington, D.C., and working with theatre organizations across Philadelphia and Northeast Ohio. He also founded and served as Artistic Director of Transforum Theatre.Dan holds a bachelor’s degree from Kent State University. Outside of work, he can often be found cycling through Rock Creek Park, exploring Hipcamps across the region, cheering on Arsenal, or hunting down exceptional coffee and bagels.Get in touch

Annual reports have become one of the most expensive—and least read—projects nonprofits produce.They’re often treated like a compliance task: dense, polite, exhaustive, and forgettable.In this episode we ask a different question: What if your annual report actually added value to your audience’s life?Drawing on principles of journalism, Hillary explores how nonprofit leaders can shift from acting like summarizers to thinking like magazine editors. She breaks down why so many reports feel like catalogs of activity instead of narratives of learning, and offers a practical playbook for building a cohesive theme, a compelling arc, and content that teaches rather than just documents.You’ll also hear from the leadership team at Moncus Park Conservancy in Lafayette, Louisiana—Executive Director JP MacFayden, Development Director Victoria Alleman, and Marketing & Communications Director Mary Allie McGoffin—as they share how redesigning their annual report changed the way their audience interacts with their work.Guests: JP MacFadyen is the Executive Director of Moncus Park in Lafayette, Louisiana, where he has led the organization since 2021. Before stepping into the role of Executive Director, JP served as Operations Director, where he helped oversee construction and built the foundation for day-to-day operations.A native of Pittsburgh, JP holds a Mechanical Engineering degree from the University of Notre Dame and an MBA in Operations from the University of Houston. Earlier in his career, he served as a space shuttle flight operations specialist at NASA’s Johnson Space Center, specializing in propulsion and de-orbit systems.Victoria Alleman is the Development Director at Moncus Park. In her role, Victoria leads fundraising and partnership development, securing more than $2 million annually from community leaders and repeat supporters. Before joining Moncus Park, Victoria worked across fast-paced industries and in investor relations at One Acadiana, where she developed a systems-level view of economic development and leadership. In 2023, she was recognized as one of Acadiana's Top 20 Under 40. Victoria earned her B.S.B.A. in Marketing in 2014 and her MBA in 2024. Mary Allie McGoffin is the Marketing and Communications Director at Moncus Park, where she leads the storytelling, brand strategy, and public-facing communications. With a background spanning graphic design, branding, digital marketing, and public-sector communications, Mary Allie brings both creative fluency and strategic discipline to her work. Before joining Moncus Park, she spent nearly a decade as a freelance graphic designer and media consultant, working with local governments, nonprofits, and political campaigns across Louisiana to design campaigns that informed, mobilized, and connected communities. She holds a degree in Organizational Communication from the University of Louisiana at Lafayette and is known for her ability to translate complex ideas into clear, compelling stories that invite people into shared civic life.Get in touch

Nonprofits tackle big problems — but often without naming the root cause that actually drives their work. In this episode, Hillary Frances breaks down how clarifying your problem statement can transform your strategy, sharpen your identity, and make your interventions more potent.Featuring Josh Jones, CEO of Neighborhood in Virginia, who has spent years reshaping his beliefs about poverty from a personal failure to systemic inequity. Josh and Hillary discuss what workforce development programming would look like if we believed it was caused by systemic forces.This episode gives you a formula to write a problem statement that identifies the real forces at play and sets you up for a unique and specific solution.Mentioned: Josh’s article published in the Virginian Pilot on “Lifting our neighbors up requires systematic change,” Feb 8, 2025.Guest: Josh Jones is the CEO of Neighborhood in Chesapeake, Virginia, where he leads a bold effort to address poverty not as a personal failure but as the predictable result of structural inequities. Under his leadership since 2018, Neighborhood has evolved from an employment-focused startup to a community organization tackling the root causes of economic instability through workforce development, advocacy, and systems change.A thoughtful and deeply reflective leader, Josh is known for challenging common myths about poverty and for inviting his team—and his community—to interrogate the narratives that shape opportunity. His work centers on expanding economic mobility, strengthening families, and creating environments where every person has a fair shot at financial stability and thriving.Get in touch

Description: Data collection inside nonprofits has become a dreaded chore.In this episode, Hillary explores how nonprofit leaders can shift data collection from a burdensome, compliance-driven exercise into a lean, human-centered practice rooted in curiosity. Drawing on her background as both a research-trained academic and a practitioner, Hillary breaks down how to design data systems that answer the questions you actually care about—rather than metrics that simply communicate how busy you’ve been.The episode offers a practical framework for building a data collection plan you don’t dread, including how to distinguish outputs from outcomes, choose the right tools for individual, group, and societal change, and keep systems simple enough that overburdened teams can sustain them.Featuring Vanessa Torres, Director of Programs at Freedom a la Cart in Columbus, Ohio, this episode grounds the framework in real-world practice. Vanessa shares how her team streamlined data collection for nearly 150 women each month—creating a system that is rigorous, survivor-centered, and genuinely useful to staff and participants alike.Mentioned: Maitreyi, A., Conner, A. L., Tumolillo, M. A., Lyons-Padilla, S., Acs, G., Patel, N. G., Markus, H. R., & Eberhardt, J. L. (n.d.). Measuring mobility from poverty toolkit. SPARQtools. https://sparqtools.org/measuringmobility/Guest: Vanessa Torres is the Director of Programs at Freedom a la Cart in Columbus, Ohio. Freedom a la cart empowers survivors of sex trafficking and exploitation to build lives of freedom and self sufficiency–this is the same organization that helped Vanessa rebuild her own life nearly 15 years ago. She oversees programs that support survivors of human trafficking through workforce development, housing, mentorship, and long-term healing. Vanessa’s expertise is shaped by more than a decade of professional experience in the justice system and in survivor-centered service delivery. Prior to joining Freedom a la Cart’s leadership team, she worked for the Columbus City Attorney’s Office, where she rose through multiple promotions in the Domestic Violence & Stalking Unit and later became the Chief Assistant to the Chief Prosecutor.In 2018, she stepped into a history-making role as bailiff for Franklin County’s CATCH Court, the specialized docket for survivors of sexual exploitation and human trafficking. Serving alongside the judge who once presided over her own case, Vanessa played a central role in implementing trauma-informed practices and supporting hundreds of participants on their recovery journeys.A gifted speaker and educator, Vanessa has presented at major national conferences including End Violence Against Women International (EVAWI), the National Association of Drug Court Professionals (NADCP), and the International Human Trafficking & Social Justice Conference. In 2023, she addressed the U.S. Chamber of Commerce in Washington, D.C., bringing survivor-informed insight to national policy and business leaders.Get in touch

What Hillary loves most about this episode: I ask horsewomen to talk about whether or not impact statements are helpful. Turns out, they love theirs and they’re using it to design their equestrian workforce program.Description: In this episode, Hillary Frances makes the case for impact statements that declare what it will take to solve a problem once and for all. Drawing lessons from tech’s 10x thinking, she explores why incremental gains rarely lead to systems change — and why definitive language can unlock sharper strategy, stronger alignment, and unexpected funding opportunities.Hillary is joined by Becca and Joell from the Square Peg Foundation, a Northern California social enterprise whose impact statement commits to a future where people with autism shift from service users to service providers within our lifetime. Together, they discuss what changed when they stopped hedging — and how a bold impact statement now guides real decisions on the ground.Mentioned: Kotashev, K. (2025, July 31). Startup Failure Rate: How Many Startups Fail and Why in 2025. Failory.Lindzon, J. (2022, March 30). TIME100 Most Influential Companies 2022. TIME.Zitelmann, R. (2019, June 17). Why successful entrepreneurs are often such difficult people. Forbes.Teller, A. (2013, February 11). Moonshots matter — here’s how to make them happen. WIRED.Shore, B., Hammond, D., & Celep, A. (2013). When good is not good enough. Stanford Social Innovation Review.PR Newswire. (2021, April 14). Certified B Corp Classy raises $118M in Series D funding to help nonprofits increase their impact. PR Newswire.Shaw, S. (2013, May 15). Google’s Page: We should be building great things that don’t exist. CNET.Guests: Joell Dunlap is the founder of Square Peg Foundation and a lifelong equestrienne with professional experience across racing, polo, jumping, eventing, and horse training. A nationally published author on humane, creative teaching and horsemanship, Joell has spent more than two decades developing a teaching philosophy rooted in inspiration, curiosity, and deep respect for both horses and humans. She created Square Peg to offer neurodivergent students and retired racehorses a second—and sometimes third—chance to thrive. Joell is also the author of the novel A Damn Fine Hand, which benefits the foundation.Becca Knopf, Square Peg’s Sonoma Program Director, is a Certified Horsemanship Association instructor and lifelong “horse girl.” Since joining Square Peg in 2015, Becca has helped expand the organization from its Half Moon Bay roots to its second location at Cadence Farm in Sonoma. Known for building trust through humor, kindness, and genuine engagement with each student’s passiGet in touch

What Hillary loves about this episode: It captures my clearest thinking on how to make donor meetings worth showing up for — and tests it alongside a young Indigenous woman fundraiser who’s done code-switching to fit white norms and is building donor relationships rooted in curiosity, respect, and shared work.Description: Many fundraisers dread donor meetings — and, truth be told, many donors do too. In this episode, Hillary Frances reframes the purpose of donor conversations and explains how to design meetings that both you and your donors genuinely look forward to. She breaks down why most meetings fall flat, the psychology behind “information-exchange fatigue,” and how centering a donor’s expertise can transform the entire dynamic.Hillary shares practical tools for crafting donor-centric agendas, choosing questions that invite real problem-solving, and matching meeting topics to different donor profiles — from family foundation leaders to venture capitalists. She’s joined by Wiliwili Foundation Founder & CEO, Koana Laimana, who reflects on her experience as a native Hawaiian woman in the fundraising field and how she facilitates donor conversations that are energizing, focused, and deeply relationship-building.Mentioned: Astro Teller, CEO of X, The Wiliwili FoundationGuest: Koana Laimana is the Founder and CEO of the Wiliwili Foundation, whose mission is to support community-led initiatives in Hawaiʻi by providing grants and resources to non-profits focused on culture, land, education, and the arts.Koana is a master resource mobilizer—she doesn't just manage donors, she is thrives in creating philanthropic pipelines that intentionally funnel much-needed wealth from the mainland directly to local changemakers on the islands. When she’s not connecting resources to the causes that need them most, you can probably find her chasing her two keiki, on the beach or in hula. Get in touch

Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs. Tailwinds is a project that brings momentum to the leaders tackling the world’s most impossible problems.Created by Flying Whale Strategies, the show delivers ideas, insight, and energy to the people doing work that often feels impossible.Each episode features brass tacks strategy that can be implemented tomorrow. Hillary Frances interviews social sector leaders who are in the messy middle of building their organizations. And since we are talking about bold solutions to intractable problems, she also brings in insight from the for-profit world. Get in touch