Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs

Flying Whale Strategies
  • 5.0 (2)
  • Entrepreneurship
  • Updated Biweekly

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. 

  1. Jul 20

    How to lead anti-racism work your team actually wants to do

    Nonprofit leaders often dread anti-racism work. It's a two-day retreat, a book club, a list of behavioral expectations — and it leaves us feeling raw, anxious, or stuck in our heads. What if that's not a personal failing, but a process problem? In this episode, Hillary Frances makes the case that anti-racism work gets derailed when we treat it as a problem to solve rather than a future to imagine. She shares what she’s learning about collective liberation — an approach to justice work defined not by what it dismantles, but by what it dares to envision. Then she sits down with Ben Garcia, Executive Director of the American LGBTQ+ Museum in New York City, who has spent 25 years building cultures of equity across museums of every size — and who brings both a practitioner's rigor and a science fiction reader's imagination to the work. Why intellectual self-policing makes anti-racism harder, not easier — and what has to shiftThe role of spirit and imagination in moving beyond anxietyHow Ben has led equity work with teams of 8, 60, and 250 — and what changes at each scaleThe specific question Ben asked his startup team that seeded their entire workplace cultureGuest: Ben Garcia (he/him) has worked for 20 years to help museums become places of welcome and belonging for all people. He started as a gallery guide and educator, moved on to exhibition development, and then served in middle- and upper-management administrative roles, before joining the American LGBTQ+ Museum as Executive Director. He has presented and published regularly on creating structural equity in museums through transparency, accountability, fair labor practices, and by adding missing voices and perspectives. Prior to joining the American LGBTQ+ Museum, Ben worked in various roles as an educator and administrator at the J. Paul Getty Museum, Skirball Cultural Center, and Hearst Museum of Anthropology. He then served as Deputy Director of the Museum of Us, and as Deputy Executive Director and Chief Learning Officer at the Ohio History Connection. He is versed in museum interpretation, operations, management, and fundraising. Ben led initiatives to return Indigenous ancestral human remains and belongings in San Diego and Ohio. He serves as a board member at Equality Ohio, working to get the Ohio Fairness Act passed. Ben graduated from the University of Massachusetts at Boston with a B.A. in Art and from Bank Street College of Education with an M.S. Ed. In Museum Leadership. He has shared his life since 1999 with his husband, Scott Fabianek, a UX/UI Designer and comic book artist. Ben is the child of a journalist and visual artist. He has six siblings, thirteen nieces and nephews, and a great-niece and nephew (as well as many beloved in-laws). He is a proud fantasy and science fiction nerd. Mentioned: brown, a. m. (2019). Pleasure activism: The politics of feeling good. AK Press. Get in touch

  2. Jul 6

    Shifting the role of the board when it's time

    If you've ever lost sleep over your board, there might be a structural reason for it — one that goes all the way back to the colonial era. Hillary shares her latest learning from helping organizations make board governance shifts. Hillary is joined by Rea Carey, a nonprofit consultant with over thirty years of experience leading organizations through some of the most significant LGBTQ+ advocacy victories of the last two decades. Rae shares what healthy boards have actually looked like at different stages of organizational life — from a scrappy founding board at the National Youth Advocacy Coalition to a governing board at the National LGBTQ Task Force — and how she learned to lead both. You'll hear: How boards developed in a power vacuum after the colonies started providing services without a monarchyWhen a working board is helpful, and when its run its courseWhat a vote on immigration reform taught Rae about facilitating generative discussions with your boardHow to have the "we might not be the right board anymore" conversation before it becomes a crisisWhy tokenism happens even when everyone means well — and what to do insteadGuest: Rea Carey (she/they) is the principal of Carey Forward, LLC, specializing in executive leadership coaching, executive staff and board succession and transition planning, and strategic advising. Rea has over 30 years of experience in fundraising, fiscal sustainability, boards of directors, non-profit management, philanthropic giving strategy, and leadership development. Rea was the founding executive director of the National Youth Advocacy Coalition and served as the longest-tenured executive director of the National LGBTQ Task Force until early 2021. In addition to serving on the American LGBTQ+ Museum board, Rea currently serves on the boards of directors of the Freeman Foundation, the Flamboyan Foundation, and has served on the board of directors for the Alliance for Justice, and other boards and advisory boards. Rea started their career as the HIV/AIDS crisis was taking hold and carries with her the lessons learned from employing strategies ranging from direct-action to advocacy, being responsive to the unimaginable, and in building organizations and mobilizing people to respond to massive challenges. Rea graduated from Smith College and earned her master’s degree in public administration from Harvard University’s Kennedy School of Government.  Mentioned:  Peter Dobkin Hall, A History of Nonprofit Boards in the United States, Board Source, 2003. Karl Mathiasen III, Board Passages: Three Key Stages in a Nonprofit Board’s Life Cycle, 1998. Get in touch

  3. Jun 22

    How to answer the scale question

    Nonprofits are asked constantly to plan for scale, and most of us answer with ambitions to get bigger. But what if the right answer has nothing to do with size? Hillary reframes the scale question entirely: scale isn't about growth, it's about influence. And sometimes the most influential thing an organization can do is change how it operates, not how large it becomes. Hillary is joined by Sarah Cryder, Executive Director of City Kids Wilderness Project, who brings her own definition of scale to the table — one that has nothing to do with serving more people and everything to do with doing the work better. You'll hear them talk about: How to answer the scale question without promising to expandThe difference between getting bigger and getting smarter — and why Sarah calls growth "getting fatter"How a shared staffing model with Outward Bound could change who gets to work in the outdoor industryNot every organization should grow, but every organization should know what role it intends to play in the long arc of change. Guest: Sarah Cryder is the Executive Director of City Kids Wilderness Project. She has an extensive strategic business planning and project management background. Prior to joining City Kids, she worked with local and national charter and district schools, foundations, entrepreneurs, and nonprofit service providers with a mission focused on improving education and life outcomes for underserved children. Sarah has also consulted with the D.C. Public Schools to implement evidence-based mental health intervention pilot programs, research successful national pilot interventions, and evaluate program outcomes through data-driven metrics. Sarah holds a Master of Public Policy from Georgetown University and a Bachelor’s degree from Boston College. Mentioned: Big Bet Bummer, Kevin Starr Scale Really Matters, Kevin Starr What’s your Endgame, Alice Gugelev & Andrew Stern Stages of Startups, Y Combinator Against Rushing to Scale, Randy Moore Get in touch

  4. Jun 8

    What If nonprofits had product designers?

    The for-profit world has product engineers, design sprints, and rapid iteration cycles. The nonprofit sector has… a debrief meeting. In this episode, Hillary asks what would happen if we closed that gap. Hillary breaks down what a "product" actually looks like in the social sector and introduces a way of testing it borrowed straight from tech startups. Then she sits down with Matteo Moore, a product designer at one of the world's largest tech companies, for a conversation that is equal parts art studio, tinkerer's lab, and science research center — Matteo's words. You'll hear them talk about: The awkward robot that delivers toothbrushes to hotel rooms — and what it taught a startup about observationHow experimentation can actually speed things up rather than slow you downThe Effort Impact Scale — a dead simple quadrant for deciding what to fix nextWhat the scientific method you learned in middle school has to do with your next program cycleGuest: Matteo Moore is a Product Designer with nearly two decades of experience designing products that people actually want to use. His career spans startups, media, education, and enterprise. He has scaled design sprint methodologies across large organizations and spent years mentoring designers at every level. Matteo's origin story is not a typical one for tech. He holds a Bachelor of Arts in Fine Arts and English Literature from the University of Colorado Boulder, a Master of Architecture from the University of Colorado Denver, and studied architecture abroad at Sapienza Università di Roma. That cross-disciplinary foundation — art, language, space, and systems — shapes the way he thinks about every product he touches. He describes his workspace as one part artist studio, one part tinkerer's lab, and one part science research center. That combination is exactly what makes him such a compelling voice on design: he brings the curiosity of an artist, the rigor of a researcher, and the humility of someone who has learned not to hold his work too precious. Mentioned:  Michael Seibel, How to build product as a small startup. Knapp, Jake, et al. Sprint. Bantam Press, 2016. Get in touch

  5. May 25

    How to build a less hierarchical org chart

    Description: The nonprofit sector is drawn to the idea of flat org charts — but most organizations don't have great examples of what that actually looks like in practice. Why do we cling to hierarchy even when it conflicts with the values we're trying to model? And what does it actually take — not just philosophically, but day-to-day — to share power inside an organization? Hillary explores the conditions that make less hierarchical structures work, and the internal work that has to happen before you ever touch the org chart. You'll also hear from three co-executive directors at All Souls Church in Boulder, Colorado, who stopped theorizing about shared leadership and started living it. You'll hear about: Teal organizations, holacracy, and mutual aid — and what each model actually looks like in practiceThe three things less hierarchical org charts require before they can workWhy collective liberation work has to come before you flatten the org chartMentioned: Laloux, F. (2014). Reinventing organizations: A guide to creating organizations inspired by the next stage of human consciousness. Nelson Parker. Mont, S. (2017, January 9). Autopsy of a failed holacracy: Lessons in justice, equity, and self-management. Nonprofit Quarterly. Valve Handbook Guests:  Leah Cousin. Leah joined the staff in 2016 after being part of the community at All Souls for nearly a decade. She enjoys reigning in the vision filled minds of those around her in the office and producing action plans to achieve those visions. She is passionate about all things vegetables: farming, cooking, and sitting around a table with friends and family to enjoy a meal.  Rachel Zylstra. Rachel is a lifelong learner, adventurer, friend, partner, mother, teacher, and 7 on the Enneagram. She’s been on staff at All Souls Church of Boulder since 2014. She is passionate about discovering and exploring faith through the lens of wonder, healing, and finding the childlikeness in all of us.  Will Forsythe. Will was born and raised in Colorado, and is now serving as the Pastor of All Souls Church of Boulder.  Will graduated from Western Theological Seminary in Holland, MI.  He has worked in youth ministry, missions, and church planting, but is excited to now call Boulder home. In his free time, Will can be found fishing, reading Russian literature, biking, or drinking a good IPA. Get in touch

  6. May 11

    How to prepare for the King Tide Era

    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 mutual aid group.  Get in touch

  7. Apr 27

    Supervisors as teachers not bosses

    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

  8. Apr 13

    Measuring the Immeasurable

    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.pdf Guest: 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

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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. 

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