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. 5d ago

    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

    41 min

  2. 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

    39 min

  3. 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

    54 min

  4. 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

    50 min

  5. 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

    40 min

  6. Mar 30

    Am I ready for Big Bet Philanthropy?

    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

    39 min

  7. Mar 16

    How to know when you're ready for your next fundraising strategy

    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

    44 min

  8. Mar 2

    Designing annual reports that people read

    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

    39 min
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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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