Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs

Flying Whale Strategies
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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. 

Episodes

  1. 5D AGO

    The problem you name is the solution you build

    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

    40 min

  2. FEB 2

    Building a data collection plan we don't dread

    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

    46 min

  3. JAN 19

    Impact statements the world has been waiting for us to write

    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 eac Get in touch

    34 min

  4. JAN 5

    Inviting donors to meetings you look forward to

    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 Foundation Guest: 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

    43 min

  5. TRAILER

    Tailwinds Trailer

    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

    3 min

Trailer

Ratings & Reviews

5
out of 5
2 Ratings

About

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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