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.

Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs is a business podcast hosted by Flying Whale Strategies, with 18 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Flying Whale Strategies hosts Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs, a business show with 18 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #17

  What reentry work teaches us about shifting public opinion

  Aug 17, 202649 minS1

  One of the most difficult parts of our work is when the mission requires changing public perception. History has proven it's possible — but we need to study the formula. This episode tracks how societies move the boundary of what's acceptable, using a framework from political theory called the Overton Window. And our greatest insight comes from two people who are living proof that it works. Shelton McElroy and George Clemens are business partners and criminal justice reformers from Louisville, Kentucky, who have spent their careers changing what people believe about incarcerated people — not by arguing, but by demonstrating. You'll hear them talk about: Why a corrections officer union in Spokane, Washington ended up being one of the best allies for downsizing a jail How a man with Nazi tattoos became 18-year-old Shelton's greatest teacher How Shelton's work training extraction officers at San Quentin becomes a model for changing minds about people we've written off Why Homeboy Industries' new Hope Village campus might be the next thing that moves the window Guests: Shelton McElroy is a licensed mental and behavioral health counselor, strategic planner, and community organizer working at the intersection of behavioral health, housing, and criminal justice reform. He is the founder of Story Group & Associates, which provides trauma-informed counseling, case management, and reentry support — and transforms vacant properties into thriving communities for people returning home from incarceration. Previously, he served as National Director of Strategic Partnerships at The Bail Project, helping launch more than 20 sites nationwide. A formerly incarcerated individual who spent more than fifteen years in the foster care system, Shelton brings lived experience to every aspect of his work. George Clemons is a behavioral health professional whose entry into this field began with his own history of substance use disorder and mental health challenges. He works directly with individuals navigating recovery, reentry, and behavioral health systems, while also advocating for system-level change. He serves on an opioid use disorder advisory board where he helps guide funding decisions for medication management — and brings the same authenticity to his criminal justice reform advocacy, where his lived experience informs both policy and practice. Mentioned: Stories Lighthouse Get in touch

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  Episode #16

  A recipe for emails people want to read

  Aug 3, 202639 minS1

  Fundraising appeals have become easy to ignore. They ask for money, lean hard on emotion, and rarely offer anything back to the reader. This episode explores what happens when appeals are designed to add value before they make an ask. Drawing on examples from standout nonprofit and for-profit emails, Hillary introduces a recipe for donor communications that contribute something useful to the inbox. We learn that being a trusted organization means becoming a source of meaning and expertise—not just urgency. In the second half, Hillary is joined by Banks Benitez, Founder and CEO of Future Forest, a firm known for producing high-ROI newsletters. Banks shares both the philosophy and the data behind emails that earn attention, trust, and action. In short, we need to figure out what we have to say and then say it with uncommon honesty. You’ll hear: A masterclass in real time: Banks walks Hillary through building a donor persona from scratch for a fictional reentry organization, landing on a fully-formed archetype named "Banks" who's mid-30s to 70, white, highly educated, and quietly wrestling with his own privilege. The give-nine-ask-one ratio: Banks's rule of thumb for editorial newsletters — five or six issues of pure value before you make an explicit ask, so the relationship doesn't feel transactional. Banks argues program staff routinely have expertise (de-escalation tactics, onboarding rituals, hard-conversation frameworks) they don't recognize as valuable Banks's favorite examples of brand journalism — Yeti's YouTube storytelling and Stripe's publishing arm, Stripe Press — show how the strongest content plays a long game that has almost nothing to do with the product itself. Guest: Banks Benitez is the founder and CEO of Future Forest , a boutique newsletter agency that helps brands and leaders build trust in the inbox through honest, human, and original content. Today, Future Forest works with a small group of clients to produce soulful, original newsletter content that cuts through the noise. Before starting Future Forest, he held roles at Urban Villages and Ezra Climate, and led Uncharted (since acquired by Common Future), a leadership incubator for social justice entrepreneurs. He holds a degree in economics from Vanderbilt University and a degree in international development from the University of Sydney. Mentioned: The New York Times Company. (n.d.). What is educational content marketing? What an education‑based marketing plan adds to your business . NYT Licensing. Get in touch

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  Episode #15

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

  Jul 20, 202647 minS1

  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 shift The role of spirit and imagination in moving beyond anxiety How Ben has led equity work with teams of 8, 60, and 250 — and what changes at each scale The specific question Ben asked his startup team that seeded their entire workplace culture Guest: 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

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  Episode #14

  Shifting the role of the board when it's time

  Jul 6, 202636 minS1

  <p>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.</p><p>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 go...

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• 

  Episode #14

  Shifting the role of the board when it's time

  Jul 6, 202636 minS1

  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 monarchy When a working board is helpful, and when its run its course What a vote on immigration reform taught Rae about facilitating generative discussions with your board How to have the "we might not be the right board anymore" conversation before it becomes a crisis Why tokenism happens even when everyone means well — and what to do instead Guest: 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

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