Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs Tue, 14 Jul 2026 12:33:17 -0600 https://www.buzzsprout.com/2561655 en-us © 2026 Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs yes 2e4be88c-46df-560c-b147-40b546702f9c Flying Whale Strategies episodic false 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. 

]]> Buzzsprout (https://www.buzzsprout.com) Flying Whale Strategies https://storage.buzzsprout.com/e4iig3peg8eii7k1tp2ubkjrwkhn?.jpg Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs https://www.buzzsprout.com/2561655 Shifting the role of the board when it's time 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 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-19363756 Mon, 06 Jul 2026 04:00:00 -0600 2140 nonprofit board governance, board transition, working board, governing board, nonprofit leadership, board management, executive director, nonprofit organizational development, LGBTQ advocacy, board diversity, fiduciary duty, nonprofit consulting, board re 1 14 full false How to answer the scale question 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 expand
  • The 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 industry

Not 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

]]> 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 expand
  • The 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 industry

Not 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

]]> Flying Whale Strategies Buzzsprout-19357682 Mon, 22 Jun 2026 04:00:00 -0600 1627 nonprofit scale, city kids wilderness project, nonprofit growth, scaling impact, nonprofit strategy, social sector innovation, nonprofit leadership, systems change, end game 1 13 full false What If nonprofits had product designers? 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 observation
  • How experimentation can actually speed things up rather than slow you down
  • The Effort Impact Scale — a dead simple quadrant for deciding what to fix next
  • What the scientific method you learned in middle school has to do with your next program cycle

Guest: 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

]]> 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 observation
  • How experimentation can actually speed things up rather than slow you down
  • The Effort Impact Scale — a dead simple quadrant for deciding what to fix next
  • What the scientific method you learned in middle school has to do with your next program cycle

Guest: 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

]]> Flying Whale Strategies Buzzsprout-19109967 Mon, 08 Jun 2026 04:00:00 -0600 2442 nonprofit innovation, product design, design sprint, social sector, program improvement, iteration, KPIs, product market fit, experimentation, user research, prototyping, social entrepreneurship, nonprofit leadership, mission-driven organizations, product 1 12 full false How to build a less hierarchical org chart 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 practice
  • The three things less hierarchical org charts require before they can work
  • Why collective liberation work has to come before you flatten the org chart

Mentioned:

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

]]> 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 practice
  • The three things less hierarchical org charts require before they can work
  • Why collective liberation work has to come before you flatten the org chart

Mentioned:

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

]]> Flying Whale Strategies Buzzsprout-19033458 Mon, 25 May 2026 04:00:00 -0600 2348 1 11 full true How to prepare for the King Tide Era 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 philanthropists
  • How we ask what’s possible versus what’s feasible and the Overton Window
  • Philanthropy’s identity crisis
  • How to identify leaders worth investing in within 5 minutes
  • How our obsession with impact might be making us dangerous

About 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

]]> 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 philanthropists
  • How we ask what’s possible versus what’s feasible and the Overton Window
  • Philanthropy’s identity crisis
  • How to identify leaders worth investing in within 5 minutes
  • How our obsession with impact might be making us dangerous

About 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

]]> Flying Whale Strategies Buzzsprout-18881139 Mon, 11 May 2026 04:00:00 -0600 3240 nonprofit leadership, future of nonprofits, social sector strategy, philanthropy trends, nonprofit innovation, systems change, leadership development, king tide era, adaptive leadership, nonprofit sustainability, funding instability, social sector transfo 1 10 full false Supervisors as teachers not bosses 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 it
  • What happened when a shift leader jumped over the espresso counter at a customer — and how that became a breakthrough coaching moment
  • Why one apprentice literally sprinted to work, and what that tells us about intrinsic motivation
  • The difference between a "blue ribbon for showing up" culture and one where people actually want to get better
  • How to build an internal certification from scratch using questions you can ask your own supervisors this week

Guest: 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

]]> 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 it
  • What happened when a shift leader jumped over the espresso counter at a customer — and how that became a breakthrough coaching moment
  • Why one apprentice literally sprinted to work, and what that tells us about intrinsic motivation
  • The difference between a "blue ribbon for showing up" culture and one where people actually want to get better
  • How to build an internal certification from scratch using questions you can ask your own supervisors this week

Guest: 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

]]> Flying Whale Strategies Buzzsprout-18996027 Mon, 27 Apr 2026 04:00:00 -0600 2994 nonprofit leadership, frontline supervisors, workforce development, employee motivation, coaching culture, adult learning, intrinsic motivation, social enterprise, apprenticeship, internal certifications, employee training, workplace culture, coaching ski 1 9 full false Measuring the Immeasurable 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18559445 Mon, 13 Apr 2026 04:00:00 -0600 2427 nonprofit evaluation, measuring impact, outcomes vs outputs, social impact measurement, nonprofit data, program evaluation, theory of change, validated frameworks, economic mobility, workforce development, homelessness solutions, criminal justice reform, 1 8 full false Am I ready for Big Bet Philanthropy? 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18408437 Mon, 30 Mar 2026 06:00:00 -0600 2312 Grants, Grant writing, International Aid, International Development, NGOs, Big bet philanthropy, Exponential impact, Transformational philanthropy, Nonprofit scale, Philanthropy and venture capital, Nonprofit innovation, Social entrepreneurship, 1 7 full true How to know when you're ready for your next fundraising strategy 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18761422 Mon, 16 Mar 2026 06:00:00 -0600 2659 nonprofit fundraising strategy, revenue streams for nonprofits, major gifts strategy, annual giving strategy, grant fundraising, event fundraising, corporate sponsorship strategy, scaling fundraising, operationalizing development, cost to raise a dollar, 1 6 full false Designing annual reports that people read 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18761418 Mon, 02 Mar 2026 06:00:00 -0700 2345 nonprofit annual reports, annual report design, nonprofit storytelling, narrative annual reports, nonprofit communications strategy, nonprofit marketing, value-add content, thought leadership for nonprofits, nonprofit journalism, editorial strategy, donor 1 5 full false The problem you name is the solution you build 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18428122 Mon, 16 Feb 2026 04:00:00 -0700 2410 Nonprofit leadership, Social entrepreneurship, Nonprofit strategy, Nonprofit innovation, Social impact, Philanthropy, Big bet philanthropy, Nonprofit boards, Organizational development, Fundraising strategy 1 4 full false Building a data collection plan we don't dread 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18521547 Mon, 02 Feb 2026 06:00:00 -0700 2774 nonprofit data collection, program evaluation, measuring impact, nonprofit outcomes, outputs vs outcomes, human-centered data, lean evaluation, program data, nonprofit leadership, social enterprise, workforce development, survivor-centered services, Freed 1 3 full false Impact statements the world has been waiting for us to write 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 each student’s passions, she brings a playful, trauma-informed approach to teaching neurodiverse kids.

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 passions, she brings a playful, trauma-informed approach to teaching neurodiverse kids.

Get in touch

]]> Flying Whale Strategies Buzzsprout-18432171 Mon, 19 Jan 2026 04:00:00 -0700 2029 bold impact statements, defining the solution, nonprofit strategy, mission vs impact statement, nonprofit growth, venture philanthropy, 10x thinking, nonprofit transformation, solving social problems, nonprofit vision 1 2 full false Inviting donors to meetings you look forward to 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18402156 Mon, 05 Jan 2026 06:00:00 -0700 2588 Nonprofit leadership, Social entrepreneurship, Nonprofit strategy, Nonprofit innovation, Social impact, Philanthropy, Big bet philanthropy, Nonprofit boards, Organizational development, Fundraising strategy, Major Donors, Major Gifts, Donor Meeti 1 1 full false Tailwinds 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

]]> 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

]]> Flying Whale Strategies Buzzsprout-18281044 Mon, 01 Dec 2025 12:00:00 -0700 163 Nonprofit leadership, Social entrepreneurship, Nonprofit strategy, Nonprofit innovation, Social impact, Philanthropy, Big bet philanthropy, Nonprofit boards, Organizational development, Fundraising strategy trailer false