Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs

Major gift fundraisers rarely get to study each other's work the way athletes study game tape — what was said, when, in what order, over how many months. This episode is Hillary's attempt at getting as close to that tape as possible: a rare three-way conversation between a fundraiser, her donor, and the host trying to reverse-engineer what actually happened between them.

Hillary sits down with Deema Salem Syed, Senior Director of Individual Giving at Central Park Conservancy, and Nadia Block, one of the conservancy’s major donors, to unpack their relationship–how it moved from an unplanned phone call to a significant multi-year commitment. You’ll hear:

• Deema's favorite cultivation question: "What's your Central Park story?"
• Behind the scenes on how Central Park Conservancy’s major gift team operates.
• How Nadia knows when she trusts a fundraiser.

Guests:

Deema Salem Syed is Senior Director of Individual Giving at the Central Park Conservancy, where she helps lead the major gifts strategy for the nonprofit responsible for the care and restoration of Central Park. She joined the Conservancy in 2020 as Director of Major Gifts and was promoted through Senior Major Gifts Officer before stepping into her current role.

Before Central Park Conservancy, Deema spent five years at Brooklyn Academy of Music (BAM), rising from Coordinator, Membership to Senior Manager, of Leadership Giving. Her development career also includes a decade-long engagement with The Public Theater’s Mobile Shakespeare Unit, bringing Shakespeare into New York City public schools, as well as experience at Roundabout Theatre Company.

Deema holds a BFA from New York University’s Tisch School of the Arts and an MFA from Pace University. Her background as an artist and her career in philanthropy have given her a firsthand understanding of both the creative and organizational sides of the cultural institutions she has spent her career supporting.

Nadia Block is a philanthropist, artist, and the Executive Director of her parents’ private foundation. For nearly twenty years, she has helped shape and lead her parents’ philanthropy. The foundation is currently on track to complete its spend-down at the end of 2026. 

Nadia holds a master’s degree in philanthropy from New York University. The family’s approach to giving is deeply relationship-based, with an emphasis on building long-term partnerships with nonprofit organizations. 

Separately, Nadia is an artist and photographer. She has helped nonprofit organizations tell their stories through powerful imagery and deeply enjoys bringing her creative and philanthropic worlds together. She is looking forward to more art and more storytelling through her art after the family philanthropy work is complete. 

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Riley Janeway and Emily Brown help run a $5.5M grant portfolio—up from $3 million in 2024, for Emma's Torch, a culinary training nonprofit for refugees and asylum seekers. Their secret isn't better writing. It's that 90% of the grants they won last year involved a real conversation with the funder first.

In this episode, Hillary Frances sits down with Riley and Emily to break down exactly how that plays out — including a funder who took years of quiet courtship before ever inviting an application. You’ll hear:

• How trust-based philanthropy is an invitation to more conversations with grantmakers
• How 90% of the grants Emma's Torch won last year involved some form of direct conversation with the funder.
• How to craft a flexible budget even for funders with specific priorities
• Riley's advice for reluctant relationship-builders
• Curious agendas for donor cultivation meetings

Guests:

Riley Janeway is the Development Manager at Emma's Torch, a New York-based nonprofit that trains refugees, asylees, and survivors of human trafficking for careers in the culinary industry, with locations in Brooklyn, Manhattan, and Silver Spring, MD. Riley leads fundraising strategy across Emma's Torch's full revenue portfolio — roughly $7.9 million annually — including its rapidly growing grants program. Before joining Emma's Torch, Riley's background spanned political and legal advocacy, including work with the National Association of Criminal Defense Lawyers and a Vermont state legislative campaign. Riley holds a degree in International/Global Studies from Colby College.

Emily Brown is the founder of Loom Partners, a grant management firm and sister company to Flying Whale Strategies. Emily previously served as grants manager at Flying Whale before launching her own firm, and has continued as Emma's Torch's grant writer for the past year. She has nine years of experience in grant writing and program development, including a role at Hope International helping raise $22 million annually, and prior work with the International Rescue Committee welcoming Afghan evacuees at Dulles Airport. Emily holds an MBA in Social Impact from Eastern University and a bachelor's degree in International Development and Political Science.

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The for-profit world is accessing capital because they know how to walk into a room and say "I don't need you to just hand me money, I need you to change the terms of another deal I have." In this episode, Hillary lays out why for-profit entrepreneurs have an easier time unlocking capital than nonprofit leaders do — and makes the case that we're missing a whole menu of creative asks beyond "grant or loan." 

She is joined by Paige Byron, development director at Colorado West Land Trust, who explains the philosophy and mechanics of capital stacks — including how she's coached foundations and venture capitalists through funding conversations that treat conservation work as an investment, not just a charitable gift. You'll hear:

• Why asking a funder to cover the interest on your loan might be the smallest ask with the biggest leverage
• How to build a capital stack for programming, not just a capital campaign
• Paige's advice for nonprofit leaders who've never done this before: build an 18-month runway, and don't be the first person in the room who's never touched debt
• A case study where a Dutch development bank promised to absorb the first $111 million of losses on a $1 billion investment fund — so private investors felt safe funding the rest

Guest: Paige Byron serves as Colorado West Land Trust’s Development Director, bringing vast experience in community engagement, philanthropy, and leadership to the team. Hailing from Wyoming, Byron most recently led efforts to protect, restore, and envision a 100-acre community park along the Wild and Scenic Snake River at Astoria Park. Prior to this effort, Paige worked for the Trust for Public Land in their Northern Rockies Department and Grand Teton National Park Foundation. Paige holds a Master’s Degree from the University of Wyoming and a Bachelor’s of Arts from Hamilton College. She is originally from the Tetons.

Mentioned: FMO. "SDG Loan Fund Mobilizes USD 1.1 Billion of Investor Capital." FMO, November 28, 2023. 

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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

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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.

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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.

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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.

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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

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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.

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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.

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