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

EPISODE · Mar 16, 2026 · 44 MIN

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

from Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs · host Flying Whale Strategies

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 ...

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

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This episode is 44 minutes long.

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This episode was published on March 16, 2026.

What is this episode about?

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...

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