Many people say yes to volunteering because they care deeply about a cause – not because they want to ask for money…
After all, fundraising often feels like something “other people do.” People with bigger networks, thicker skin, or a natural comfort with asking for money…
But at some point, volunteer leaders, board members, and advocates are often invited into major donor conversations. And that moment can feel intimidating if you’ve never done it before!
In this episode, I am joined by my wife Eileen Opatut, volunteer fundraiser, first-time major-gift asker, and longtime advocate, for a discussion about what happens when a thoughtful, values-driven person decides to raise money – not because it’s easy, but because it feels necessary.
This is a candid, practical conversation about what it really looks like to step into fundraising for the first time. Eileen shares why she chose to fundraise for Lambda Legal, how she prepared herself to make the ask, and what surprised her most once she actually began.
Together, we walk through the real mechanics of relationship-based fundraising, including how to:
- Identify prospects when your network feels small,
- Reach out without over-engineering the message, and
- Approach conversations with curiosity rather than pressure.
We’ll also talk openly about the emotional moments that come with fundraising, the silence after the ask, the fear of follow-up, and the relief of realizing that “no response” is rarely personal. Eileen will share her first major yes, the power of multi-year commitments, and how fundraising becomes less intimidating when it’s rooted in shared values and honest storytelling.
This episode gives a clear look at what works in fundraising and development work. Whether you’re new to fundraising or supporting board and volunteer fundraisers, this conversation demystifies the process and reminds listeners of a simple truth: asking for money is not an imposition, it’s an invitation to participate in work that matters.
TUNE IN TO LEARN:
- Why people step into fundraising when it feels uncomfortable: How conviction – not confidence – is often what finally pushes a volunteer fundraiser to make their first ask.
- How to prepare without over-preparing: What actually matters before a fundraising conversation – and what doesn’t.
- Why silence isn’t rejection: How to interpret “crickets” without taking it personally, and what to do next.
KEY QUOTES:
- “I’m really not the perfect candidate to be a fundraiser. But if I can do it, so can anyone. And knowing that, that makes me even better.” – Eileen
- “[M]y passion for the mission…is greater than my fear of asking or hearing no.” – Joan
- “I think it’s okay because it’s not about me. It’s really about them. You know, I’m giving them an opportunity to really stand up and rise.” – Eileen
- “[I]f you are really passionate about the cause, that when you ask, it actually feels good.” – Joan
ABOUT GUEST:
Eileen Opatut is an Emmy award winning television executive with over four decades of experience with the start up and transformation of cable channels. She began her career at Nickelodeon and from there developed a new documentary form with National Geographic Explorer. Her signature accomplishment was the transformation of The Food Network where, thanks to her eye for talent and what makes great television, she made Iron Chef, Ina Garten, Rachel Ray and Tony Bourdain household names. In keeping with her commitment to LGBT equality, Eileen was also a part of the launch team for LOGO, the first LGBT cable channel. Eileen is now retired, a master gardener and a volunteer fundraiser.
RESOURCES:
- Eileen Opatut LinkedIn
- Eileen Opatut Facebook
- Nonprofit Leadership Lab
- Joan Garry’s Guide to Nonprofit Leadership – 2nd Edition by Joan Garry
- FREE WORKSHOP: Let’s Build the Nonprofit Board of Your Dreams!
- FREE WORKSHOP: The 5 Practices of Outstanding Nonprofit Leaders
- Music by Jukebox the Ghost
Disclosure of Material Connection: Some of the links in the post above are “affiliate links.” This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”
Sponsored By DonorPerfect
DonorPerfect provides nonprofits with powerful fundraising tools to drive success. Built on a foundation of integrity and innovation, the company prioritizes its clients over investors, cultivating a culture of collaboration, continuous improvement, and a commitment to making a difference. Check out their resource(s) below.
Sponsored By DRG Talent Consulting Experts
DRG is a talent advisory group helping nonprofit organizations to identify, attract, and nurture innovative, diverse leadership. Our team of 40+ experts serves over 200 nonprofits a year of all sizes and in various sectors across the country. Learn more at drgtalent.com.
Check out their resource(s) below.