Intro
Welcome to the Fit Fundraising podcast, where we bring you game changing fundraising topics direct from our meetings with major donors and nonprofits nationwide. We don’t interview consultants who haven’t met a donor in decades for fundraising stays on the front lines with nonprofit donors and leaders. This podcast is a glimpse into our work with nonprofits as we get on the field of them and successfully modeled fundraising.
Roy Jones: Hello, I’m Roy Jones, and welcome to the Fit Fundraising Podcast. We’re going to have some fun in fundraising today—talking about a really important topic for people who manage direct mail programs, marketing programs, or major gift development. That topic is generational giving. What’s happening? What are the differences between Boomers like me and younger generations? How do we give differently? Which channels do we use? What’s going on in the marketplace, and how does it impact our marketing plans? I’m excited about our guest today. She has become a dear friend of mine and is very involved—and I have to admit, a great student as well—at City Vision University. Cheryl Hackett is the Director of Development at the Wyoming Rescue Mission. Cheryl, thanks so much for joining us today. We’re so honored to have you.
Cheryl Hackett: Thanks, Roy. Thanks for having me.
Roy Jones: We often talk about the shift to digital communications—especially the use of email. I mention this all the time: the average donor gives to seven to ten different charities. Some nonprofits send an email every day. Not all of them are appeals, but that’s still a lot of communication. If you do the math—even just two emails a week per charity—that’s 80 emails a month landing in someone’s inbox. How do you cut through that clutter?
Cheryl Hackett: I think a few things matter. First, using the donor’s name in the subject line—something like: “Roy, help provide a hot meal for a neighbor in need today.” Make it specific, heartfelt, and actionable. Digital campaigns should be catchy, colorful, and succinct. But what really cuts through the clutter is a story that makes you stop and think. Not in an exploitative way, but in a human one. For example, tell me about Christina—what her life looked like before she came to the mission, and how partners like you made her transformation possible. Then, close with a clear call to action. Strong writing, emotional storytelling, and powerful visuals—brief but moving—can break through all that noise.
Roy Jones: Talk to me about the subject line—it’s got to be right. It’s got to be punchy. I’ve even seen you use an emoji every now and then.
Cheryl Hackett: laughs I think they’re fun. That might be my Gen X side showing. But I’ve also learned from my kids that emojis don’t always mean what I think they mean—which is another nuance of modern communication! Subject lines should be personal and provocative. For example, “Roy, you can provide meals” might get scrolled past. But “Roy, will you help provide a hot meal for a cold and hungry neighbor today?”—especially in a Wyoming winter—makes you pause. Or if it’s summer in Phoenix, maybe it’s “Roy, will you help provide water and shelter for a neighbor in need today?” Asking a question engages people—it makes them think.
Roy Jones: That’s exactly it—you’re getting them to think. And what I hear you saying is that storytelling crosses all generational lines. Whether it’s Boomers, Millennials, or Gen X, it’s always the story that connects.
Cheryl Hackett: I’m so passionate about stories. At Wyoming Rescue Mission, we’re people of faith—and God is a God of stories. For 2,000 years, people have been reading the stories passed down to us in the greatest story ever told—the Bible. The gospel changes lives. Just last week, I was connecting with a major donor—a Boomer—whose son is in recovery for the first time in 20 years. He’s now four months sober. I realized she wasn’t in the right emotional place for a major gift conversation, but I wanted to support her. I sent her a few testimonial videos—real stories of transformation. She went from giving $500 every few months to a single gift of $3,000—her largest ever. Stories sell themselves. And across all generations, people are hungry for radical relationships. There’s so much brokenness in the world—Wyoming has one of the highest suicide rates in the country. People need to know they’re not just ATM machines. They matter. Whether it’s a Boomer, Millennial, or Gen Xer, the timeless principle is the same: be donor-centric. Ask, “How can we serve this person where they are?”
Roy Jones: That’s powerful. Let’s pivot for a moment. We’ve talked about connecting with donors by generation. What about inside the organization—how do you see generational dynamics playing out in your team and office culture?
Cheryl Hackett: Well, this is going to sound a bit stereotypical, so forgive me! Our Executive Director is a Boomer. He wants an omnichannel approach—direct mail, digital, email—all working together with consistent branding. He may not understand the technology behind how we execute it, but he has a clear vision for integration. My father, from the Greatest Generation, had only a flip phone. He’d never have gotten an email appeal! Our Executive Director is older than me, while my marketing coordinator is a Millennial. I enjoy learning about new technology—and for what I don’t know, we rely on our digital consultants. They’re on top of what’s current and help bring that vision to life. Digital is also far more cost-effective than traditional advertising and lets us segment messaging—like delivering customized ads to lapsed donors through streaming or online platforms.
Roy Jones: So inside your organization, you’re balancing communication styles across generations. From Boomers to Millennials, it’s about communication, right?
Cheryl Hackett: Exactly. And for anyone listening who might have an Executive Director resistant to change—because change is hard—emotional intelligence matters. Know your audience. What’s important to your leader? Gather data that connects digital outreach to mission impact. For example, digital can reach more people for less cost—which means more money available for guest services. Present it that way, and it resonates.
Roy Jones: So it’s an incremental process—prove one channel, then add the next.
Cheryl Hackett: Right. If you’re already doing radio ads, try adding streaming audio—it’s much cheaper. We’ll produce a streaming ad, then share it with radio partners who might run it as in-kind support. The same goes for video. Produce a short 30-second streaming spot, share it with local news outlets, and negotiate lower rates since the content’s already produced. That way, you meet your leadership where they are—keeping the traditional methods they value, while introducing digital innovation that saves money.
Roy Jones: That’s great advice. Any final thoughts before we wrap up?
Cheryl Hackett: I’d just emphasize using a mix of strategies. In my role, I’m seeing the wealth transfer among Boomers. Many major donors tell me they’re transitioning wealth to their children. That makes relationships with the next generation—those inheriting the wealth—more important than ever. Combine that relational focus with the power of storytelling, told through every available channel—mail, digital, social, and email. Just keep telling the mission of your mission.
Roy Jones: That’s so good—and fishing for the mission, too! Cheryl, thank you so much. If listeners want to learn more about your ministry or reach out to you, how can they do that?
Cheryl Hackett: The easiest way is through our website, wyomission.org. I’m on Facebook, Instagram, and LinkedIn—but not on TikTok yet! I’d love to connect.
Roy Jones: Thank you again, Cheryl. And thank you to everyone listening to the Fit Fundraising Podcast. If you need fundraising support, go to fitfundraising.com. I built this company by helping organizations raise money—often for free at first—and many of those went on to become long-term partners. If we can help strengthen your fundraising, reach out to us at fitfundraising.com. I look forward to talking with you soon. See you next time.
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