In Part 2 of this Fit Fundraising Podcast conversation, Roy Jones and Cheryl Hackett, Director of Development at the Wyoming Rescue Mission, dive deeper into what truly connects donors across generations—stories and relationships.
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Generational Giving with Cheryl Hackett: Bridging Boomers, Gen X, and the Next Wave of Donors
In this episode of the Fit Fundraising Podcast, Roy Jones sits down with Cheryl Hackett, Director of Development at the Wyoming Rescue Mission, to explore how giving habits are evolving across generations. From Boomers who still love their direct mail to Millennials and Gen Z donors who live online, Cheryl shares how her team bridges the gap through multichannel fundraising, storytelling, and faith-driven connection. It’s a practical, hope-filled conversation about building trust, embracing innovation, and inspiring generosity that lasts.
From Boomers to Gen Z: Sustainers, Segmentation, and the Future of Giving with Kyle Gorman
From sustainers to segmentation, today’s fundraisers face a world of change. How do we connect with Boomers who still carry the wealth, while preparing for Millennials and Gen Z who are shaping the future of philanthropy?
From Boomers to Gen Z: Branding, Giving, and Generational Shifts with Kyle Gorman
From Baby Boomers writing checks to Gen Z giving online, every generation engages with philanthropy differently. In this episode, Roy Jones sits down with Kyle Gorman, Executive Director of Advancement at the Evansville Rescue Mission, to unpack the trends shaping donor behavior across the ages.
Kyle shares lessons from leading a $9 million capital campaign, insights on balancing direct mail with digital, and why branding matters more than ever for nonprofits. Whether you’re trying to reach loyal boomer donors, middle-aged givers blending mail and online, or younger supporters building lifelong habits, this conversation will help you navigate the shifts and grow stronger relationships with every generation.
The Power of Mastermind Groups: Iron Sharpens Iron for Fundraisers
What if the secret to breakthrough fundraising wasn’t another conference, but a small circle of peers sharpening one another? In this episode of the Fit Fundraising Podcast, Roy Jones sits down with marketing professor and nonprofit strategist Dina Jones to unpack the power of mastermind groups. Together, they explore how masterminds go beyond networking, providing nonprofit leaders, fundraisers, and CEOs with a safe, faith-centered space to share challenges, spark creativity, and build confidence. From her first experience in Nashville to co-leading groups today, Dina shares how masterminds can transform isolation into innovation—and how this cutting-edge approach is shaping the future of fundraising.
From Boomers to Gen Z: Communicating in a Multi-Gen World with Carrie Lynn Wright (Pt. 2)
In Part 2, Roy Jones and Carrie Lynn Wright dig deeper into the communication gaps, giving habits, and leadership challenges across generations. Hear real-world stories—like the viral “Tony the Paint Guy” moment—that reveal how embracing change, adopting new technologies, and fostering open dialogue can help nonprofits engage donors and rally multi-generational teams for long-term success.
How to Navigate Your Fundraising Team in Times of Uncertainty
Navigating uncertainty isn’t about having all the answers. It’s about leading with clarity, compassion, and confidence with the people beside you. Your team is your greatest asset—cultivate them well and lean on one another even when seasons seem to be changing.
Writing Appeals in Uncertain Times
You can’t control what happens in the world or your neighborhood, but you can control what happens in your shop. Focus on your donors, what are their needs and
goals. There are always hills and valleys, the biggest drop comes when you don’t stick to the schedule. Keep asking and they will give.
From Boomers to Gen Z: Communicating in a Multi-Gen World with Carrie Lynn Wright (Pt. 1)
In Part 1, Roy Jones sits down with workplace culture expert Carrie Lynn Wright to explore the defining traits of Boomers, Gen X, Millennials, and Gen Z—and how these differences shape nonprofit teams and donor relationships. Learn how understanding generational perspectives can strengthen workplace culture, improve communication, and build stronger connections across every age group
Stay the Course – Development directives for turbulent times
It has been a year of starts and stops, peaks and valleys for the nonprofit industry. The year following any presidential election presents challenges for philanthropy. Changes and uncertainty do impact giving; when new administrations put new programs in place, it can take time for donors to assess and adjust accordingly.
