What really happens when nonprofit CEOs step out of the boardroom and into one-on-one conversations with their donors?

In this episode of the Fit Fundraising Podcast, Roy Jones sits down with Michelle Porter, CEO and Co-Founder of Souls Harbour Rescue Mission, to unpack what she learned by personally meeting with key supporters—without a large fundraising staff or a formal major gifts department.

Michelle shares how Souls Harbour grew from serving one meal to becoming a $17 million, multi-site mission, and how intentional, relational donor meetings from the C-suite transformed both donor engagement and internal culture. You'll hear practical insights on involving program staff in donor stewardship, shifting from fundraising to friend-raising, and discovering what truly motivates long-term supporters to give.

If you're a nonprofit leader wondering whether major donor meetings are worth your time—or how to start without "doing it wrong"—this conversation will give you clarity, confidence, and a proven path forward.

In this episode, you'll learn:

• What surprised Michelle most when she began meeting donors one-on-one

• Why major donor programs don't have to start with professional fundraisers

• How involving staff and clients strengthens donor relationships

• The most common motivations donors shared—and how to listen for them

• Why CEOs play a critical role in major donor engagement

In Part 2 of our conversation with Jordan Smith, Executive Chief Development Officer at Tree of Life Ministries, we explore what it really takes to reach donors from Boomers to Gen Z. Jordan breaks down the communication habits of different generations, how Tree of Life grew from a small online presence to more than 13,000 followers, and why social media is now the front door to donor engagement.

Jordan also shares how strategic events — including something as simple as a community pickleball tournament — are bringing in brand-new supporters, and how thoughtful follow-up, prayer, and authentic relationships turn first-time donors into long-term partners.

If you want to understand the future of donor engagement and how to connect meaningfully across generations, this conversation gives you a clear, practical roadmap from one of the leading young voices in nonprofit development.

In this episode, Roy Jones sits down with Jordan Smith, Executive Chief Development Officer at Tree of Life Ministries in Purcellville, Virginia. Jordan shares how a moment of compassion in the aftermath of Hurricane Katrina inspired his family to launch a ministry that now partners with more than 40 churches and serves thousands each year.

Together, Roy and Jordan explore what it means to lead with humility across generations—how younger leaders can introduce innovation while honoring the wisdom of those who came before them. From implementing new technology to building bridges between Boomers and Millennials, Jordan offers powerful insights on faith-driven leadership, generational teamwork, and keeping Christ at the center of every mission.

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.

Cheryl shares how faith, authenticity, and storytelling cut through today's digital noise and unite Boomers, Gen X, Millennials, and Gen Z donors alike. From crafting irresistible subject lines to blending traditional and digital outreach, she explains how to engage supporters meaningfully in a world crowded with messages.

You'll also hear how nonprofit leaders can bridge generational gaps inside their teams, embrace innovation without losing trust, and keep their missions at the heart of every message.

🎧 Listen now and discover how timeless storytelling can transform your fundraising across every channel.

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 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?

In this episode, Roy Jones sits down with Kyle Gorman, Executive Director of Advancement at the Evansville Rescue Mission, to talk about:

• Why the first gift is the most critical moment for lifetime giving

• How younger donors respond to frequency and messaging

• The challenge of leading and listening on multi-generational teams

• What the coming wealth transfer means for nonprofits

Kyle shares candid insights from leading campaigns, managing a cross-generational team, and meeting with donors across every age bracket.

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.

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. Don't miss our Giving Tuesday Mastermind on September 20th, more information at fitfundraising.com/clearwater

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.

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.