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Sharing insights, strategies and inspiration you can use right now.

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This is where I share strategies, action steps, and ideas for scaling major gifts, and answers to questions that matter most right now. 

Trent Thompson Trent Thompson

Making the Ask: Why Learning To Ask for Major Gifts Is Like Building a Plane in Flight

What if you could practice high-stakes donor conversations in a safe space before the real thing? In this edition of Scaling Major Gifts, I share the strategies I wish I'd known before my first big ask, plus how new AI tools are changing the game for fundraisers like us. Read this edition and share it with your team—because we all need to fly together in this mission-critical work.

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114. Becoming Ken: What Fundraisers Can Learn about Dignity, Trust, and Self-Worth
Trent Thompson Trent Thompson

114. Becoming Ken: What Fundraisers Can Learn about Dignity, Trust, and Self-Worth

In my recent conversation with Ken Miller, CFRE—author, fundraising consultant, and dynamic speaker—I was reminded that behind every smiling face in our sector, there’s a deeper, often untold story. Ken’s path has taken him from the heights of Ivy League success to the depths of prison, and back to a life of impact and integrity. The lessons he’s learned aren’t just about survival—they’re about thriving, leading with love, showing empathy, and building resilience in the face of setbacks.

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113. How to Build Trust and Stand Firm in Fundraising
Trent Thompson Trent Thompson

113. How to Build Trust and Stand Firm in Fundraising

Have you ever wondered what it would feel like if the nonprofit sector truly centered trust, collaboration, and empathy at its core? What if we reimagined fundraising and leadership in a way that put people—and their dignity—ahead of rigid power dynamics and outdated models? I’ve been giving a lot of thought to these questions lately, and after my recent conversation with Martha Schumacher, I’m more convinced than ever that the future of philanthropy depends on boldly embracing trust-based relationships as well as the courage to rewrite old narratives.

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Trent Thompson Trent Thompson

From First Gift to Forever: Proven Retention Strategies for Major Gifts

After nearly three decades in the world of major gifts, I can say with absolute certainty: securing that first major gift is a triumph, but transforming that initial generosity into a lifelong partnership is where the real magic—and challenge—happens. Whether you’re a major gift officer, development director, executive director, or board member, donor retention isn’t just a metric; it’s the heartbeat of your mission’s sustainability.

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112. Bridging the Gap: Blending Donor and Community-Centered Fundraising
Trent Thompson Trent Thompson

112. Bridging the Gap: Blending Donor and Community-Centered Fundraising

In this episode, I’ll share how blending the best of donor-centered and community-centered approaches, building diverse teams, and leading with courageous empathy can drive real, human-centered change. You’ll leave with practical steps and the inspiration to transform not only your fundraising but your entire organization.

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111. From Overwhelm to Opportunity: AI and the Modern Fundraiser
Trent Thompson Trent Thompson

111. From Overwhelm to Opportunity: AI and the Modern Fundraiser

Have you ever wondered if all the noise about artificial intelligence in fundraising is just hype — or if it truly holds the key to the next big leap for your organization? If you’re a major gift officer, development director, executive director, or board member, it’s easy to feel both overwhelmed and skeptical about another “revolution” in how we work. But here’s my promise: this conversation isn’t about buzzwords or tech for tech’s sake. Instead, we share hard-won insights, surprising research, and practical strategies from my experience and my conversation on The Intentional Fundraiser podcast with Nathan Chappell, a nonprofit AI leader. You’ll walk away seeing how curiosity — not fear — can turn today’s uncertainty into tomorrow’s advantage for your mission and your donors.

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Trent Thompson Trent Thompson

Why I Wrote "Calling All Heroes": A Letter to All Nonprofit Stakeholders

My book, Calling All Heroes, is my invitation—and my challenge—to all of us who believe in the transformative power of philanthropy. I wanted to offer a roadmap that blends the best of donor-centered and community-centered fundraising, grounded in real-world experience and a profound respect for every stakeholder in our missions.

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110. Honoring Voices: Building an Ethical Storytelling Culture in Nonprofits
Trent Thompson Trent Thompson

110. Honoring Voices: Building an Ethical Storytelling Culture in Nonprofits

I’ve spent years navigating the world of nonprofit storytelling, and I’ve made my fair share of mistakes along the way. But what I’ve learned—especially from inspiring voices like Carly Euler—is that there is a path where your fundraising goals and ethical responsibilities not only coexist but powerfully reinforce one another. In this episode, you’ll discover practical, actionable ways to transform your storytelling approach to raise more money and build deeper, more respectful community relationships.

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Trent Thompson Trent Thompson

First Impressions, Lasting Impact: The Path to Major Gifts

After nearly three decades in the world of major gifts, I can say with certainty: the journey to securing transformational support begins long before a check is written. It starts with that very first impression—an interaction that can set the tone for a relationship that lasts years, even decades. Whether you’re a major gift officer, development director, executive director, or board member, how you approach those initial moments with a potential donor can make all the difference.

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109. Digital Heartbeats: Engaging Major Donors in a Virtual World
Trent Thompson Trent Thompson

109. Digital Heartbeats: Engaging Major Donors in a Virtual World

Donor expectations are shifting fast, and the old playbook just doesn’t cut it anymore. In this post, I’ll share hard-won lessons, practical strategies, and inspiring stories that will help you rise above the digital clutter and create authentic, transformational connections with your donors—no matter the medium. By the end, you’ll walk away with actionable insights you can use right now to deepen engagement and inspire generosity.

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Trent Thompson Trent Thompson

Engaging Major Donors in a Digital Age

After nearly 30 years in major gifts, I’ve seen our field transformed—sometimes overnight—by technology. But one thing has never changed: major donors want to feel seen, valued, and connected to our missions.

Today, as executive directors, development leaders, and board members, we face the challenge (and opportunity) of building authentic relationships in a digital-first world. Let me share what I’ve learned, the pitfalls I’ve witnessed, and the practical solutions that keep donors engaged, loyal, and inspired—no matter the medium.

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108. Embracing the Subscription Model in Nonprofit Giving
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108. Embracing the Subscription Model in Nonprofit Giving

In this episode, we share how embracing sustainable, recurring giving—rooted in the subscription economy—can transform your fundraising, your organization, and even your own sense of possibility. By the end of this conversation, you’ll walk away with actionable insights and renewed confidence that you can build a thriving recurring giving program, no matter your starting point.

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Trent Thompson Trent Thompson

Navigating the Fine Line Between Fundraiser and Donor

After thirty years in major gifts, I’ve seen the transformative power of strong donor relationships. But I’ve also seen the pitfalls when those relationships cross from professional stewardship into personal friendship. Let me share why, in my experience, maintaining professional boundaries isn’t just best practice—it’s essential for the health of both your organization and your own well-being.

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107. Drawing a Line Between Fundraiser and Donor
Trent Thompson Trent Thompson

107. Drawing a Line Between Fundraiser and Donor

After nearly three decades in major gifts, I’ve seen the transformative power of strong donor relationships. But I’ve also seen the pitfalls when those relationships cross from professional stewardship into personal friendship. Let me share why, in my experience, maintaining professional boundaries isn’t just best practice—it’s essential for the health of both your organization and your own well-being.

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Trent Thompson Trent Thompson

DAFs Demystified: Practical Steps for Major Gift Teams

After nearly three decades in major gift fundraising, I’ve seen countless trends come and go. But few have reshaped the landscape quite like donor-advised funds (DAFs). If you’re a major gift officer, development director, executive director, or board member, understanding DAF donors isn’t just a “nice to have”—it’s essential for your organization’s future.

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Trent Thompson Trent Thompson

Why Now Is the Time to Engage, Not Retreat

If you’ve been in the nonprofit trenches as long as I have—nearly three decades—you know that economic and political uncertainty isn’t new, but it always brings fresh challenges. I recently read in The Chronicle of Philanthropy (by Ben Gose) that online donations have dropped sharply since President Trump’s latest tariff announcements. This year, President Trump’s tariffs and the resulting stock market volatility have sent a chill through online giving. As major gift officers, development directors, executive directors, and board members, you’re likely asking: Should we pull back on fundraising appeals, or is now the time to double down?

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106. Bold Fundraising During Tumultuous Times
Trent Thompson Trent Thompson

106. Bold Fundraising During Tumultuous Times

Have you ever found yourself staring at a fundraising plan, wondering if now is the right time to ask—or if you should wait for calmer days? If you’re a major gift officer, development director, executive director, or board member, you know that uncertainty is part of our nonprofit DNA. But when economic and political storms hit, those questions become even more urgent. In this post, I’m sharing hard-won lessons and actionable strategies from my latest podcast episode, “Bold Fundraising During Tumultuous Times” Stick with me, and you’ll walk away with the confidence and practical tools to fundraise boldly—even when the ground feels anything but steady.

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Trent Thompson Trent Thompson

How AI Can Supercharge Your Major & Planned Gift Fundraising—Without Losing the Human Touch

After nearly three decades in major and planned giving, I’ve learned that our work has always been built on three pillars: trust, timing, and tailored conversations. Relationships are the heart of what we do. But today, artificial intelligence (AI) is giving us new tools to deepen those relationships—by helping us uncover hidden prospects, personalize stewardship, and make data-driven decisions that move high-value donors from interest to investment, all without losing the human connection that matters most.

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105. Ten Toes Down: Building Bold, Inclusive Philanthropy in Uncertain Times
Trent Thompson Trent Thompson

105. Ten Toes Down: Building Bold, Inclusive Philanthropy in Uncertain Times

The world is watching how we show up—not just in our fundraising goals, but in our values, our courage, and our willingness to lead through uncertainty. In this conversation, I share what I learned from Maia McGill, a trailblazer in inclusive philanthropy, about how we can embed equity and intentionality into every facet of our work. Take a listen, and you’ll walk away with practical strategies, renewed inspiration, and a powerful reminder that the future of fundraising belongs to those bold enough to build it differently.

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