From $25k to $1M: Mindset Shifts That Accelerate Major Gift Fundraising Success

By Jeremey Cramer

This month, I want to tell a story about a recent client of ours: a nonprofit that went from receiving $25k annually from a donor to $1 million.

This client had a clear vision and a detailed understanding of their cost assumptions, but they didn’t yet have the confidence to ask donors with serious philanthropic potential for the leadership gifts that would set them up for long-term success.

In other words, they were behaving too small.

Enter TGP.

The work we’re privileged to do with clients is to help nonprofit leaders share a philanthropic narrative with confidence and conviction, so they can make the big asks that transform their organizations and, ultimately, their impact.

 

MAJOR GIFT FUNDRAISING SUCCESS: HOW IT STARTED

For the particular donor this organization was speaking to, our research revealed liquidity in the billions.

Their instinct was to increase the annual gift from $25,000 to $100,000, which is a meaningful jump, but far below the donor’s true potential.

When Lisa and I began working with the CEO on strategy, our job was to provoke her thinking and help her see what was actually possible.

Through a few strategic questions, we uncovered that this donor family had transformational philanthropic potential, and that the organization had been underestimating what they could inspire on behalf of their mission.

The CEO herself is an extraordinary leader who had taken the organization from start-up to scale, but she didn’t yet see her organization as deserving of transformational philanthropy.

The plan she had developed required more than $50 million to fully realize. So, when she saw that the math simply wouldn’t work without transformational gifts, she made a courageous pivot: instead of asking for $100,000, she prepared to ask for $10 million.

 

THE RESULTS OF THE BIG ASK

While the donor family wasn’t positioned to give the full $10 million, they responded with something even more powerful:

They increased their annual giving from $25,000 to $1 million.

And what the donor said afterward was even more meaningful:

“That was the most meaningful ask I’ve ever received.”

That’s how you know the organization got it right.

They aligned the request with the donor’s motivations and aspirations.
They asked with both conviction and humility, grounded in the organization’s values.

I could not have been prouder of that CEO and her team.

 

INSIDE THE STRATEGY: HOW TRANSFORMATIONAL GIFTS ARE WON

While our job is to lead leaders through a process that enables them to ask for a donor’s full potential, it ultimately takes real courage to do this work.

There’s rigor and discipline behind every transformational ask. It’s not as simple as asking for more money.

It requires:

• Deep research and analysis
• A strong cultivation strategy
• Connections built on trust
• Opportunities for donors to experience impact up close
• And of course, making the ask

This CEO and I spent ten hours together before making a single move.

We reflected on every email, rehearsed every conversation, and examined each next step carefully. And ultimately, she deserves full credit for the outcome. She made a genuine, powerful connection between the donor’s aspirations and the vision of where her organization was headed.

That’s what transformational giving looks like in practice.

 

YOUR TURN: SHIFTING THE FUNDRAISER’S MINDSET

Even the most seasoned fundraisers need to pause and do their own inner work before engaging high-net-worth donors.

Here are two mindset shifts that make all the difference:

Overcome imposter syndrome.

Many fundraisers feel nervous in rooms filled with wealth. But here’s the truth: you’re the expert.
You understand your mission, your impact, and your community better than anyone. Wealthy donors are looking for someone to help them make wise, meaningful investments in the world.
Lead from that place of confidence and clarity.

As someone said at a recent TGP Consulting workshop:

“Recognize power without being controlled by it.”

Check your own relationship with money.

Many fundraisers hesitate with high-wealth donors because they carry their own money stories, feelings of intimidation, scarcity, or fear of offending.
But here’s the truth: you are the guide in this conversation. They’re looking to you for clarity, confidence, and leadership.

Transformational giving requires emotional maturity as much as technical skill.

 

READY TO MAKE YOUR OWN MAJOR GIFT BREAKTHROUGH?

If you’re ready to make a transformational move  that could change not just your revenue, but your organization’s future…let’s talk.

At TGP, we help leaders ask bigger, think bolder, and lead with the conviction their missions deserve.

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