What if generosity was not only about asking for donations but instead changing how we think about giving altogether? Too often, fundraising is treated as a tactic. But true generosity is a mindset, one that requires nonprofits to reframe ‘the ask’ so it aligns with donor intentions and fuels lasting impact.

That’s the heart of “The Generosity Shift.” In conversation with Joanna Hogan, Founder & CEO of Inspire Generosity, and Infinite Giving’s CEO & co-founder, Karen Houghton, we explored how nonprofits can move beyond traditional approaches in fundraising. Instead, by shifting to generosity, nonprofit leaders are centering conversations around trust, authentic connection, and experiences that make giving joyful and deeply meaningful.

Because here’s the tension: generous people want to give from their assets, not just their bank accounts. Yet most nonprofits aren’t prepared to receive those non-cash donations, or they’re unsure how to invite them. 

Even when the technical systems are in place, stock or crypto donations don’t automatically roll in. That leaves leaders wondering if the effort is worth it. The truth? It is. Your biggest supporters do give this way but only when they’re invited with confidence and clarity.

In this post, we’ll unpack how to move from scarcity to abundance by shifting both your mindset and your message. You’ll learn how to:

• Think of donors as "giving partners" and speak to them in ways that feel aligned, not awkward
• Highlight the tax-smart efficiencies that make non-cash giving attractive
• Build readiness that’s not only technical but relational

Because when nonprofits embrace The Generosity Shift, they not only capture bigger gifts but, more importantly, they create deeper, lasting impact.

Replay our webinar to learn more about how to shift generosity
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The Difference Between “Fundraising” vs “Inspiring Generosity”

As Joanna explained, fundraising is usually about getting money from people so you can accomplish your mission. “It often creates a one-sided dynamic,” Joanna said. “You’re the one with the need, and they’re the ones with the resources. That setup can make everyone feel a little off.”

In this situation, the nonprofit leader ends up feeling like they have to persuade or convince someone that their cause is worthy. It becomes about strategy, technique, persistence. Sometimes even desperation.

Inspiring generosity is completely different. “It’s about finding giving partners in people who care about the same things you do,” Joanna said. “They see the issue too, and they want to be part of the solution. When that happens, it’s not one person giving and the other receiving—it’s a partnership.

“They bring financial resources, you bring vision, leadership, and on-the-ground impact," Joanna exaplined. "And you care just as much about their experience as a giver as you do about meeting your organization’s goals.”

When this happens, the focus shifts. It’s not about the money. It’s about what becomes possible when people come together to do something meaningful. Generosity can take many forms: time, skills, relationships, or funding. But none of it puts one person on a pedestal. No one’s the hero. Everyone belongs. And that’s what makes it so powerful.

‍“Once I experienced the difference for myself (when giving felt mutual, not transactional) I knew I could never go back."

The Underlying Issues

Considering the upcoming Great Wealth Transfer with nearly $124 trillion to be passed down to the next generation in the U.S., it’s clear that we don’t have a generosity problem but instead we have a generosity bottleneck. 

As Joanna explained, there are plenty of people who want to put their wealth to work solving problems, funding cures, and fueling dreams. And there’s certainly no shortage of need: budgets are being slashed, leaders are stretched thin, and programs that took decades to build are vanishing overnight. 

“The gap isn’t money, it’s mindset and training,” Joanna explained. “Too many nonprofit leaders haven’t been equipped to inspire generosity, so they default to simply asking for cash. That leaves everyone feeling awkward, uncomfortable, and stuck in a cycle that can’t be sustained.”
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The Heart of Generosity 

In traditional fundraising, we often refer to people as “donors,” which, in Joanna’s opinion, is like calling them a wallet. “I prefer terms like supporters, contributors, or—my favorite—giving partners,” Joanna said.

“When someone shows interest, the typical fundraising approach jumps straight to the ask. We ‘hit them up for money,’ often before we’ve really built any kind of relationship. And if it’s a large request, it can feel a lot like asking someone to marry you on the first date.”

Inspiring generosity takes a different path. For nonprofit leaders, this means you start by making sure you’re talking to the right person, someone who not only has the capacity to give, but who truly cares about the issue you’re trying to solve. Someone with a track record of generosity, because not everyone who’s wealthy is generous. From there, it’s about building a genuine, authentic relationship over time, Joanna explained.

In traditional fundraising, we talk about donor fatigue—and it’s real. People get tired of being asked again and again, especially when they haven’t felt truly thanked or seen the impact of their previous gift.

“Generous people will tell you: one of the biggest reasons they stop giving to organizations they care about is because the thank-you note included another ask, or they only hear from someone when money is needed,” Joanna said.

‍“When you’re inspiring generosity, you’re not just asking for help. You’re inviting someone into something meaningful. You’re creating a relationship, not a transaction. And that changes everything.”

Why Assets Matter

At Infinite Giving, we’ve seen how nonprofit leaders often find themselves stuck in a chicken-and-egg scenario when it comes to asset giving, specifically around stocks and crypto. We often hear comments such as: “No one’s asking to give this way, so we don’t need it.” Or, “We have the ability to accept non-cash gifts, but no one uses it—so maybe our donors aren’t interested.”

Both mindsets are understandable, but they’re holding us back. Because the data tells a different story:

• Over 90% of wealth is held in assets like stocks, not in checking accounts.
• The average online cash gift is around $128, while the average stock gift is over $8,000.
• Stock giving has grown 135% over the last 8 years.
• And research by Dr. Russell James shows that nonprofits who invite both cash and stock gifts raise 55% more over five years.

Asset giving presents a huge opportunity in generosity that nonprofits simply can’t afford to miss.

Upskilling and training to invite asset gifts

As Joanna explained, many nonprofit leaders are financially illiterate when it comes to non-cash gifts such as stock or other types of assets. “They might have heard the terms, but if you don’t understand something yourself, it’s hard to confidently talk to a giving partner about it—let alone encourage someone to make a gift using it,” Joanna said.

“I remember the first time someone told me they wanted to give from their IRA. I smiled and said, “Okay—great!” but inside I was scrambling. They ended up telling me what information they needed—like the mailing address, tax ID, and all the stuff I should’ve already known. I was embarrassed, because they were ready to be generous… and I wasn’t ready to receive it.”

Joanna also shared her candid story about the first time someone told her she should be inviting gifts from donor-advised funds (DAFs).

“I smiled and nodded like I understood, but I had no idea what they were talking about. It wasn’t until I opened my own DAF that I truly understood what a powerful tool it is. And more recently, I learned that there’s over $250 billion already allocated to charity sitting in DAFs—undesignated and waiting. That’s staggering. And it’s another example of the generosity bottleneck in this country.”

Knowledge isn’t power until it’s applied, which is exactly why Joanna created the Generosity Lab. “It’s a safe, supportive space where my students practice these conversations with real people who have significant capacity,” she explained. ‍

“So by the time they’re sitting across from a giving partner who could make a transformational investment, they’ve already practiced, refined, and gained confidence in their approach. They’re not winging it. They’re ready.”

Reframing the Invitation to Unlock Bigger Gifts

It’s up to the nonprofit leader to reframe the giving conversation so that it feels like an invitation rather than a request. But what language shifts help create trust and inspire action to be more generous? 

“Like many people responsible for raising money, I used to believe that if I just had the right words, everything would fall into place,” Joanna said. “So I read the books, took the webinars, and paid close attention to all the different ways you could make the invitation to your giving partners.”

Joanna shared that one of the approaches she felt most comfortable with was saying, “Would you consider a gift in the amount of…” and then naming the number. “That felt respectful. And asking permission to make the invitation beforehand was a great strategy—because you’re not putting people on the spot,” she explained. “You’re giving them space. You’re honoring their process. And often, they’ll share valuable insight about when and how they like to give.”

But that still sounds like traditional fundraising, doesn’t it? However, Joanna said that when you’re inspiring generosity, you’ve already created the conditions for generosity to happen.

“It’s not a surprise. It’s not pressure. It’s the next natural step—and in many cases, they bring it up before you do. So it honestly doesn’t matter what words you use. It’s not about the words. Just like it’s not really about the money. What matters is the relationship. The alignment. The trust that’s already been built.”

The DREAMS framework generosity

Joanna created a practical framework for how generosity is actually inspired. These 6 steps in the DREAMs framework help to create conditions for shifting generosity.

• Discover is about finding the right people. You don’t need more names—you need the right ones.
• Research is about keeping the end in mind, understanding your giving partners, and knowing what truly drives their generosity.
• Engage is about using language that fosters partnership. It’s asking the right questions so you can truly understand what someone wants to accomplish with their money that’s meaningful to them, and being able to explain not just what you do but why it truly matters. Why you, why them, and why now?
• Activate is about making giving fun—moving from asking to inviting so that giving conversations feel good instead of awkward. It’s also about helping people give in ways that work best for their financial situation, like gifts of stock, real estate, or business assets.
• Multiply is about turning your supporters into passionate advocates and making it easy for them to share your mission so they can help expand your reach and broaden your base of support.
• Sustain is about making gratitude unforgettable—not transactional—and showing impact through stories. When supporters feel seen, inspired, and connected, generosity doesn’t just continue, it grows.

“The DREAMS framework isn’t about tactics,” Joanna said. “It’s about creating space for generosity to do what it does best—flow.”

Making it easy to inspire generosity

One of the biggest challenges we hear from nonprofit leaders is: 'I don’t even know where to start.' We asked Joanna, what would you say to a nonprofit leader who wants to step into these conversations but feels overwhelmed or underprepared?

Joanna said if you’re feeling overwhelmed, start small. “Identify one conversation this month where you’ll practice asking better discovery questions—just one. That alone can shift the way you connect.”

We were also reminded us that nonprofit leaders don’t have to figure it out alone. “Reach out for training,” Joanna advised. “Learning by trial and error is painful, and it’s one of the reasons the turnover rate for fundraising professionals in the U.S. is just 14 months.”

“Knowledge isn’t power until it’s applied. And when you’ve had space to practice, reflect, and try again, you start to show up differently. You trust yourself more. You stop second-guessing. When that happens, generosity conversations start to feel like what they were always meant to be—natural, joyful, and deeply human.”

Next Steps for the Generosity Shift

If this conversation is sparking ideas for you, but you’re wondering how to actually do it, Infinite Giving is here to serve you.

We come alongside nonprofits as your financial partner to help set up brokerage accounts, create stock gift workflows, and steward those gifts well, with no transaction fees on stock donations. We believe receiving generosity should be as joyful and easy as giving it.

Whether you’re getting your first non-cash gift or ready to scale a strategic giving strategy, we’d love to be your partner in shifting generosity into transformational impact. Let's get started.