What if the fundraising practices that feel most natural are actually the ones holding you back?

After more than four decades in fundraising—and helping raise more than $3 billion for important causes—Kevin Gentry has reached a striking conclusion: much of what works best in fundraising is counterintuitive.

In this episode of You Are What You Give, Kevin and I explore what separates transactional fundraising from transformational giving.

Why doesn't simply demonstrating greater need necessarily inspire greater generosity? Why can it sometimes be easier to raise $1 million than $10,000? And what changes when we stop viewing donors primarily as sources of money and begin treating them as genuine partners in solving a problem?

Kevin makes the case for thinking beyond the next gift. That means understanding a donor's values and aspirations, inviting their knowledge and experience into the work, and building relationships that can develop over years rather than around the next ask.

We also discuss why fundraising is a skill that can be learned, the importance of authentic vision, what Kevin wishes he'd understood 40 years ago, and why the best donor conversation may sometimes be the one in which you don't ask for money at all.

Kevin shares free weekly fundraising advice and additional resources at TENXStrategies.com.

Special thanks to Victoria Hearst for her generous support of this season of You Are What You Give.