When Giving Goes Wrong
What happens when trust collapses inside a nonprofit - and what responsible giving actually requires
Many conversations about philanthropy focus on generosity. But there’s another side to giving that people rarely discuss:
What happens when trust breaks?
Not theoretically, but inside a real organization, with real donors, real beneficiaries, and real consequences.
In my conversation with Yael Simon, we explored exactly that.
Within weeks of stepping into a nonprofit leadership role, Yael found herself navigating the fallout of a major fraud crisis. Investigations, broken credibility, donor confusion, and an organization unraveling in real time.
And while the story itself is dramatic, the deeper value of the conversation lies beyond. Because this episode is not really about scandal. It’s about stewardship.
Giving Is Built on Trust
There’s an assumption that sits underneath most philanthropy:
You find a cause you believe in, you trust the people running it, and then you let go.
Most of the time, that works. But when things fail, it becomes very clear that giving is not only about generosity. It’s about responsibility.
Not responsibility in the sense of becoming suspicious of every organization. And not responsibility in the sense that donors need to micromanage the causes they support. But responsibility in the sense of staying engaged.
Asking questions.
Understanding where resources are going.
Recognizing that trust is something that must be built and protected intentionally.
Why This Matters Beyond One Organization
One of the most important parts of this conversation is that Yael does not reduce failure to “bad people doing bad things.”
Instead, she points toward something more challenging:
How systems fail.
How oversight weakens.
How organizations drift.
How assumptions replace accountability.
And perhaps most importantly: how trust, once broken, affects everyone involved. Donors. Beneficiaries. Staff. Entire communities.
That’s what makes stewardship so central. Meaningful giving requires more than emotional reaction. It requires intentional awareness.
Philanthropy as Stewardship
The conversation also moves beyond crisis itself.
We discuss:
what sophisticated donors look for
why some organizations struggle to sustain support
the role of young professionals in philanthropy
and how philanthropy works best not as a complete solution — but as a catalyst
Because healthy philanthropy is not built only on urgency. It’s built on relationships, clarity, communication, and trust over time.
Watch, Listen and Engage
This episode with Yael Simon is one of the more difficult — and important — conversations we’ve had on You Are What You Give. Join us for an important conversation about better giving.
If you’d like to contact Yael Simon, you can visit her website: https://arakura.co
And as always, thank you to Victoria Hearst, whose generosity helps make these conversations possible.
