Case Files
Behind every nonprofit failure is a story.
A decision that seemed reasonable at the time.
A risk no one flagged.
A policy that didn’t exist until it was too late.
Case Files traces those stories… through court records, regulatory actions, and the wreckage left behind… in order to understand what went wrong and what it means for the rest of us. It’s how I teach governance at Seattle University, and it’s how I keep learning in my own work. Because the sector gets stronger when we’re willing to study our failures, not just celebrate our wins.
📖Season 1 (2026)
Case 1 - Flipcause | What the Flipcause bankruptcy teaches us about technology & good governance.
Donors gave to nonprofits. But their money ended up with Flipcause, a fundraising platform that filed for bankruptcy earlier this year, disclosing nearly $29 million in donor funds hanging in the lurch. For more than 3,200 organizations, that money is probably gone. It’s a story about a piece of technology, but it’s also a story about a blind spot in nonprofit governance: the gap between how boards think about technology and the financial risk it actually carries. We start with a current case dominating todays news cycle before looking back over the last decade.
Case 2 - NaNoWriMo | How NaNoWriMo’s Board Failed Its Community — And What Yours Can Learn From Ithttps://caitlinpontrella.substack.com/p/the-governance-failures-that-brought
or 25 years, NaNoWriMo brought hundreds of thousands of writers together every November to attempt the impossible: a 50,000-word novel in 30 days. Then, in March 2025, the board announced it was shutting down. It wasn't one bad decision or one bad year that killed it… it was a cascade of governance failures that went unaddressed until the community walked out the door.
Coming Up: Lessons from organizations like the LA Museum of Contemporary Art, Berkshire Museum Art Sale Controversy, Whitney Museum, Smithsonian, American Folk Art Museum, and More.
*Case Files draws from publicly available sources: Court documents, regulatory filings, news coverage, and editorials. The goal isn’t to litigate or condemn, but to learn. These cases don’t capture everything about the organizations involved, and circumstances may have changed. If you have corrections or additional context, I’m glad to hear it.