Ask This Question Before You Send The Letter
A board member once came to me with a plan: write one letter, send it to every high-net-worth person in town, and raise a few hundred thousand dollars for their brand-new nonprofit.
No staff. No donor relationships. No idea whether a single person on that list had ever given to a cause like theirs.
Before we wrote a word, I asked one question:
“Does anyone on this list actually know you?”
Not “knows of you” — actually knows you, or knows someone close enough to open the letter. That question did more work than anything else. It also led to two more: Are these people philanthropic? Have they given to something similar? The honest answers narrowed a wishful list into a real one. We led with information, not an ask. Then we sent something built for the ten people who actually mattered.
They raised close to $100,000. Their first appeal ever.
I've also sat across from development teams who send the same letter every year, to the same list, in the same voice — then act surprised when the number doesn't move. Different problem, same root: no plan built around who's actually listening.
Here's what both stories tell you: a strong year-end appeal isn't about reach. It's about knowing exactly who you're talking to, and building a plan around them — not a template.
That's the whole premise behind the Year-End Appeal Kickstart. Over 30 days, working alongside 11 other EDs and development leads, you build one real plan: a qualified list, sequenced asks, a timeline that survives October. Not theory. Not a swipe file. Your actual appeal, built start to finish.
Who it isn't for
You're hoping a bigger mailing list solves the problem. You want someone to write the letter for you without doing the qualifying work first. You're not ready to look honestly at what hasn't worked.
Who it's for
You already have some donor relationships. You know the appeal needs to change — you just haven't had the structure, or the hours, to rebuild it alone. You want this handled before Q4 swallows your calendar.
If that second one sounds like you — the Kickstart starts September 9, caps at 12 people, and is $297.
Not sure yet? That's fair. Shoot me an email or send a DM — I'll tell you honestly whether it's the right fit. No pitch required.
Now go ask fearlessly.
