← All insights

Jan 27, 2026 · 2 min · fundraising

My barista won't stop upselling me

I've been going to my local coffee shop more than usual lately, and every morning the barista hits me with something new. First it was a bag of beans. Then a seasonal latte instead of my regular drip. Then a diner mug. We are going on three straight weeks of upsells, and at this point I'm half expecting an offer on the table I'm sitting at.

It's funny until you see the mirror in it. The barista is us, blasting the donor file. The upsells are the asks stacked into every email, every touchpoint, every season.

What the asks add up to

No single ask is wrong. That's what makes this trap comfortable. Each one is reasonable, justified, on-calendar. But the person on the other end doesn't experience your asks one at a time. She experiences the accumulation, and the accumulation has a message of its own: what we want from you matters more than what you came here for.

If all you ever do is ask, people stop showing up.

I still love that coffee shop, for the record. The coffee's good. But I've started bracing slightly on the walk in, and that tiny bracing is exactly what we should fear in our donor relationships, because it precedes every unsubscribe and every quiet lapse. The alternative isn't asking less out of timidity. It's serving more out of conviction: stories worth reading, encouragement worth opening, value that has nothing to do with this month's target. Brand is the drink worth coming back for. The ask works best when it's the exception in a relationship, not the substance of it.

Before you go

Where is your growth really coming from?

Find out in three minutes. Eight honest questions, a straight read on whether your growth is built to last, and free moves you can run whether we ever talk or not.