$3 payments, Karen emails, and remembering people are people

Remember how I promised to Venmo everyone who filled out my consumer validation survey $3 for coffee at their local shop? Well, I did that. But accidentally toggled on the "for goods/services" option for every single payment. Which means Venmo charged each recipient a fee to receive the $3 I was trying to give them as a thank-you.

I didn't realize I had charged people a fee for their coffee gift until I got one email. A passive-aggressive masterpiece: "Great, thanks for charging us fees for our own coffee money."

It was 16 cents. My bad, lady.

She was also worried about having to pay taxes on the $3 (you don't pay taxes on this stuff until it's over $600, but whatever). The whole thing had big "I need to speak to the manager" energy, except I am the manager, and also the intern who fucked up the Venmo settings.

My initial reaction was defensive. Like, it's $3, it was an honest mistake, and you're really coming at me like this over 16 cents? But then I caught myself, fixed the error by sending everyone an extra 20 cents to cover the fee, and sent out a "whoops, my bad" email explaining what happened.

And then I sat with it—the email, the exchange, the time it took to undo my fuckup. Because that one bitchy email actually contained a really important reminder I need to hold onto as I build this thing.

Here's what that single interaction reminded me about interfacing with the general public:

This shit will happen. You will fuck up small things. You will fuck up big things. Systems will glitch. Toggles will be toggled wrong. Emails will go to spam. Payments will get delayed. There is no version of running a consumer-facing product where everything works perfectly all the time.

Most people don't remember there's a real person on the other side. When they're interacting with a business entity or brand—even a tiny pre-seed startup like mine—they forget there's an actual human reading their messages, fielding their comments, pulling the levers. They're not thinking about the solo founder who's learning Venmo's UI for the first time (jk) while also trying to figure out product market fit. They're thinking about The Business.

People don't expect to be treated well. This one hit me. Most people's default assumption when dealing with a business is that they'll be treated as a number. That their complaint will be ignored. That the company doesn't actually care. They come in hot because experience has taught them that's the only way to get attention.

And honestly? That person who sent the passive-aggressive email probably has too much time on their hands and needs to channel their energy into something productive. But also, they're not wrong to be annoyed. I did mess up. The fact that I'm a scrappy founder learning as I go doesn't make the mistake less annoying for them.

At the end of the day, I want to build something different. I want people to remember there's a real person here. And that I see them as real people too. I want to set the expectation that you'll actually be treated like a human, not a metric. But that means I have to be ready for the learning curve—the fuck-ups, the Karen emails, the small mistakes that reveal big truths about how people interact with businesses.

I mean, I’ve run a small biz for roughly ten years now. But it’s different. I have clients for whom I create things and collaborate with. Not customers, and not at this scale.

It also means I need systems. Real ones. Checklists. Double-checks. The boring shit that prevents these avoidable mistakes. Because "learning in public" is one thing, but repeatedly making the same preventable errors isn't scrappy—it's just unprofessional.

Links your algo won't surface:

The Mom Test — My friend and future CTO sent me this one—Rob Fitzpatrick's essential guide to customer conversations that actually teach you something. Stop asking leading questions and start learning what people actually want.

Strong Opinions, Weakly Held — The original 2006 (very short) blog post on holding strong opinions while staying open to being wrong. Essential for founders who need conviction but can't afford delusion.

First Round Review: Customer Service as a Growth Engine — Why treating customers like humans is actually a competitive advantage, not just nice-to-have.

The Kano Model — A framework for understanding which features delight customers vs. which ones they simply expect. Helpful for thinking about what "good" actually means in your product.

The Gervais Principle — Venkatesh Rao's classic on organizational dynamics. Not directly about customer service, but illuminating for understanding how companies lose touch with humans.

PS: Subscribe now if you're into this messy build-in-public energy. Miss the last issue? It’s right here. Also literally none of this is ever advice. I’m sharing what I learn through Babe, and perhaps you’ll learn from my mistakes. Hopefully, maybe, who knows, ily. Also if you’re not already, come hang with Babe on insta, Farcaster, and TBA 🟦.