My Stripe Tax Story

My dad owns a successful chain of bicycle stores in Texas. He’s been in business for almost 51 years and he’s one of the largest bike dealers by volume in the country. He has nearly a hundred employees and a bookkeeper. Despite having a proverbial dozen balls in the air at any time and despite having people on the payroll to do bookkeeping, he sits down at his computer every night at home, logs into the ERP system, and reviews sales and receipts. He catches all kinds of crazy things. Credit card fraud (before the chargeback even comes), internal theft, mis-priced items, mistakes, you name it. He has great employees but even the best make mistakes and he’s learned this habit over the decades the hard way. I remember sitting next to him as a kid, watching him pour over cash register journal tapes that were yards long, looking for problems.

My point: if you let this kind of fuck-up go undetected for over three months, you have to at least assume some of the blame and acknowledge that you probably could have caught it if you scrutinized transactions. Every good business owner does it.

(I work at Stripe but don’t in any way speak for the company. This purely personal.)

I don’t mind them publishing this. It doesn’t feel unfair or dramatizing or in bad faith (etc.)

At the end of the day we build things to try and make other humans’ lives easier; to wrap the complexities of “global financial internet infrastructure” so business owners like the OP can focus on things that are not “collecting Canadian taxes”.

Whether Stripe ended up making the “right” changes in this case or not, we didn’t hit that bar.

And as “someone who works for Stripe but absolutely in no way speaks for Stripe”, it’s a productive reminder of the downstream effects of what we build. What we build has real world implications, ones people at Stripe take very seriously.

It hurts to read about the misses, but I would 10000% rather read about it on the front page of HN than us not know about it. And in this case, again, what they wrote doesn’t feel like it’s in bad faith, so it’s useful feedback.

Sad to see Stripe fall to the bean counters instead of staying focused on customers. They were coming out with some cool innovations a few years ago. Even "don't be evil" Google is moving in this direction. Not sure why companies always evolve this way. Boeing is another prime example. Apple has maintained its focus on the customer and thrived, bucking the trend, which seems like it would be motivation for others to stay focused on the customer. Especially given when Apple hired the Pepsi guy to run things in the bean counter way, the company nearly died.

> if you let this kind of fuck-up go undetected for over three months, you have to at least assume some of the blame and acknowledge that you probably could have caught it if you scrutinized transactions.

I work in eCommerce and occasionally there will be something like a script or config gets messed up and an issue with billing will happen. And being the "expert" I'm usually the one called to fix it.

I wish I could count the number of tense discussions I have had that are along the lines of:

  Them: We haven't been charging tax in Canada for three months because the config was wrong. Fix it!
  Me: (some more polite variant of) So just to confirm, this has been wrong in your ERP... hundreds of thousands of CAD of uncollected VAT... for 3 months and you're just now noticing?

It is, unfortunately, an extremely common discussion. That or some close variant of.