Yup, I'm working with an accountant to better understand what's going on. Last year I was in a grace period but this year I'm going to have to file. Luckily it's just me, no employees and no cofounder to worry about. But man tax law is complicated and I don't like not knowing every part of what I'm doing.

Part of the reason I started working at Stripe is that I remember going through exactly this and it freaking sucked. Building a product and finding customers for it is hard enough without also having to cross-class as an expert in international taxes of software sales.

(Drop us a line if you need a referral to an accountant; we can introduce you to an accountancy that works with a lot of Internet businesses. We also have some guides about it at https://stripe.com/atlas/guides to demystify it a bit.)

Out of curiosity, are you guys thinking of something like an UpCounsel for startup/technology-focused accountants?

We have a number of accounting firms which we work with that we refer Atlas customers to. This lets us explain the Atlas concept once, prepare the firms for "You're going to have a high volume of companies who will often have the same set of issues so let's research and brief those in advance", build out tools to assist with information gathering, etc.

It also lets us help refer companies to accountancies whose sweet spot most closely corresponds to the facts of the company.

And don't skimp on a quality accountant. I "saved" $2k one year by shopping for a bargain accountant. I've since learned his advice cost me between $50k and $100k in unnecessary taxes.

What was the advice about? I’m curious what led to such a big difference.

LLC vs S-Corp. Trump muddied the waters though. Now it's unclear which is better.

S-Corp is still strictly better for tax purposes for companies with net profit before owner salaries north of $100k.