Specifically, sales tax is a nightmare.

I’m trying to sell to people all over the world, and I have no idea where to even start on figuring out what to charge them. Sales tax is the U.S. alone is an atrocious mess, but when you include global sales, it is ridiculous. And software to help calculate it is extremely expensive and confusing in its own right. I would think taxes, something that governments all of the world want you to pay, should be simpler. All I want to know is how to charge my customers properly, and who I have to pay what taxes to. That doesn’t seem to difficult in my mind, but clearly that’s just me.

Well, at least I found an alternative. For those who are hitting this problem on their own start-ups, try finding a site which will act as the vendor on record, and handle sales tax for you. Trust me, it is worth whatever they charge you to avoid that mess. Personally, I’m using FastSpring. They don’t have a great API or functionality, but at least I don’t have to worry about it anymore. If anyone else has suggestions, I’m all ears.