I'm a firm believer in remote work – I have spent the past 20 years as a remote employee for many different organizations and there's no way that you could ever convince me that remote work isn't the best way to structure an engineering organization. Now, that said, there is one horrible, awful aspect of remote workers for startups – the damn state.
Any U.S. startup is generally structured as a C, an LLC or a sub chapter S corporation. And that gives the company the correct legal structure to operate as a business. The problem is that while the company is a federal level entity, employment is fundamentally a state level thing. And every damn state has some screwy accounting, legal or training thing that will reach out and smack you in the ass – hard. I've seen this repeatedly and I've even heard my accountant say things like "Damn Boston; I hate Massachusetts".
Let's say that you have a startup with three founding employees who live in:
This is three sets of state level paperwork with which you have to comply. And even if you use a payroll company like PayChex, I guarantee that there will be some level of state paperwork that you, the founder, will be find annoying / incomprehensible / ass maddening.
I have read that Stripe is trying to make creating startups easier with the Stripe Atlas program and I hope so but I am honestly dubious.
Bah! States! A pox upon them. Begone!