Thread by @Shpigford

1/ Massive lesson learned today regarding running a remote company: you must register as a foreign entity in every state you have employees.

I incorrectly assumed that using a PEO absorbed all the tax nonsense.

2/ It absorbs it for payroll taxes. It does NOT absorb the taxes/fees every state charges for the "privilege" of hiring someone that lives there.

And boy do states love to get greedy with those charges.

3/ I'll be writing checks for the following amounts. Roughly 90% of these are purely late fees/penalties.

Texas: $3,666 (2 employees)
Tennessee: $2,026 (1 employee)
California: $816 (1 employee)

4/ I called the the SoS of each state to try and figure out a reduction in those penalties...nobody was event remotely interested in even having a discussion about it.

5/ This is one of those scenarios where I feel like a complete amateur idiot. I've been self-employed for 15 years and have been painfully aware of how terrible every state treats small businesses. I should have known better.

6/ I legitimately don't understand how anyone would ever be able to figure all of this out. Every single year I stumble upon some new obscure tax/fee/penalty/regulation I have to abide by.

It's just incredibly demoralizing.

7/ For all the pro's of building a remote team, there's a huge hairy pile of con's that come with every city, county, state and country having their own set of taxes/laws.

It's a complete dumpster fire.