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Wouldn't it still be possible to do contracts for $599, but like... one for each jira ticket/github issue or something? You could hypothetically set things up to not know who was resolving tickets, right?

I mean it seems like a ridiculous way of getting work done, but fundamentally possible.

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No, if you (as a contractor or employee) make more than $600 from the same person/business, you'd be obligated to report it, which would in turn make them obligated to report it, even if they didn't realize you had done more than a single contract for them. For this to work, you'd have to have independent shell corps make each chunk of work as well, which .. is probably also illegal.

What could work is a middle man (ala upwork), but then you'd have to accept the middle man knowing you.

That makes sense -- I'm assuming the company is going to follow the letter of the law, because they are a known entity, but the anonymous/pseudonymous individual is trying to break it.

you'd have to spin up an LLC for each engagement to do this, 1099 forms are based on your entire (contractor) relationship with the company for the tax year.

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