Sure, but if by that company having to treat him as an employee he got paid three times more plus benefits, without having to burn the candle at both ends on 5+ dystopian gig economy companies, he would probably come out on top.

Why wouldn’t they be able to multi-app? As far as I can tell this is double talk. “If we have to W2 them we will make a condition of employment that they can’t be clocking hours in multiple apps at once.” That is the only explanation I can see for why there’d be any issue. At least in California there is no law that would restrict either company or employee in such a way, in fact the case law on non competes seems to lean the other direction with preference given to workers not being restricted from practicing their trade except in very limited circumstances. So they’re creating a straw man unworkable situation that would only be created by them pushing an unworkable system and supporting employment agreement.

There are many alternative ways to structure this relationship. Many with just as much or more chance of being long term sustainable for all parties than the current model which definitely works for one party but we have good evidence is not sustainable and workable for all the workers some of whom are being chewed through and exploited.