I don’t think Hacker News faces liability for posting non-compliant ads. (Not a lawyer!) But if it turns out to be a trove of them, HN’s essentially a honey pot.
> any actual cases brought for enforcement will end up in court in NYC
Precisely what you want your early-stage portfolio dealing with.
Agree that investors should not tolerate illegal behavior from their portfolio companies, but realistically VCs can't manage every day-to-day detail of their portfolio. And even when they do get involved they can't always control the management -- see Uber, for example. Sometimes the VCs provide the legal cover for questionable behavior because the potential profits outweigh the potential fines and risk of enforcement by well-intentioned but ultimately toothless laws, as I suspect the NYC law will turn out.
New York City has no shortage of investigators with overlapping jurisdiction looking for troves of targets.
> VCs can't manage every day-to-day detail of their portfolio
These are job postings on Hacker News!
The law in question only has vague enforcement provisions that include fines "up to $250,000," which means any actual cases brought for enforcement will end up in court in NYC. A civil judge will then get to decide what "good faith" means in each specific case, and also decide questions of jurisdiction and responsibility.