Examples that would cause this to resolve to yes:
Customers cannot withdraw their assets for ≥14 days (e.g. due to a hack)
Major loss of customer funds (>1% of total assets held on Polymarket, or similar), not just a few individuals affected
Files for bankruptcy in a way where customer assets are affected
Markets are blatantly resolved incorrectly, in a manner that is widely regarded as fraudulent or grossly incompetent (rather than minorly incompetent)
Any other major incident that would cause investors not to want to put their dollars on Polymarket in the future
2023 market: https://manifold.markets/JonasVollmer/will-polymarket-fail-by-the-end-of?r=Sm9uYXNWb2xsbWVy
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https://manifold.markets/JonasVollmer/will-polymarket-fail-by-the-end-of?r=Sm9uYXNWb2xsbWVy