The biggest mistake reddit made was not cracking down on the fundamentalist trans activists of /r/shitredditsays back in the early-mid 2010's when it started becoming a problem. It was a crossroads and reddit took the wrong path, probably because it seemed like less of a hassle at the time. The TRAs were somehow able to cozy up to reddit leadership and the rest is history. If the tide ever turns to the point where journalists find the courage to investigate this stuff, they should probably start with BardFinn.