Most studies suggest that between 1-4% of the general population are sociopaths. That is not exceedingly rare, but rather people we will encounter on a daily basis. In certain professions, it's likely much higher.

The overall scope of accusations against Caldbeck (including the rather detailed court filing of former employee Ann Lai, which includes disturbing documentary evidence in the form of text messages) is, at this point, substantial.

Your choice to interpret and minimize this as mere 'poor judgment' and 'signals got mixed up' is questionable given the preponderance of evidence, and certainly does seem to minimize the scope of harassment reported by the victims. I mean, for heaven's sake, he had to leave Lightspeed because of his harassment of one of their founders! They took a big financial hit with StitchFix. This was clearly widely understood and swept under the rug.