Don't forget that Uber burned through VC money at a peak rate of something like 500 million$ a month to subsidise their low prices until they drove competitors out of business and/or established themselves as ubiquitous. In the olden days it was called dumping, now it's disruption.

craigslist served as a prostitution and drug trafficking forum for most of its' popular existence.

ebay used to allow the sale of presription drugs, prescriptions themselves, body parts , animal cadavers , pirated software, and shipping of weapons to restricted global areas.

ebay was also an unreported tax-haven-ish thing for a few early years.

(ebay was great fun to browse around in the mid 90s.)

the production of the model T had some interesting quirks. When production ramped he essentially bought the entire workforce from certain regions and caused all sorts of social issues. He had his employees self-tattle on each other for 'moral standards'.

The model-t itself was also produced off a different patent that was held by someone else and ignored; it was fought for later and won by Ford in 1911.