First rule of security: There is no perfect security. You need a multilayered strategy. Tor is a start. Anonymized OSs like Tails are another aspect. Not releasing personal info on the web -- to the extent you can do that -- is another.
I guess his job does not involve participating in projects that have git repositories or public mailing lists.
What was the benefit to having no electronic record? Was he a lawyer for the mob?
It makes sense though, so many people run companies that sell, exploit, mismanage, abuse user data, or outright ignore privacy issues that it's bound to leak into HN as well. It's unfortunate.
I will ask.