I'm going to go out on a limb here. I think he's right. It's a red flag, not the only red flag. Like, if you use strong encryption, have associated with known drug traffickers, and served time in prison on a felony charge, someone might want to keep an eye on you. It's one of many factors that may or may not be worth considering. The use of strong encryption alone should not be considered bad.
It's super clear that we're on the cusp of a total informational transformation in the West in terms of how life is lived, and a consequence is that there are deluges of personal data.... and a lawful, diligent and trustworthy law enforcement or spy officer will want to use that to do their jobs better. Unlike many in the tech world, I don't buy into either left or right anarchism: I think the office of the State is a valid one.
So we have to start looking to the future and how to properly safeguard rights in the Information Age.