Making the argument is the wrong phasing. Instead, what he should have said is "I can almost certainly get away with breaking the non-compete, and it is unlikely that anyone will notice".

Tech companies are not sending private detectives to follow every engineer that left the company.

This fantasy world, where major tech companies are preventing random engineers from leaving to work for other big tech companies, is just not true. It happens all of the time, and almost nobody gets sued.

Like, I don't know what to tell you. Like half of the engineers that I know, have job hopped, sometimes multiple times, between these top tech companies. They aren't being sued.

They go work at microsoft, and then leave for Facebook, or uber, or "insert rando prestigious tech company here", and I don't know of a single one, of all of my friend that I know, who has ever been sued for job hopping between top tech companies as an engineer.

It just does not happen, for the average tech employee, outside of weird, extreme, egregious cases.