Criminal prosecution for fraud? Does that really happen with any regularity? I think by far the most common consequence of being caught lying about a felony is firing with cause.
I'm not a lawyer but I think a fraud prosecution is very unlikely. However, there are a bunch of torts involved.
The real consequence I'm referring to here though is a firing for cause. Real for-cause firings are rare in our business, so I think we tend to forget that they are a big deal.
The major consequence of "termination for cause" is that you don't get severance, and the company will probably fight unemployment claims.
I grant you that if he gets fired over this, he shouldn't expect a package. His life is already in a state of fucked-up-ness that is beyond worrying about that he might get fired without severance. He needs to get a job, first and foremost. Severance is almost a Maserati problem, where he is.
Right now, severance is nice to have but not a huge deal. Fifteen years from now when he's getting large (~1 year) contractual severances due to being in highly strategic roles-- he can be cut for reasons that aren't his fault, and job searches take years at his level-- he will want to start coming clean about the felony. By that time, he'll have a track record and can come clean because no one will care about a 15-20+ year old felony conviction.
You are providing what I believe to be --- pragmatically --- terrible advice in this thread. It is not impossible to find employment in tech with a felony conviction; in fact, by all outward appearances, the opposite is true; people with CFAA convictions are employed at a rate higher than that of the overall population; they are, as a general rule, employed.
What you're saying is that you think the job market is so inhospitable to people with criminal convictions that they should endanger their career to weasel their way into jobs. We could debate how unwise that advice was if you were right about the employment market. But you're wrong about the employment market, which makes the risk/reward on what you're suggesting so far out of whack that your suggestion isn't worth entertaining.
I don't have strong opinions about what you do with a prospective employer who at no point asks you about your criminal record. But if you're asked about it, you're crazy if you lie.
Again, let me (tediously) repeat that I don't know you personally; you happen to spend a decent number of words on HN articulating ideas that I find worth disputing, but on the street I wouldn't know you from Adam and I have no issue with you personally.
It is not impossible to find employment in tech with a felony conviction; in fact, by all outward appearances, the opposite is true; people with CFAA convictions are employed at a rate higher than that of the overall population; they are, as a general rule, employed.
This may be. That's why I suggested the "odds and evens" (full disclosure with half, full omission with half) strategy. Not only is it hedged but it will also give him data-- which we don't have.
It's obviously better if he can disclose and still get a job. Then he has nothing to worry about.
To be honest, I feel like we're both suburban kids arguing about inner-city gang life. :) We both think we're tough, and we both are tougher than most people in our neighborhood, but we haven't actually been in the slums. We don't have the data. I guess that's a good thing, given the nature of what we're arguing about.
I'm glad that you're arguing the other side of this, though, because we're talking about Serious Shit and OP needs to hear all sides.