Yeah, that looks similar to the one that I got. But I don't remember it having the shares outstanding listed, because I specifically remember asking around to try to figure that number out. But that was years ago and maybe my memory is bad.
Fraud is hard to prove because it requires providing intention, but certainly some of the elements of fraud are present.
I don't remember who was buying, but I think it was literally on "Second Market" before they were acquired by NASDAQ (iirc)... I wanna say that was in the summer of 2015, and was the only official liquidity opportunity that was offered for employees, at least in the last few years that I was aware of. I know some of my colleagues got out with sharespost sales, but those were only the ones who had enough shares qualify for that sale (which, again screwing the lower compensated employees, wouldn't be the customer service teams).
In my mind, there's two things that should change: first, and most importantly, we need better protections for employees in these kinds of situations; second (and a distant second, but still salient since it's the only thing that you really can do to protect yourself), people should be more wary. I totally agree that you can't protect yourself from these kinds of deals done in secret. But, you can look for the kinds of warning signs and stay away.
I know people who were laid off during one of the multiple rounds of layoffs, and still went back to buy their shares. That's some strong Kool-aid, and it makes very little sense to me why one would do that in this context if they weren't being given some strong misinformation.
The company played some nasty mind games with their employees regarding equity. They did a 7 (I think?) for 1 split, and then had the recruiters telling employees that they had "never seen a company give out so many shares before." They sent out spreadsheets with calculators that would let you estimate the value of your shares, and just casually let you know that Apple was trading at ~$700/share. iirc, they even pre-filled in the line for potential value with Apple's current share price (so, 5000 shares * 700 Apple-level share price = 3.5M). At every company meeting, they'd get really pumped about how they were going to IPO. They would throw parties celebrating their 100 millionth patient life covered, even though it seemed pretty obvious those numbers weren't real. No 401k match, since you're not going to need it after we IPO.
There was even a second market offering to let Ryan sell enough shares to pay his taxes and maybe buy a nice house in South Park.
I don't feel bad for the engineers, since they were generally exposed to enough information that they should have been able to call bullshit. I feel bad for the customer success team, who were often given a tenth of the amount of shares as engineers but would still frequently talk about retiring when we IPO. Hopefully the exec bonuses will be voted down, and there'll be a class action lawsuit.
This is a problem that faces a lot of startups. We should all be more wary of information that's given out, and be more demanding of transparency. Learn a less from all of us PF employees: the more a company talks about their IPO, the less likely it's going to happen.