Except a liquidity event rarely happens.
When they do, it's often a shell game for the investors to mask losses. The early stage employee's options are from the common pool; the investors get preferred options which are paid out first. Generally it's quite easy for the board to zero out employee options if things aren't going as well as hoped.
Many years ago, at the first company I worked for that IPO'd, I think I was something like employee number 30. Employee number 1 was a good friend of mine, and after the event we and a few others decided "I'll show you mine if you show me yours". Jewel was big at the time, total honesty was all the rage. Now I had made "a bit" of money on my stock options, not an amount to be sniffed at, but far from a life-changing amount. Think on the order of, a car, or a year's tuition, or an amazing vacation. What was shocking tho' is that we'd all made that much. We all had exactly the same options package.
Executives hired well after me, mere months before the IPO, were buying racehorses. Go figure.
Yeah. I've worked at a company where I was middling employee 250 but had the same number of options as important employee 8 simply because I was bros with the founder. I think hackers think the non-technical side of the business is going to be merit based and "fair" but that's generally not the case in my experience.
The difference here was 5-figures for the technical types who'd been there for years vs 7-figures or more for business types who'd been there for months. If nothing else it was a real eye opener into how the world really worked. Not that I'd had any illusions that I was going to retire there and then, mind. But still.
I believe they were "bros" with the VCs rather than the founders, tho'. The founders didn't do too badly but today, they aren't retired either...
