> I have yet to hear a single case of an employee purchasing their options when they left and thinking it was the right decision later on.

I know at least a dozen ex-colleagues of mine who fit this criteria. When the company in question exited, it created 400 millionaire employees.

that's the problem with anecdotal evidence - you can't really tell for sure a company is going to become a massive unicorn often until very close to the point it does. I've worked at companies that raised many millions of $s and seemed very promising and a few years later went out of business. Who becomes a winner is also not always completely "fair" (as in it depends somewhat on circumstances/fortunate happenstance).

> you can't really tell for sure a company is going to become a massive unicorn often until very close to the point it does.

I don't contest this point.

> I've worked at companies that raised many millions of $s and seemed very promising and a few years later went out of business.

The only narrative I contest with my anecdata is drawing a universal truth from this experience of yours.

As a sibling comment said:

> Salt of the Earth folk love to share their stories of financial misery, but generally keep quiet about their embarrassment of riches.

I think it's the other way around - we comparatively hear a lot more about the successes than the failures. For every unicorn that made 400 people millionaires there are probably >1000 startups that either went out of business, never had a liquidation event, or never at the scale that rank and file employers got anything significant.

Obviously not literally "nobody", someone at some point joins google/microsoft/facebook/amazon/etc at an early stage and exists a millionaire many times over. Just like every week somebody wins the lottery. It's just not as likely to happen to you personally as the people selling you on joining their early startup would like you to believe.

> I think it's the other way around - we comparatively hear a lot more about the successes than the failures

Not here on HN.

I was prompted to post on this thread after reading comment after comment about failures.

aye - latecomers to a company may have massive financial/product impact but have less equity when the IPO happens vs. those who were there initially and left after 12 months. On the other side the board and others can dilute early equity holders at their leisure.

At the end of the day you're really throwing money into a black box which may turn out to contain a trash can. There is more financial transparency in penny stocks.

I've personally had great success with RSUs, but those are ultimately part of your comp even if you discount them to zero - there is no requirement to put in additional money.

I won't claim that it's the expected outcome for most, but I've exercised options well into AMT territory on multiple occasions, and it seems to have worked out favorably to the point that I could probably skip the ping pong and shrimping boat phases and jump straight to mowing lawns for fun like Forrest Gump.

Also, I have heard stories of former employees that didn't exercise their options or cashed out early, and I wouldn't say regretted it, but reflected on the fact that the stock did a lot better than they predicted it would.

Salt of the Earth folk love to share their stories of financial misery, but generally keep quiet about their embarrassment of riches.

I purchased options. Some didn't pan out. Some did. Was an early employee on all of them, purchase price was relatively low, and I don't regret any of them.