I worked at a promising mobile-app startup whose gigantic ambitions didn't pan out; I figured they'd be an acquisition target and bought my options for like $4K. At some point the founders decided to cash out, but instead of selling, they started paying out dividends.

That first check alone more than tripled my money - and came with a cap table, too, so I could see the $1m+ payouts to each founder as a nice little lesson in the disparity between founder and early-employee outcomes.

Not that I'm complaining - this has turned into the single highest-performing investment I've ever made :) Career-wise it launched me into the big leagues. A+, would do it all again.

The only other startup that paid me equity money, I got enough to buy a used motorcycle. Yay.

Depends on your definition of unicorn. I did quite well out of options at a previous gig. They IPO'ed shortly before I left and are now trading at >50x the exercise price.

Several close friends have had their options worth $1M+ at Splunk, Slack, JFrog and more - I know the numbers because they've called me for financial advice.

Did that in the past in the UK at BT.A (and the forced split of cellnet) and RELEX more recently and I am in an EMI scheme at the moment that will pay out on the sale of my current employer

Having said that there are significant protections in UK law for employee share schemes

I was part of a startup for a few days short of a year. We got acquired by Apple and I walked away with ~$400k after taxes (no 83-b election benefit). I’d say that was a significant amount for me for 1 year of work.

It's very common to sell stock at > 30x exercise price when you get into a growing company at the right time. A lot of imponderables in that, and all of that risk is borne by you. You end up making VCs and founders rich: they get to sell stock at even higher multiples, and at much lower risk: they get to sell on the day of IPO, and they also get preferred shares, which have more protections (founders used to have Common Stock only, as the article states, but that has changed, and they also get to sell stock during intermediate financing rounds, which also considerably reduces their risk).

Significant is $, not %. 10% of $1M beats 100% of $10k.

Why would you expect options to pay big for a non-unicorn? Unicorn means the startup investment succeeded in its goal. No one gets rich when their investment fails.

20x at a startup recently acquired for 1B (assuming they hit earn-outs), right at the unicorn threshold.

I have. Twice.

My situation is far more common than the people making millions from unicorns at IPO.

The majority of exits don't come from IPOs. They come from acquisitions of small-ish companies by big or medium size companies. These don't make headlines because they're not very noteworthy for the average person.

Pretty sure a ton of people have done this via acquisition.