Unless you wanted to be acquihired into Google/Instagram, you likely wouldn't have made any money in equity. This acquisition is $200M less than their most recent valuation from 4 years ago, the investors are probably taking everything and most employee options are likely underwater.

If it makes you feel any better, "business sense" is nonsense in situations like that. No need to feel bad about buying the wrong lottery ticket.

It happens. I turned down a job at Shazam very early on because I couldn't understand what on earth their business model was. They were recently acquired by Apple for (coincidentally) $400m. https://en.wikipedia.org/wiki/Shazam_(application) The actual start up I founded instead fizzled into administration.

Right but Shazam was founded in 1999 and took almost 20 years to exit.

You can't look at these numbers in a vacuum.

But also Shazam took about $100m in funding with no down rounds.

It wouldn't have been life-changing money for you, it would have been a minor bonus. Usually, only the founders make life-changing money from big deals except in very rare instances, like Microsoft and Google. I doubt any but a few very early employees did well at Shazam. Meanwhile, I'm sure what you learned at the startup you joined was far more valuable than whatever the bonus was. You made the choice with the information at hand.

Equity for employees is trash value. You would do well to just pretend it doesn't even exist when factoring decisions about where to work or if to change jobs. I never ask for equity, I never care about equity. I care about the salary.

Those were innocent times. When it founded it seemed like a stupid toy, and no one on the general public was talking about it's now obvious eventual use case as a surveillance tool.

Well to be fair, no one still talks about that publicly as a selling point, they use other words instead like "collecting aggregate data on user purchasing trends"

Statistically you were still right

eh, it's silly to have those kinds of regrets. You can't predict the future, and you made a reasonable decision based on the information you had. I wrote this a few years back when thinking about what it means to regret something: https://battlepenguin.com/philosophy/science/time/

I've got a few stories like this. One was with Peloton. People buying expensive stationary bikes to work out at home? Ridiculous! )))

I would say never regret your decision when the future turns out unexpected. You made an educated guess, and you could have no idea that they would be success.

this is a horribly irrational and generally unwise way to live your life, imo

I mean, I'm not really crying over it, just mildly annoying.