Any stories of employees with equity successfully taking home over $1m? $500k?

Not faulting your decision making process, but have you kept track of the startups you declined offers from?

I would be curious if that paradigm changes in 10 years, not that I will remember to ask you :D

I joined a startup several years ago as an early engineer. The company was acquired last year, and my equity was worth more than $1m after investors were paid.

Yes, my first startup job got me into the high end of that range, as employee #5, with a relatively small acquisition.

I know several people who took home much more from employee roles (albeit in larger acquisitions) in the recent past.

A lot of it has to do with who you work with. In every case I can think of, windfall money for employees came from founders with a track record of accomplishing that (or, in my case, a founder who would soon develop that track record, and was, in the company I was at, extremely committed to making sure his team was well compensated at liquidity).

This is one of the reasons I don't love Paul Graham's hacker startup thesis, about working very hard for 5-10 years so you can take it easy for the rest of your life. There are a lot of problems with that idea, but one of them is that it generates a lot of loss aversion instinct for founders.

Facebook and Google both created literally thousands of millionaires, IIRC. Bad news, though: power law distributions of startup returns have some really toothy consequences for employees as well as for investors.

There exist some less famous answers I could give here but they would be socially embarrassing to friends/colleagues. Let's put it this way: IPOs are public, right? Each of them allocates 10%ish of the market cap to employees. If you guessed employees 1 to 100 split half of that you wouldn't be insanely off base. If 5% of market cap is $100 million...

Another thing you could do, if you're interested, is look up the Angels participating in an early round in a recent startup and check out their LinkedIn profiles. Most have an obvious tuple of (Company, Start Date) which itself explains accredited investor status.

This is a side effect of companies filling coffers via investors instead of via customers. If you're part of a high growth company with reasonable earnings, that sales multiple means you'll likely get a taste of the action. If you're in a high growth VC funded company with no revenue, then that multiple goes to the VC and maybe one or two people they might like to work with again.

You can restate this via all sorts of dilution and complex shareholder classes and endless paperwork and HN blogposts, but that's what it boils down to.

Chances are you're in a no-growth or modest-growth company so none of this matters and you should read a basic business book from the 1960s instead, serve your customers well, and charge a reasonable fee for the goods and services you deliver.