It sounds like your startup was unfortunately an outlier with respect to the level of dilution experienced. 99% dilution over 6 rounds is far from 'usual reality'. More common is 20% dilution per round.

It was also an outlier, in the sense that it had a valuable exit.

You've only got one lifetime to pull the equity slot machine, hoping that the reels come up all sixes.

6 rounds of 20% dilution will get you to 74% total dilution from the initial grant.

Which in this case nets you >$1M [0] vs the 80k quoted above. This also assumes no retention grants over 6 rounds.

  [0]: 0.02*0.8^6*$200,000,000 = $1,048,576

Something I am always curious about is, was your company / CEO open and honest with you about how your shares were doing? If you worked somewhere for 5 years, it could be easy to think you're safe but meanwhile the CEO is diluting your equity to fractions of what it originally was? Don't they have to report that to employees?

In my experience both as that employee, and sometimes the executive - they're not. There are frequently legal, secrecy, or other corporate reasons for the lack of disclosure. It kinda sucks - but it's understandable.

To be fair, I'm someone who has never chosen shares over base salary. The equity slot machine is fine, but I (firmly) believe that over the long haul, the only thing that matters is index investing. Benjamin Graham is always right.

I appreciate shares - I work either way. They're just not my motivation. If that works for others - great.

Every round of financing, the shares got diluted but the total value of shares should increase. Otherwise, the company is not doing well and taking a down turn.