[Sohcahtoa82]

My biggest problem is that I dislike my job but it has potential to pay off big and allow me to retire (Or at least, semi-retire) in ~5 years off the stock options.

Retiring at 45 seems pretty appealing. I could finally catch up on my massive library of games I've been wanting to play, not to mention reducing my alarm clock usage to likely 10 times a year, rather than 5 days a week.

[p1esk]

it has potential to pay off big

I hope you’re not talking about a startup lottery

[Sohcahtoa82]

I am.

And I do recognize that it's just that - a lottery. We could fail and I end up unemployed with nothing. Or a funding round could dilute my stock options to worthlessness.

[p1esk]

It does not make any sense to suffer through 5+ years of unsatisfying job with (relatively) low pay, just to have a very small (<5%) chance to make enough money to retire. This chance is actually much smaller if you own less than 5% of the company (i.e. not a founder or C-level).

Source: worked for 7 startups in the last 20 years.

[Sohcahtoa82]

My base salary is actually above market by a decent margin.

Total compensation is a little lower than market if you assume the options are worthless. But if we get to a $5B valuation, the value of my options would put me to a significantly over-market compensation, though not enough to retire. If we reached $30B, then that would give me ~$6M assuming no dilution.

[p1esk]

What is the current valuation, or how much money have you raised, and how many rounds?

[Sohcahtoa82]

Our current valuation is not public. I can't disclose it.

But we've had 4 rounds of funding totaling $131M.

[tw98521358]

Or just regular old recession