“if” is the key word there. Most companies don’t make it to IPO, and even if they do it would be a long wait. In the mean time your shares are illiquid, the paper they are written on is worth more. I’d prefer to take the cash alternative and put it into safe investments.

AND there could be any number of rounds of funding before a successful Exit.

It’s best to value the options at $0 and consider them a lottery ticket.

Oh yeah, it's a lotto ticket for sure. Even starting the job, I told my wife I was playing the startup lottery. She's fine with it since we have over 6 months of expenses in savings, and work in security, I won't have a hard time finding a new job if we went belly up.

The company is very transparent with the numbers, though. Every month we have an all-hands meeting and the CEO goes over numbers, including current ARR, burn rate, balance, and runway.

We received a $75M Series C in May, and in our last fiscal year we 4X'd our ARR. We're doing pretty well.

The main thing to remember is that typically early stage options for an engineer will make you a bundle iff everyone else gets paid (often first).

When things go badly, or even just not well, it doesn't matter what your plan was or how transparent everything is - the founders/board may be staring down a choice between folding the company up or decimating the equity of everyone currently holding it. It's a pretty easy decision usually. The good ones will take it on the nose with everyone else, the others ... well they aren't taking the same hit.