Would you exercise your options in this situation?

Hi there, I’ve been working at a startup for the past 3 years and we’ve grown rapidly from a team of less than 10 to more than 230 today.

I’ve been thinking about whether I should exercise my stock options. I’ve vested 25k/35k total so far, but haven’t exercised any. I have the ability to exercise up to 25k. The current exercise price is $0.01 which means it would cost $250 to exercise.

The company shared their 5 year strategy today, which mentioned preparing for IPO in 2025 with the intent of an IPO in 2026.

I know a few managers have exercised all their options, and are only sticking around with the intent of cashing out their stocks when we are acquired, IPO, etc.

Would you exercise in this case?

If exercised today, would I pay taxes every year until IPO?

Is there any way to predict how much taxes THIS may cost?

If you’ve exercised your options, what was your experiences? Why did you exercise?

If you exercise and quit, and the company later IPO’s, do you still benefit?