[wonderthrowaway]

Bah...if you had skills that could guarantee you could retire at 55, and equity that might let you retire at 30 (best case) or 45 (worst case), why not take the chance if you believe in your work, your company and your mission?

If you know what your company is making is bullshit, then by all means bail as soon as you can. If it is important work, then the risk is far less.

[loumf]

2.5 million in a well managed (even conservative) portfolio is practically guaranteed to be enough for retirement in 10 years with passive oversight. You would be adding to it with savings as well.

I guess if you're hell bent on being all in, I'd recommend some kind of insurance in the form of a Put option that you hope expires worthless (assuming this is a public company).