Never worked at a tech start up so take with grain of salt. I have been in recruiting for a few years so seen how it affects candidates monetarily. I'm answerin

Never worked at a tech start up so take with grain of salt. I have been in recruiting for a few years so seen how it affects candidates monetarily. I'm answering this question based on benefit = money. Depends on the company. If the company is unstable (no profit or losing money as is a lot of tech) it's never certain. If they are already showing profit or a way to profitability I would do a year or so before you think they'll IPO. This gives you likely upside on the stock, you'll vest a portion of your stock and be able to sell after the employee lockup period. This isn't a guarantee, look at Zynga's IPO and flop right after. My opinion maximizes on safety before an IPO exit. You likely don't want to play acquisition unless you know you'll get a retention offer from the new company (you run the key feature/product for the acquired company).