So if you don't foresee being at the company for at least 5 year or foresee having the money to purchase the options you have accrued after the 1+ years then you are better off asking for cash. Companies of course don't like this because it costs them nothing if they pay part of your comp in options that you then leave on the table when you leave the company. This is calculated, the companies know this.
How many startups can you expect to work in your career where you stay for 5 years? Lets say you work for which would be 20 years of your career. How many of those 5 are going to actually IPO? The math suggests you leaving a lot of money on the table. If you take the comp in cash you can put that money to work for you in other ways.
Personally I've made way more from stock options than I have from wages. Google stock has appreciated 7x since I joined in 2009, so you can do out the math for various fractions of equity compensation. And this was for a company where I valued that equity at zero, because it already had 20,000 employees, it was in the middle of the financial crisis, its stock was dropping like a rock, and 89% of employees were underwater in their stock options.
You could argue that if you take cash compensation, you could then invest that in public market stocks (like GOOG etc.), and there's a pretty good argument for diversification and not holding your net worth in your paycheck. OTOH, when it's your company stock, you also have an information advantage: for example, the press was very down on Google for most of 2009, thinking that they'd tapped out on growth and the web was basically over, and after the initial post-crisis bump it basically traded sideways until mid-2012. Having seen the energy there, the products under development, and the query growth rate numbers, I knew this wasn't true, but if you'd worked for cash in another company and then tried to invest in the public markets you would've had a very distorted picture of reality.
The employee got what they wanted (cash for their stock).
What infuriated me was that I had to do all the leg work and paper work and it was only when the money for the sale went into an escrow that the company rejected the offer. So they wasted a lot of people's time unfortunately - mine, the broker and the buyers time. The companies "preferred buyer" turned out to be some Hollywood big wig. And my guess is that they never had any intention of letting my proposed sale go through.
One curious thing I learned is that although this practice of selling options on the secondary markets by "worker bees" was strongly "discouraged" because it was seen as a sign of not believing in the company, it turns out the execs were all selling their options left and right and had been doing so for years.
ROFR isn't that bad. What is bad is some contracts have a call option on your stock at FMV price, even when you exercise.
This means that ISOs can probably be exercised tax free, but NSOs require you to pay taxes on the spread from strike to the fair market valuation.
If your strike price is low enough you may be able to save and afford to exercise the ISOs, the NSOs will probably be too expensive with the tax burden.
There's also a 10yr expiration on options anyway so it's possible that you could lose them even if you're waiting for an IPO while holding unexercised NSOs.
