Worth pointing out that when people throw numbers around the stock value alone may sound impressive but that has to be compared against the opportunity cost that's usually associated with that route. Usually those options are handed out because the employee is accepting less cash or other compensation than another employer might pay then for similar work. Walking away with $750k after 5 years might sound fantastic, b…
I would argue there is value in the bubble payout itself. Even if you're good at saving & investing over the course of many years the assets and liquidity you have when you cash in your equity gives you a chance to take risks and meet potential business partners that you don't have as a salaryman who's good with his money.
For the sake of argument, let's say that you have two positions which will pay the same total cash compensation. BigCorp's job will pay it out in equal amounts over 5 years, whereas NewCo's job will pay out 10% each year for 4 years, and then 60% in year 5.
BigCorp will almost certainly result in a lower overall tax bill because much of each year's income is taxed at lower rates. NewCo will result in a lower tax bill for 4 years due to the lower income, but year 5 will probably put a large amount of compensation in the top marginal tax bracket.
Also, the BigCorp job will afford more opportunities for outside investing (stock market, real estate, whatever) and possibly more free time to do it in. So with BigCo you'll have had four years of compounding investment growth before NewCo really gets started on it.