But $800M in USD is worth only about $1.2B today. Keeping the money invested in Apple is convenient if you're already paid in stock, but beyond the lock-up period we have to keep in mind that it's just one of many things he could have done when accepting the money

Though I think it fair to speculate that if he had taken the deal he would likely have more money today, at the cost of less status

Yeah but who can say Steve Jobs bought their company so early on, the early Dropbox design was so Apple-esque.