Depends on the type of shares you are getting and at what price your are buying them vs their current and anticipated worth. In general, most of these deals will hand out B shares to new associates valued less than the original A shares given to founding partners but still worth quite a bit. At the time of a second sale you have the option to cash out a portion or keep them as they increase in value and cash out at a later time. As with any investment, there is risk either way. You should be able to negotiate some if not all of these shares be given as part of signing the contract. You should also have the option to buy more shares if you wish. By most accounts, though not a hard and fast rule, most second sales can yield a 2-4X return on investment. Can be more of course, or turn to zero. Odds are in your favor if this is a solid PE firm that you will be able to gain a profit on the shares. Have to do some due diligence.