It all depends on what the investment was in. If the company you invested in is doing very well, you always want to convert that investment into equity if you feel the company is going places. If you feel that it is going bad and you have an option to be a) bought out at your original investment or even at a small loss, I would do it. b) If you are offered a ROI then definitely take it and run (if the company you feel is not going to make it)