Of course the first one because you took a risk and it ends up in a loss is not going to be much painful but regret of playing safe would always be with you once you realize that you could have made huge profit by taking that risk. In life most of us try to stay away from the risks and that's a realty, but we don't know that those risks might be helpful for us to make profits. However, despite knowing all those things we will try our best to avoid risks and stay safe, that's human nature. Only few lucky ones take risks and in end they make profit.