Paying lawyers? It isn't like he has the power to shut them down. He is just giving the aggrieved a voice to have their time in court.
If the courts and society deem releasing sex tapes, constant slander and non-stop privacy violations are OK, then nothing will come of it.
But their methods certainly deserve to be put on trial. It isn't like he is suing the NY Times, it is Gawker specifically because of how toxic their journalism is.
And Thiel is 1 of the leading libertarians in the country that rejects many of the dogmas on the left, of course outing him is going to have some political warfare comeuppance to it.