We tackle the problem of the randomized generation of slowly synchronizing deterministic automata (DFAs) by generating random primitive sets of matrices. We show that when the randomized procedure is too simple the exponent of the generated sets is O(n log n) with high probability, thus the procedure fails to return DFAs with large reset threshold. We extend this result to random nondeterministic automata (NDFAs) by showing, in particular, that a uniformly sampled NDFA has both a 2-directing word and a 3-directing word of length O(n log n) with high probability. We then present a more involved randomized algorithm that manages to generate DFAs with large reset threshold and we finally leverage this finding for exhibiting new families of DFAs with reset threshold of order $ Ω(n^2/4) $.