I disagree that you need a solid founding in information theory. Almost all that I've seen about IT in ML is minimizing the KL divergence, which can be learned by browsing the wiki page.
KL(P,Q) = E_P[Q_length(X)] - E_P[P_length(X)]
stealing
ha ha ha!
If your salary is going to depend on how many models you pushed out and not how well they continued to perform, many will optimize over the number of models pushed out.
A major source of problem (and sometimes a gift) is that you cannot prove a empirical statistical claim true or false in finite time. There is always this non-zero probability that the weirdest thing would happen. It could be just sheer bad luck that the model did so poorly in this cycle.
This is like saying, "You don't need to really know calculus, just integrals."