> paralysis by analysis (of which uber-complicated and rigid typing is a sort).
How "paralysis by analysis" has anything to do with typing? And how is typing uber-complicated to begin with? This is ultra basic logic... And why exactly you you think dynamic langages are exempt of typing?
How does all of that has anything to do with a competitor shipping "buggy RoR-based systems a few months earlier"? You can do all kind of shit even in more statically checked langages if you really don't care about quality, and ship buggy products sooner too.
How is a system that prove that some aspects of your program is free of some class of defect should be considered "training wheels"? Do you also consider that compiler warnings are a bad thing for time to market, and so should be disabled? How can you gain any time from not using an automatic checker? Your brain is faster than a microprocessor to do repetitive tasks? This makes no sense. You do not abstain to put on your seat-belt just because you thing you know how to drive, nor do you disable all safety feature of whatever equipment just because you kind of think, without even the beginning of a reasoning to backup that, that you are going to do things "faster". And while the logic telling that what you are going to do is more dangerous is immediate and irrefutable. And while the studies about costs of discovery of bugs depending on the phase of dev clear.
Arguably there are some meta-programming aspects of Ruby which can let you program faster than with a language without equivalent features. But in no way we can deduce from this that "Advanced typing/static analysis" are "training wheels". This is one the the thing that is just so wrong in our industry that I sometimes just don't really know what to answer. I mean I could as well see a claim that the earth is flat and try to convince the crazy claimer that this is not the case, but I have the feeling that people making such claims are not sensible to logic to begin with.