For software, the tooling and the abstractions are so powerful that you can make incredible software without knowing what's really happening under the surface. Imagine an "abstraction ladder", with each level building on the previous level. Frequently in software development, you only need to understand a single level n, and maybe a little of n-1, to make great software. So the advice of "just jump in" is often great advice because you're jumping into a "shallow pool".
(P.S, I love the work you're doing with MathAcademy, though I wish there was discounted price for "casual" learners that only have an hour or two a month)