As someone who learned on python (many years ago), I think the balance of being allowed to shoot myself in the foot, while only having to learn complexity when complex concepts came up, was a good combination rather than a bad one. Trying to learn C++ and Java before, having to type everything was an impedement. On python, you find out that types still matter when you try to add a string to an integer, for example. The moment the type matters to you is when you need to dig into those details. I'm not sure I would have the career I do if it hadn't been around to be the one language that fit my 16-year old brain.
You don't have to compete with C++. If switching the interpreter allows you to save 20% server costs at ~0 development cost that's a no-brainer. Rewriting your stuff in C++ might allow you to save 95% of your server costs, but development cost is a lot higher.
My gut feeling is that Python is just not safe or static enough to ever be worth trying to compete with (say) C++ with. Python sure is easy but I think the asymptotic cost of using it for a big project (in my hands at least) is just not worth it.
I like Python's syntax quite a bit but I feel bad watching people learn to program using it - partly because it's an oddly low-level language (It's closer to being C than Haskell) and there's no compiler to stop you shooting yourself in the foot (If I write something fundamentally unsound I want to know about it now not when the process has been running all day)