Nate, man — these are valuable lessons. Some of them I’ve learned the hard way, even as a low level manager.
Also, my other tip is — don’t be afraid to reinvent the wheel. There are many products out there, and surely a lot of designs might just be improvement on something else. Remember, the wheel didn’t start off as a rubber tire on aluminum or steel rims — It probably started off as a round rock or log on a shaft, and took several stages to get where it is now. I see a lot of people shy away from ideas because there is something that is already somewhat like that. Instead of making them feel stupid for having an idea that’s already done, I try to help them compare their way to the other product’s way, and help them to think along the lines of “how could we make it better” — if any of that makes sense