HI:"So why aren't more smart Canadian kids with great educations growing up to become entrepreneurs "
They have not been taught how to fail.
Its ok to fail but get up, dust yourself off, and go and win.
The educational system is like a house league sports situation where everyone gets a medal(diploma).
I taught at a GTA college in the STEM areas.
The students would design a prototype and I would judge its viability(that's what I did before teaching).
I would be positive before pointing out the deficiencies but in doing so initiated a fire storm because criticism was viewed as detrimental. 
Our middle-class is made up of public servants and workers in the natural resource areas.
If we don't strengthen our future generations intellectually (at all levels) we will be doomed when oil/NG,lumber, minerals become less valuable in tomorrows world.