1) For those of who did not start off your life as libertarians please say a little bit about your evolution.
Didn’t care till 9/11. Always hated the police state and public school system. Thought I was an anti-war/anti-bush liberal until I found out that I was actually an anti-war libertarian, thanks to Ron Paul. It wasn’t long before I was a property rights ancap. I have recently rejected the idea of rights, after reading an essay someone posted on here about the myth of the rule of law. My subjective morality is that whatever the market produces is whatever is just and most efficient, no matter what.
3) Would the collapse of society as we know it be necessary for libertarianism to get a full hearing?
I don’t know if that’s what it takes, but I do know that that is exactly what we WILL get when society DOES collapse. I’ll be full of I-told-you-so’s.
4) Is focusing on education and changing people’s minds an approach that is fast enough to keep enough with government growth?
I don’t think so, but it is definitely necessary. Getting the word out is what it’s all about.
5) Given the anti-intellectual nature of capitalism, i.e. they’re not paid as much as they’d like, how do you establish a broader base of support for libertarianism among academics given the ability of the state to use tax dollars to bribe them?
It already exists. You just used it to ask this question.
6) Are you optimistic or pessimistic about the future in terms of liberty?
I’m nervous about the short-term. Economic collapse seems imminent. I just hope the crash is bad enough to take the military-industrial complex/police state with it. If it doesn’t, I’m sure we can look forward to another war. I still can’t decide whether I should invest in stocks or in survivalist materials. 
Ultimately, though, I think “invisible” technology (internet, computation, IT, virtual reality, nanotechnology, encryption, etc) will drastically reduce the reach and magnitude of state power, worldwide. I actually agree with what most transhumanists have to say about our future technologically, so I’m definitely optimistic. Once it becomes clear that liberty is the only mode of society effective and efficient and sustainable enough to make these technologies a reality, most people will fall in line.