“Libertarians” who are trying to use politics to achieve their goals I would argue have a massive contradiction in their heads, which is why videos like this become a great agony to watch (about 5 minutes of pain will prove my point):

How about this approach to discussion:

“People love social security and medicare, and I respect that. I think it’s good that people engage in the program to experience what it’s like to live with a government funded system. I might be wrong, but I do see a financial problem down the road. If I’m right, there will be huge inflation in the currency, which means the old people will experience a significant drop in the standard of living, and might have to work until they drop. If I’m wrong, then old people will have a good time and can play golf in their retirement. I think financial problems will increase in significance between now and 2030.”

See what’s going on here? Instead of making it a battle about “I’m stupid”, “I’m smart”, “you’re wrong”, “you’re right”, you’re just making a prediction. You don’t pass any judgement on whether it’s good or bad, you let people make their own conclusions. And make room for being wrong, then it’s much less offensive. Make use of the tools of freedom: reason, humor, experimentation, science… you know all these.

I’ve made more than my fair share of mistakes, so I’m not claiming that I haven’t tried using discussion and political means to achieve what I want. But if you listen to this libertarian, he wants to dismantle the most popular government program in the US; social security.
Imagine you’re a woman in her 50’s. You’ve been working all your life, and your husband is dead. You haven’t prioritized studying politics, all you have taken the time to do is catch some evening news on mainstream media. Then up comes this libertarian guy and says he wants to shut down your pension plan. How is that going to make you feel about libertarians?

Libertarians seem to often forget very important parts of their own philosophy. Freedom means freedom to make your own mistakes, with judgement from reality, not from libertarians and other humans. Sure, people who have studied finance might know that social security is a ponzi scheme that’s been going on for 80 years, but many people think it’s a legit program. Why fight them? Let them have the freedom to find out for themselves.
How about letting them have freedom from libertarians? What if libertarians are not wanted in the US? Why should you force yourself into that society?
What I have done for myself has made my life so much better; I packed my bag and I’m watching the progress in different countries from afar, at a safe distance. Maybe you should try that too?

The US was NOT started as an anarcho-capitalist society, not even close. It’s an experiment in having a government limited by a constitution. Why not just leave the experimenters alone? If you want a ancap society like I do, let us start our own. Why are you messing with other people’s experiment when you can make your own? And why not learn about seasteading?

I’ll make my own predictions:
My hypothesis is that libertarians are never going to win using the political system, by voting or by trying to change government. I think there’s a contradiction in believing in freedom and using politics at the same time, and it cannot work.

If I’m wrong, Rand Paul is going to win, he’ll not be corrupted once in power, he’ll make the US a bastion of freedom, he’ll change the course of the US, he’ll fix the budget and pay down the debt, people will not be annoyed when the biggest depression in the history gets underway and libertarians won’t have to flee the country to save their lives like the Jews had to flee Weimar/Germany.

Feel free to prove me wrong, I’ll be watching your explosive chemistry project from a safe distance; from a country far, far away.
I’ll leave you free to fail.