One of the biggest challenges for libertarians is convincing others of their viewpoints. It is especially hard persuading family members, because they already know your flaws and do not necessarily think you are any smarter when it comes to politics. Regardless of whether it is a family member, a friend, a co-worker, or just someone you happened to sit next to on a plane, it can be quite difficult to get someone to be open-minded about libertarianism. There are a lot of people stuck in the Republican/ Democrat paradigm. It seems to make people not think clearly.
One approach I have found that actually opens up some people's minds is to talk about investing. Every individual is different, so no one approach will work the same. But I've found that talking about investments gets some people to think differently.
I am a big advocate of the permanent portfolio, as discussed in Harry Browne's book Fail-Safe Investing. If someone asks me for investment advice, I often refer them to the permanent portfolio, or at least the mutual fund (PRPFX). If someone looks at the performance of PRPFX, they can see that it has been a good and consistent performer. It is an opportunity to explain to people why diversification is so important. You can explain that it doesn't just mean diversifying in different stocks. It also means diversifying so that you are hedged against a weak dollar and high price inflation.
It is fairly easy to explain to someone that the overall general price level goes up over time because money is created out of thin air by the Federal Reserve. It is easy to explain that gold and silver (but gold in particular) are good hedges against inflation. Therefore, it makes sense to have them as part of a portfolio.
It is important to remember that it is rare that someone is converted into a libertarian based on one conversation. Even if you did supposedly convert someone in one conversation, does the person really understand libertarianism? Hardcore libertarians understand that it is an ongoing learning process. They also understand that you probably would not have a full grasp on the subject after one conversation. It takes most people many books and articles and YouTube videos, etc. before they are converted and have a good understanding.
So, most of the time, the best you can hope for is to move a person one step closer to your ideology. But the first step may just be a matter of opening up the person's mind.
There are a lot of people who are frustrated with their own government and they are also frustrated with investing. The stock market has been a roller coaster ride and it has barely provided any return in the last 12 years (if you bought and held), while most prices have continued to go up. People are looking for explanations, other than the same old Keynesian lines. They are also looking for sound investment strategies.
So why not help a friend and let him know about the permanent portfolio? Why not tell your friend about the importance of gold? You are appealing to their self interest. You are helping them out. And you may be opening up their mind to more libertarian ideas.
The one thing I would caution against is being too aggressive. It is important to talk to people when they are ready. It is probably not a good idea to offer unsolicited advice. People around you can know that you are interested in investments and interested in libertarianism. It doesn't mean you have to sell them. Some people become ready in their own time and will come to you for advice. Some people will never be ready.
For those people who are looking for answers, it is important for libertarians to be there for them. I have found that a good way to open minds is by talking about investments and avoiding the subject of politics, at least directly. It may work for you too.