Its been a miserable failure. I've come to the conclusion that programming is hard, and I've been incredibly privileged by having a computer since I was 2 (C64!) and I have so much built in knowledge that I don't even realize I have.
Also, this stuff just isn't fun for a lot of people. Sometimes its downright painful for them and they just can't push themselves through the tough parts motivation-wise. I can imagine it being a bit like doing Crossfit (or any exercise). I know I'd be a lot healthier if I did it for a year. But the upfront expense, the pain, and being incredibly bad at it for the first few months just makes it so I don't even try- even though I know the benefits could be life changing.
I bought a copy of Agile Development on Rails and gave it to such a friend. He didn't know how to pull up a command prompt, and I realized that he didn't know what a text editor was. Or that you'd run things from the terminal, and type them in the text editor. I helped him get past that, but he never focused in on it and never saw the beautiful and amazing parts of it.
Another friend got a little farther. But I soon realized how much 'background' knowledge he was missing. I pointed him toward some free online CS courses, which helped. But life got in the way and it just wasn't the #1 thing for him, so he got distracted and quit when he moved to a new (small) city.
Another friend wanted help getting started. He was motivated, but we hit a major problem. He's a student with an older iBook. We had huge issues setting up Ruby due to various environmental problems. I didn't have the time to really redo his entire system, but I wasn't able to get Ruby installed easily since he was on 10.3 or something ancient.
Just telling people that there are boatloads of money to be had, and that there are tons of resources out there doesn't always work. They really have to love it to get through that first painful year or so.
Now perhaps having more jobs (these knowledge factories) that will give people an environment to work in, the tools, the training, etc... might help. But otherwise, I've just seen that I have personally been a complete and utter failure at helping friends get into programming. I'm thankful that I have a background that makes it easy for me to do and learn, but many just don't have that background and I don't know how to help them get past that.