How remote the chances are of making money from a startup depend on the person. The probability ranges from a snowball's chance in hell to maybe 90% in the case of someone like Bill Gates. (He was not necessarily going to be the richest man of all, but the likelihood of him not even making enough to be independently wealthy was pretty small.) I can't tell what the chances would be in your case without meeting you, but certainly there are some people for whom starting a startup is a reasonable gamble.
It definitely wouldn't take decades to find out. When startups fail they usually fail in less than 2 years.
It's not impossible, it's just adding another degree of difficulty. I did exactly this in the second half of my twenties. Working on my projects, doing consulting when I had to to support myself and my family. I believe the impetus that drives "family men" to seek shelter in a "normal" job can also drive you to be relentless in making your startup work. More skin in the game.
Also, team comes into play here. Personally. I know that if I wouldn't have had such a wonderful and supporting partner at home, the startup issue would have been a non-starter.
Team first =)
Being free and being broke is what I think his direct route is. You can say that the pan handlers have more or less freedom than a business owner, depends on how you define the words.
In many ways intellectual freedom can only be found once material mastery has been achieved. There are a few famous examples from history that say otherwise, like Diogenes, but I doubt you're at his level. I also doubt you really believe in what you're saying, otherwise you would go straight to "abandoning" instead of posting on Hacker News.
I would argue that there is a threshold for this material mastery. I don't think is necessary for it to be exorbitantly rich. I can look at researchers who enjoy their work, and are working on problems interesting to them. They usually don't have a big monetary profit. Just a thought
