Almost everything about this angers me. It's presumptuous, arrogant, intellectually lazy and fallacy driven. And worst, Alex not only thinks he's correct, but morally right! Absurd!
Lets start at the top.
1. "If selling subscriptions to a small web application to cover my mortgage and subsidize my hobbies is “freedom”, then I’ll happily risk incarceration." - All Alex is really saying is that he defines "freedom" a different way than x person. You can't really judge that. Perhaps be perplexed, maybe inquisitive, but don't judge. In this regard, to each their own. And please don't confuse what makes you happy with what makes someone else happy. Alex is saying that obligation makes him happy. Great! Go for it. Someone else is saying that taking care of their family and living a simple live makes them happy. Cool...
"Seek first to understand, then be understood".
2. "When I read statements like this, my secular humanist streak flares up. ... We should endeavor to improve the lives of as many people as possible in a lasting and significant way, making the most of our own skills in the process." - Uhm...wow? This is nearly a nonsensical statement, saved merely by the fact that I _think_ I know what he is trying to say. Several problems arise from this statement, the first being that he brings in Humanism. Humanism, meant to enlighten perspective, only clouds the statement with doubt. Secondly, "should" is a word that will always get you into trouble with regard to other people. "Should" implies "I know better than you" or "let me tell you why you are wrong" not "hmmm..interesting perspective but I've always been of the mind that " which is a conversation, not an attack.
Lastly, it is worth noting that the statement is cute in that it provides an ego boost for the person espousing it, the statement itself is nearly worthless alone. I suspect that the statement serves to boost ones ego more than it serves to guide ones life. It also smacks of a statement made by someone with very little life experience.
3. "Building a business around maximizing your individual happiness is not particularly useful or admirable. That is my position, and I’m well aware that it may be unpopular with some." - Equivocation. Alex is not using the "term" happiness to talk about this side of things, but that is what it is. He is striving to find meaning/happiness on his own terms in his own way: by going big and making an impact. Deriding someone for doing the same thing in a different way is, at best, silly, at worst, narcissistic.
I would like to leave with a story about a country doctor I knew. He worked for 40 years in the bush in Australia. He loved living there and it was where he grew up. He was able to make a good living working there and being the small town country doctor and generally found happiness doing it. He told me about when he did a rotation in the UK and was offered a job starting a new hospital. He would have been able to reach massively more people in one year than he could in his entire work life in the country, make tons more money and have a hugely beneficial impact. He turned it down and went back to Australia. His reasoning "someone other than me would have taken and done that job, but that same person was unlikely to help these people in this town."