The biggest take-away for me was that, at the least, he acknowledged that it's irresponsible to gamble his family's well-being on a long-shot startup idea. Tech culture right now prizes irresponsibility. The youth fetish is one aspect of it, but more generally, it's founded on unrealistic (irresponsible) promises and mostly bad decisions (drop out of school to work for a startup! move to the most expensive city in th…
lastly, is it because you are 'smart as fuck', that why you are so jaded now because the value you brought to the startup would have taken you much further in a traditional job, as opposed to an average person who has much more to gain from a startup being successful?