The core of what he was trying to convey was the sooner you get to understand real user / customer problems the better off you'll be in life as an entrepreneur.
He stayed away from this in his early days as he opted for stability and that he seems to regret.
Many Hacker News submissions get flagged to death for such tactics alone.
In this case the substantive aspect is at least partly that Garry has had a close relationship with HN over the years. And vice versa.
It "worked" in that that it got people's attention but distracted from the post's main message.
And sometimes you're better off learning this at an actual company that ships products to millions of people than grinding away at a startup that won't exist in a year or two, with options that are worth nothing and a salary much lower than you'd get at a more established company. And there's a good chance the startup never ends up shipping anything of value. Startup vs Big Co isn't always a no brainer, lots of factors to consider.