I feel a lot of the folks here are focusing on the wrong parts here. The $200M loss was a cheap way of getting user attention, but hey it worked! 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.
> The $200M loss was a cheap way of getting user attention, but hey it worked! 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.