Prospective acquirers will often pursue potential targets simultaneously and, if they go silent on you, this may have little or nothing to do with whether you followed up diligently or not. In my experience, when an acquiring company wants to move, they know how to do so quickly, at least to engage in sufficient due diligence to see whether they might want to do the deal. Thus, when you do get in a situation where you are getting slow or evasive responses after an initial expression of interest, or where things go silent after an initial set of exchanges, I am not sure there is much you can practically do about it unless you have options to sell to others and use this as a lever to speed the process. You can be as aggressive as you like in such cases but, if the acquirer is simply trying to keep options open, you won't be able to force things absent a credible threat of going elsewhere.
That said, this one may have simply fallen through the cracks owing to the early failures to follow up more aggressively. Only the Google people can know for sure.
There's probably a way to phrase that without implying that HN is a "gentleman's-only" club. (With every romantic interest we entertain?) Or that the learning is limited to the 15-30 age range -- I know people my father's age who are learning some very painful lessons in this department...
Regardless, the point has merit, and in either context you can't win (or even gain the experience you need to win) unless you're in the game. :)
It does look like apart from building a great product in an exciting space Jay may not have done a bunch of things required for making an acquisition happen. Things like being on the radar of a clearly articulated internal champion in the acquiring company, getting multiple outside sources to recommend the acquisition, getting all the stakeholders on board and committed, getting personal and professional growth arrows of stakeholders aligned, getting a stalking horse to create competition for the acquiring company, etc
That said, this one may have simply fallen through the cracks owing to the early failures to follow up more aggressively. Only the Google people can know for sure.