Let's say it's ~2 million every 5 years. That might sound like a lot of money, but it's couch cushion level of expenditure for a large organization. YC easily extracts enough value to keep it running.

Like Wikipedia the vast majority of value is from free content. That trend continues across my browsing habits. I need to use an ad blocker because I frankly don't see a lot of them.

> HN does have ads, in the form of job posts for the YC companies.

I don't really agree with how you're defining portfolio company job links as ads.

AFAIK they do not charge portfolio companies for job links, so is it really an ad if they don't charge for it / it generates no revenue? The companies and tech mentioned in their descriptions are often just as interesting as other stories posted here. They are more in a gray area of content marketing or sponsored content than native advertising.

I suppose you could make an argument around it potentially increasing the value of their equity stake in a company by making that company more valuable. It seems a bit roundabout — I don't consider them ads any more so than a link to your blog post is an "ad" for your blog, or the comment posts in the monthly job threads are "ads".

Ryan didn’t make a leap; that’s the literal definition of the word. First definition I found: a notice or announcement in a public medium promoting a product, service, or event or publicizing a job vacancy.

Ryan’s link to his blog is 100% an ad, IMO. So are YC portfolio job postings.

Where do you drawn the line between when a link to a blog post is / isn't an ad? Is every submission that links to any site an ad? This seems like a gray area to me.

I don't think a job posting is ever not an ad. Whether pasting a link to one's blog is or isn't for me depends on the motivation.

If the motivation is "I might forget my blog address; better record it here", it's not an ad. If the motivation is, "I want people to be able to find out more about me/drive awareness of me or the blog," it's an ad.