Ask HN: Recommend book(s) about monetizing a web site/application?

I have a web application in the early development stage. I have a (humble but ambitious) plan to achieve reasonable amounts of traffic compared to the competitor sites or the sites with similar functionalities.

Let's assume (fast-forward when version 1.0 of the site is online) that the amount of visitors of the site are according to the plan. Since the functionality offered by the site is completely free, how does one monetize the traffic to the site? And more specifically, are there any books that discuss the general methods/mechanisms for making money out of "popular" sites?

I've researched for books about monetizing but I've found mostly books about making a product/site popular (something that I humbly assume that is already a fact).

Thank you for your time.

If it's a web site/blog that provides content to a specific niche, I'd recommend listening to some of what Gary Vaynerchuck (search on Youtube) has to say. More than anything, he just encourages you to market yourself, cold call, and really be personal with your visitors.

If you're building a web application, there's Don't Just Roll the Dice (http://businessofsoftware.org/ebook.aspx), which provides an excellent guide to software pricing. Unless you're serving a specific niche that advertisers will like, add a price to your application. Actually, even if you're serving a specific niche, add a price. If you're looking to sell eyeballs, you'll need a ton of eyeballs before you'll even recover your costs.

Your question was a bit vague, so I can't really give a specific answer. But assuming you are able to get hundreds of thousands of people flooding your site daily, you can slap some ads on it at any time.