“Bob” is a GMail user and uses the Google search engine. Google knows:

1. What Bob is searching on via a cookie on his computer. (if he types a url that doesn’t exist into the Google toolbar, that URL gets sent to Google).
2. What domain names he visits (Search + Analytics).
3. Who owns those domains (Google is an ICANN-accredited registrar).
4. What pages he clicks on (Analytics) .
5. What ads he clicks on (Adsense).
6. The content of emails he receives (unlimited data retention from Gmail).
7. Who is sending Bob emails (via “content extraction”).

Of course, in the recent email from Google describing benchmarking, Google said they want to provide “you with transparency, control, and new services”.  I think this was a typo made by Google, they should replace the word “you” with the word “Google”.