The main rule in contextual advertising is simple:
Ensure that your contextual advertising is done on right context.
Sounds redundant but it isn´t. Let me show an example of advertising aimed at particular time-of-the-day:
Hmm, it is 11AM on Monday morning. I have barely woken up. I don´t necessarily want to be up, but generally if you work at the office you don´t have choice. Or are you referring to my stand-up desk?
I don´t even know what I will do tomorrow, not to mention knowing will I oversleep or not. I was planning to go sleep early, but do you know more about my Netflix addiction?
I have already eaten breakfast and I am already dreaming about my lunch. Would you have any lunch deals? Or will you be targeting those ads at my dinner time?
This ad was definitely at the right place because I noticed it. Probably in the media report it will also be really effective because I replayed it zillion times to get proper screenshots. So probably we will get more of this kind of lazy targeting in the future.
In many ways the opportunities in digital media are really interesting right now: ability to target people at the right place, right time and to retarget based on their behavior is fascinating. Unfortunately media and the media agencies are too often just too damn lazy to really utilize these opportunities, or just plain creepy.
This experience was not without silver lining, it reminded me to listen this awesome song by Dr. John to cheer up my Monday:
Stand-Up Strategy 