Except saying you are fat and ugly when you're actually Brad Pitt doesn't really do anything. Getting sued for BS causes undue stress, time, money, etc.
Kayak could copy this UX in a day if they wanted. I don't think even $15mm (even if it was all spent on marketing) is going to see much of an uptick for hipmunk. I bet priceline, kayak, etc. spend close to that a month.
I swear he is the world's luckiest person. Implodes Digg, somehow gets $ out and does angel investing. Gets his next pos start-up bought out for an ungodly sum for doing nothing and not making a cent. And now a VC. This guy should play the lottery.
I'm so sick of these DDG stories. The truth is no one uses them, 99.9999% of people outside SV have never heard of them and currently there is no reason to switch to them.
Offline ads for direct response are easily measurable with tracking numbers. Branding ads - well - I have no clue how they track any of that - but then again how do you track a CPM media buy just designed to increase brand awareness online... (note: I come from the DM world).
I've never used turntable, thought it was dumb, but did it ever make $? Did they ever even have a plan to make $? Seemed like a giant fad to me and can't believe they raised $ successfully - especially with having to deal with music licensing.
Only way I can see them fitting into $100bn valuation is if they come out with an AdSense competitor that not only is contextual, but if you are signed into FB also based on your likes/social graph.