Bebo: 850 million dollars to 0 million dollars in less than two years. There's betting the farm and being wrong, and then there's just burning a giant pile of one billion dollars in a field.
Pets.com: a mere 300 million doggy dollars down the litter box.
The sock puppet toy was the last item available for order on the Pets.com site at the time of its shutdown in 2000.
Broadcast.com: pictures, videos, words and not even numbers are suited to take this one on. It seems like a practical joke that went horribly wrong, a stunt that backfired, a Springtime for Hitler attempt that never materialized, a drunk dial in the middle of the night that somehow cost 5.7 billion dollars. I'm not sure 5.7 trillion dollars would have seemed any crazier for a deal like this.
The glaring exception is Yahoo's famous purchase of Mark Cuban's Broadcast.com in 1999, which paid nearly $10,000 for each of their 520,000 monthly active users, ten times any other startup. (Broadcast.com skewed the chart so much, I had to leave it off.)
The word you were looking for there is infamous, not famous.
When Mike and I started Instagram nearly two years ago, we set out to change and improve the way the world communicates and shares. We’ve had an amazing time watching Instagram grow into a vibrant community of people from all around the globe. Today, we couldn’t be happier to announce that Instagram has agreed to be acquired by Facebook.
You had me at "change the world."
I guess I won’t have to worry about the kids education any more.
Who turns down a billion dollars? What does the second million will really mean after the first? The 400th after the first 399? I went to lunch recently and was handed back the equivalent of a penny which I intentionally tried to overpay. If you've put yourself in a position where there's no way to know what your value is then you probably made a wrong turn some place very long ago.