GMail Deja Vu
Back in 1999, we thought we should try incubating a company. It was all the rage at the time. I've since sworn it off and will rely on entrepreneurs to do what they do best and i'll stick to the funding/mentoring part of the VC equation.
But it was a heady time. A guy named David Kent came to see me with an idea that he wanted to start a business around. He couldn't be the entrepreneur because he was a practicing surgeon. David had a neat idea. He wanted to provide a free-email service for consumers that ran ads in the emails based on the content of the message. We bought into it. And incubated a company called FaveMail.
Needless to say, nobody has heard of FaveMail. Our execution stunk. The idea was years ahead of its time. And so we took the failed investment, used what was left of the business to buy a troubled email service provider called Bigfoot Interactive, brought in an experienced management team, and built a very nice company that is one of the leading email service providers. So there's a happy ending to this story.
The lesson i take away from the whole thing is great ideas don't make great investments - great entrepreneurs do.