This post is about Jason Calacanis's appearance on TWIT 105: The Day the Music Died.
Listen about 31.5 minutes into TWIT where he talks about paying $75,000 for a domain name. And then says that he wouldn't sell it unless he was getting $7.5 million.
First off, it comes out as conceited. He prefaces it by saying "you can have her on your show every week" about a new employee of his. I would have no interest in working with someone who thought like that, but even less so someone who talks like that.
Second, is this 1999? Did you not notice little sites like Digg, Flickr, del.icio.us? What would possess you to invest in a company where the leadership is eager to spend that kind of money? It reminds me very much of the parties and penthouse office spaces that were a great way to fritter away money in the last tech boom.
You're only interested in 100X return on investment? It's going to be hard to build a fundamentally sound company when you're only interested in that kind of return. Unless you're only putting in $1,000, and clearly that's not you.