Download the MP3. There are not many entrepreneurs who have spent their entire 10-year careers starting new ventures in online media, but Jason Calacanis just can’t help himself. Jason rode the dot com wave in New York by starting Silicon Alley Reporter. His publishing company Rising Tide Media grew to $12 million in sales. Unfortunately Jason also rode that wave down after the bubble burst. He ended up selling his first business to Dow Jones for a lot less money than he could have gotten before the crash. Undeterred, Jason started Weblogs, Inc. to make money by selling ads in blogs they pay people to write. In only 18 months he grew the business to a point at which AOL (TWX) bought it for a reported $25 million. Now he’s re-launched Netscape as a news website where users vote for what’s important. Jason’s caused a lot of controversy by paying top users of competitive sites such as Digg (whose CEO Jay Adelson was on our last show) to switch to use his service. Hear what’s been driving Jason’s entrepreneurial career.