Today’s media executives plotting to charge for their content would do well to hear how Larry Kramer beat Jim Cramer’s TheStreet.com by resisting pressure to put most content behind a pay wall while not relying entirely on advertising. To the average consumer, MarketWatch.com seemed to have come out of nowhere during the late 1990s to quickly establish itself as one of the leading sources of online financial information. For MarketWatch founder Larry Kramer, it represented the last chapter of his 15 year journey as a first-time entrepreneur. Larry started his career as a journalist, going from reporter to the top editor of the San Francisco Examiner in just 10 years with stops at the Washington Post and Trenton Times along the way. Larry founded DataSport Inc. (the company that would eventually morph into MarketWatch though a series of mergers and partnerships) with $500,000 from friends and family. He almost ran out of money early on. After a wild ride on the public market, Larry sold MarketWatch to Dow Jones for over $500 million in 2004 and went on to become the president of CBS Digital Media until 2006. Hear how Larry lived though two different careers and what he’s planning next.