The cantankerous founder of American Lawyer magazine, CourtTV, Brill's Content, and Clear, Brill's latest venture is Journalism Online, an online payment system for news websites, which he sold in 2012.

The son of a Far Rockaway liquor store owner, Brill skipped the bar exam and took a job in journalism instead, starting his career in the early '70s writing for Clay Felker at New York. Combining his legal background with his interest in journalism, he later approached Esquire's owners about financing a magazine dedicated to the legal profession, discussions that led to American Lawyer. The title caught on quickly as Brill shook up the prim world of high-powered litigators with gossipy features and the scoop on salaries and firm profits. Brill expanded the company during the 1980s before taking his act to TV in 1991, when he raised capital from Time Warner, NBC, and Cablevision to launch CourtTV. The timing worked out nicely: Soon after the network's debut, the nation was consumed by legal coverage of the William Kennedy Smith rape trial and the OJ Simpson murder case, both of which helped turn CourtTV into a household name. In 1997, Brill sold his stake in CourtTV and American Lawyer to Time Warner for a reported $30-40 million.

After his next venture, the shortlived magazine Brill's Content, the serial entrepreneur launched Clear a service that offered biometric I.D. cards so travelers could bypass airport security and pass through a special (and much quicker) security line. Although it managed to rack up 65,000 or so members and a dozen or so participating airports, Brill mysteriously stepped down as the company's CEO in February 2009 and shut down four months later. He's since started Journalism Online, an online payment system for news sites and newspaper publishers, but sold his stake in the company 2012.

The cigar-chomping, suspenders-wearing Brill has long had a reputation as a ferocious editor and brutal boss. Among journalists who used to work for him, he's best known for the vicious notes he used to jot down in the margins of reporters' copy, including "Is English your first language?" and "You should be fired." Brill should not be confused with Steve "Wildman" Brill, author of The Wild Vegetarian Cookbook and the leader of popular wild-food-foraging tours in New York City parks. [Image via Getty]