Wenda Harris Millard is convergence incarnate. She's currently the president of advertising consultant firm Media Link LLC, where she advises companies including MySpace on their advertising strategies. Before that, she was co-CEO and media president of Martha Stewart Living Omnimedia Inc. (NYSE:MSO), which she joined in 2007 after six years as chief sales officer at Yahoo! Inc. (NASDAQ:YHOO). But at 11 a.m. Monday, Jan. 10, 2000, when Steve Case and Gerald Levin held a jubilant press conference to announce America Online Inc.'s $164 billion bid for Time Warner Inc. (NYSE:TWX), Millard was at DoubleClick Inc. (NASDAQ:GOOG). There, she was a founding executive of the pioneering provider of Internet ad services that was ultimately acquired by Google Inc. (NASDAQ:GOOG) for $3.1 billion last year.

In this episode of our Decade of The Deal video series, Millard recalls feeling "extremely skeptical" of the natural fit AOL and Time Warner purported to be. Millard's skepticism drew not only from her new-media experience but also from such analogue-era stints as publisher of Family Circle and executive VP/group publisher of Adweek, Brandweek and Mediaweek. As Martha Stewart put it, Millard's "strong grasp and understanding of emerging platforms, combined with her in-depth knowledge of traditional publishing, make her the perfect choice." Stewart shared this insight on welcoming Millard to MSLO's executive ranks. But it also serves to introduce our commentator on a merger that many less astute than Millard considered, if only briefly, "the deal of the century."

As we celebrate The Deal's 10-year anniversary, we are featuring monthly video interviews with personalities from each year of our history. Click here to watch venture capitalist Fred Wilson's take on the dot-com boom in 1999. And click here to see how Ted Turner explains his bizarre comment that the AOL-Time Warner deal was better than sex. See the video below or download it on iTunes. - Richard Morgan