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Today's Fail Week story features Kevin Ryan, president and CEO of DoubleClick from 1996 up through the time of its $1.1 billion sale to Hellman and Friedman in 2005 (a couple years before its $3.1 billion sale to Google) and the founder of luxury flash sale pioneer Gilt Groupe. Ryan talks about the lowest time in his career, when he held a total of seven painful rounds of layoffs while shepherding DoubleClick through the dot-com bust. Having to show so many hard-working employees the door meant "losing total credibility" as a leader.
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