Fail Week: When Kevin Ryan Held 7 Ugly Layoff Rounds — And Lost ‘Total Credibility’ As CEO

As the Discovery Channel’s Shark Week celebrates the ferocious creatures that inhabit the ocean, TechCrunch TV is holding a week-long homage to the dangers swimming under the surface in our own industry: Fail Week, which is a five day long video series that shines some light on the dark days that even the most successful entrepreneurs go through. We in the tech press don’t talk nearly as much about failures as successes, and this is a small step toward changing that.

Today’s Fail Week story features Kevin Ryan, who has one of the most star-studded track records in the tech industry, having been the 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, among other things.

In the video above, 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. “It was ugly,” he said.

Hear about how that time felt, what kept him going through the dark days, and what lessons he’s learned.