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Obsessing Over A Giant Failure Can Be A Good Thing (Really)

Martin Hosking's LookSmart was a poster child for the late-'90s Silicon Valley boom and bust (but mostly bust). With his new e-commerce company with a twist, RedBubble, Hosking once again looks very, well, smart. Watch brain power overcome the most brutal collapse.

Any conversation that involves digging through past failures is generally a CEO's worst nightmare. Martin Hosking is an exception—a leader who revels in the opportunity to dissect his previous catastrophes.

In 1995 Hosking cofounded LookSmart, an online advertising company that became a poster child for the late-90s Silicon Valley boom and bust. LookSmart rose to prominence with a multimillion-dollar Microsoft contract and a meteoric IPO, but within a year, the dotcom bubble burst, crippling the company and revealing its shaky foundation. A major class-action suit over its core product devastated the entire operation by 2003.

RedBubble became Hosking's new obsession three years later. The company had a fresh retail model focused on custom-designed products and user-submitted artwork. The cautionary tale of LookSmart's demise directly informed the process in creating his new venture—as a lesson of one idea that never needed repeating.

Martin Hosking

"The only thing that's a real failure is if we tried something that didn't work and then we go try the same thing again," says Hosking.

Seven years in, RedBubble is alive and well, and Hosking readily admits that none of it would have been possible without that first setback.