Kevin Roose observes that “Silicon Valley has managed to turn failure into a bragging right”:
Why talk about failure at all? In part, the trend may be a concession to Silicon Valley’s messy reality. Even during a historic tech boom, the fact remains that the vast majority of start-ups die in their infancy. (Shikhar Ghosh, a senior lecturer at Harvard Business School, studied more than 2,000 venture-backed start-ups and found that roughly 75 percent of them failed to return investors’ capital.) But these missteps, numerous as they are, are rarely KOs. At many failed start-ups, defeated founders and engineers quickly move on to other ventures, investors write off their losses, and the tech world absorbs the hit without cascading into an industrywide crisis. Given the gentle funeral that awaits many start-up deaths, the postmortem trend can also be seen as a psychological prophylactic, a clever way to shrink the stigma around failure and ensure that entrepreneurs keep gambling on crazy ideas, despite the likelihood that they’ll lose. It’s also a hopeful reminder that what starts as failure can morph into success. After all, Steve Jobs ran NeXT before he built Apple into a colossus, and Twitter was spun out of a DOA podcasting start-up called Odeo. If they kept going, the pep talk goes, so should you.
At its best, the start-up postmortem offers a founder the chance to self-reflect and apologize for mistakes made along the way. At worst, it’s a job application in disguise. Some tech retrospectives are so filled with humble-brags and hubris (if only we hadn’t been so far ahead of the curve!) that they don’t read like failure stories at all. “We built a world-class team of engineers, designers, marketers, and operations specialists,” wrote the Outbox founders, while eulogizing their mail-scanning start-up earlier this year. “Together, we made a product that was as beautiful as it was complex, and overcame nearly every obstacle in our path.”
The Dish 