Before Google, Sergey Brin tried (and failed) to let us order pizza by fax
Before Google co-founder Sergey Brin started the work that would make him famous, he tried to remake the business of pizza delivery. In a Solve for X talk recently posted online, he describes coming up with what seemed like an elegant solution to ordering food: find the publicly posted fax numbers for restaurants, then build an online form and write a script that faxes it as an order. But his plan was derailed by the fact that while his local pizza place had a fax machine, it was quite reasonably being ignored. "The challenge of a problem, or the importance, isn't really that related to how likely you are to achieve it," he says. Of course, even in a talk about the value of failure, his plan failed exceptionally quickly: it luckily took just one order for him to realize people weren't using their fax machines. The full talk is below; you can catch the story at around 2:00 in.

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