Webvan, ahead of its time.

The idea of having your customers order their groceries online, buying their food for them, and delivering it to their homes was a horrible business model back in 1999 when Webvan tried it and failed miserably in 2001 going bankrupt.

However, with the advent of mobile-web and smartphones, that can do virtually anything, Webvan's idea could very well be a profitable business model in the post iPhone world.

In 2001 I had never traded a single stock in my life so I don't know much about how Webvan operated but I do know that back then the idea of carrying around a pocket-sized phone that had a blazingly fast wireless internet connection (relative to 56k dial-ups) and had a big enough screen where you could actually see full-color high res pictures (and you could magnify them) was an idea that nobody except, maybe, Steve Jobs had in his head (but probably not since the iPhone debut in 2007).

Back in those early days the internet was very immature and not fully developed. So if you wanted to order your groceries online you basically just typed-up your grocery list in a Webvan text-box and then prayed that he would get you the right brand or flavor that you wanted. For example if you just wrote down that you wanted Total WholeGrain cereal the Webvan employee would shit his pants when he got to the cereal isle when seeing that there are fully 5 different versions of that cereal (Honey Almond Flax, Blueberry Pomegranate, Cinnamon Crunch, Raisin Brand, & Cranberry Crunch). He would have no F-ing clue which one you wanted and would either get you the wrong kind or not buy anything at all. Either of which would piss you off and rightfully so.

With today's internet though, the cloud, and smartphones instead of just writing down a vague, ambiguous grocery list of the foods you want, you could browse through pictures and select the specific brand you want. With pictures there is no ambiguity of what you want and the Webvan employee would be equipped with an iPad or iPhone and have a picture of the exact item you want. If it's not there he could even Tweet you to find out if you would like him to get you another similar brand or not get anything at all. You could even personalize the experience by taking the customer with you on a shopping trip and take pictures of them holding the brands they like. Then the next time they are putting together their grocery list, they could click on a picture of themselves holding the brand!

This simply wasn't doable back in 1999 but I think it is doable now. Maybe that's why Jeff Bezos bought Webvan in 2009 (for probably nothing) and now Amazon owns them (Check Wikipedia).