Drew Houston attended MIT and wanted to get into one of the most prestigious startup accelerator programs in the world, Y Combinator, in 2005. He eventually got in with the idea for Dropbox in 2007. But two sessions before that, he applied and was rejected. The reason he was rejected was because the company he wanted to start wasn't very good.
Sam Altman, who now runs Y Combinator in place of the accelerator's co-founder, Paul Graham, told the story of Houston's rejection on stage at TechCrunch Disrupt in New York this morning.
According to Altman, Houston applied with an SAT prep startup idea. His rejection letter noted that Houston seemed really smart, but "there has got to be something better you can build than an SAT prep company."
Houston spent the next few years thinking of harder problems to solve and came up with a file storage company in the cloud which could get rid of thumbdrives altogether.
Here's the Y Combinator application he submitted in 2007 that finally got him in the door. Now his company is worth $10 billion and it's one of the two most valuable startups YC has ever had in its program, along with Airbnb.