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Before Dropbox, Drew Houston ventured into the world of startups with Accolade, an online SAT prep company.

"My first company was called Accolade, and it was doing online SAT prep because we realized that back in the day the SAT was changing and no one had really built a good online course."

He applied to Y Combinator with Accolade but faced rejection.

"We were rejected without an interview... Largely because we were both, my co-founder and I, were both part-time on it, a couple other reasons—market size, probably some other stuff."

This setback didn't deter him but instead fueled his determination to succeed.