The second "May 2008" above should be "May 2009".

At the Imgur comments link are many other infographics for entrepreneurs.

Including how Airbnb and Instagram got started. 

I think it's fair to say that there's almost an INVERSE correlation between how great a startup is after 5 years, versus how hard it was to get there. We could write a gigantic essay about this, but the long and the short of it is: great companies are taking bigger risks, and it's harder to see whether they will be successful in the early stages. Or another way to say it is what a young entrepreneur friend recently told me: "No one starves to death to start a company that makes monitoring software."

You're very right. Here's the equivalent infographic for Airbnb and it matches what you say.