How Did Airbnb Make Y Combinator Write Bigger Checks?

On The Peel, Dropbox becoming a billion-dollar startup around 2011 was called one lucky year. Airbnb becoming a billion-dollar company in 2010 and 2011 was the second hit, and YC then went from giving founders $12,000 and $15,000 to $100,000, $120,000, and $175,000.

Garry Tan was a software engineer at Palantir, employee number 10, and he designed the Palantir logo. Palantir had only 10 people and tried to hire YC alumni, which is how he found out about YC. YC started in 2006 and 2007. Back in 2007 and 2008 he already saw YC as where smart engineers went to start a company, and he wanted to be like Steve Huffman, Drew Houston, and James Lindenbaum, who created Heroku. Around 2011 Dropbox had become a billion-dollar startup, and a lot of people said one year lucky. In 2010 and 2011 Airbnb became a billion-dollar company, and the line was one you're lucky, two you're good. Suddenly everyone in the Valley realized YC was a place to pay attention to, and Turner Novak said Airbnb put YC on the map because YC had done it twice.

The second billion-dollar company is what made the larger checks follow. Garry Tan had already treated YC as the destination for strong engineers in 2007 and 2008.