Hipmunk, the online travel site that digs up discount plane tickets on the Web, announced on Friday a $20 million investment led by Oak Investment Partners.
The investment doubles Hipmunk’s previous funding, bringing the total investments to about $40 million since the company was founded in June 2010 in San Francisco. Ren Riley, a general partner with Oak Investment, which has offices in Palo Alto,will join the Hipmunk board of directors, the company said.
Hipmunk is a Y Combinator alumni — one of the startups to exit the elite accelerator, and boasting with a prestigious list of entrepreneurs behind it. Hipmunk was co-founded by Steve Huffman, who also co-founded the microblogging site Reddit, as his second Y Combinator project. He was joined by MIT graduate Adam Goldstein, who was recently named one of Forbes’ “30 under 30″ in technology. Huffman, who was adored by Y Combinator founder Paul Graham, was able to skip the application for his second stint at the accelerator in 2010. Huffman said Graham essentially gave them a free pass to YC, because he was a repeat entrepreneur who had already proven himself with Reddit.
“We called (Graham) up and asked him to get dinner and asked to do Y Combinator,” Huffman said. “He said, ‘What do you want to do?'”
The men explained their travel website idea to Graham, who responded, “Oh, how much money do you want?” according to Huffman.
But Hipmunk, while a popular consumer tool to find cheap airfare and plan international travel, hasn’t attracted the attention of investors the way some of its fellow YC alumni have. By comparison, Stripe, the online payments platform that joined YC in 2010, has raised $120 million; Airbnb, which completed YC in 2008, has raised $776 million; and Dropbox, a 2007 YC startup, has raised about $1.1 billion, according to CrunchBase.