The site’s audience grew rapidly in its first few months, and by August 2005, Huffman noticed their habitual user-base had grown so large that he no longer needed to fill the front page with content himself.[11][14][15] Huffman and Ohanian sold Reddit to Condé Nast on October 31, 2006, for a reported $10 million to $20 million.[3][16] Huffman remained with Reddit until 2009, when he left his role as acting CEO.[17]
Huffman spent several months backpacking in Costa Rica[18] before co-creating the travel website Hipmunk with Adam Goldstein, an author and software developer, in 2010. Funded by Y Combinator,[19][20] Hipmunk launched in August 2010[21] with Huffman serving as CTO.[22] In 2011, Inc. named Huffman to its 30 under 30 list.[22]
In 2014, Huffman said that his decision to sell Reddit had been a mistake, and that the site’s growth had exceeded his expectations.[23] On July 10, 2015, Reddit hired Huffman as CEO following the resignation of Ellen Pao[24] and during a particularly difficult time for the company.[25] Upon rejoining the company, Huffman’s top goals included launching Reddit’s iOS and Android apps, fixing Reddit’s mobile website, and creating A/B testing infrastructure.[3]
Since returning to Reddit, Huffman instituted a number of technological changes including an updated mobile site and stronger infrastructure, as well as new content guidelines.
I don’t think that he’s had a whole lot of faith in Reddit as a business since early-on.