During spring break of his senior year at UVA, Huffman and college roommate Alexis Ohanian drove to Boston, Massachusetts, to attend a lecture delivered by programmer-entrepreneur Paul Graham. Huffman and Ohanian talked with Graham after the lecture and he invited them to apply to his startup incubator Y Combinator. Huffman came up with their original idea, My Mobile Menu, which was intended to allow users to order food by SMS. The idea was rejected, but Graham asked Huffman and Ohanian to meet him in Boston to pitch another idea for a start-up; it was at this brainstorming session that the idea for what Graham called the "front page of the Internet" was created. Huffman and Ohanian were accepted in Y Combinator's first class. Huffman coded the entire site in Lisp. He and Ohanian launched Reddit in June 2005, funded by Y Combinator. 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. At 23, Huffman and Ohanian sold Reddit to Condé Nast on October 31, 2006, for a reported $10 million to $20 million. Huffman remained with Reddit until 2009, when he left his role as acting CEO. Huffman spent several months backpacking in Costa Rica before co-creating the travel website Hipmunk with Adam Goldstein, an author and software developer, in 2010. Funded by Y Combinator, Hipmunk launched in August 2010 with Huffman serving as CTO. In 2011, Inc. named Huffman to its 30 under 30 list. In 2014, Huffman said that his decision to sell Reddit had been a mistake, and that the site's growth had exceeded his expectations. On July 10, 2015, Reddit hired Huffman as CEO following the resignation of Ellen Pao and during a particularly difficult time for the company. 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. Since returning to Reddit, Huffman instituted a number of technological improvements including a better mobile experience and stronger infrastructure, as well as new content guidelines. These included a ban on content that incites violence, quarantining some material users might find offensive, and removing communities "that exist solely to ... make Reddit worse for everyone else". Shortly after returning, Huffman wrote that "neither Alexis nor I created reddit to be a bastion of free speech, but rather as a place where open and honest discussion can happen." In a 2012 interview, Ohanian had used the same phrase to describe Reddit, as noted by The New Yorker and The Verge. Huffman also worked to make the site more advertiser-friendly and led efforts to host video and images on site. In late 2016, Huffman was the focus of controversy for altering posts on a subreddit popular with supporters of Donald Trump, /r/The Donald. Following criticism from Reddit users, he undid the change and issued an apology. Beginning in 2017, Huffman led the redesign of Reddit's website with its first major visual update in a decade. Huffman said the site had looked like a "dystopian Craigslist" whose outdated look deterred new users. Development of the new site took more than a year, and the redesign launched in April 2018.
Net neutrality activism
Huffman is an advocate for net neutrality rules. In 2017, Huffman told The New York Times that without net neutrality protections, "you give internet service providers the ability to choose winners and losers". On Reddit, Huffman urged redditors to express support for net neutrality and contact their elected representatives in Washington, D.C. Huffman said that the repeal of net neutrality rules stifles competition. He said he and Reddit would continue to advocate for net neutrality.
