During spring break of his senior year at UVA, Huffman and college roommate
Alexis Ohanian delivered by English programmer-entrepreneur
Paul Graham. Huffman and Ohanian talked with Graham after the lecture and he invited them to apply to
Y Combinator, his
startup incubator. 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. 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 as CTO. 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. In a 2012 interview, Alexis Ohanian had used the phrase "bastion of free speech" specifically to describe Reddit, as noted by
The New Yorker and
The Verge. Huffman also worked to make the site more advertiser-friendly 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 Huffman said the site had looked like a "dystopian Craigslist" whose outdated look deterred new users. In anticipation to Reddit's
initial public offering, it was revealed that Huffman’s compensation package for 2023 was worth $193.2 million, which included a salary of $341,346, stock awards worth $98.3 million and stock options valued at $93.8 million. In September 2024, Huffman was named by
TIME as one of the 100 most influential people in
AI. ==Controversies and criticism==