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1983-11-12
Reddit co-founder/CEO. Coded the site solo in Lisp at 21 after YC rejected his first pitch, sold it for $10M at 22, left for 6 years to build Hipmunk, then returned in 2015 to fix Reddit — IPO'd it in 2024, became a billionaire in 2025.
Roomed with Huffman at UVA, co-drove to the Paul Graham lecture that started everything, co-pitched Y Combinator, and co-built and co-sold Reddit through its first sale to Condé Nast
Timeframe: 2001-2009 as active partner; remained connected as Reddit's profile grew through the 2010s-2020s
Huffman's programming idol; rejected their first pitch but personally handed them the 'front page of the internet' concept and funded it with $12,000 as part of YC's first-ever batch
Timeframe: 2005-present
Fellow member of YC's first batch; as a Reddit board member and investor, publicly announced and backed Huffman's 2015 return as CEO
Timeframe: 2005-present
Partnered with Huffman on Hipmunk for six years, with Goldstein as CEO and Huffman as CTO, through funding rounds, the Concur sale, and the eventual shutdown
Timeframe: 2010-2020
Her turbulent interim CEO tenure and resignation amid the 'Great Reddit Blackout' directly created the opening for Huffman's 2015 return
Timeframe: 2014-2015
Data quality: 8/10 completeness, 8/10 confidence
Based on 22 sources • Last updated: 2026-08-21