As an active contributor to the open-source developer and hacker culture, most prominently in areas involving the programming language Ruby, he has written enthusiastic articles regarding his philosophies and opinions on various issues. He has been featured as a guest on podcasts, including Rubyology and SitePoint, and he often speaks out about his conviction that developers should seek to collaborate more, and the measures which would promote such collaboration, such as writing better documentation and contributing to other people's projects. In 2008 Tom Preston-Werner spoke about the application of conceptual algorithms to higher-level thinking patterns, rather than solely to coding patterns. Preston was one of the initial members of the San Francisco group IcanhazRuby or ICHR, after he became a regular member of the San Francisco Ruby Meetups. He continued until the meetings became overwhelmed by venture capital investors searching for talent; this prompted him to seek more private gatherings. On April 8, 2011, he also started a conference called CodeConf, by means of GitHub's influence in the coding community. Preston-Werner is the creator of the TOML configuration file format.
Career
In an article published by Hacker Monthly in 2010, Preston wrote about his passion for ensuring that developers document the code they write so others can easily understand how it works. In 2004, Preston-Werner founded Gravatar, a service for providing globally unique avatars that follow users from site to site. The company grew to about 32,000 users in 2007, when Preston-Werner sold the company to Automattic. In 2005 he moved to San Francisco to work at Powerset, a natural language search engine. Powerset was acquired by Microsoft. Preston-Werner declined a $300,000 bonus and stock options from Microsoft so that he could focus on GitHub.
GitHub
Preston-Werner co-founded GitHub in 2008 with Chris Wanstrath, PJ Hyett and Scott Chacon, as a place to share and collaborate on code. Architects, musicians, city governments, builders and others are currently using GitHub to share and collaborate on projects beyond software code. In 2010 Preston-Werner read a comment on Twitter insulting the quality of GitHub's search function. This prompted him to overhaul the service's search, drawing on his experience having worked at Powerset.
Resignation from GitHub
Julie Ann Horvath, a GitHub programmer, alleged in March 2014 that Tom Preston-Werner and his wife Theresa engaged in a pattern of harassment against her that led her to leave the company. GitHub initially denied Horvath's allegations, then following an internal investigation, confirmed some of the claims. Preston-Werner resigned. GitHub's new CEO Chris Wanstrath said the "investigation found Tom Preston-Werner in his capacity as GitHub's CEO acted inappropriately, including confrontational conduct, disregard of workplace complaints, insensitivity to the impact of his spouse's presence in the workplace, and failure to enforce an agreement that his spouse should not work inthe office."
After GitHub
Following his resignation from GitHub, Preston-Werner sold his shares in the company to Microsoft. Along with a team of former GitHub co-founders and executives, Preston-Werner then cofounded Chatterbug, a software for language-learning. In 2018, Chatterbug cofounder Scott Chacon announced an 8 million series A funding round for the company, financed by himself and Preston-Werner.