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Dick co-founded Burning Door Networked Media, a web design and development consulting company.
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Dick co-founded SpyOnIt, a web page monitoring service.
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In 2004, Costolo, Eric Lunt, Steve Olechowski, and Matt Shobe, founded the web feed management provider FeedBurner.
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Dick began working in other areas of Google. In July 2009, he left Google.
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In July 2009, Dick left Google, and in September 2009, it was announced that he was joining Twitter as its COO.
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Dick was joining Twitter as its COO. Although his 2010 takeover as CEO was supposed to be temporary, while CEO Evan Williams was on paternity leave, it eventually became a permanent position.
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In May 2011, it was announced that President Obama had appointed Costolo to the National Security Telecommunications Advisory Committee, along with the Corporate Vice President of Microsoft’s Trustworthy Computing Group