James started honing his interviewing skills as a college student in 2007 when he hosted presidential candidates on his dorm-room video blog. The Economist said he was "probably the world's foremost expert on YouTube videos posted by presidential candidates."

During the 2008 election, he wrote, hosted, and produced an award-winning video series for Politico. In 2012, he wrote and hosted videos for The Daily, a first-of-its-kind newspaper for tablets and smartphones.

He later served as Head of Communications at Automated Insights, an internationally-recognized software company turning raw data into polished stories.