Shipman attended Queen Elizabeth's Grammar School, Horncastle in Lincolnshire, and studied History at Churchill College, Cambridge, graduating in 1996, where he was part of a losing Cuppers darts team, beaten by a Robinson team in the finals.

[1] He worked for the Sunday Telegraph as a Washington DC political correspondent, covering the 2008 United States elections and Barack Obama's campaign and subsequent victory.

[1] In March 2019, Shipman reported an alleged coup in the Conservative Party to remove the Prime Minister, Theresa May from office.

[8][better source needed] In February 2022, Shipman lost a libel case brought by Baroness Chapman, paying her substantial damages and legal costs.

In May 2021, Shipman had posted two tweets on Twitter, one attributed to an unnamed Labour party source, that the court determined meant he had falsely suggested Chapman had a “secret adulterous relationship” with Labour leader Keir Starmer.