He is half of the double-act, The Pin, with Alexander Owen, with whom he has made four series for BBC Radio 4, picking up nominations at the 2017 Writers' Guild Awards.

He went to the Haberdashers' Aske's School for Boys[5] and performed with the Chicken Shed Theatre Company before studying English Literature at Trinity Hall, Cambridge.

[7][8] Ashenden and Owen then performed with the Cambridge Footlights, as part of the first troupe to tour America, in a show directed by Liam Williams and Daran Johnson.

His TV credits include Avenue 5 (HBO), The English Game (Netflix), W1A (BBC1), Stath Lets Flats (C4), Brotherhood (Comedy Central), Plebs (ITV2) and Sky Christmas special, Cinderella: After Ever After.

In 2020 The Pin released “The Special Relationship”[11] an 8-part series on Audible, co-starring Fred Armisen, Cecily Strong, Jamie Demetriou, Lolly Adefope and Kate Berlant.