Toby attributes his love of comics to his family having moved frequently for his father's army career. He started making his own comics at seven while off school with a broken leg.

Toby is the author of The Spinoff's non-fiction comic series The Side Eye, which won the Voyager Media Award for Cartoonist of the Year for 2019. In 2020, his Covid-19 collaborations with Dr Siouxsie Wiles were shared around the world. He has published several books, including collections of his cartoons depicting daily life: Alledaags: A Year in Amsterdam and Don't Puke On Your Dad: A Year In The Life of A New Father; and two children's books: Capsicum, Capsi Go and The Day The Costumes Stuck.

Toby lives in Auckland with his wife Sonya and their two sons.