Dolmond was born into the Hornwort family of Bree, not necessarily a rich family but not necessarily poor either. Dolmond learned things with ease and soon became known for his vast expanse of knowledge from botany to history. He knew the language of ravens and at least two other languages (besides Westron). 

When he was 20 Dolmond got a job at the Scholar's Stair Archives, cataloging and sorting books. Soon, though, he grew bored. He had successfully sorted all of the books and there was nothing, in his mind, for him left to do, so he went and joined a group of adventurers and his life began.

When his adventures ended, Dolmond attempted to start a new life in Bree. He, however, was lame in his left leg, due to a particularly rough adventure with wargs, so he could not find work. He became a merchant for a time, and would ride in a cart (so he would not have to walk), but eventually his business went bankrupt. Dolmond, far past his prime, settled down in a tent in Beggar's Alley. 

It would seem that despite his vast expanse of knowledge and wisdom, Dolmond does not know how to manage his own personal finance. That can be a problem.