She had seen her father's death many times in her head since she was six years old. She remembers hiding under the bed in her little sister's room, staring out through the crack in the door. Her mother was screaming, crying, begging, praying. The noise echoed through the house and bounced between the buildings around them. Then came the sounds of something breaking. A crash, followed by a thud. After that, silence.
The next thing she remembers is crawling out from under the bed and running into her parents' room. They were lying on the floor, covered in blood. One of them was still breathing, the other wasn't moving. She looked up at her brother standing beside the bed. He was just a little boy, about ten. His eyes were wide and filled with tears. She could tell he had been crying, but he didn't seem to care anymore. He was too shocked to cry any longer. He knew his father was dead.
The death of her mother granted Widow's Watch to her brother. He was now Lord Desmond II Flint-Ironsmith, Lord of Widow's Watch. Widow's Watch is a cold, wretched place. The winter's were tough and the fields were lacking. It was difficult to even muster five thousand men.
Widow's Watch is surrounded on three sides by mountains. On the fourth side it is bounded by the sea. The only way into the castle was through a narrow strait guarded by two gates. This was the key to Desmond's inheritance. The real prize was not his Flint birthright, but the bequest of his father's shares in the Ironsmith Trading Company. His father's rule via jure uxoris over Widow's Watch and consequently control over a coastline he filled with trading ports. He grew the Ironsmith Trading Company into a power thought by many to be greater than even lordships. The marriage between their father the first Desmond and Lyessa Flint may have been simply a brilliant strategical decision at first but over the years he saw them grow to love each other truly. Lyessa Smith had already seen too much tragedy. She lost her heir at the Red Wedding and now to die like this...
Desmond was not a bad man. He tried to be gentle and kind but the weight of his destiny was too heavy for him to bear. He knew he had to take up his father's mantle and name to protect the realm, but the only thing he could think of was vengeance. A vengeance he could not direct to anybody. He was obsessed with finding the man who destroyed his family. He wanted to become renowned enough to find the man who killed his parents and then he wanted to become powerful enough to face the man who ordered it.
So he aspired to become the greatest trader in all of Westeros. He wanted to build his dynasty's company into an empire. He wanted to be known as more important than the Kings of Westeros. He wanted to be the one to bring the Iron Throne to its knees. It was all he could think about.
He set sail with ships full of ironmongery, weapons, horses and livestock from across the Narrow Sea. He traded with everyone from Dorne to the Free Cities. He became a merchant prince in his own right, though he paid homage to his father's legacy. It was on one of these expeditions where he met Lord Daemon Waters, Lord of Malarqovos, First Captain of Braavos, and Lord Minister of Daenerys Targaryen's Queen's Council.