Barrie was the younger of two children, whose parents were the most prominent members of the board of directors of a shipbuilding company, Ferryfolk Lines. Actually, the company built and operated various watercraft, ranging from paddle-boats and canoes which might be rented for short periods of time by individuals for fun, to larger ships which might be leased by traders, transporters, etc. However, the mainstay of the business was a line of ferryboats, on which the company itself employed crews, to transport people between Tanq and either Jump Village or Shipsister. Barrie's family was fairly comfortable, financially, though far from wealthy; the expense of building and maintaining ships took up much of the profits of operating or letting them. The family also wasn't large enough to be considered a "clan," as are many of the wealthier families on The Land. It was essentially just Barrie, his older brother Jim, and their parents. However, their ancestors had been among the settlers of Tanq in 380, and among the founders of Ferryfolk.
Barrie spent much of his youth around boats and ships, as one might expect, and sometimes worked on various crews, as did his brother. However, he also spent much of his free time in a local street gang called the Sea Monogs. He was basically just killing time, trying to have some fun while he could, knowing that someday he'd have to get serious and take a full-time job in his parents' company. Of course, his parents weren't the only people on the board of directors, and when one of the others retired in 898, his spot went to Jim. Barrie himself didn't expect to start out on the board of directors, but he knew he'd get there eventually. Meanwhile, by an interesting coincidence, the head of the Sea Monogs retired from the gang around the same time Jim joined the board. (Being a young man, he was ready to start doing something serious with his life.) Barrie wasn't much younger than the outgoing leader (he was 18 at the time), which was old enough to quit the gang himself, but instead he accepted the position as new leader, voted by the other members of the gang. He didn't expect to keep at it for more than a year or two, though the following year, he began to hear of intervillage gangs forming. This interested him, so he began working to make the Sea Monogs more prominent in Tanq. In 901, his gang officially joined LandOrder.
But as fate would have it, Barrie was subjected to another coincidence. This time, it was the fact that his brother and their parents were all killed in a tragic boating accident shortly after Barrie joined LandOrder. He inherited their share of Ferryfolk, but because of his gang activities, most of the rest of the board formed a voting block to prevent him from attaining any real power in the company, even though he was now technically its highest official. (His only ally on the board was Haruka, of the clan that would later take the name "Nearwright.") In frustration, Barrie sold his share of the company to the board (for less than it was worth), and Haruka would soon be forced out of the company, herself. Finding himself with no job prospects, he realized he had no choice but to continue as don of LandOrder's Tanq branch (a position he had always intended to give up).
Once the Sea Monogs joined LandOrder, most of the other gangs began breaking up, realizing they couldn't compete with an intervillage gang. However, in 902, those that remained joined to form a new branch of InterGang, under the leadership of Lydia. Tanq was never considered a major branch of either gang, and both Barrie and Lydia were considered at best "competent" by their respective capos. This led the two of them to feel a certain empathy for each other, and so there was never much conflict between the two gangs, in Tanq.
In 904, when the surname law was passed, Barrie chose the name "Ferryman," in honor of his late family's ferrying business.
In 912, Lydia was fired from InterGang by her capo, and subsequently was recruited by don Larami Illuminatus of Tonad to join her in the new intervillage gang she was starting, called the Illuminati. This unexpected upheaval allowed Barrie to make some strides in enhancing LandOrder's position in Tanq, though these strides were somewhat minimized by the efforts of The Syndicate, which started becoming more active that year than ever before.