It was the end of the year 291 AC when the money began to flow properly. Still, summer of course, as it likely would be for another six and a half years, but then the cosmology of Westeros, and likely the entire planet, was very odd. At any rate, there were now two Galleons at sea, the Great Stag, and the Dragonstone Keeper, and while they didn't make as many voyages as the cutters each one was worth ten or fifteen times what one of their smaller brethren could provide. It didn't take all that long at all for me to start paying back my loan as it turned out, and I was glad for that at least. Relations with Bravo were a necessity, especially as I began trading further afield, with the Galleons going as far as the Westerlands and Skagos, though I wanted more marines trained up before I started making a play in the Stepstones. Interestingly one of my sloops made a trip down from the Northern route to Pentos. The Targaryen's weren't in the city at the time, having been last spotted in Volantis, but the trio was informative nonetheless. The three sisters seemed to be hiring mercenaries for something, apparently rumors of another war breaking out in the disputed lands.
I would keep an eye on all that for now. Any major disruption in the Free Cities would let me dodge reprisal in the Stepstones long enough to build up my defenses.
Still, time continued rolling by, and eventually the third Galleon the Righteous Guardian was sent out to join its sisters on the waters of the narrow sea, it's destination was Braavos, with a cargo full of Dragonglass.
Amongst all this the industry on Dragonstone expanded, new wharf opened as more people continued to pour in, and soon enough the town was a small city, just over fifteen thousand strong. It was nothing compared to the greater cities of the realm, but it warranted walls, or more accurately earth and brick ramparts, to protect my production base.
They weren't yet finished by the time my father arrived from King's landing to celebrate my twelfth nameday.