"Matron" Willina Brandyberg
This wizened elderly halfling lady is wearing simple and dark clothing, although close inspection reveals it is of excellent fabric and make. Though her face is wrinkled, her eyes are especially sharp.
“Matron” Willina Brandyberg married young, to an aspiring itinerant halfling merchant named Phillit. Although Phill and Willina started out with just a single ox-cart and some (arguably quite good) barrels of wine, Willina’s shrewdness and business acumen swiftly came to the fore, convincing her husband to invest in a riverboat for trade up and down the Tibre, and when Phil died 6 years later he left her with 3 children and a river-van of 6 barges and boats.
In the years since then, she’s had 3 husbands, 8 more children, 16 grandchildren and 11 great grand-children, most of whom either still work as part of the family business, along with their partners and employees. The Brandybergs commercial empire spans a quarter of the known world, and their riverboats and caravans routinely bring goods to port to meet their oceangoing vessels to spread their goods further, and increase their profits accordingly.
Despite their commercial reach, the Brandybergs are unassuming people, tending towards humble displays of wealth if any are required. Those who deal with them respect their integrity, and they are known to be as honest as a trader can be expected to be. Willina herself is quick to judge, both for good or for ill, and quite boisterous and generous with those she considers friends.