St. Paul's was not one of the more well-endowed cathedrals, although it was medieval England's largest, longer and higher than the present-day replacement. Its estates were mostly in the regions just north of London or in Essex. Some of their produce was brewed into ale or baked into bread for the canons in the St. Paul's brewery and bakery, which are believed to have stood opposite each other in Godliman Street, a north-south street below the churchyard, west of the palace of the Bishop of London; the canons allowance was 21 loaves and 30 gallons of ale a week. The cathedral precinct was a walled area in the east side of the city, large enough so that those entering or leaving the city by its western gates had to circumvent or pass through the precinct.

This medieval equivalent of a shopping mall built near the brewery would have brought St. Paul's valuable annual income in rents. It was not the first initiative of this type by the Dean and Chapter. In 1369 they had contracted with two carpenters for the construction of a row of twenty shops with solars above near the cathedral bakery, facing onto Godliman Street. These shops were each to be about 12 feet wide and were all to have the same appearance. The carpenters would be paid £303 for this work, out of which they had to furnish all the materials. It is hard to imagine that this work and that of 1370 were not both part of the same plan, creating in effect a shopping street – although both rows of shops were so long they appear also to have turned the corner onto an adjacent street and taken an L-shape. The carpenter's contract, to complete the structure above the groundworks that Webbenham would take care of, has not survived to us.

In 1410 a contract between St. Paul's and a timber-merchant and carpenter had the aim of building a row of three houses in Friday Street (a little east of the precinct), each with a ground-floor shop, incorporating counter and a partitioned space (workshop?). In the first half of the fifteenth century however we hear relatively little of rows of shops being built. It was from the early fourteenth century that we find the construction of such complexes, and the same period when "Row" starts to appear in street names; Lady Row in York is an extant example of a string of combination shops and dwellings. In 1373 the Prior of Lewes had two opposing rows of shops built on property he held in Southwark; whether the larger St. Paul's venture was an inspiration cannot be said. Entrepreneurial initiatives to construct new buildings for their rent revenues were common enough that they must have had a significant effect on the redevelopment of many townscapes.