Evidently Cole dealt in cloth, for in 1395-6 he was assessed for alnage on four broad cloths sold at Weymouth. He also exported it (for example, in November 1403, in a cargo shipped on Le Marie of Weymouth). He probably also traded in Gascon wines, for in November 1408 he received bonds for the payment of £10 by Nicholas Bridge, a merchant of London and Bordeaux. But he was locally active in other ways, too: in 1397 he had provided assurances to the earl of March’s bailiff at Wyke Regis that Philip Brice would pay the £2 owing on his account as ‘messor’ of the manor; then, in May 1404, he and others, including the sheriff of Dorset, were ordered to distribute a tenth part of the ransoms for Frenchmen taken prisoner during a recent assault on Portland among those who had helped defend the coast but had not themselves made captures.
In 1406, following the death of his second cousin John Engleby of Bridgwater, Cole had added to his holdings in Weymouth two messuages in Ilchester and lands in North Petherton and Lymington (Somerset). He began disposing of his property in 1409, by conveying a house in Weymouth to John Abbot of Melcombe and John Mey of Dorchester, and then, two years later, he settled on his second wife burgages in Ilchester and Lymington.
