More may be added to the earlier biography.
Hebbe followed a family tradition of service at the staple court of Chichester, succeeding his grandfather and namesake Geoffrey (who was periodically constable of the staple in the years between 1365 and 1378),
More has been discovered about Hebbe’s mercantile dealings, which at the beginning of his career appear to have progressed satisfactorily, albeit not without encountering difficulty in gaining satisfaction from his debtors. In the late 1390s he was in partnership with William Overey* the Southampton merchant. In May 1398 in the staple court at Chichester (conducted by Hebbe’s father as mayor) they received from the Sussex esquire Robert Tauk† a bond in £9 12s. 4½d. Tauk failed to repay them before he died, and it was not until June 1410 that the two creditors were given temporary possession of his manor of Westhampnett and other holdings worth £7 p.a. as compensation. Similarly, in 1399 Hebbe and Overey had received a bond for £6 for merchandise sold at the staple to John Slyfhurst of Midhurst and John atte Mill, but in this case their debtors escaped justice for more than five years, and even then although Slyfhurst was imprisoned at Guildford his associate could not be found.
As noted in the earlier biography, Hebbe’s trading concerns started to run into serious trouble in 1418. Further details about his subsequent financial difficulties are revealed in the records of the court of common pleas. While his second Parliament was in progress, in the Michaelmas term of 1423, he was sued by creditors for relatively small sums of money, but following his service on the expedition sent to relieve Le Crotoy in the next year (on which he had embarked shortly after the dissolution), the suits brought against him were for much larger amounts. For instance, in Easter term 1425 the executors of Richard Salter, a former mayor of the staple of Chichester, brought a plea of debt against him for £33. Attempts to diversify his sources of income may be discerned in the various descriptions given to him on the plea rolls: ‘merchant’, ‘draper’, ‘husbandman’ and ‘soldier’.