The family of Respryn took its name from a hamlet in the parish of St. Winnow, immediately to the north of Lostwithiel, and in 1337 an ancestor and namesake of Richard’s had held some 26 acres of wasteland, as well as other more fertile acres, on the nearby manor of Penlyne, which belonged to the duchy of Cornwall. The Respryns were evidently related in some way to Clarissa, the second wife of John Fortescue (father of the future chief justice); not only were various members of the family in possession in 1408 of properties which formed part of her inheritance, but in 1421 Richard himself was party to a settlement made by the couple on Fortescue’s eldest son, Henry. It may well be that the lady concerned was Respryn’s mother. He himself held property within easy reach of both of the boroughs which he represented in Parliament: his father had acquired land in the parishes of St. Just in Roseland and Ruanlanyhorn near Truro, and there were family holdings in Penkneth and Fowey as well as at Lostwithiel itself. In addition, he possessed a reversionary interest in premises in the parishes of St. Enoder, St. Kew and St. Teath, and the 1428 assessments for parliamentary taxation show that he owned parcels of land scattered over central Cornwall.
Respryn’s career as a lawyer began a few years before his first return to Parliament in 1390. He was up at Westminster in 1388 and 1389, and it was there that he witnessed a deed for Nicholas Trenewith concerning holdings in Cornwall, entered into recognizances for £31 6s.8d. payable to the feoffees of the same property, and stood surety for John Breton I of Bodmin when the latter was required to appear in Chancery. His father, John, who had served on various royal commissions in Cornwall over the past few years, had failed to act on one to investigate illegal shipments of tin; consequently, when the Chancery officials persisted in prosecuting him, in June 1391 he sent Richard to Westminster to take on his behalf an oath that he had never received the writ. Respryn also had business nearer home, at the Launceston assizes; and at Michaelmas 1391 he was at Lostwithiel acting on behalf of Sir William Talbot† in presenting, at the duchy exchequer, both Sir William’s and the late Sir John Reskymer’s accounts for the shrievalty of Cornwall. Talbot probably made Respryn his executor, for after his death it was the latter who submitted a formal declaration in Chancery excusing his failure to act on royal orders for the supervision of mines in Devon and Cornwall. Other prominent west country figures by whom Respryn was employed at one time or another, as attorney, feoffee or surety, included John Colshull I, John Hawley I of Dartmouth, Stephen Trenewith, Thomas Nanfan, and the Bodulgates. His stewardship not only of the town of Dunheved (a duchy appointment which perhaps dated from as early as 1400), but also of the Cornish estates of Bishop Stafford of Exeter, adds to the impression of a busy, competent lawyer, becoming increasingly more expert in estate management and advocacy as his career progressed.
All the same, Respryn’s reputation came into discredit on at least two occasions: one of them in 1424, when John Fursdon alleged that he had been among those who joined Richard Trevanion in breaking into his manor-house at Fursdon, nearly killing him and his wife, and causing the latter to suffer a miscarriage. However, by the time a commission of oyer and terminer came to be set up to investigate the complaint, Respryn’s name had already been dropped from the charge (though a servant of his was still implicated).