He married Margaret, sister of Sir Rhys ap Thomas.
Like many members of the Welsh gentry, Herbert was a notable bardic patron.
He hosted a bardic debate at Coldbrook House between Deulwyn and Bedo Brwynllys.
He was eulogized by Ieuan Deulwyn, Bedo Brwynllys, Hywel Dafi, and (jointly with his brother William) Huw Cae Llwyd.
He fought alongside his brother at the Battle of Edgcote (a victory for rebels who supported the Earl of Warwick and the Duke of Clarence), where he was captured and executed.