He would use examples from the everyday lives of his listeners, introducing anecdotes and even jokes. Schupp employed these devices and techniques not only when addressing his own congregations, but also when appearing as a guest preacher in other churches nearby, greatly swelling congregations in the process. His approach was, by the standards of the times, truly innovative, and by many criteria highly successful. But not everyone was impressed. There were those who interpreted rebukes in his sermons as personal insults and other who thought their life choices were no business of this tiresome preacher. From fellow clerics, steeped in the traditions of a more baroque approach to sermons and written religious pieces, came the criticism that the colloquial syntax of his delivery was inconsistent with the serious purposes of a sermon - any sermon. It soon became evident that as his sermons became ever more widely discussed, Schupp would have to learn to face criticism from both wings of the Christian faith among the good Protestant citizens of Hamburg. Personal tragedy struck on 12 June 1650 when Anna Elisabeth, his wife, died, possibly following a long period of poor health. His second marriage was to Sophie Eleonore Reincking and took place on 10 November 1651. She was a daughter of Dietrich Reinkingk, a friend from Schupp's time as a diplomat in Osnabrück whose fortunes had been enhanced after his friend and employer Prince Frederick succeeded to the throne of Denmark towards the end of 1648. Dietrich Reincking was no longer a senior diplomat representing Bremen: he was the Danish chancellor. The poet-pastor Johann Rist honoured both Schupp's bereavement and his second marriage with a warmly sympathetic poem, indicating that the two men were already in contact with one another. There were those who surmised that Schupp's marriage to his second wife was less amicable than his first marriage had been, but these are countered with suggestions that these negative reports were no more than malicious rumours put about by rival churchmen and others who found Schupp threatening or annoying. It was probably in 1654 that Balthasar Schupp started to produce a string of written pieces in the German language that are, for scholars of satirical writing, his most important and enduring contribution. Of those pieces for which the date can be ascertained, the first was "Der lobwürdige Löw" ("loosely, "The commendable Lion""), which was an extended letter of congratulation addressed to Schupp's friend Marcus Pensin in Stade (just to the west of Hamburg) in celebration of Pensin's marriage to Catharine, the daughter of the Hinrich Schwelund.