He made money

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First recalling an old proverb, Deasy then invokes no less a figure than the Bard to justify his love of money: "If youth but knew. But what does Shakespeare say? Put but money in thy purse." Thornton cites the old proverb, "If youth but knew what age would crave, it would both get and save." The italicized phrase comes from act 1 scene 3 of Othello, where Iago repeatedly urges Roderigo to sell his lands, claiming that with the money's help he can persuade Desdemona to love Roderigo. This is hardly an instance of thriftily saving up for old age, and in any case Iago is a sociopathic liar who is cheating Roderigo of his wealth. (He confides to the audience that the money will end up in his purse: "Thus do I ever make my fool my purse.")

Ancient Greeks often approached the Homeric epics as if they were owners' manuals for human life, and many modern Christians oddly persist in viewing the Bible this way. In Joyce's time there was a widespread cultural conviction that life wisdom could be found in Shakespeare, and he implanted that mindset in both Deasy and Bloom.  Ithaca notes that Bloom has often "reflected on the pleasures derived from literature of instruction rather than of amusement as he himself had applied to the works of William Shakespeare more than once for the solution of difficult problems in imaginary or real life." "Had he found their solution?" the catechism asks. "In spite of careful and repeated reading of certain classical passages, aided by a glossary, he had derived imperfect conviction from the text, the answers not bearing in all points."

The narrative's mockery of Bloom here echoes Stephen's earlier contempt for Deasy, which he expresses so politely that Deasy does not notice the rebuttal:

     — Iago, Stephen murmured.
      He lifted his gaze from the idle shells to the old man's stare.
      — He knew what money was, Mr Deasy said. He made money. A poet, yes, but an Englishman too.

Shakespeare did make money, and not accidentally. He was one of a handful of "sharers" (i.e., shareholders) in the Lord Chamberlain's (later the King's) Men, in the Theatre (later the Globe), and in the plays that the acting company produced in those theaters. The partners split obligations and profits according to their stake in the whole. Shakespeare's share was originally one eighth, 12.5%, but at the time of his retirement he held about 7%. His shares must have produced a sizeable income, because as he aged he purchased a lot of real estate in and around his home town, Stratford. He did exactly what the proverb recommends, saving up for a time when money would be important, and in much the same way as Bloom has done by purchasing Canadian railway stock paying a 4% dividend.

Stephen's utter lack of thrift means that he could learn something from both Deasy and Bloom, but the odds that he will do so anytime soon are vanishingly small. Accepting Deasy's point about Shakespeare's love of money, he makes this "English" quality an object of derision rather than admiration in Scylla and Charybdis: "He drew Shylock out of his own long pocket. The son of a maltjobber and moneylender he was himself a cornjobber and moneylender, with ten tods of corn hoarded in the famine riots. His borrowers are no doubt those divers of worship mentioned by Chettle Falstaff who reported his uprightness of dealing. He sued a fellowplayer for the price of a few bags of malt and exacted his pound of flesh in interest for every money lent."