He who loves wisdom makes his father glad, but a companion of prostitutes squanders his wealth.
It's unclear whether the antecedent of "his" in the second half of the verse ("his wealth") is the father of this "companion" (similar to how the first half mentions the father of "he who loves wisdom") or the "companion" himself.
The connection between this verse and the Parable of the Prodigal Son in Luke 15, where the son does squander the father's wealth, suggests that the antecedent is an implied father. Additionally, in this reading, the two halves of the verse parallel each other: "he" with "companion," "wisdom" with "prostitutes" (in an inverted sort of way), and "father" with "his."
Alternatively, this "his" could indicate the "companion" himself ("his [own] wealth"), and this understanding results in an-other contrast between these two men. The first half ("he who loves wisdom makes his father glad") contains three characters: "he," personified "wisdom," and "father." If "companion" is the antecedent of "his" in the second half, there are only two entities there (although, admittedly, one is plural): "companion"/"his" and "prostitutes." The first man ("he who loves wisdom") maintains his familial relationships, but the second (the "companion of prostitutes") lacks them.
I lookt up this verse in languages that have distinct forms for "his" and "his own" (reflexive possessive) and discovered that both follow this second reading ("his own").
Norwegian:
En mann som elsker visdom, gleder sin far; men den som holder vennskap med skjøger, øder sitt gods.
Esperanto:
Homo, kiu amas saĝon, ĝojigas sian patron; sed kiu komunikiĝas kun malĉastulinoj, tiu disperdas sian havon.
I'm not sure to what degree (if any) all of this applies to the original Hebrew text, though, because it has no "his" in the second clause; it's just "a companion of prostitutes squanders wealth":
אִֽישׁ־אֹהֵב חָכְמָה יְשַׂמַּח אָבִיו וְרֹעֶה זוֹנוֹת יְאַבֶּד־הֽוֹן׃
