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Answer: When considering involvement in "non-Shabbat-friendly" fields on Shabbat without a forbidden action per se, one has to look at four Shabbat prohibitions.
1. Hachana (Shulchan Aruch, Orach Chayim 323:6) – Doing something on Shabbat so that it does not need to be done after Shabbat, even if no melacha is needed after Shabbat. This issue does not apply to this case, because the opportunity that arose on Shabbat is unique and is not instead of something you would have had to do after Shabbat.
2. M’tzo cheftzecha (Shulchan Aruch, OC 306:1) – Taking steps to advance a specific melacha after Shabbat. Here, there is no specific melacha on the horizon, as your son would just be amassing information, with no actions related to it on the horizon.
3. Shitrei hedyotot (Shulchan Aruch, OC 307:13-16) – Reading matters that could cause problems on Shabbat. There is discussion in the gemara (Shabbat 149a) as to the exact concern, but the Rambam (Shabbat 23:19) and Rosh (Shabbat 23:1) both connect it broadly to weekday-like activity (see this column, Mishpatim 5784, dealing with newspapers. There is a consensus (see Dirshu 307:70) against reading commercial advertisements, even if one is not intending to thereby "shop.") However, shitrei hedyotot does not apply to oral exchanges.
Bemare Habazak - Rabbis Questions (654)
Rabbi Daniel Mann
677 - Ask the Rabbi: Gluten-Free Diet and Shabbat Considerations
678 - Ask the Rabbi: Stock Market Talk on Shabbat
679 - Ask the Rabbi: Bedikat Chametz for Guests at a Hotel
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Thus, just discussing the stock market generally avoids all of the above prohibitions. However, as a kind of composite of these issues, it is accepted among bnei Torah not to engage freely in nitty gritty economic discussion. This is in line with the halacha (Rambam, Shabbat 24:4; Shulchan Aruch, OC 307:1) that one should not speak at length about idle matters. Commerce matters are "worse" in this regard than many idle matters (see Mishna Berura 307:63). While most of the strict sources discuss reading commercial matters, not speaking, speech is worse than thought (Shabbat 113b).
It is too draconic and not in line with halacha to forbid a passing statement about the stock market or a business. Even regarding more serious discussion, like the people you mentioned, a conversation about stocks can be justifiable because the Rama (OC 307:1) says that one may talk at length about idle matters if he gets enjoyment from such discussion. For some people, discussing stock trends is enjoyable like for other people discussing the NBA playoffs is. However, we do not recommend to people (including your son) to center a discussion on Shabbat on the stock market.
Does the mitzva of teaching your son a profession change the picture? It is permitted to arrange on Shabbat for a son’s professional training (Shabbat 150a; Shulchan Aruch, OC 306:6), as the mitzva creates an exception in the laws of m’tzo cheftzecha. However, this leniency permits only discussing engaging the educator, not negotiating a contract. We also do not find that a student of the field should be involved even in training that does not directly violate Shabbat. Thus, to the extent that listening to the discussion is your son’s vocational training, it should under normal conditions be off-limits on Shabbat. The content of some fields, e.g., medicine or some areas of social sciences, is ennobling and likely Shabbat compatible. Commerce, while a perfectly fine professional field, is generally not. If you see these men as potential mentors, mentorships can probably be arranged at a different time or manner. However, if your son enjoys and gravitates on his own to such a conversation, it would likely not be wise to stop him.
Bemare Habazak - Rabbis Questions Ask the Rabbi: Omitting Tachanun in Selichot in the Presence of Simcha
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D'varim Judaism’s Social Vision
Re’eh
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
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Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
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