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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.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
Rabbis in Midrash
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Kuzari -Rabbi Ari Shvat Kuzari class 9 - "Seeing is Believing" (parag. 21-30)
These paragraphs elaborate on the theme that seeing and knowing is better than any attempt to prove logically, and begins explaining the difference between Israel and gentiles.
Ein Aya Various Universal Stages of the Geula Process
Rav Kook examines the various stages of redemption, explaining how (in addition to the obvious oft-mentioned stages of ingathering the exiles, reviving the Hebrew language, army, state etc.) the messianic dream of world prosperity, the State of Israel and world unity can and are realistically and logically gradually coming true.
Kuzari -Rabbi Ari Shvat Kuzari class 8- "Answering Questions on the Kuzari's Proof from Mass Revelation
How do we know that the "claim" of mass revelation to 2,000,000 witnesses at Mt. Sinai is really true? This important class answers all of the questions skeptics ask about this claim of the Kuzari.
Ein Aya Armies Still Necessary for Balance & the War Against Wars
Rav Kook explains why the world was originally divided into the various seemingly contradicting ideologies and cultures, in order to develop each one respectively. Swords or armies symbolize how each respective ideology defends themselves, as well as deters their opposing ideologies and cultures. On the other hand, the messianic era will be one of peace, and Rav Kook explains the transition to that stage, which mankind is already undergoing.
The Land of Israel LGBT'S IN ISRAEL
The question was asked, how can one make Aliyah with the LGBT parades?
Kuzari -Rabbi Ari Shvat Kuzari class 7 - Five Accumulative Proofs of G-d
As a preparation for the Kuzari's classic proof of G-d from the mass-revelation at Sinai, we start here with 5 other directions to strengthen our belief which also contribute to what the Kuzari will present as well.
Ein Aya Muscle & Meaning: The Dual Nature of Gevurah (Physical Strength)
Is physical strength and fitness a necessity or an ideal? Although it if often totally overlooked among topics of Judaism, Rav Kook writes that it clearly is also a necessity to deter the many enemies of Israel, but even in Y'mot HaMashiach, in the Messianic era, to a certain extent, it's ideal continues even after our enemies will have been finished off.
