Rabbi Yosef Dovid Josilowsky
Answer:
Everytime you lend money, there is some sort of risk that at the end of the day you won't get it back. However, even though nothing is 100% guaranteed, since there are certain assets that are guaranteeing my investment (my assets are being insured by the owners assets), it can be viewed as having an issue of ribbis.
It doesn't say anywhere that if the loan is structured with only specific places to get it back, it's not an issue of ribbis. (For example, if an LLC goes bankrupt, we don't have anywhere that it says clearly that now there is no issue of ribbis, because there was such a risk from the beginning that this could've happened.)
Reb Moshe has a famous heter that you may be allowed to lend with ribbis to a corporation. But there are numerous achronim who disagree with this assertion for a variety of reasons, some mentioned below.
One example that the Rishonim talk about, is where someone sends a mashkin (collateral) for a loan. Even if he doesn't take any responsibility for it, it is a problem, as you are guaranteeing the loan. Tosafos mentions a heter that if it is done through a goy, and the goy takes responsibility for the loan, it would be ok.
Another typical example, which brought down in the gemara is batei arei choma (places that had a wall since the time of Yehoshua Ben Nun). These places have a special halacha that I can sell you a house and I can come back and redeem the house within a year even though it is ribbis. However if I do that, I should be able to collect rent, as otherwise he was just using my house for free? The gemara says that although he was using the house for free and it is ribbis, there is a special heter in this case. There is no personal liability for this loan, the only thing is that if you don't redeem the house, he'll take the house from you. If the house falls down, he will lose his money, so why doesn't that risk make it not ribbis? It seems to be that as long as there are some assets that are guaranteed it is ribbis.
The gemara says that this is true even by benai hair, where people are selling a shul with the right to buy it back. If the sale is negated afterward, lemapahrea (retroactively) it would be viewed as a loan, and is ribbis. The question is, if it is retroactively viewed as a loan, who would be responsible to pay the money? The kehilla? It seems not, and that it would be ribbis, but there is a special heter in this case. This would seem to be comparable to a corporation, as it is not a single individual, rather an entity that has the responsibility of the loan, and is still considered ribbis. For this among other reasons, the Minchas Yitzchak has an issue with Reb Moshe's heter to lend to corporations.
Personally, I believe that anytime there is some sort of security or guarantee up front, like perhaps a case of preferred equity, it may be more stringent. Perhaps even Reb Moshe would agree in this case that the heter to lend to corporations would not apply.
Question: So if the person with the aforementioned situation came to you, are you telling him to stay away from this deal?
Answer: No, there is always a solution with Ribbis. The heter iska has to be structured in the proper way for the specifics of each individual case. But usually if you prepare in advance, know what you want to do, and discuss it with Rabbanim who have knowledge in Chosen Mishpat there will be a way to do it in accordance with halacha.
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