1. Sure, I agree that nothing is actually no risk, but this is close enough that I can call it that comfortably. I have zero doubt that he would make things right no matter what, based on past experience and knowing him well.
2. I have negative money there, so I'm not worried about it. Even if I had positive money, there is SIPC coverage of both securities and cash.
3. I would never get into a situation with a single point of failure. IBKR could die and I'd be fine. I don't mind the extra step of having to liquidate something in the extremely unlikely event that IBKR disappears.
A conversation
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I see. I understand what you're saying but I think we might be talking about different categories of risk here. Have you read any of NN Taleb's books? He explains these things better than I could.
I think you might enjoy Fooled by Randomness or The Black Swan (the latter is most relevant here). I'd recommend only reading the first 2/3 as he tends to waffle on at the end!