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I wonder what he uses for seed storage/backup.
Just imagine him (or anyone of us, for that matter) losing the master wallet seed.
Historically he had been accused of ONLY holding all the keys at Coinbase, and then he hinted at having several custodians, so it seems that his custodial solutions are not very clear - though maybe I am missing any further disclosures that he had made in more recent times - since I would speculate that anyone investing in his various bitcoin accumulation (and HODL forever) strategies would want to have some assurance that he is not going to end up losing the coins.
I can't say I remember him ever specifically mentioning his personal (or his company's) security practices. Such things could be considered private matters, not to be disclosed and/or discussed publicly, which makes sense. Being in control of over 330,000 Bitcoin puts a heavy burden on the owner(s) in terms of making sure nothing gets leaked or lost.
[...as above...]
he once said they use an institutional custodian
Really? I would think this would be against his principles ("not your keys, not your coins" and all...), but with such amounts to deal with, I can (kind of) understand him. Also, it's MicroStrategy, not Saylor personally.
To date, Saylor has not been much of a vocal advocate of NYKNYC, and he has been greatly criticized for making statements to the contrary, including criticizing cryptobros who insist on holding their own keys.. including that he had to walk back some of the levels of the harshness of his statements that seemed to overly criticize those advocating self-custody.
It is possible that Saylor might come around on this self-custody point (especially since a lot, if not all of bitcoin's power comes from abilities to self-custody it), yet it is a bit of a problematic area with Saylor, his practices and what he seems to be advocating, at least up until recently.
I agree with you that it would be quite powerful if Saylor were to lose access to a big chunk of coins...probably contributing to some turbulence in the BTC markets too, depending on how it plays out, even though as we realize positive side effects of taking coins off of the market does increase the value of the coins actually held by others... Saylor knows about that, since he also talked about dying with his coins... though he would not be able to die with MSTR's coins unless there were flaws in their custodial arrangement in which ONLY he had the keys.
Reminds me of a bit of a joke and it would be funny if Saylor was giving some presentation and then mentioned that he had all of his coins on a ledger that was dangling on his neck (and you know how so many bitcoiners don't have very good impressions of the security of ledgers - but also the OPsec would be a strange sight too).. or if he said that he had all of the seed words memorized.. would he use 12 words or 24 words? He's got a big brain, so he could probably handle 24 words, and scatter them through at random points in his various presentations... 331,200 BTC hidden in plain sight.
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OT -- Your last paragraph reminded me of a riddle someone uploaded many years ago on the net: an image containing clues leading to a wallet containing something in the order of 325 BTC (IIRC). The riddle was extremely hard to solve (for me at least, would not even dream of being able to solve it). Still, someone allegedly managed to solve it pretty quickly (maybe in the first month of posting the riddle, again, IIRC). Some people (were they posting in this forum/thread?) had suggested a conspiracy theory of the owner and the solver being the same person, doing this to pass the coins as earnings being donated to him by some mysterious big coiner wanting to play a game.
As for Saylor, I do enjoy watching him talk about monetary energy and thermodynamically sound money, and buzzing hornets and all that stuff. He certainly has a charisma of communicating his ideas in a very entertaining and persuasive style. He does a good service educating the masses about Bitcoin, I like him for this reason and I do point inquiring friends to his videos.
Having said the above, I still do consider him (to a degree) as part of the "establishment", in terms of his role as exec. chairman of MicroStrategy and his entrepreneurial background. He certainly is no anarchist trying to demolish the traditional monetary establishment. If anything, he is pushing for compliance, legislation, regulation and acceptance of Bitcoin by the traditional players, and, perhaps, that is a more realistic approach to the future of Bitcoin than some anarchist trying to change the world. So, in that sense, I would not be surprised if he was not so much in favor of NYKNYC and used an institutional custodian for managing the bulk of his coins.
For small players, fish and such, like most of us, I would consider NYKNYC and related security practices as absolutely essential in securing our stash. I would not permanently park more than single-digit BTC amounts in an exchange.
