I believe that he is planning on holding bitcoin longer.. but yeah, he might not even be alive by then.. 21 years from now, he must be pretty close to 80 by that time, if he were alive.
But, surely no problem for a person or a company to project out their own plans, even though surely there is no commitment that any person or company would have in order to have to stick to such commitment in terms of if facts might change that end up influencing changes in opinion and/or actions.
Yeah, there's no telling what's going to happen that far into the future--especially when you're talking about bitcoin, which we all love but in truth is a relatively new and very controversial asset. And by controversial I mean there are still a lot of skeptics in addition to whatever regulations governments might put into place that could hurt it.
But man, with bitcoin at $75k Michael Saylor must be tap dancing on the ceiling right now, and I'd bet that it's going to go much higher. As far as what MSTR might do with its bitcoin holdings 20+ years into the future, the question reminds me of what the future of Berkshire Hathaway is going to be once Warren Buffett dies and his successor takes the helm. It's possible that in the case of Saylor's death, a new CEO might not be such a big fan of bitcoin and could start unloading it....but obviously that's pure speculation. I don't have a crystal ball, and I don't think anyone else here does either.
*GO BITCOIN!!*
For sure, Saylor has not been silent in regards to stating his investment thesis and the various reasons behind his investment thesis on a fairly regular basis, and it seems to me that largely with the passage of time, he has gotten more aggressive and more convicted including coming up with more and more strategies to double down on his previous levels of conviction, so in some sense, he has contributed towards putting himself and his company into "the" kind of go-to place for certain kind of investors to get into a certain kind of bitcoin price exposure, including that the larger and larger his stake becomes and the more that he had been actually following through with his previous plans, the more credibility that he gainz in regards to someone who stays convicted towards following through with any statements that he makes.
Saylor and/or MSTR could waffle, yet there is no real reason to expect that they are going waffle absent to strong justification for doing so, and some mere changes in regulations here and there or some other price difficulties are not likely to shake him out of his position, since historically he has already shown that he is not shaken easily and when in doubt he errors on the side of buying more rather than hesitating.
For anyone studying and looking into bitcoin, even in the 4.5-ish years that Saylor/MSTR has been into bitcoin, many aspects of bitcoin have been playing out at least as bullish as expected, so there are likely ways in which conservative (and even worse scenarios have been expected), yet bitcoin largely has been continuing to deliver as good as could be expected.. even though of course, we could imagine even more bullish scenarios that could have had played out in bitcoin, yet even the scenario that has been playing out is nothing to really complain about, even if there are more bullish scenarios that could have had played out.
But man, with bitcoin at $75k Michael Saylor must be tap dancing on the ceiling right now, and I'd bet that it's going to go much higher. As far as what MSTR might do with its bitcoin holdings 20+ years into the future, the question reminds me of what the future of Berkshire Hathaway is going to be once Warren Buffett dies and his successor takes the helm. It's possible that in the case of Saylor's death, a new CEO might not be such a big fan of bitcoin and could start unloading it....but obviously that's pure speculation. I don't have a crystal ball, and I don't think anyone else here does either.
*GO BITCOIN!!*
In the case of Warren Buffet, I don't know how BH will perform after his death but he has left advice to the trustee of his estate to put 90% in the S&P 500 and 10% in short-term government bonds.
Between now and 2045 we do not know what may happen, so if Saylor dies then many things may have changed. On the other hand, if he dies soon, whoever takes over the reins has no choice but to follow the plan Saylor has laid out for continued success, especially with the institutional adoption that is coming. Deviating from the plan in the slightest would mean cascading stock sales.
It seems to me that any deviation from the MSTR plan laid out by Saylor would likely have to be well justified and well within the spirit of the original plan... and of course, Saylor would have more credibility to deviate as compared with any successor, absent the successor building his own credibility.