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Speaking as a tax attorney, when someone does something like this, it is motivated by liquidity concerns. Meaning, that the person has a lot of valuable assets

Speaking as a tax attorney, when someone does something like this, it is motivated by liquidity concerns. Meaning, that the person has a lot of valuable assets but not in a form that can actually be spent, and they want cash they can actually spend on something. While most similarly situated individuals normally would take out a loan against their assets, in some situations that may be impractical or not possible. For example, the banks may be unwilling to make further loans if the individual already has a large amount of such loans (as Elon does), or if the underlying asset (Tesla stock) is viewed as overvalued (which many analysts have argued).

ryzvonusef 5y ago
If I may have a bit of your time, usually sales like this are pre-arranged. Billionaire goes to a Bank (like GS or whatever) tells them I need to sell X number of Shares by Y date on Z price, the Bank gathers up the buyers, and then the the transaction is committed in one fell swoop, on market down, GS takes their commission and it's over by the time the markets open next Monday What are the pros/cons of doing this bit by bit, over such a long period of time, on the public market? He is still not done and will be selling well into next week.