I don't see Jack going the path that Michael went. Jack has far too many hurdles and he holds or controls only 2% of Twitter's stock while Michael holds 22.6% of Microstrategy.

Jack is also in the cross hairs of activist hedge fund Elliott Management who in an agreement with Twitter put 2 members on the board. This hedge fund will squeeze every nickle of value out of Twitters stock after taking a 1 billion dollar stake. I would see no reason for Elliott Management to support value creation from moving Twitters cash to BTC as it would be diluted. They would be better off directly buying BTC. Activist shareholders generally are not long term holders, they will drive up the stock price and sell, push up dividends or spin off assets.

Jack also said he was moving to Africa for 3-6 months this year because he sees Africa as a good opportunity for BTC. He later walked that back in light of COVID. Point being it was a psychological tell in that he is ready to move to the next adventure in the business world. He left the CEO seat at Twitter for 7 years after being pushed out with the interesting part being rumors of why. Further consider his training.

While he is pro BTC I don't see Twitter as the business vehicle he will use to develop a strong BTC enterprise but I could be wrong.

Jack may however be able to move some cash from Square treasury to BTC, I have not reviewed their board.

However applying a little game theory to the approach of companies taking large positions in BTC is interesting. I can't put it all here, but what will happen to Microstrategy in say 10 years assuming BTC is a million dollar coin? Their 38,250 BTC would be worth over 38 billion dollars far eclipsing the current value of the company. This would put them and any other company that did this in the similar position as Yahoo.

The sale of Yahoo's digital assets to Verizon created a shareholder revolt due to Yahoo's 50 billion dollar stake in Alibaba. Any company having major cash or cash equivalents on the the balance sheet has always created problems. The same thing happened to Apple.

Also consider why it took the Yahoo holding company years while spending million to sell off the Alibaba stake, tax.

These companies and whales that have large holdings of BTC will almost become vassal states. This will drive governments to use regulation and laws to extract that value from the holders. And with US politicians, as well a others proposing "wealth taxes", what will they do when BTC is at 10 million a coin?

In the end governments are in a good position to become stackers.

Cheers