I think Mike Saylor has way more Bitcoin in his own stash than his company does. He probably bought Bitcoin throughout its whole existence and started the company to bring in outside investors. This way, he's not only promoting Bitcoin to the masses but also making a lot more money from his investments. Of course, I could be wrong, but for some reason, that's how I see the whole story.
In 2013, Michael Saylor compared and likened bitcoin to gambling, he did not believe in its future. He only really changed his mind about bitcoin after spending time learning about it and the crypto market in 2020, and that was also when the covid pandemic hit our economy.
Although no new information was mentioned, according to his previous statement, he personally owns 17,732 Bitcoins and this is the Bitcoin that he asserts will never sell. Not the amount of bitcoins the company holds because he doesn't have full control over them.
MicroStrategy was founded in 1989 and they also started investing in 2020.
https://x.com/saylor/status/413478389329428480
The best decision Michael Saylor and MicroStrategy took was to invest in bitcoin after they saw its future potential growth. I may be wrong but i think that even as Michael Saylor criticized Bitcoin as gambling, he may have secretly be holding bitcoins why trying to scare people away from investing. Besides even if bitcoin was a gambling as he stated in 2013, people still win and become successful through gambling but the only thing that paints gambling bad is due to the fact that most people fail while few win.
If someone has once made criticisms about bitcoin and later found out that what he criticized is the sure way to financial liberation and at the time of discovery, continued investing since 2020 till now, it means he has really identified a long term value in it and he is ready to take all the risks to get to the top. Today, once a bitcoin critics have now become one of the biggest holder of the asset he once criticized while many who are believers in bitcoin couldn't even own much in their portfolio and others are just fans and no coiners.