I think Mike Saylor has way more Bitcoin in his own stash than his company does.
As of the last time when Saylor made his bitcoin holding public, he owned less than what the company holds; it was 17,000 bitcoin, but that has been long, and the number has not been updated, and he also owns up to 10% of the total company share in MicroStrategy.
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.
I think otherwise. I'm not sure when exactly Saylor started investing in bitcoin, but he did not start on time. At first he was sceptical about bitcoin and was said to be a critic of bitcoin. Back then, it was during 2020, if I recall correctly, that his stance on bitcoin started changing positively, unless he had been accumulating it in the background while criticizing it openly.