In 2013 he had completely different views on it, so he didn't do it through its whole existence for sure.
From 2013 to 2020 when Michael Saylor changed his mind and actually started MicroStrategy investment in Bitcoin, there are enough time for him to change his mindset on Bitcoin and take action. It's luckily that he changed it years ago, and had enough time for accumulating Bitcoin at many cheaper prices than in 2024 and 2025 as well as in future years.
Other institutional investors who came in this market cycle and future ones will surely feel a little bit of jealously with Michael Saylor and Strategy which are like a role model for tech giants and institutional investors in Bitcoin market.
Although MicroStrategy has an advantage over other organizations when it comes to investing in bitcoin in 2020. At that time, there weren't many institutions interested in bitcoin and ETFs weren't available yet. But they only really started buying bitcoin like crazy from 2024 and so far they hold 568,840 BTC at an average price of nearly $70k per bitcoin. That means they are holding onto about 50% of the unrealized gains (about $20 billion) over a 4-year holding period. This is a dream profit for individuals and small organizations, but still not attractive compared to large corporations. That may be why the largest corporations in the United States as Apple, Meta, Microsoft, are still in no rush to invest in bitcoin.