While MicroStrategy is indeed holding its BTC at a roughly $520M unrealized losses, their strategy clearly shows how even after buying at the top you can be successful.

I think nowadays there does not go one single month without the news of MicroStrategy buying some more Bitcoin and increasing their holdings to even more absurd numbers, to some numbers where I believe no big company will be able to catch up to anymore. But MicroStrategy has not always been the smartest in buying BTC and they seemingly don‘t care:

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MicroStrategy Portfolio tracker, chart from Bitcoin News on Twitter/X

Here we can see each purchase of BTC for MicroStrategy over the last two years and we can also see the current average purchase price of roughly $29k. It's pretty low, but as we can see they also bought BTC quite often at the very top of 2021 at prices of roughly $55k+.

Their strategy seems to be akin a DCA strategy, we often meme about “MicroStrategy is DCAing“, but this is pretty much the reality. Even if we can‘t really see where exactly they buy BTC, as MicroStrategy usually makes many small purchases over the course of months and weeks. Their goal most definitely is to just average down their purchase price, that is also why we saw many more purchases of them in this bear than in the 2021 bull market.

So, if Micheal Saylor can go buy the top and still be pretty much a successful trader, even after remaining $520M in unrealized losses, we can surely do that too. Buying the top at BTC actually is no issue at all, you can quickly prevent a “Buy high Sell low“, by occasionally buying BTC at low prices and you will usually have over one year to do that in a bull market.