Saylor strategy about Bitcoin is working fine. He has 193,000 Bitcoins bought at 6 billion usd and his current holdings has value of 13 Billion. So as long as his strategy is working, he doesn't have to worry at all.
Saylor's strategy?
It's what many of us have been preaching for years:
Buy, hodl, don't sell unless you must, get rich in the long run.
Easy peasy.