it will only work as long as they continue to find people who want to buy their bonds and that implies that people don't have access to buying bitcoin directly, that is the simple strategy -- if institutions cannot buy bitcoin, but can buy stocks and bonds then microstrategy will continue to work
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As long as bitcoin price moves up every cycle, $MSTR stock price will move up faster than bitcoin price, their bonds will make gains also. As hundreds of trillion dollars currently invested in toxic assets, and a lot of these money canโt invest directly into bitcoin, wonโt they want to invest in an asset growing even faster than bitcoin? I will, and invest as much as I possibly can. As the cycle continues, money will keep coming to MSTR as it has a BTC yield and the best performance.
The other reason that their bond will be in high demand is as the treasury bond market in a slow train wreck, $MSTR bond will serve as escape valve for the bond investors. This also applies as other kinds of bonds caters.