They take a bath in FIAT...but bitcoin per share doesn't change. Thinking of MSTR priced in terms of NAV, is an incorrect framing. What is Microsoft stock price to NAV? 30 times? 3x NAV is crazy low risk compared to betting on NVDA or MSFT that 95% of the stock price is forward expectations that they will continue to have radical breakthroughs and continue growing.
TLDR: MSTR, because 95% of its assets are BTC, has the most volatility of almost any stock. Issuing the convertible bonds is a bridge to traditional finance, especially the bond market, which has been saddled with artificially low interest rates for 30 years. Due to government and non-government regulations, many of the funds that are buying these bonds can only buy bonds, which previously were underperforming in real terms (7-15% inflation, 5% yield even on junk bonds). The bonds are basically 100% of bitcoin upside, and 0% downside...you can't lose, and the demand for these is only going to increase. Even in a bitcoin bear market, the bonds are dated like 5+ years out - they will still sell.
As long as the Fed keeps interest rates artificially low (below the inflation rate) which THEY HAVE TO, until currency collapses, I think MSTR is the only company that can do what they are doing. Sure Apple or MSFT could buy bitcoin, but it would be such a small percentage of their business, they would not have the wild volatility that MSTR has - MSTR is the only way to do this now, he has a 4 year head start, and 400k BTC. Yes, I think its more risky than just holding BTC, but I have strong conviction that bitcoin will go up forever, and therefore MSTR has a good chance of continuing to be a bridge from the huge pools of assets stuck and bleeding out in traditional finance, to bitcoin. I want to own part of that because right now it is the highest performing stock in terms of bitcoin per share than anything else.
I measure my wealth in bitcoin, and I want to continue to have more bitcoin every year - I wouldn't risk my real bitcoin, but my ETF bitcoin (not even redeemable for real bitcoin, yet) I figured why not. If bitcoin breaks, and the world gets worse, governments are coming for retirement accounts and its gone anyway. I had about 1k shares of MSTR from when it was cheap, and I bought more when it was $400, for every ETF "bitcoin" I sold, I'm only getting 0.4 BTC in MSTR, but if that even returns 10% BTC per year for the next 15 years? It will be 1.6 BTC per 1 sold now (at $400/share).
How long does hyperbitcoinization take? If it takes 30 years to drain the bond market (I think its the first domino to fall to bitcoin), then how much will my MSTR be worth, averaging 10% BTC per year? 6.4 BTC per 1 BTC invested now.
If it only takes 15 years to drain the bond market, then I would expect higher bitcoin returns in MSTR - maybe 25% over 15 years. So in only 10 years, that 0.4 BTC becomes 3.2 BTC (Rule of 72 - divide 72 by the CAGR and that is the number of years it takes to double, also works for inflation: 72 divided by inflation rate is the number of years for your purchasing power to be cut in half)