Why MicroStrategy Will FailIf you listen to Michael Saylor, watch what he is doing with his financial engineering, and "learn about Bitcoin" it seems incredibly obvious that... MicroStrategy WILL NOT fail . At least, that is what I have been told by those that stand to gain massively from Bitcoin's price appreciation. It makes a lot of sense: corner the market of Bitcoin supply => force the price into "discovery" mode and everyone that believed in him and Bitcoin will be rich to the point they feel they deserve for being so prescient with their wisdom.
The history of finance does not bode well for such absolute certainty...
I began shorting Microstrategy with Puts over a year ago. "Being early and being wrong are often indistinguishable in trading/investing." I've lost money. But that did not dissuade me from calling BS on this scheme.
Up until November 22, 2024 it had been a small trade that had not worked out so far. But on that day Saylor gave a CNBC interview (highly recommend looking it up) where he talked about their "core business", their "Bitcoin reactor", "selling volatility", and lots of complex financial jargon. To some, this might come across as brilliance. To me, having been in markets for a long time and studying their history it was patently obvious he was doing the classic, "if you can't amaze with brilliance then dazzle with bullshit" tactic. This was not a scam, nor a ponzi, nor a fraud... in absolute terms. We don't actually have a word for it. But it needs a derogatory term because people are going to lose money buying into it.
I don't believe in karma. What I believe is that people cannot help be themselves and repeat their character flaws and patterns. This is not the first time Saylor has engaged in "financial engineering". Over 20 years ago MSTR (same company, same symbol) got caught by the SEC for doing much the same thing a Enron in their accounting practices. They were levied a big fine and the stock dropped -60% in a single day. Roughly two weeks later... the entire dot-com bubble imploded. Was MSTR the catalyst for this collapse? Unknown. But it certainly did not help keep the bubble going...
Once again Saylor is exploiting the financial system. Or as gamers would call it; "clever use of game mechanics." There is nothing illegal about what he is doing (that is apparent). It's all out in the open. But it's leverage. Lots of leverage. MSTR ran out of simple debt and have found other ways to make cash to buy Bitcoin. Every week they keep "buying the top" as cheerleaders for this asset; Bitcoin. Trying to get others to join in their crusade to... I guess get it to $1 million now. Still valuing it in fiat terms while claiming to be changing finance (do they still want to do that anymore with Blackrock being their best backer? Unknown.
I left all my Bitcoin Maxi chats as part of a New Year's Resolution to argue less with people on the Internet after 2024. When I left I was still defending my short while they were eagerly buying the dip. With all investments... time will tell.
The Trade
I have been purchasing Puts in different traunches with different strikes going out all the way to 2027. These long term Puts have their theta offset by selling shorter duration options to keep myself theta positive. This has been great over the last 2 months with increased IV. During the recent drop to $285 I actually found myself delta positive for a day. I wanted to get "more short" and added as much risk as I felt comfortable on the last push up to $380. Now delta negative/theta positive.
Where I stop out: $390 is a key volume profile level topside. If price gets back above there I consider myself wrong... for now... and start to unwind risk or hedge more
How I manage: I will continue to manage my delta/theta as long as IV makes it fun while always trying to stay negative. Buy long dated puts on pops up; Sell some Puts on every move down. The goal is for MSTR's debt to start getting called this year and they be forced to make some hard choices. This may require Bitcoin and/or the equities market to collapse in 1-2 years. If so; MSTR will be hurt tremendously.