Uber seed investor and executive producer of the All In podcast Jason Calacanis has been publicly sounding the alarm bell about Microstrategy's bitcoin treasury strategy and the cheer leading exhibited by the company's CEO, Michael Saylor. Calacanis believes that Microstrategy's bitcoin acquisition techniques are a Ponzi scheme waiting to implode. Going as far as to question whether or not Microstrategy is the next FTX.

Earlier today, Jason spent a section of an episode of This Week in Startups to discuss his worries about MSTR's bitcoin treasury strategy, Saylor's overt pumping of the strategy, and the fact that there are other companies like Marathon Holdings beginning to deploy similar convertible debt strategies. While I can see how this can be unnerving for many, I do think there is a fundamental misunderstanding of what Microstrategy is doing. Last week I explained the strategy in a tweet, which I'll reiterate here:

Whether you like it or not, Saylor and Microstrategy have found a way to give pools of liquidity (particularly pools with mandates to allocate to fixed income) exposure to bitcoin’s volatility via convertible notes. The converts are performing better than any other fixed income product on the market.

Other investors have noticed this and have piled into MSTR as well understanding that demand for the converts will increase and enable Microstrategy to accumulate more bitcoin. Those investors feel comfortable with the premium to mNAV MSTR is trading at because they believe the demand for a high performing fixed income product will remain high and likely increase.

Microstrategy can continue doing this until viable competition comes to market because there is no one else offering this type of bitcoin return exposure to fixed income investors at scale.

Another important detail, the convertible notes have a duration of 5 years or more while bitcoin’s lowest 4-year CAGR is 26% and its 50th percentile 4-year CAGR is 91%. If you think this will continue then this is a pretty safe bet for Microstrategy and the convertible note holders.

In a world were central banks and governments have gone mad with currency debasement and debt expansion it is pretty safe to assume that bitcoin adoption will not only continue but accelerate from here.

What do I think about Microstrategy accumulating this much bitcoin? It makes me a bit uneasy but there’s nothing I can do to stop it and bitcoin will survive in the long run. Even if Microstrategy blows up somehow (I don’t think this is likely). Bitcoin was designed to be anti-fragile.

This is a classic case of “don’t hate the player, hate the game”. Or better yet, join the game. After all, the only winning move is to play.

Essentially, Michael Saylor is taking a long-term bet on bitcoin's continued adoption/monetization and trying to accumulate as much as possible by issuing convertible notes with a 4+ year duration, which should increase the likelihood that Microstrategy is in the black on their bitcoin buys over time as history has shown that anyone who holds bitcoin for more than four years has performed well. This should, in turn, be reflected in their stock price, which should increase alongside bitcoin and convert the debt they've accrued into newly issued shares of MSTR. Through the process, if the strategy is executed successfully, increasing the amount of bitcoin per share for MSTR shareholders. (This is the only metric shareholders should care about in my opinion.)

Yes, this may seem crazy to many and extremely risky to most, but that is the nature of free markets. Every company takes calculated risks in an attempt to increase shareholder value. Michael Saylor and company are betting on the fact that bitcoin will continue to be adopted and are utilizing pools of capital that don't have the ability to buy bitcoin directly, but want exposure to its volatility to achieve their goals. To me it looks like a perfectly symbiotic relationship. Microstrategy is able to accumulate more bitcoin and increase their bitcoin per share while fixed income investors are able to access a product that performs well above their benchmark due to the embedded volatility of the exposure to bitcoin Microstrategy provides.

This won't be a surprise to any of you freaks, but I think it's a pretty smart bet to make. Bitcoin is almost 16-years old. It has established itself as a reserve asset for individuals, companies and countries. A reserve asset that is completely detached from the whims of central planners, transparent, predictable, scarce, and can be transmitted over the Internet. Bitcoin is an idea whose time has come. And more people are beginning to recognize this.

This is one of the beautiful aspects of the public company convertible-note-to-bitcoin strategy that Microstrategy has deployed over the last few years. They are able to harness the benefits of forces that are external to their core business to provide shareholders with value. Michael Saylor could stop buying bitcoin tomorrow and it wouldn't affect bitcoin's adoption in the medium to long-term. He continues to buy bitcoin, and encourages others to do the same, because he recognizes this.

Bitcoin is the apex predator of treasury assets for every individual, company, non-profit or government. The assets competing to be treasury assets are all centrally controlled, easily manipulable, and quickly losing favor. Earlier today, Federal Reserve Board Governor Christopher Waller came out and admitted that inflation is kicking the Fed's ass. They cannot tame it.

Waller may posture by saying that "submission is inevitable", but that doesn't make it true. There is simply too much debt and not enough dollars. The annual interest expense on the US Federal debt is now larger than our spending on national defense. The Fed, whether it wants to admit it or not, is going to have to monetize that debt via the debasement of the dollar. If you are using dollars as a treasury asset it is very important that you understand this and react accordingly by adopting a bitcoin strategy. This is what Michael Saylor is trying to make his peers in public markets understand.

Sure, his marketing tactics may seem a bit uncouth to many and the way in which he's expressing his belief through Microstrategy's accumulation strategy may seem risky, but it's hard to argue that his core thesis is flawed. Especially when you consider the fact that bitcoin has officially climbed to the strata of being seriously considered as a treasury asset for the most powerful nation state in the world.

I listen to the All In podcast quite frequently and genuinely like the show. It is a good way to gain perspective on how Silicon Valley investors view the world. If I were to give Jason any advice it would be to take a step back and to view bitcoin through the lens of one of the most frequently discussed topics of the last twelve months on his show, the emergence of AI and the importance of incorporating AI into your business and workflow as quickly as possible before you get left behind. The same mental model applies to the emergence of bitcoin as a dominant reserve asset.

Bitcoin Treasury - The Fourth Lever to Equity Value Growth

Most companies do not hold enough bitcoin There is a saying you often hear in bitcoin circles that “you can never have enough bitcoin.” This is typically expressed by those who have spent the time to both understand bitcoin’s unique and superior monetary properties and also to appreciate why tho

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It is imperative that every individual, company and government adopts a bitcoin treasury strategy if they want to be able to succeed moving forward without the inherent resistance that is introduced from storing the fruit of your labor in a money or money-like asset that does not preserve purchasing power over time. Just because Saylor has recognized this, moved aggressively to effectuate his understanding via his company's balance sheet, and vociferously markets the strategy to others doesn't mean he's wrong.

As I said in my tweet last week, I personally prefer to hold actual bitcoin. That doesn't mean that Microstrategy and others haven't honed in on something unique and legitimate given their circumstances and access to certain financial tools.

Final thought...

I apologize for the extended hiatus. I hit a hard wall of writer's block over the last month. I think the time away from the keyboard has been good for me and the quality of this rag moving forward.