The Bitcoin community’s opinion about Michael Saylor and Strategy ($MSTR), formerly MicroStrategy, seems to be just as volatile as the company’s stock. And honestly, I get it. I bought my first Bitcoin in 2014 and have closely followed the space ever since. Along the way, I’ve seen many heroes rise and fall. Eventually, skepticism toward any large player in the industry becomes natural—and rightly so. Remember: don’t trust, verify. Before we dive into verifying Strategy’s plans together, TBL Pro readers, I want to acknowledge something about Michael Saylor. Whether you like him or not, agree with him or not, his willingness to lead from the front is undeniably admirable. Recently, I listened to an interview between Tim Kotzman and Strategy’s CEO, Phong Le. While I haven’t fact-checked every statement, it seems clear that Strategy has consistently remained at the forefront of innovation for a long time. Innovation appears deeply embedded in the company's culture and DNA—and I'm almost certain that's largely due to "Mike," as Phong likes to call him. But what truly defines a pioneer? At their core, pioneers venture into the unknown, driven by curiosity, vision, and determination. They challenge established norms, embrace uncertainty, and often endure significant setbacks. Not all pioneers achieve immediate success—many face failures, obstacles, and doubts. Yet, even during setbacks, pioneers adapt, learn, and pave the way for others. Ultimately, the legacy of pioneers is defined less by their successes and more by their courage to push boundaries and inspire progress, regardless of the outcome. We’ll revisit this idea a few times, I'm sure.
As bitcoin's role in the global financial landscape evolves, understanding its potential impact on your wealth becomes increasingly crucial. Whether we see measured adoption or accelerated hyperbitcoinization, being prepared for various scenarios can make the difference between merely participating and truly optimizing your position. This is why Unchained developed the Bitcoin Calculator – a sophisticated modeling tool that helps you visualize and prepare for multiple bitcoin futures. Beyond traditional retirement planning, it offers deep insight into how different adoption scenarios could transform your wealth trajectory. What sets this tool apart is its integration with the Unchained IRA – the only solution that combines the tax advantages of a retirement account with the security of self-custody. In any future state, maintaining direct control of your keys remains fundamental to your bitcoin strategy. Start with WhyTo understand Strategy better and what they are trying to achieve, it helps to paint the bigger picture first before diving into the details. I appreciate some of Simon Sinek's concepts, especially his principle of ‘Start with Why.’ The Wright brothers were true pioneers. Yet, if Polymarkets had existed in 1903, the odds would have been nearly 0% that they would achieve powered flight before Samuel Pierpont Langley. Simon Sinek argues that the Wright brothers succeeded where Langley failed because of their internal motivation—their Why. While Langley was largely motivated by fame, prestige, and financial gain, the Wright brothers were driven by a deep, passionate belief in the transformative power of flight. Their unwavering sense of purpose inspired perseverance, experimentation, and innovation despite numerous setbacks. Unlike Langley, whose approach primarily focused on what (creating a successful airplane), the Wright brothers clearly understood their why—a vision of changing the world through flight.
Another example comes from Jocko Willink, an ex-Navy Seal who, in my opinion, embodies true leadership. If you asked him about the most important factor in successfully completing Navy Seal training, he would emphasize the Why. You must know why you're doing it. If your reasons are wrong, you'll quit along the way. In my last article for TBL Pros, I distinguished between people who are Holding On for Dear Life and those who Hold Onto Decentralized Liberty. The difference between these groups lies in their Why. Why are you holding this asset? Is it for a quick profit, or to improve your life—and perhaps the lives of others? I understand not all bitcoiners would agree with me, and I'm humble enough to admit if I need to reconsider my heroes, but I genuinely believe Michael Saylor chose this path because he sees Bitcoin as a solution to problems caused by manipulating the money supply. He views Bitcoin as the best proxy for money and believes humanity thrives under a sound money standard. Another reason I think Saylor acts from genuine intent is his statement that he considers ‘burning his personal bitcoin’ to increase the value for all other bitcoin holders. As Simon Sinek suggests, the right Why, combined with proper execution, results in profit for the company, ultimately increasing shareholder value. However, profit shouldn't be the primary goal. When the Why resonates, people naturally want to buy your products, use your services, or lend you their money. They want to be part of your vision, will remain loyal, and may even form a community around your company. Volatility is VitalityWe’ve explored the Why. Now, let’s proceed to the How. Forgive me for being blunt here, but I think you'll get the reference: ‘It’s the volatility, stupid!’ Michael Saylor famously stated that “volatility is vitality,” highlighting how publicly traded companies often experience increased investor engagement and heightened stock demand during periods of significant price fluctuations. Strategy leverages Bitcoin holdings on its balance sheet specifically to introduce volatility into its stock, creating strategic opportunities. Meanwhile, analyst Stephen Perrenod conducts comprehensive mathematical analyses of Bitcoin’s price movements. According to Perrenod, the beauty of Bitcoin’s volatility lies in its positive skewness—meaning that while significant volatility and downside risks certainly exist, Bitcoin historically experiences larger and more frequent upward price movements. Because of this positive skewness, among other favorable characteristics, Bitcoin stands out as the ideal asset for corporate strategic investment. The options market plays a crucial role in driving greater investor demand, largely because options trading revolves around probabilities. Higher volatility increases the likelihood that certain strike prices will be reached before a given expiration date. Without delving deeply into option pricing and trading, the key takeaway is this: the higher the probability a strike price will be met within a certain timeframe, the more valuable the option becomes. Highly valuable options attract traders of all types employing various strategies. Typically, however, assets with high volatility also suffer from low liquidity. Institutional investors usually avoid illiquid markets because they need to take substantial positions. Entering a market with insufficient liquidity can trap institutional investors if the trading volume dries up, especially if momentum turns against their positions, exacerbating their losses. Yet, Bitcoin presents a unique opportunity by combining high volatility with high liquidity. With a market capitalization around $2 trillion, Bitcoin is large enough for institutional investors to enter and exit positions worth billions of dollars without significantly impacting the market price, provided the trades are executed strategically. Bitcoin's liquidity is further enhanced by its 24/7 trading availability, making it one of the most liquid assets in financial markets today. Strategy is capitalizing on these unique merits. Although anyone could pursue this path, Strategy was among the first to recognize the opportunity and brave enough to commit fully to an all-in, Bitcoin-only treasury strategy, positioning themselves as pioneers on a new financial frontier. Financial EngineeringYou better refill that cup of coffee because you might need it. Next up: the What... Subscribe to The Bitcoin Layer to unlock the rest.Become a paying subscriber of The Bitcoin Layer to get access to this post and other subscriber-only content. A subscription gets you:
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Tuesday, April 1, 2025
Pioneers: A Deep Dive Into Saylor's Strategy
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