From Dot-Com Crash to Bitcoin Kingpin : Story of Michael Saylor
Rise, Fall and Rise again of MicroStrategy co-founder
Introduction
Before everything, let me share you a price chart of a NASDAQ listed stock from 1999 - 2025.
Wait what? That thing took 23 years to reach same level of prices? The ticker we are talking about is $MSTR. MicroStrategy, a software company founded by Michael Saylor in 1989, initially gained prominence during the dot-com boom of the late 1990s by providing business intelligence, mobile software, and cloud-based services. Saylor, known for his visionary yet controversial leadership, saw MicroStrategy's stock soar in the late 90s, only to crash in 2000 due to accounting discrepancy controversies and the bursting of the dot-com bubble. This is headline in front page of Daily News on March 21, 2000.
Part 1: The Rise
In the early 2000s, MicroStrategy wasn’t alone in facing a crash—many major tech stocks, particularly those tied to the dot-com boom, saw their valuations plummet. Companies like Amazon, Alphabet (Google), and others eventually recovered by focusing on product innovation and building sustainable business models, leading to rising stock prices over the years. However, MicroStrategy's story was different. Despite its continued focus on business intelligence and software, the company struggled to regain the market's favor, and $MSTR remained well below its previous highs for nearly two decades till 2020 and covid-19 crash threatening to put the final nail in the coffin. Then Saylor made a bold move.
On August 11, 2020, MicroStrategy announced that it would adopt Bitcoin as its primary treasury reserve asset, marking a historic move as the first publicly traded company to do so. At that time, Bitcoin was priced around $15,000. This decision represented a dramatic shift for Michael Saylor, who had previously criticized Bitcoin, suggesting it was a fad likely to fail.
The turning point came as Saylor reassessed the macroeconomic landscape, particularly concerns about inflation. Influenced by his friend and fellow entrepreneur Eric Weiss, a Bitcoin advocate, Saylor became convinced that Bitcoin offered a superior hedge against inflation compared to traditional assets like cash or gold. This change in perspective led to MicroStrategy's initial $250 million Bitcoin purchase, sparking a series of further acquisitions that have since solidified the company as one of the largest corporate holders of Bitcoin.
Following MicroStrategy's initial investment, Michael Saylor continued to accumulate Bitcoin, making multiple high-profile purchases that drew widespread attention. Around this time, a confluence of factors fueled a crypto bull run. The Federal Reserve's policy of lowering interest rates, combined with extensive money printing to counteract the economic impact of COVID-19, spurred investor interest in alternative assets, including cryptocurrencies. Bitcoin’s price surged from around $15,000 to nearly $60,000. Global adoption also gained momentum—El Salvador became the first country to officially purchase Bitcoin, recognizing it as legal tender, while Elon Musk announced that Tesla would accept Bitcoin payments, further boosting market confidence.
Part 2: The Fall (SPOILER: It’s not)
By the Fall of 2021, MicroStrategy stock started rallying as bitcoin reached an All-time-high (ATH) of 60000$ and Saylor started getting attention. However, all assets that experience a bull market, will experience a bear market as well. Enthusiasm cooled, and the market began to correct. To make matters worst, Fed announced they would hike the interest rates back to normal, the honeymoon period of low interest rates for companies to borrow money and focus on expansion since covid crash is coming to an end, a bad news for equity and crypto markets. Sentiment is circulated such that MicroStrategy’s aggressive buying signaled a "temporary top" for Bitcoin’s price, casting doubt on the sustainability of the rally. This sentiment, coupled with macroeconomic uncertainties and regulatory crackdowns, led to a significant downturn, initiating a bear market that challenged even the most fervent believers in Bitcoin’s long-term promise.
Then came a brutal bear market, with companies falling like dominos as they do not have liquidity to be solvent by the end of 2022. A cascading effect took hold—each bankruptcy of a company holding significant Bitcoin reserves pushed BTC's price lower, triggering further collapses among those struggling to maintain solvency and liquidity. The downfall was sparked by major failures such as $LUNA, FTX, Celsius, Three Arrows Capital, and Voyager, all facing liquidity crises. This chain reaction sent Bitcoin plummeting from $60,000 to $16,000. The situation was even worse for many altcoins, with some losing as much as 99% of their value. Also most of the people were invested in altcoins, thinking it would outperform Bitcoin in short term. Sentiment turned overwhelmingly negative; for many, "crypto" became synonymous with "scam." The financial devastation was so severe that it led to tragic consequences, including cases of suicide.
What about MicroStrategy? It had a significant impact on MicroStrategy, and its stock price took a major hit as Bitcoin's value plummeted. Michael Saylor was once again in the spotlight, this time facing scrutiny and speculation about MicroStrategy's future. Rumors spread that both Saylor and MicroStrategy might be forced to liquidate their Bitcoin holdings due to the staggering losses. The pressure was mounting—Tesla had already sold most of its Bitcoin due to investor concerns and environmental criticisms, leading to widespread assumptions that MicroStrategy might follow suit.
Yet, despite the fears, Saylor held firm, refusing to back down from his long-term conviction in Bitcoin, even as the market spiraled and critics grew louder. In fact, he started buying more aggressively. Wall Street began to view him as a mad man with a mad obsession.
Part 3: The Rule
The market sentiment began to improve and the Federal Reserve shifted its strategy, easing interest rates to achieve a soft landing. This change rekindled optimism not only in Bitcoin but across the broader blockchain space. A wave of innovation swept through the crypto world, with DeFi (Decentralized Finance), DePIN (Decentralized Physical Infrastructure Networks), and DeSci (Decentralized Science) gaining traction. The aim was clear: to decentralize industries traditionally dominated by a few major players, leveraging blockchain technology as the backbone for this transformation.
Layer 1 networks like Ethereum and Solana emerged as the foundational layers for this new economy, building the financial infrastructure necessary for a decentralized future. Yet, despite the rise of these alternative blockchains, Bitcoin remained the uncontested "King of Crypto." Its appeal lay in its unique commitment to scarcity—unlike any other asset, Bitcoin’s maximum supply is forever capped at 21 million coins. This immutable limit, along with the assurance that no one could fraudulently create more or seize an individual's Bitcoin, solidified its reputation as a secure and uncorrupted store of value, like gold or maybe better, anchoring its enormous significance in the financial landscape. What is Saylor doing? Still buying more BTC !!
Once again this is reflected in Valuation and price of MicroStrategy. After an year of ups and downs, BTC reached a new ATH of 70000$. But, but, but… this is just the beginning. There is a dinosaur about to arrive. Enter Mr. Donald J. Trump.
In the 2024 U.S. Presidential elections, Donald Trump emerged as a clear winner, riding a wave of pro-crypto stance. His victory sparked a surge of euphoria in the crypto community, bringing renewed hope for regulatory clarity and reform. Under the previous administration, the SEC, led by Chairman Gary Gensler, had been criticized for its handling of cryptocurrencies. Many crypto companies faced lawsuits, with the SEC labeling them as securities, subjecting them to strict regulatory scrutiny. Trump's campaign had been vocal about his dissatisfaction with the SEC's approach, even promising to remove Gensler from his position if elected. With Trump in office, the expectation was for a more favorable regulatory environment, one that could support innovation and attract investment in blockchain space. You definitely guessed what is going to happen next.
NINETY NINE THOUSAND UNITED STATES DOLLARS. This is Bitcoin, but what about MicroStrategy ? They are the only public company that kept on buying bitcoin from the lows, right? They finally hit a new all-time high. Wall street is still not digesting this.
Yet still, Saylor is still doubling down. MicroStrategy is planning to raise $1.6 billion of convertible notes at 0% coupon and 55% premium, with a strike price of 672 $. It’s trading at 421 $ right now, when this article is published.
In short, Investors are giving him money in exchange of MSTR shares, they would get shares if MSTR reaches 672$, otherwise he need to return the money back, but without any interest. Essentially, investors are betting that MicroStrategy stock price goes up and gives him money. He buys Bitcoin. If BTC goes up, MSTR goes up. He gives away more MSTR shares, buys more bitcoin, which in-turn increases the BTC price, and the show goes on.
Yes, this is a risky scheme, as he can simply choose to keep buying bitcoin with cash reserves, increase the holdings and outperform the traditional finance corporations without needing to sell $MSTR, MicroStrategy already holds over 1.5% of total bitcoin supply (331,200 BTC / 21,000,000 BTC). If something goes wrong, BTC, MSTR both plummets and he might not have enough liquidity to pay back the loans and MicroStrategy have to file for Bankruptcy. You never know about any upcoming and sudden black swan event.
The demand of convertible note offerings is so high that they completed a $3 billion offering instead of planned $1.6 billion. We wouldn’t be discussing about his story if he didn’t take his first risky move of buying bitcoin. People are defined by their bold moves. As usual, some people think this would be bad for MicroStrategy, but only time will tell.
Conclusion
Reading Saylor's journey from tech CEO to Bitcoin evangelist hits home because we all are feeling that same despair watching our savings slowly die in traditional finance before finding the orange pill of Bitcoin. Yes, people hate you or do not agree with your stance, you can’t convince everyone. But you should have conviction on your beliefs. He didn’t sell the holdings like others in the times of extreme panic, he doubled down because he believed. Keep in mind that people care only when your plan works, so no need to care about their opinions.
"At some point people will realize that they have more to fear by not embracing this technology than by embracing it." - Michael Saylor
In the end, here are two clips of Saylor speeches I really like.
Yes, there are lot more events unfolding in this article that might need more explanation. To get answers to all the questions like Why is bitcoin valuable, how is it mined? What was the drama in FTX, LUNA collapses? What are Ethereum and Solana? What are DePIN and DeSci?, you can subscribe to get all these upcoming articles directly to your mailbox.