NUMBER ONE: Michael Saylor
Now I don’t know much about sorcery, but I do know this: if a man in a fine suit tells you he can turn your paper into gold, you best check your pockets before he disappears in a puff of logic. We’ve seen snake oil salesmen, dot-com dreamers, housing hucksters, and crypto cultists—but none quite like Michael Saylor. He ain’t selling stock. He’s selling belief. And the way Wall Street’s buying it, you’d think faith finally got listed on the NASDAQ.
The Rise and Reinvention of a Fallen Billionaire
Michael Saylor’s story reads like the financial equivalent of Icarus—with a twist. After soaring during the dot-com boom, he crashed hard when the SEC accused his company, MicroStrategy, of inflating revenue. He lost billions in days. But unlike most tech titans who vanished into TED Talks and meditation retreats, Saylor stayed. He waited. He watched. And then he did something nobody saw coming.
In 2020, as the world drowned in pandemic panic and stimulus checks, Saylor took MicroStrategy’s spare cash—$250 million of it—and bet it all on Bitcoin. That wasn’t the end. It was the beginning of a new identity. He wasn’t just buying crypto—he was building a machine.
By 2025, MicroStrategy—now simply called Strategy—held over 550,000 Bitcoin. That’s more than 1% of all the Bitcoin that will ever exist. More than the United States, China, or any government on earth. As of this writing, their holdings exceed $50 billion. And yet the company’s market cap has ballooned to over $100 billion—twice what its Bitcoin is worth.
Why? Because Strategy isn’t a software firm anymore. It’s a belief engine.
How the Machine Works: Reflexivity and Risk
Saylor’s system runs on a concept called reflexivity—a feedback loop where rising Bitcoin prices fuel rising stock prices, which allow him to raise more capital, buy more Bitcoin, and do it all again. It’s like spinning straw into gold—until the belief falters.
He funds this loop with convertible debt—bonds that can turn into shares if the stock price rises high enough. If it doesn’t, they stay bonds, and the debt accumulates. Right now, Strategy holds over $8.2 billion in such obligations, much of it raised at 0% interest.
It’s leverage disguised as genius.
And genius is a fragile thing.
Because if Bitcoin stalls—or worse, drops—the feedback loop reverses. The premium evaporates. The debt doesn’t convert. And to repay it, Strategy might have to do the one thing Saylor swore he’d never do:
Sell.
And if the biggest Bitcoin evangelist becomes a forced seller? That’s not just a financial event. That’s a psychological earthquake. The myth dies. The story breaks. And with it, potentially, the whole market.
Why It Matters
Michael Saylor isn’t running a company. He’s running a narrative. And for now, it’s working. Traditional investors are buying in—some through the backdoor via convertible bonds, others directly into the stock—chasing yield, momentum, or just the dream that this time, the system really has changed.
But it hasn’t. Not really.
Underneath the orange logo and the Twitter threads lies the same old truth: when a financial model depends entirely on sentiment, it doesn’t bend. It snaps. And the louder the belief, the harder the fall.
Whether Saylor’s creation becomes the Amazon of Bitcoin or the next FTX, one thing is certain—he’s changed the game. Maybe forever.
They say history repeats itself—first as tragedy, then as farce. But on Wall Street, it often comes back dressed up as a genius with a PowerPoint and a plan. Michael Saylor may very well be the next Rockefeller. Or he may be the next cautionary tale told in business schools under the chapter titled “When Belief Becomes a Liability.” Either way, he’s no longer just playing the game. He is the game.
So the next time you see a stock doubling just because the man behind it said the word “Bitcoin” with conviction, ask yourself: Is this brilliance? Or is this belief in costume?
And remember—when belief is the product, the selloff is the punchline.
NUMBER TWO: Satoshi Nakamoto – identity unknow.
EXTRA CREDIT: A brief history of Bitcoin followed by a price timeline with major milestones.
📜 The History of Bitcoin
🔹 2008 – The Genesis
- October 31, 2008: A person or group using the pseudonym Satoshi Nakamoto published the Bitcoin whitepaper:
“Bitcoin: A Peer-to-Peer Electronic Cash System.” - It proposed a decentralized digital currency using blockchain, avoiding traditional financial institutions.
🔹 2009 – The Birth
- January 3, 2009: The Bitcoin network launches with the Genesis Block (Block #0).
- Embedded in it: “The Times 03/Jan/2009 Chancellor on brink of second bailout for banks”—a protest against fiat money systems.
🔹 2010 – The First Real Transaction
- May 22, 2010: Laszlo Hanyecz buys two pizzas for 10,000 BTC.
Today, it’s celebrated as Bitcoin Pizza Day. - First known market price: ~$0.003 per BTC.
🔹 2011–2013 – Growing Pains
- Other cryptocurrencies begin to appear.
- Bitcoin gains attention among technologists and libertarians.
- 2011: Reaches parity with the US dollar (~$1).
- Silk Road, an online black market using BTC, accelerates Bitcoin’s infamy.
🔹 2013 – First Big Spike
- Bitcoin hits $1,000 in November.
- But crashes quickly due to exchange shutdowns and regulatory uncertainty.
🔹 2014–2016 – The Crash and Rebuild
- Mt. Gox, the largest exchange, collapses after a massive hack.
- BTC stays mostly below $1,000.
- Development continues quietly with the rise of wallets, hardware security, and growing merchant adoption.
🔹 2017 – Mainstream Mania
- Bitcoin hits $10,000 in November, driven by retail investors.
- December 2017: Peaks near $19,783, then crashes hard in 2018.
🔹 2018–2019 – Crypto Winter
- Prices tumble below $4,000.
- ICO scams and regulation crackdown.
- Institutional interest starts to brew behind the scenes (e.g., CME futures).
🔹 2020–2021 – Institutional Adoption & All-Time Highs
- COVID-19 and money printing drive renewed interest.
- Tesla, Square, and MicroStrategy announce BTC buys.
- October 2021: First Bitcoin Futures ETF (ProShares) launches.
- November 2021: All-time high near $68,990.
🔹 2022 – The Crash Again
- Luna, Celsius, Voyager, and finally FTX collapse.
- Price drops below $16,000 by the end of the year.
🔹 2023–2024 – Recovery & ETFs
- Bitcoin rebounds on ETF optimism.
- January 2024: The first U.S. spot Bitcoin ETFs approved.
- Price crosses $45,000, then $60,000, leading to renewed institutional interest.
🔹 2025 – Where We Are Now
- As of August 2025, Bitcoin trades around $100,000, driven by ETF flows, institutional interest, and the belief in Bitcoin as “digital gold.”
📈 Bitcoin Price Timeline (Key Dates & Values)
Date | Price (USD) | Event / Milestone |
---|---|---|
Jan 2009 | $0.00 | Genesis Block |
Oct 2009 | ~$0.0007 | First exchange rate published |
May 2010 | $0.01 | First real-world transaction (10,000 BTC = 2 pizzas) |
Feb 2011 | $1.00 | Bitcoin reaches parity with USD |
Jun 2011 | $31.00 | First major bubble, followed by crash |
Nov 2013 | $1,000 | Hits $1k, then crashes after China bans exchanges |
Dec 2017 | $19,783 | First all-time high, mania phase |
Dec 2018 | ~$3,200 | End of crypto winter |
Dec 2020 | $28,000 | Institutional adoption begins |
Apr 2021 | $64,000 | Coinbase IPO, Tesla buys BTC |
Nov 2021 | $68,990 (ATH) | Peak of the 2021 bull run |
Nov 2022 | ~$15,500 | Post-FTX collapse low |
Jan 2024 | ~$45,000 | Spot ETF approvals |
Apr 2025 | ~$75,000 | Saylor’s strategy in full motion |
Aug 2025 | ~$100,000 | Current level (estimated) |
© 2025 insearchofyourpassions.com - Some Rights Reserve - This website and its content are the property of YNOT. This work is licensed under a Creative Commons Attribution 4.0 International License. You are free to share and adapt the material for any purpose, even commercially, as long as you give appropriate credit, provide a link to the license, and indicate if changes were made.