Michael Saylor is a quirky businessman and inventor with a hint of genius.He bleeds Bitcoin.
For a long time, I've been captivated by his eccentric, almost peculiar, ability to dismantle every counterargument no-coiners have against the world's largest digital currency.
My favourite interview was when Tom Bilyeu told Saylor: "You represent to me somebody who has tremendous conviction, possibly a lot of risk tolerance."
In typical Saylor fashion, he responded to a complex topic in a way a 5th grader could grasp.
Michael Saylor — Source
“How many chairs are you sitting on right now? Are you all in on the chair? The point is really that you put on one pair of glasses, you’ve got one pair of AirPods, you’re looking at me through one screen, and you’re using one microphone. Do you trust it? Is that conviction? It seems kinda scary. Why don’t you diversify? Why don’t you use ten microphones?”
It's beyond thought-provoking.
Saylor's clever narratives aren't typical clichés —every time I hear him speak, it's like he uncovers a hidden truth or reveals a new perspective I hadn't heard before.
He says this ability to work around problems comes from being taught early in life to search for answers and figure things out.
When he was 18, his MIT professor, a NASA consultant who designed the tiles on the space shuttles, stood up at the front of the class and held up one of the tiles, which was burned with a streak up on it, and said:
“You know, on this space shuttle’s last reentry, this tile burned off. Nobody at NASA knows why, and we’re unsure how to fix it. What do you think?”
M.Saylor says everybody looked at each other with glum faces, and it suddenly dawned on the class that the answer to the question would not be in the back of a textbook.
The expectation that an 18-year-old would solve a problem no one else in the world had worked out, even people at the top of their profession, injected confidence in him.
You can see this same mindset influencing his Bitcoin thesis.
Let's dive into it.
Micro Strategy owns 1% of the entire supply of Bitcoin.
They're relentless.
Whenever I check my X account, MicroStrategy doubles down on Bitcoin, and there's no sign of them slowing down.
The company, which now has 214,246 tokens valued at around $14 billion, has had its fair share of controversy. Some articles accuse MS of causing the start of the 2000 Dotcom bubble to burst when its stock tumbled 62% in a single day.
It was right after the SEC brought and settled accounting charges against Saylor and two other company executives.
Republishing the correct financial figures caused the company's stock to plummet and Saylor's net worth to fall by $6 billion.
Saylor paid the SEC $350,000 in penalties but never admitted to wrongdoing. He was then required to pay an additional disgorgement of $8.3 million, which involved reclaiming extra funds from the company's future profits. Ouch.
Things got worse in 2022. The Attorney General for the District of Columbia tried to sue Saylor for alleged tax fraud.
They accused him of illegally avoiding $25 million in taxes by pretending he lived in another state. MicroStrategy is also charged with collaborating with Saylor to facilitate his tax evasion by lying about his address.
Saylor responded:
“I respectfully disagree with the District of Columbia’s position and look forward to a fair resolution in the courts.”
Despite being marred with some controversy, mainly around what looks to be tax reporting, I tip my hat at Saylor's longevity — navigating MicroStrategy through multiple recessions.
It's a testament to his resilience and long-term vision.
"Even if you were 200 years late to buy property in New York, you would have still made money."
Crypto has a strange way of tricking your brain.
Whenever I saw parabolic prices rise for an asset I owned, the hairs on my neck stood up to attention.
I'd think to myself, "You absolute genius, Jay".
The opposite sinking feeling in the pit of my stomach would always accompany inevitable drawdowns, and I'd think to myself, "What a bloody idiot."
What this chaotic mix of confusion highlighted was my perspective on time.
I had no time horizon in the future to peg myself to, so instead, I'd react to the volatility of daily price charts. I can tell you those stomach-churning butt-clenching drawdowns suck when you watch the chart minute by minute.
It wasn't until Michael Saylor put this all into perspective with a clever comparison to buying New York property 200 years ago.
It's the most significant explanation I have heard on investing in Bitcoin because every word is accurate.
Michael Saylor — Source
“Just like buying into New York City 250 years ago — yeah, sure, you’re late, people got there 100 years before you.
Okay, well, in this case (Bitcoin), someone got there 14 years before you. I once tweeted, very famously, I said I think Bitcoin is going the way of online gambling and I think Bitcoin was at $100 a coin, then.
I was wrong, but I didn’t realise it at the time. When I needed Bitcoin, Bitcoin was $9,500 to $10,000 a coin, and so I bought it at ten thousand dollars instead of one hundred dollars.
People will buy it at a hundred thousand, they will buy it at a million, they will probably buy it at 10 million, right?
How much does an apartment in Manhattan cost? People pay 10 million dollars for four thousand square feet. Ten million dollars, right? All of Manhattan was purchased for what, like, twenty-nine dollars in beads or something if you roll the clock back far enough.
You can’t get caught up in what the unit price is. You have to ask the following question: What is the dominant Network in cyberspace?
Bitcoin is the dominant Network.”
Final Thoughts.
The message is to have a long-term time horizon and make a solid, concentrated bet on the dominant Network.
Diversification doesn't help.
If anything, it's a distraction from the top-performing assets.
Having said all that, my Bitcoin position is tiny compared to what I hold in Ethereum and Solana because these assets are rising optically together. Still, ETH and SOL are less liquid than BTC and increase by a higher percentage.
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