The lively atmosphere belongs to the "Epstein circle," but Saylor just wants to hoard coins.

Author｜Kuri, Deep Tide TechFlow

It’s no coincidence that one person can hold onto 710,000 Bitcoin.

Last Friday, the U.S. Department of Justice released 3 million pages of documents related to the Epstein case. Politicians, billionaires, celebrities—names kept popping up from these files. Michael Saylor, founder of MicroStrategy (now Strategy), was also mentioned.

However, Saylor’s appearance was a bit unusual; he was at the disliked table.

From publicly available information, in 2010, Epstein’s PR Peggy Siegal once complained in a private email:

“There’s a guy named Saylor who spent $25,000 on a dinner ticket, and I was supposed to socialize with him. But he was completely unengaging, like a zombie on drugs. I couldn’t stand it and left halfway through.”

Peggy’s main job was Hollywood film PR, and her side gig was arranging dinners for Epstein—basically, scouting wealthy people to pull into the circle.

Socializing with the wealthy, helping them meet the right people at parties and dinners, making sure they have fun and spend comfortably. After decades in the game, she probably thought she’d seen all kinds of billionaires.

But Saylor, she couldn’t handle him.

It’s not because of his character; it’s because he’s too dull. Spending money to get in, sitting there unable to chat, showing no interest in socializing.

Peggy’s words were, **"**I don’t even know if I can charge him, I don’t know where to start with him… he has no personality, completely clueless about social etiquette."

Now Epstein’s case has exploded, and the people on the list are busy distancing themselves. As for Saylor, he was never part of that scene to begin with.

Being overly bored and introverted has instead become a kind of armor.

But when this kind of “boredom” is placed in a different context, it’s another story.

Saylor’s company, Strategy (formerly MicroStrategy), is the publicly listed company holding the most Bitcoin worldwide. In January this year, when Bitcoin was still fluctuating around 90,000, they bought over 37,000 more Bitcoin, spending $3.5 billion.

Almost weekly, without fail.

As of now, Strategy holds 712,647 Bitcoin, with an average cost of $76,037. Today, Bitcoin just dipped below $76,000, meaning Saylor’s position is right at break-even.

The market’s fear index hit a 20-week high, and the crypto world is in chaos. Strategy’s stock price has fallen 60% from its peak.

But Saylor tweeted “More Orange,” implying he plans to keep buying next week.

Back then, Peggy said he was like a zombie. Now, it seems, only a zombie could do this kind of accumulation.

No explanations, no timing, no selling. Completely indifferent to the outside world, feeling good about himself.

Back then, Peggy said she didn’t know how to help him spend money. Now, Saylor has clearly found his way—buy only Bitcoin.

From that email, it’s clear Saylor is an outsider in the fame and fortune scene. He can’t sit still, doesn’t chat, and a night with him feels like he wasn’t there at all. But this kind of person is surprisingly steady in trading.

No socializing, no relationship management, no second-guessing others’ intentions. Just focus on one thing: buy every week, never sell.

Boring, dull, indifferent to the outside world… These traits are flaws in social settings, but perhaps they are a gift when it comes to holding Bitcoin.

After this story spread, a classic meme appeared on Twitter, suggesting that Saylor isn’t interested in minors but is extremely obsessed with unacquired assets.

From a hindsight perspective, this exposure has, to some extent, helped Saylor build a positive image.

After Epstein’s case broke in 2019, Peggy, responsible for PR, lost contracts with clients like Netflix and FX, effectively ending her PR career; meanwhile, Saylor became one of the world’s largest Bitcoin holders.

The person disliked is still buying coins, while those who disliked him have already dropped out.

But on the other hand, Saylor’s current situation isn’t so easy either.

The new Federal Reserve Chair Warsh is hawkish, and market expectations are that he won’t aggressively cut interest rates upon taking office. When rate expectations shift, all kinds of assets worldwide come under pressure.

Gold fell, silver fell, and Bitcoin dropped even harder.

Adding to that, tariffs, US-EU tensions, and capital fleeing to traditional safe-haven assets, the narrative of Bitcoin as “digital gold” is gradually fading.

If Bitcoin continues to fall, Strategy’s ability to raise funds through new stock issuance will weaken, and the rotation in crypto stocks could turn into a vicious cycle.

But Saylor seems to really not care about these—perhaps that’s another side of “boredom.”

Ordinary investors can’t do what Saylor does, not because they lack money, but because they are too “normal.” Normal people watch news, analyze charts, listen to others. When fear rises, their hands get itchy, and their hearts hurt.

Every day, they make decisions, each decision draining their willpower.

But Saylor’s strategy seems to have no “decision” step. Buying is the only action; not selling is the only principle.

As he puts it: “Bitcoin is the best asset mankind has ever invented. Why would I sell?”

You could say it’s faith, or you could say it’s obsession. But from an execution perspective, the biggest advantage of this system is:

It doesn’t require you to be smart, only to be bored.

Of course, this isn’t advice for you to imitate him. Saylor’s confidence comes from being a listed company with stocks to issue and bonds to borrow. Ordinary people don’t have these, and trying to copy his approach will most likely only lead to losses.

But there’s one thing that might be worth learning.

In investing, “interest” is often the source of losses.

Frequent trading, chasing hot topics, following news, leveraging… these behaviors that make investing “fun” are actually the enemies of returns.

The real profitable strategies are often so boring they make you want to sleep.

Saylor’s case is extreme, but the logic holds. In a noisy market, “boredom” might be the rarest skill.

Those who used to be social butterflies at parties are now either distancing themselves, under investigation, or have disappeared entirely.

Perhaps, holding coins and being a person follow the same principle:

Don’t stay long in lively places; boring things are worth doing long-term.

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