The Most Famous “Insider Buy” On Wall Street Is A Myth
Michael Saylor, executive chairman of Strategy (MSTR) just bought another $101 million of Bitcoin, and you should ignore it.
The headlines are calling it the ultimate insider signal. The world’s biggest Bitcoin bull, backing up the truck on the dip, buying about 1,550 coins right after Bitcoin slipped under $60,000.
He’d even sold a sliver of his stash a week earlier, his first sale in four years, and then turned around and bought roughly 48 times more than he let go.
“This is smart money loading up while everyone else panics,” they say. “Follow the insider.”
There’s just one problem. Saylor isn’t an insider, not in a way that should matter to you.
I’ve built much of my track record on insider buying, so let me tell you what the signal actually is, because almost everyone gets this wrong.
A real insider buy is a CEO or a chairman putting his own money into his own company’s stock. The reason it matters is information.
That CEO knows his earnings before you do. He knows the order book, the pipeline, the deal that hasn’t been announced yet.
When he buys, he’s betting his own cash on what he knows and you don’t, and that gap is the entire edge.
Now apply that to Saylor and Bitcoin. What does he know about Bitcoin that you don’t?
Nothing.
There’s nothing to know.
Bitcoin has no earnings to see early, no revenue, no pipeline, no order book. It doesn’t even have a CEO. Nobody knows who Satoshi is. There is no inside, which means there is no such thing as a Bitcoin insider.
Saylor isn’t buying on information, because there is no information to buy on. He’s a man with an enormous bet who’s just making it bigger.
That’s conviction, and conviction is not the same thing as knowing something. His company’s average cost is about $75,680 a coin, Bitcoin’s trading in the low $60,000s, and that position is more than $10 billion underwater right now.
Some signal.
Here’s What Real Insider Buying Looks Like
A CEO buying his own company because he knows what’s coming. I told my readers to buy Palo Alto (PANW) at around $154 after its CEO put millions of his own money in, and a few weeks later, it was over $300.
Insiders at Southwest (LUV) gave us a signal we traded four separate times for as much as 109%.
And the one I keep coming back to is Rolls-Royce (RYCEY), where insiders buying their own shares first pulled me in, and we’re now up over 1,400%.
Every one of those was a person with real knowledge of a real business, betting real money on it.
That’s an edge. Saylor doubling down on a coin is not.
That line, between an edge and a guess, is the whole reason I treat Bitcoin the way I do.
I have no problem trading Bitcoin. I’ve done it and done it well. Back in 2024, I took 194% on a Bitcoin ETF in 123 days, a clean sell-the-news play around the halving, and I’d do it again tomorrow if the setup were there.
What I won’t do is call it an investment, because I can’t analyze what has no fundamentals. There’s nothing to value. There’s only price and mood.
And right now, the mood should worry you.
We’re in the most crypto-friendly environment in history, with the full weight of the U.S. government behind it, and Bitcoin is still down tens of thousands of dollars a coin from its highs.
So, answer me one question.
If everyone pushing it is right, who’s selling?
I’ll tell you who. It isn’t the regular guy. It’s the people who pumped it to the top, quietly selling all the way down while still going on television to tell you it’s the future.
That’s the oldest game on Wall Street, running in plain sight. Bitcoin’s trend is broken. It broke 75,000, and the next real stop is the 50s.
That’s not a doomsday call, it’s just what the selling is telling me, and I’d rather say it out loud than sell you a dream.
Trade Bitcoin if you want. Speculate with it. Just never with money that matters to you.
And never confuse a speculator doubling down with an insider who knows something. One is a bet. The other is an edge.
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