Insiders Ring the Cash Register

There’s an old Wall Street saying: “They don’t ring a bell at the top.”

But that’s not entirely true. Corporate executives are ringing – the cash register.

They’ve become record sellers of shares of the companies they operate:

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That sea of red isn’t the stock market – yet – it’s company insiders heading for the exit (Source: Bloomberg)

In the most recent week, there were a total of 200 insider transactions, as measured by Form 4 filings with the SEC. Only 2, or a mere 1%, were buys.

That’s a sharp contrast to just over 100 days ago, when insiders got bullish on their company’s own prospects amid the fearful fallout of President Trump’s “Liberation Day” announcement and market crash.

“Insiders have many reasons to sell,” notes our Portfolio Director Andrew Packer, who has – literally – written the book on the subject. “They may want to pay off a mortgage, put a kid through college – or may even be financing a divorce. Insiders only buy for one reason – they find their shares a compelling value here.”

“Typically, you’d expect insiders to be sellers about 75% of the time. It’s part of their compensation. Today’s ratio is totally out of whack.”

If only 1% of corporate insiders – the CEOs, CFOs, and other high-level employees – are considering buying here, but 99% are selling, that’s at odds with retail investors, who are doing the opposite.

We’ve seen this level of insider selling before – in 1999 at the height of the dotcom boom. So we’re not in uncharted territory.

With insiders ringing the cash register, it’s a sign we’re in the late stages of a bull market – and investors may be on a crash course with higher volatility.

~ Addison

P.S. from stocks to crypto: Grey Swan Live! returns Thursday at 2 p.m. ET with Ian King.

Ian’s hot on an upcoming event that he forecasts will trigger a new crypto boom, sending the market cap of the space to $8.5 trillion by 2030. We’ll be looking at his latest moves in the cryptocurrency market – including the rise of Ethereum as the rally in bitcoin takes a pause. What’s it all mean? And where do we stand regarding President Trump’s plans for a Strategic Bitcoin Reserve?

All that and more. Ian will also cover his list of the top token opportunities in the cryptocurrency space as this asset class continues to push higher and gain regulatory guidance.

Remember the new time!

Grey Swan Live! with Ian King will begin at 2 p.m. ET/11 a.m. PT tomorrow, Thursday, September 4, 2025.

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If you have any questions for us about the market, send them our way now to: feedback@greyswanfraternity.com.

There’s an old Wall Street saying: “They don’t ring a bell at the top.”

But that’s not entirely true. Corporate executives are ringing – the cash register.

They’ve become record sellers of shares of the companies they operate:

Turn Your Images On

That sea of red isn’t the stock market – yet – it’s company insiders heading for the exit (Source: Bloomberg)

In the most recent week, there were a total of 200 insider transactions, as measured by Form 4 filings with the SEC. Only 2, or a mere 1%, were buys.

“Typically, you’d expect insiders to be sellers about 75% of the time. It’s part of their compensation. Today’s ratio is totally out of whack.”

We’ve seen this level of insider selling before – in 1999 at the height of the dotcom boom. So we’re not in uncharted territory.

With insiders ringing the cash register, it’s a sign we’re in the late stages of a bull market – and investors may be on a crash course with higher volatility.

~ Addison

P.S. from stocks to crypto: Grey Swan Live! returns Thursday at 2 p.m. ET with Ian King.

All that and more. Ian will also cover his list of the top token opportunities in the cryptocurrency space as this asset class continues to push higher and gain regulatory guidance.

Remember the new time!

Grey Swan Live! with Ian King will begin at 2 p.m. ET/11 a.m. PT tomorrow, Thursday, September 4, 2025.

Turn Your Images On

If you have any questions for us about the market, send them our way now to: feedback@greyswanfraternity.com.

Back in April, when we published what we called the Trump Great Reset Strategy, we described the grand realignment we believed President Trump and his acolytes were embarking on in three phases.

At the time, it read like a conceptual map. As the months passed, it began to feel like a set of operating instructions written in advance of turbulence.

As you can expect, any grandiose plan would get all kinds of blowback… but this year exhibited all manner of Trump Derangement Syndrome on top of the difficulty of steering a sclerotic empire clear of the rocky shores.

The “phases” were never about optimism or pessimism. They were about sequencing — how stress surfaces, how systems adapt, and what must hold before confidence can regenerate. And in the end, what do we do with our money?!

Relative to GDP, the net international investment claim on the U.S. economy was 20% in 2003. It had swollen to 65% by 2023. Practically every type of American company, bond, or real estate asset now has some degree of foreign ownership.

But it’s even worse than that. As the federal deficit has pumped up the GDP figures, and made a larger share of the economy dependent on government spending, the quality and sustainability of GDP have deteriorated. So, foreigners, to the extent they are paying attention, are accumulating claims on an economy that has been eroded by inefficient, government-directed spending and “investments.” Why should foreign creditors maintain confidence in the integrity of these paper claims? Only to the extent that their economies are even worse off. And in the case of China, that’s probably true.

As global government interest expense climbed, gold quietly followed it higher. The IIF estimates that interest costs on government debt now run at nearly $4.9 trillion annually. Over the same span, gold prices have tracked that burden almost one-for-one.

Silver has recently gone along for the ride, with even more enthusiasm.

Since early 2023, Japan’s 10-year government bond yield has risen roughly 150 basis points, touching levels not seen since the 1990s.

Over that same period, gold prices have surged about 135%, while silver is up roughly 175%. Zoom out two years, and the divergence becomes starker still: gold up 114%, silver up 178%, while the S&P 500 gained 44%.

According to the American Association of Individual Investors, the average retail investor has about a 70% allocation to stocks. That’s well over the traditional 60/40 split between stocks and bonds. Even a 60/40 allocation ignores real estate, gold, collectibles, and private assets.

A pullback in the 10% range – which is likely in any given year – will prompt investors to scream as if it’s the end of the world.

Our “panic now, avoid the rush” strategy is simple.

Take tech profits off the table, raise some cash, and focus on industry-leading companies that pay dividends. Roll those dividends up and use compounding to your overall portfolio’s advantage.

Back in April, when we published what we called the Trump Great Reset Strategy, we described the grand realignment we believed President Trump and his acolytes were embarking on in three phases.

At the time, it read like a conceptual map. As the months passed, it began to feel like a set of operating instructions written in advance of turbulence.

Silver has recently gone along for the ride, with even more enthusiasm.

Since early 2023, Japan’s 10-year government bond yield has risen roughly 150 basis points, touching levels not seen since the 1990s.

A pullback in the 10% range – which is likely in any given year – will prompt investors to scream as if it’s the end of the world.

Our “panic now, avoid the rush” strategy is simple.

Take tech profits off the table, raise some cash, and focus on industry-leading companies that pay dividends. Roll those dividends up and use compounding to your overall portfolio’s advantage.