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Ripple Effect

Insiders Ring the Cash Register

Loading ...Addison Wiggin

September 3, 2025 • 2 minute, 15 second read


Insider Trading

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.


The Grand Realignment Gets Personal

January 13, 2026 • Addison Wiggin

Sunday night, Powell addressed the probe head-on in a video post — a rarity. He accused the White House of using cost overruns in the Fed’s HQ renovation as a pretext for political interference.

The White House denied involvement. But few in Washington believed it.

What followed was bipartisan condemnation of the investigation. Greenspan, Bernanke, and Yellen co-signed a blistering rebuke, warning the U.S. was starting to resemble “emerging markets with weak institutions.”

The Grand Realignment Gets Personal
A Rising Sign of Consumer Stress

January 13, 2026 • Addison Wiggin

Estimates now indicate that the average consumer will default on a minimum payment at about a 15% rate – the highest level since a spike during the pandemic lockdown of the economy.

President Trump’s proposal over the weekend to cap credit card interest at 10% for a year won’t arrive in time to help consumers who are already missing minimum payments.

Not to fret, the other 85% of borrowers continue to spend on borrowed time. Total U.S. household debt, including mortgages, auto loans, student loans, and credit cards, reached record highs in late 2025, exceeding $18.5 trillion. This surge was driven partly by rising credit card balances, which neared their own all-time peaks due to inflation and higher interest rates.

A Rising Sign of Consumer Stress
Protest Season Amid the Grand Realignment

January 12, 2026 • Addison Wiggin

There’s an old Wall Street maxim: “Don’t fight the Fed.”

This year, you could add a Trump corollary.

A wise capital allocator doesn’t fight that storm. He doesn’t argue with it. He respects it the way sailors respect the sea: with preparation, with humility, and with a sharp eye for what breaks first.

In 2026, the things that break first are the stories. The narratives. The comfortable assumptions.

Protest Season Amid the Grand Realignment
Breaking: Government Budgets

January 12, 2026 • Addison Wiggin

Total municipal, state and federal debt service costs soared to nearly $1.5 trillion in the third quarter of 2025. Debt’s easy to accumulate when rates are low. Trouble is, you are obligated to refinance them even after rates go up.

It’s also a key reason why the Trump administration is demanding lower interest rates – even if it means reigniting inflation.

Breaking: Government Budgets