GSI Banner
  • Free Access
  • Contributors
  • Membership Levels
  • Grey Swan Forecasts
  • Video
  • Origins
  • Sponsors
  • My Account
  • Sign In
  • Join Now

  • Free Access
  • Contributors
  • Membership Levels
  • Grey Swan Forecasts
  • Video
  • Origins
  • Sponsors
  • Contact

© 2026 Grey Swan Investment Fraternity

  • Cookie Policy
  • Privacy Policy
  • Terms & Conditions
  • Do Not Sell or Share My Personal Information
  • Whitelist Us
Ripple Effect

Insiders Ring the Cash Register

Addison WigginAddison 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:

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.

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.

Turn Your Images On

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


Housing Shortage? Hardly.

September 11, 2026 • Addison Wiggin

The dollar may be losing purchasing power, but housing prices aren’t getting the memo because buyers can’t afford the financing…

Housing Shortage? Hardly.
Bessent’s Three-Part Gambit

September 10, 2026 • Addison Wiggin

Bessent lost round one with the bond vigilantes, but he could take another route involving the world’s most heavily shorted major currency…

Bessent’s Three-Part Gambit
The Sapporo Strategy

September 9, 2026 • Addison Wiggin

Like the development of AI applications, the Sapporo model relies on allied capacity rather than on a single state-directed machine…

The Sapporo Strategy
Dollar “Debasement” Meet AI Buildout… Play Nice!

September 8, 2026 • Addison Wiggin

When other countries weaken their own currencies alongside the dollar, the result can become a global race toward lower purchasing power…

Dollar “Debasement” Meet AI Buildout… Play Nice!