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
Beneath the Surface

From Permission to Possession

Loading ...Addison Wiggin

December 12, 2025 • 3 minute, 55 second read


CryptoStablecoins

From Permission to Possession

“If someone gives you permission, they can take it away. I give myself permission.”

– Lucille Clifton

 

December 11, 2025 —For the first time in history, Americans will be able to transact freely without fearing political disfavor or the legacy financial system. The architecture itself enforces neutrality. There is no “cancel” button.

The end of fiat regimes controlled by politicians and central bankers is a reasonably imaginable prospect.

This is precisely what Kirk meant by the preservation of order. The founders balanced power between branches; today’s coders balance power between servers.

In both cases, the goal is the same: to prevent centralized concentration and preserve liberty. Peer-to-peer transactions will introduce a whole new level of competition into the banking system.

Instead of putting money in a savings account with a bank, earning partly (if any) interest, you can lend directly. And then you can get a market rate for your capital, not a rate imposed by today’s big banks, which are effectively gatekeepers for the legacy financial system.

Dollar 2.0: Our Grey Swan Working Thesis

On October 21, the Fed hosted its Payments Innovation Conference and formally opened the policy spigot on stablecoins, cryptocurrency, and tokenization. We’ll continue to track and flag investable edges as the guardrails are implemented.

We’ll be watching opportunities in three categories:

  • The issuers — companies that create digital dollars backed by real cash or short-term U.S. Treasuries, and prove it every month. Think of them as safer, faster payment systems that don’t depend on weekend bankers.

    • The builders — firms designing the plumbing and legal framework that make those payments work. They’re the picks and shovels of the new financial gold rush.

    • The adapters — traditional banks that plug into the new system instead of fighting it, using faster settlement to cut costs and (in theory) pass the savings on to customers.

In short: the new money rails are coming, the infrastructure is investable, and the smart banks will ride them instead of watching from the station. 

🌍 And… The Global Shift

Across the world, nation-states are taking notes. China’s digital yuan is built for surveillance; Europe’s digital euro is built for compliance. The American model is being built for freedom — a multi-issuer, transparent, competitive system anchored in law. Chaotic in its disruption.

At the Fed’s Payments Innovation Conference, Governor Christopher Waller floated “skinny accounts” to allow approved stablecoin issuers direct settlement access—a constitutional bridge between central banking and market innovation.

Hamilton meets Satoshi.

Love it.

And it’s a reason for optimism. Refreshing for me in a career critiquing the failures of fiat currencies and insurmountable debt that it encourages at all levels of society – government, corporate and individual.

🧭 Back to First Principles

Kirk wrote that liberty “endures only when linked to order, and order only when linked to justice.” That’s what’s being rebuilt here: not a new ideology, but a new infrastructure for old freedoms.

Trump’s conversion to digital money wasn’t the result of his kids following a tech fad — it was a rite of passage the nation had to witness. That is, if they bothered to pay attention to what was happening to the man behind the ghoul’s mask painted over his public face.

Trump was the test case. The debanked president who learned, painfully, that political power doesn’t guarantee financial access — and that the only real safeguard against tyranny is a system that cannot discriminate.

The lesson? Freedom cannot depend on parties or courts… but it can be preserved on digital monetary architecture.

🌄 The Optimistic View

America has consistently reinvented itself in times of crisis. The founders survived monarchy. Lincoln survived disunion. We’ve survived bank panics, oil shocks, stagflation, and disco. We’ll survive deplatforming, too.

The Second American Revolution won’t be fought with muskets or manifestos. It won’t be fought with petty violence and street demonstrations. It will be written into code. And available to those who wish to take advantage of it.

Russell Kirk called the first American Revolution “a revolution not made, but prevented.” The second will be the same. We’re not tearing down the house — we’re going to rewire it in code.

The result may not be utopia. But it will be freedom you can bank on.

Addison Wiggin

 

Grey Swan Investment Fraternity

 

P.S. This piece first appeared in our November Grey Swan Bulletin. Today, we’re continuing our review our 2025 Grey Swan forecasts and planning out our best new ideas for 2026 this week… and putting together our final Bulletin of 2025.

Next week, we’ll be back at it with a sneak preview of what we expect in 2026 and solid moves you can make before year-end.


The Hindenburg Five

February 24, 2026 • Addison Wiggin

The stock market “rebalancing” is a polite way to put it. Energy and health care are getting a healthy boost. But tech hardware and software makers are still getting dressed down and have been asked to report to the principal’s office.

The great rotation underway has triggered a series of “Hindenburg Omens.” Five have occurred in recent weeks.

The Hindenburg Five
Piercing The Veil

February 23, 2026 • Addison Wiggin

The S&P 500 has traded in a 3.7% range over the past two months — less than half the 20-year median of 8.6%. One of the tightest ranges in modern history.

In trader parlance, the indexes are “flat,” a setup that often materializes before a sell-off at the top after a multi-year bull market.

Goldman Sachs told its own traders to be aware that institutional trading activity resembles a VIX reading near 35. Rather than a reading of 20, where the VIX has been trading over that same 2-month period.

The U.S. software ETF, IGV, tested its April 2025 lows last week and trades roughly 35% below its peak. The “SaaS-pocalypse” in software companies reflects the fear of Citrini’s 2028 scenario happening in real time.   That divergence now exceeds the spread seen at the peak of the Great Financial Crisis.

Under the surface, the “great rotation” we wrote about last week is threatening to widen.

Piercing The Veil
Oh. Canada

February 23, 2026 • Addison Wiggin

Despite its overly-educated 40-million-plus population, on a GDP per capita basis Canada is null. Collectively, the Great White North would rank as America’s second-lowest state, coming in above Mississippi, but below Alabama.

Oh. Canada
Matt Milner: SpaceX + xAI: What It Means for You

February 20, 2026 • Addison Wiggin

SpaceX is the most valuable private startup in history — and if its success continues, it might become the most valuable public company in history.

After all, as Musk famously said in 2023, “I have never lost money for those who invest in me and I am not starting now.”

For investors, SpaceX has been a wild, joyful ride — and now the journey continues!

Matt Milner: SpaceX + xAI: What It Means for You