1998, Redux

October 31, 2025 • 54 second read

In his press conference after lowering interest rates a quarter point this week, Federal Reserve Chairman Jerome Powell laid out the case that the AI boom was nothing like the dotcom bubble.

There’s just one problem. The market is following the dotcom boom nearly perfectly – with 2025 following closely to 1998:

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Stocks continue to rally like the middle stage of the dotcom boom. (Source: Mark_ungewitter via X)

If this trend continues, stocks are likely to peak late next year, possibly form a double top – then give back the bulk of their gains.

With today’s high valuations in stocks already, it may be a good time to move to more defensive and better-valued stocks.

~ Addison

P.S. Yesterday’s Grey Swan Live! with John Robb provided a rich discussion on AI, new defense technologies, and an overall picture of what the next few years could look like.

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

Ripple Effect

1998, Redux

Addison Wiggin

October 31, 2025 • 54 second read

AI Boom dotcom boom

In his press conference after lowering interest rates a quarter point this week, Federal Reserve Chairman Jerome Powell laid out the case that the AI boom was nothing like the dotcom bubble.

There’s just one problem. The market is following the dotcom boom nearly perfectly – with 2025 following closely to 1998:

Turn Your Images On

Stocks continue to rally like the middle stage of the dotcom boom. (Source: Mark_ungewitter via X)

If this trend continues, stocks are likely to peak late next year, possibly form a double top – then give back the bulk of their gains.

With today’s high valuations in stocks already, it may be a good time to move to more defensive and better-valued stocks.

~ Addison

P.S. Yesterday’s Grey Swan Live! with John Robb provided a rich discussion on AI, new defense technologies, and an overall picture of what the next few years could look like.

Turn Your Images On

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

The Internet Just Got Its Own Money

November 20, 2025 • Ian King

Every major tech shift has followed a similar pattern. As information moves faster, the money follows.

The telegraph made news global and opened up a world of investment opportunities. Radio, and then television, ignited a new wave of prosperity for investors. And the internet made communication instant, creating fortunes for those who saw what was coming.

Now standards like x402 are doing the same for AI and digital payments, potentially putting Jamie Dimon’s empire in jeopardy.

If you have Coinbase building the payment rails, Circle handling settlement and projects like Worldcoin and Particle Network solving for identity and wallets — do you really need a bank to validate transactions and keep track of who owns what?

All of these companies are helping to build a new layer of fintech infrastructure. And they’re all working toward an economy that runs continuously, without the need for corporate scaffolding.

Jensen Huang’s Double Exhale

November 20, 2025 • Addison Wiggin

“What if you held a bond auction and nobody showed up?” That’s the perennial question plaguing a Treasury Secretary.

Yesterday’s $16 billion auction of 20-year Treasurys didn’t go as well as Bessent would have liked.

High yield: 4.706%

Bid-to-cover: 2.41 (below the 10-auction average of 2.71)

Demand is softening at the exact moment the government needs to roll over debt at record levels.

The Carry Trade Meltdown

November 20, 2025 • Addison Wiggin

With Japanese yields soaring, the returns on the carry trade are lower. Carry trades are likely getting unwound, pushing Japanese bond yields even higher.

The unwinding of the carry trade also helps explain why many individual stocks listed on the New York Stock Exchange have crashed by 40-50% from their recent highs. Investors are selling the target assets of the trade in order to pay back their yen-based loans before their profits get squeezed.

Coinbase Wants to Dominate the Internet Capital Markets

November 19, 2025 • Ian King

On November 10, Coinbase announced a new platform that lets users buy crypto tokens before they list on the exchange.

The company calls it: “a more sustainable and transparent way for projects to distribute tokens.”

In other words, we’re moving into ICO 2.0. But this time there will be more rules.

The Internet Just Got Its Own Money

November 20, 2025 • Ian King

Every major tech shift has followed a similar pattern. As information moves faster, the money follows.

Now standards like x402 are doing the same for AI and digital payments, potentially putting Jamie Dimon’s empire in jeopardy.

All of these companies are helping to build a new layer of fintech infrastructure. And they’re all working toward an economy that runs continuously, without the need for corporate scaffolding.

Jensen Huang’s Double Exhale

November 20, 2025 • Addison Wiggin

“What if you held a bond auction and nobody showed up?” That’s the perennial question plaguing a Treasury Secretary.

Yesterday’s $16 billion auction of 20-year Treasurys didn’t go as well as Bessent would have liked.

High yield: 4.706%

Bid-to-cover: 2.41 (below the 10-auction average of 2.71)

Demand is softening at the exact moment the government needs to roll over debt at record levels.

The Carry Trade Meltdown

November 20, 2025 • Addison Wiggin

With Japanese yields soaring, the returns on the carry trade are lower. Carry trades are likely getting unwound, pushing Japanese bond yields even higher.

Coinbase Wants to Dominate the Internet Capital Markets

November 19, 2025 • Ian King

On November 10, Coinbase announced a new platform that lets users buy crypto tokens before they list on the exchange.

The company calls it: “a more sustainable and transparent way for projects to distribute tokens.”

In other words, we’re moving into ICO 2.0. But this time there will be more rules.