Wall of Worry, Indeed

Last week’s market weakness — with a big selloff Thursday, and a pre-market decline on Friday — brought out the bears.

Based on the latest sentiment survey, investors are fairly neutral overall:

Turn Your Images On

Investors are mixed on the market’s returns in the next six months (Source: AAII)

This is good news for our “most terrifying bull market” thesis.

Wall Street traders have a term for this phase: the wall of worry. As long as investors get fearful enough, the market top isn’t in.

At the top, investors will go all-in – in what’s known as the “blow of top”, like they did with dotcom stocks in 1999, or as many did with SPAC companies in 2021.

We haven’t quite gotten to the “this time is different” mentality that causes investors to throw on the blinders – yet.

~ Addison

P.S. So what do you do with your money before the blow-off top? Glad you asked.

This week on Grey Swan Live! we’re planning a special two-fer for you. On Thursday, October 23, 2025 at 2 p.m. ET we’re going to do a run down of all the historical records this terrifying bull market has already hit — including retail investor buy-in, record margin debt and capital concentration at the top of the S&P 500.

We’re going to lay out in simple terms the AI crash scenario. Mostly, so you’re aware of what’s at stake, where we are in the mania and exactly what we expect to happen.

As Andrew Ross Sorkin, author of Too Big To Fail, said this week while promoting his new book “1929,” if we’re all in agreement this is a bubble in AI stocks, the trick is to “know when to get on [and more importantly] get off, the wave.”

Then, on Friday, October 24, 2025 at 2 p.m. ET, we’re going to do a comprehensive asset allocation and model portfolio review for paid-up annual members of the Grey Swan Investment Fraternity.

During the review session on Friday, we’ll be giving you access to an exclusive Plunge Protention Plan (for annual members only) including ways you can protect your money against a stock market correction and a few aggressive ways you can make money like the pros when the stock market goes down.

We’ll be providing more details throughout the week. But for now mark your calendar for these two dates:

Thursday, October 23, 2025 @ 2 p.m. ET — comprehensive overreview of the “terrifying bull market.”
Friday, October 24, 2025 @ 2 p.m. ET — a comprehensive review of the Grey Swan asset allocation strategy and model portfolio. (For paid up annual members only)

The time to prepare for a market correction is before it happens, not while or after. If you wait to long, the the exits will get crowded in a hurry… and you don’t want to be worrying about your money if and when that happens.

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

Last week’s market weakness — with a big selloff Thursday, and a pre-market decline on Friday — brought out the bears.

Based on the latest sentiment survey, investors are fairly neutral overall:

Turn Your Images On

Investors are mixed on the market’s returns in the next six months (Source: AAII)

This is good news for our “most terrifying bull market” thesis.

Wall Street traders have a term for this phase: the wall of worry. As long as investors get fearful enough, the market top isn’t in.

At the top, investors will go all-in – in what’s known as the “blow of top”, like they did with dotcom stocks in 1999, or as many did with SPAC companies in 2021.

We haven’t quite gotten to the “this time is different” mentality that causes investors to throw on the blinders – yet.

~ Addison

P.S. So what do you do with your money before the blow-off top? Glad you asked.

We’re going to lay out in simple terms the AI crash scenario. Mostly, so you’re aware of what’s at stake, where we are in the mania and exactly what we expect to happen.

Then, on Friday, October 24, 2025 at 2 p.m. ET, we’re going to do a comprehensive asset allocation and model portfolio review for paid-up annual members of the Grey Swan Investment Fraternity.

We’ll be providing more details throughout the week. But for now mark your calendar for these two dates:

Thursday, October 23, 2025 @ 2 p.m. ET — comprehensive overreview of the “terrifying bull market.”
Friday, October 24, 2025 @ 2 p.m. ET — a comprehensive review of the Grey Swan asset allocation strategy and model portfolio. (For paid up annual members only)

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

A 50-year mortgage doesn’t make housing cheaper. But by stretching the repayment period over time, it DOES lower the monthly payment on your principal. That lowers the percentage of your total income you’re spending on repayment. And in a strange way, it makes sense.

With a fixed rate mortgage and inflation running in the high upper digits, the real value you of your total debt goes down over time (inflation pays off your loan, as long as your income rises faster in nominal terms). Of course you pay off a lot more interest over 50 years than 30 years. And it takes a lot longer to build up equity (assuming also that house prices don’t fall).

Last night’s 60–40 Senate vote shoved the government back toward “on.” There’s apparently a shutdown truce… for now.

A bloc of Democrats “crossed the aisle” after weeks of getting nowhere on health-care demands. “We had no path forward… and SNAP beneficiaries were losing benefits,” Sen. Tim Kaine, one of the 7 who conveniently aren’t up for reelection, said.

The new deal funds Washington only through January, tacks on three bills to keep parts of Defense, Ag, and the Capitol complex humming through 2026, reverses shutdown-era RIFs, and restores back pay.

The House is next; the president says he’ll sign it fast when it gets to the Oval Office.

The S&P 500 Quality Index ranks companies not by market cap or a compelling AI story, but rather by fundamentals. Earnings, profit margins, and financial leverage. Reasonable debt.

You know, the kind of stuff that makes your eyes glaze over. And the type of companies we like to hold for the long haul in our model portfolio.

If I were to sum up the mindset of New Yorkers who elected Zohran Mamdani as mayor of New York City, it would be We want something for nothing, and we want the rich to pay for it. Instead, they will get nothing for something, and they will pay for it with a degraded quality of life.

Mamdani’s victory was paved with ingratitude for the blessings New Yorkers receive daily. The mindset demanding “something for nothing” from society is not just a political phenomenon, but a profound lapse in economic understanding and moral character.

Last night’s 60–40 Senate vote shoved the government back toward “on.” There’s apparently a shutdown truce… for now.

The new deal funds Washington only through January, tacks on three bills to keep parts of Defense, Ag, and the Capitol complex humming through 2026, reverses shutdown-era RIFs, and restores back pay.

The House is next; the president says he’ll sign it fast when it gets to the Oval Office.

The S&P 500 Quality Index ranks companies not by market cap or a compelling AI story, but rather by fundamentals. Earnings, profit margins, and financial leverage. Reasonable debt.

You know, the kind of stuff that makes your eyes glaze over. And the type of companies we like to hold for the long haul in our model portfolio.