The Late-Cycle Signals I Watch — And How I'm Positioned

I called my dad in Vietnam last week, and he asked me on stock advice. And if you've been following me for a while, especially in my most viral video, you would know that anytime any of my elder family members ask me about investment opinions, it tends to be a very grim sign of what to come.

Not a chart. Not a Fed meeting. My dad — who has lost money every single time he invests into stocks or crypto — asking me how to get in. The last three times that happened, the market topped out around eight months later. Every time.

You've been asking me the same thing all year. When do I, Ace get out? When do I de-risk? When do I raise cash? It's the number one question in my inbox. I sat on it because The answer that I could give you at that time could change literally one week after. How I position changes literally week by week, depending on how my view and how my opinion about the market changes based on market events.

Let’s start with where we are. I'm not going to repeat it but you already know the 18 by 60 year real estate cycle that I have been preaching about. Land moves on an 18.6-year rhythm — roughly 14 years up, 4 down — and we're about year 14. Stage 4. The Winner’s Curse, the peak where leverage is maxed, everyone piling in, "new era" stories everywhere. And here's the part most people miss — land doesn't peak with the stock market. It peaks first. Then credit. Then the broader economy.

I believe that most people get one thing wrong about exits: they wait for confirmation. They want to see the crash before they believe it. But by the time the headlines agree it's a bubble, the move that mattered already happened, the investor would have seen their portfolio drop by 30%.

So here's the order — and it's the same every time. Debt is tightened. Refinancing gets harder. Turnover slows down — deals stall before prices even move. Then prices of assets flatten. And only after all that do the forced sales show up and it finally looks like a "crash." Watch how it actually went:

In 1928–29, the Fed hiked to curb the speculation. Property had already peaked in 1926 — the stock market got one last wind into '29, then the credit was already gone when it broke. In 1973, everyone blamed the oil shock. But the oil embargo landed on an economy already weakened by tighter credit — it pulled the trigger on a gun that was already loaded. In 2005–06, subprime froze and home prices peaked in 2006 — a full two years before Lehman made it obvious. The damage is always done early, in the quiet. Prices collapse last. Waiting for the price is choosing to be late.

Now line the tops up. 1929. 1973. 1989. 2007. Every one of them had the same four things: credit quietly tightening while spreads stayed low, asset prices rose to the top of the range, a "this time is different" story everyone believed, and a famous trigger that got the blame. Four boxes. In 2026, all four are flashing.

There's a longer echo too. Major tops cluster about 60 years apart — 1906, 1966, 2026. The one almost nobody remembers is 1966: the S&P fell about 23%, peaking in February and bottoming in October, as funding markets seized in what one economist called a "controlled panic." And notice the timing: the peaks tend to land in years ending in 6, but the decisive breaks come in years ending in 7 — 1907, 1937, 1987, 2007. That's why I read 2026 as the peak, and 2027 as the more likely year for the real break.

And the first crack already showed. June 5 was the biggest one-day drop in US stocks since last October. One bad day isn't a crash. It's the kind of day that tends to show up first.

Could I be wrong? On the timing — yes, easily. Governments have gotten very good at stretching cycles past where any old playbook said they'd break. The break could be 2027, not now. The direction I'm confident about. The exact month, I'm not. That's the honest gap.

Here's one signal you can watch yourself this week — free. Since land turns first, you'll see it in housing supply before any headline. Watch months-of-supply (the Fed publishes it free on FRED) and days-on-market in your own city. When listings start to go up and homes start to sit, the turn has started. Make it a monthly habit. Do that and you'll see the shift on the ground before the national data ever rings the bell.

That's the method. Now the part I actually do with it.

Every Tuesday I pull three readings from Smart X Terminal and write down where they sit. Right now two of the three are giving me warnings — and one of them is a credit signal that hardly anyone reads correctly, and the one real-economy number that just turned negative — plus exactly how I've moved my own money, including the most cash I've held at any point this cycle.

Quick note: these readings are as of June 20. Markets move, so I keep Smart X Terminal updated in real time for the live picture.