Philoinvestor

Philoinvestor

3 Worries for 2026 (and their analogies)

The Bill is Coming Due.

Dec 20, 2025
∙ Paid

To be honest, I am not worried personally.

In fact, I am excited to see these setups unfold and create opportunities for us going forward. Those who should be worried are those with backward-looking perspectives that cannot adapt to current realities.

Some thoughts on what will break investors (and their pocket’s) going forward.

  • the infinite belief (to the point of dogmatism) in passive investing

  • sovereign bonds and fiat money remaining sound regardless

  • those that continue to extrapolate the recent past to the future

The Misunderstanding 🪃♠️

I’ve spent more than twenty years occupying myself almost exclusively with finance and money, and I’ve come to a simple conclusion: most people get the focus backwards.

Nearly all effort goes into making money, while very little goes into keeping it. But the thing is, long-term outcomes are driven less by how money is made and more by how it is lost.

Outcomes are non-linear to amounts. i.e. It won’t matter as much to your future self or the current and future generations of your family whether you have $5mln or $15mln (today’s value!), but it will matter if you have $5mln or $0.

What follows are my thoughts on the market’s three greatest traps — illustrated through historical analogies.

Some of the analogies are: 1) The Oil Crash and OPEC crisis of 1985, 2) the official end of Bretton Woods and the transition from the Gold Standard to the Dollar Standard and 3) the Canary Wharf-induced bankruptcy of the Reichmann Brothers property empire.


By the way, the 3rd worry is on AI.

I listened to Jim Chanos’s interview with Jack Farley and realised Jim Chanos’s team used the same method we used last year in Downside at AI to calculate Cloud profitability 👇

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