Thiel’s Exit: Or, How I Learned to Stop Worrying and Maybe Sell Everything

Right. So, Peter Thiel. Billionaire, Palantir founder, and apparently, a man who enjoys a good portfolio purge. Honestly, the drama. He still owns a chunk of Palantir, don’t get me wrong – about 100 million shares. It’s his safety blanket, I suspect. But his hedge fund, Thiel Macro? Cleared house. Everything gone. Poof.

The SEC filings are… revealing. Q3 2025, they had $74 million spread across Tesla, Microsoft, and Apple. A perfectly reasonable spread, if you ask me. Then, Q4? Nada. Zip. Zilch. Not a single stock. It’s like he woke up one morning and decided the whole market smelled faintly of regret. I get it, actually. It often does.

Now, everyone’s scrambling for a reason. Is he seeing something we’re not? Did he have a particularly bad avocado? Honestly, I suspect it’s a bit of both. He probably looked at the valuations, did a quick calculation, and thought, “You know what? I’m going to go lie on a beach.” And good for him, frankly. Though, it does suggest a lack of confidence in the tech giants. Or maybe he just really needed the cash. Don’t judge.

The S&P 500 was looking a bit… frothy in Q4. Expensive, historically. Like that dress you bought online that looked amazing on the model but… doesn’t quite work on you. It’s a feeling. So, he bailed. Smart? Reckless? Depends on your tolerance for risk… and your access to a private island.

But here’s the kicker. He did this before. Back in late 2019. Sold everything, sat on his hands for five years. The S&P 500, predictably, went on a tear. A 91% return. He missed out. Massively. Though, to be fair, he was busy betting against the market with put options. Which, you know, softened the blow. It’s a bit like losing a tenner on a bad date – annoying, but not exactly life-ruining.

The real irony? He missed the AI boom. ChatGPT dropped in Q4 2022, and suddenly everyone was convinced they could build the next unicorn. He was sitting there, hands empty, watching the madness unfold. I’m picturing him with a very expensive glass of wine, muttering about the irrationality of markets. I’d be doing the same.

Let’s talk valuations, shall we? The S&P 500 had a CAPE ratio of 39.1 in Q4 2025. That’s… high. Like, really high. The 30-year average is 28.5. It hasn’t been this expensive since the dot-com bubble. Which, let’s be honest, feels like a distant, slightly embarrassing memory. And it’s only gotten more expensive since then. February 2026 saw it creep up to 39.2. Lovely.

Here’s a handy table, because everyone loves a good table. It shows what happens when the CAPE ratio gets this frothy. Prepare for disappointment.

Time Period S&P 500’s Best Return S&P 500’s Worst Return S&P 500’s Average Return
1 Year 16% (28%) (4%)
2 Years 8% (43%) (20%)
3 Years (10%) (43%) (30%)

Basically, if history is anything to go by, we’re looking at a decline. A 4% dip by February 2027, a 20% tumble by 2028, and a full-blown 30% plummet by 2029. Cheerful, isn’t it? Though, of course, past performance is no guarantee of future results. It’s just… a pattern. And I, for one, am a sucker for a good pattern. Especially when it confirms my deepest anxieties.

But here’s the thing. AI might change everything. Maybe companies will magically become more profitable. Maybe earnings will soar. Maybe pigs will fly. JPMorgan’s Kriti Gupta says AI adopters are seeing margin expansion. Which is… promising. Though I suspect it’s mostly hype. Still, it’s a good story.

Wall Street, predictably, doesn’t agree with Thiel. They think Tesla, Microsoft, and Apple are undervalued. Bless their optimistic little hearts. Analysts are predicting upside of 22% for Tesla, 51% for Microsoft, and 21% for Apple. It’s like they’re deliberately ignoring the warning signs. Or maybe they just have a vested interest in keeping the party going. Who am I to judge?

So, where does that leave us? Thiel Macro has a mixed track record. He beat the S&P 500 last year, avoided losses with those put options, but missed out on gains by sitting on the sidelines. The S&P 500 is expensive, history suggests a correction is coming, and Wall Street is stubbornly bullish. It’s a mess, really. A beautiful, chaotic mess. And honestly? I wouldn’t have it any other way.

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2026-03-15 10:54