Writing · Capital / Finance / Investing

2025-09-14
Why do we still worship fortune tellers in suits? Since the beginning of man, we’ve chased predictions. Witch doctors tossed chicken bones. Romans wouldn’t fight until the entrails said “go.” Now? We dress it up with charts, models, and media segments. Same impulse, shinier packaging. The problem isn’t predicting—it’s pretending those predictions mean much. If every forecaster had to publish their batting average, most would look like a blindfolded kid swinging at piñatas. Imagine a tarot card reader forced to show the results of their last 1,000 readings. The line would vanish. Yet the boldest, most confident voices are the ones on TV and in white papers. They’re usually the ones who miss the most. We remember their rare hits and forget their constant misses. Next time you’re tempted to say “the Fed will do X” pause. Ask yourself: what’s my own track record of being right? Odds are, not great. That doesn’t mean you stop thinking about the future. It means you stop mistaking forecasts for facts. This reminds me of a conversation I had with a very rich real estate investor. The sponsor had all these fancy reports and predictions too, the investor was trying to get me to invest in another deal. We are sitting in the sponsor’s office, a large Class C operator in the Southeast. They controlled over 10,000 units. He bragged about the money they made. I asked: “How much did they improve NOI? During the 4 year period” He laughed “NOI actually got worse. Insurance up. R&M up. Payroll higher, Bad debt worse. But cap rates fell, so we sold for a huge number. Now it’s the next guy’s problem. I don’t know how they’ll even breakeven.” Don’t kid yourself—real estate is a cyclical business. Everyone looks smart in a boom. The trick is not drowning when the tide goes out. Discipline is walking from deals that don’t pencil under realistic assumptions. I’ve never lost sleep over the deals I didn’t do. I’ve lost sleep over the ones I did!
Capital / Finance / InvestingOperations / Property ManagementReal Estate (general)

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