Welcome to The Nightcrawler, a weekly collection of thought-provoking articles and analysis on technology, innovation, and long-term investing. The Nightcrawler is published every Friday evening by Eric Markowitz, Managing Partner of Nightview Capital and the firm’s Director of Research. Follow him on X.
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In this evening’s email…
Quote of the week: “To be uncertain is to be uncomfortable, but to be certain is to be ridiculous.” — (I’m uncertain of the origin of this quote.)
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My interview with Barry Ritholtz on luck, humility, and how (not) to invest
For my Long Game column over at Big Think, I spoke with Barry Ritholtz about his excellent new book, How Not to Invest — a sharp, funny, and deeply insightful guide to the behavioral traps that trip up even the smartest investors.
In our conversation, Barry unpacks the real culprits behind poor decision-making: overconfidence, hindsight bias, and the seductive pull of “this time is different” thinking. His advice? It’s better to look dumb and actually learn than fake it and lose money.
How Not to Invest is a masterclass in behavioral humility — a reminder that long-term success comes down to three things: luck, curiosity, and humility. As he puts it: “Better to look stupid and learn than pretend and lose money.” A lesson for investors — and for life.
- Key quote: “The book is ostensibly about investing. But if you strip it down to its most basic form, it’s about decision-making, judgment, and behavior. If I’m explaining this to a three-and-a-half-year-old, I’d say: we want to teach you to make good decisions — not just ones that work for now, but over time. Think of your life as a long arc, and the better your decisions across that arc, the better your life will be. And when people tell you life is simple, it’s often more complicated than that. Beatrice needs to think critically and be aware of people who may not have her best interest at heart. My area is investing, but at its heart, this book is about making better choices.”
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Howard Marks on why uncertainty is a feature, not a bug
In his latest memo, Nobody Knows (Yet Again), Howard Marks offers a characteristically lucid meditation on uncertainty—both in markets and in life.
The memo draws a throughline from 2008 to COVID to today’s trade turmoil. He emphasizes that real investing happens in the fog—when predictions fail and doubt reigns. It reminds me of an idea I often return to: the poet John Keats’s notion of negative capability—the ability to remain “in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason.”
Here, Marks argues that the best investors act not necessarily from conviction, but from clarity about what can’t be known. Tariffs may aim to support U.S. industry, but their ripple effects—higher prices, job losses, global instability—remain dangerously unpredictable. Acting only when the dust settles is, itself, a costly choice. This theme is central to The Nightcrawler: to think long-term, we must resist the urge for premature answers. Instead, we embrace ambiguity, stay grounded in first principles, and move forward—especially when it feels most uncomfortable.
- Key quote: “I can’t claim to have analyzed the future. In fact, I consider the phrase “analyze the future” one of the great oxymorons. The future has not yet been created, and it’s subject to millions of complex, unquantifiable, and unknowable factors that will always be in flux. You can ponder the future and speculate about it, but there’s nothing to “analyze” and certainly there wasn’t in the early days of the Global Financial Crisis.”
A few more links I enjoyed:
Rules Of Thumb Vs. Rules Of Big Toe – via Matt Zeigler (Cultish Creative)
- Key quote: “Next time somebody gives you some smart sounding advice, labeling it as a Rule of Thumb, be sure to check if it matches one of your own Rules of Big Toe. If not, brace yourself if you embrace putting their rule into practice, because you might have to get hurt before you figure out if it works.”
The Foundations of Investing: You Cannot Time The Market – via Michael Cordaro
- Key quote: “There are times when it gets very tempting to listen to the voices around you telling you they know where the market is going next. This is where the discipline really needs to kick in because in order to successfully time the market, you have to be right twice. Let’s say you go with a gut feeling and liquidate your entire portfolio at or near a market peak. You feel pretty good about yourself as stocks fall and crisis sets in. That is until you start to feel the pressure of when to get back in. Those that have lived through the bad times know that the market usually turns around right when you’re ready to throw in the towel.”
Trade, Tariffs, and Tech – via Ben Thompson / Stratechery
- Key quote: “This, more than anything else, is what has hollowed out U.S. manufacturing. The cost of cheap consumer goods and a seeming inexhaustible capacity for U.S. debt was the shifting of ever more manufacturing abroad. Yes, things like lower costs and different labor standards played a role, but it’s the structure of the world economy that matters most; indeed, China’s labor costs are significantly higher than they used to be, but China’s manufacturing dominance is actually accelerating.”
From the archives:
Morgan Housel – via Acquired (H/T Matthew Stafford)
- Key quote: “There’s now a very famous Bezos quote, where he says, ‘People always ask me what’s never going to change. But what’s more important is what’s not going to change.’ The more nuance to that question that he said a couple sentences later, is he said, ‘You can never imagine a world in which consumers don’t want cheap prices, fast shipping, and big selection. It’s impossible to imagine a world where people don’t want that. Because of that, you can put so much confidence into investing in those things, knowing they’ll be relevant in the future.'”
