Investing & Strategy

Trust Me, Bro Finance- Why Social Media Makes Adverse Selection Worse

“Trust Me, Bro” Finance: Why Social Media Makes Adverse Selection Worse

The stock market used to be a place where information asymmetry worked in predictable ways. Professional investors had Bloomberg terminals. Retail investors had newspapers and whatever their broker told them over the phone. Everyone understood the pecking order of who knew what when. Then social media arrived and promised to level the playing field. More […]

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What Happens When You Start Dollar Cost Averaging $10 of Bitcoin Every Day for 5 Years?

What Happens When You Start Dollar Cost Averaging $10 of Bitcoin Every Day for 5 Years?

The interesting thing about buying Bitcoin every single day is not what happens to your money. It’s what happens to you. Most articles about dollar cost averaging treat it like a math problem. They show you charts with lines going up. They calculate returns. They compare strategies. But somewhere between the spreadsheet and the real

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Why Your Long-Term Strategy is Failing Your Monthly Returns

Why Your “Long-Term” Asset Allocation is Failing Your Monthly Returns

Every investor has heard the gospel of long-term thinking when it comes to asset allocation. Buy and hold. Stay the course. Time in the market beats timing the market. These mantras get repeated so often they’ve become financial scripture. But here’s the uncomfortable truth: while you’re busy being patient and strategic, your portfolio might be

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Why Your 10-Year Portfolio is Probably Betting on a Dead World (Secular Trends)

Secular Trends: Why Your 10-Year Portfolio is Probably Betting on a Dead World

The average investment portfolio is a museum of the present disguised as a bet on the future. Look closely at the holdings in your retirement account or your carefully diversified index fund, and you’ll find something uncomfortable: most of these companies exist to serve a world that is already disappearing. This isn’t about predicting the

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How to Own the S&P 500 and Still Feel Like a Hedge Fund Manager

How to Own the S&P 500 and Still Feel Like a Hedge Fund Manager (Core-Satellite)

Most people think investing is binary. You either park your money in an index fund and accept mediocrity, or you become a stock picker and pretend you’re Warren Buffett at a cocktail party. The first option feels like defeat. The second feels like delusion. But there’s a third way that lets you have your cake

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Bordeaux vs. Bitcoin: The Unlikely Investment That Doesn't Crash on a Tuesday

Bordeaux vs. Bitcoin: The Unlikely Investment That Doesn’t Crash on a Tuesday

There’s something profoundly absurd about comparing a bottle of fermented grapes to a string of mathematical code. Yet here we are, living in a world where both can be considered serious investment vehicles. One sits in a temperature controlled cellar in France, quietly aging. The other exists everywhere and nowhere, pulsing through servers and changing

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The Bitcoin Problem: Where Does Crypto Fit into a Modern Portfolio Theory Strategy?

Harry Markowitz won a Nobel Prize in 1990 for work he published in 1952. That work, Modern Portfolio Theory, changed how we think about investing. Now, seventy years later, a technology he could never have imagined is forcing us to reconsider what his theory actually means. Bitcoin presents a peculiar challenge. It behaves nothing like

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