Archive
Risk
+1
Feb 28, 2026
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10 min read
Gradually and Then Suddenly
Our story begins in the late 1990s. When software started ruling the world. We're now in the middle of what's being called the "AI Scare Trade" or SaaSpocalypse. Software stocks are down. Private equity down. Private credit down. This is how we got here. And what you might want to be thinking about.
Markets
+1
Feb 14, 2026
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10 min read
Certainty is Poison
Let's talk about resilience. In markets, as we get deeper into 2026. For our kids—because the clock has started, whether you like it or not. And why Vineer Bhansali's least favorite word is greed.
Markets
+2
Jan 31, 2026
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12 min read
Inflation, Markets, and Precarity in America
For a brief window, you could earn 5% on Treasury bills and actually build wealth after taxes and inflation. That's over. Now people are back to saying "there is no alternative to stocks"—but history tells a different story. In this piece: TIPS as an inflation hedge, what really happened to stocks in the 1970s (spoiler: down 50%+ in real terms), and my conversation with Mike Green on passive investing's endgame and why the poverty line might actually be $140,000, not $40,000.
Markets
+1
Jan 17, 2026
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8 min read
Life Is Full of Hard Choices
People often say "there is no alternative" to stocks. But the US equity market is trading at its second-highest valuation in 145 years—only the Tech Bubble was pricier. History shows that starting from extreme valuations compresses future returns, sometimes for a decade. And T-bills? Barely breaking even after taxes and inflation. Both options present uneasy trade-offs. But here's the thing: there's always a choice to make. That's far more productive than pretending there isn't one. Plus: my conversation with Devin Shanthikumar on why sell-side analysts "speak in two tongues" and how AI is changing security analysis.
Markets
+1
Dec 20, 2025
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5 min read
The Future Is Unwritten
Looking back at 2025, I'm reminded that the strongest bull markets are built on diminishing bad news, not good news. But what about looking forward? I sat down with Paul Solman—50 years explaining economics to America, eight Emmys, five Peabodys—and he cut to the chase: "It's a stochastic universe. I have no idea what's gonna happen next. So you come up with strategies that protect you as best you can." Then he offered something deeper: be here now, small acts of kindness, there's more good in the world than bad. The future is unwritten. Grab a pen.
Markets
+2
Dec 6, 2025
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5 min read
On Doing the Right Thing
Against all odds, 2025 is almost history. And the lesson? It's always the right time to do the right thing—never a better or worse moment. That simple truth guided me through April's chaos, when Jason Zweig at The Wall Street Journal asked me what investors should do. The answer: prioritize doing no harm, manage regret risk, don't panic into something worse. Life must go on, even in uncertainty. That was the work this year. It will be again in 2026.
Markets
+2
Nov 8, 2025
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11 min read
“Up and to the Right” + Advanced Tax Strategies
People love to say "stocks go up and to the right over the long run" like it's a law of physics. It's not. The U.S. stock market's 150-year run required exceptional circumstances—no foreign occupation, no revolution, stable institutions, and relentless value creation. Eleven other markets literally disappeared in the 20th century. For prices to rise, "steady" isn't enough. Businesses must generate more value, more revenue, greater efficiency, more cash—every decade. A lot has to go right. We shouldn't take any of it for granted. Plus: my conversation with Brent Sullivan on tax alpha strategies and why tax comes after risk, return, and diversification—not before.
