You Think You Own “The Market.” You Mostly Own Seven Companies.
There’s a number that changed how I think about passive investing: 34%. That’s the share of the S&P 500 that the ten largest companies represent as of 2026. In 2010…
Nobody Told You the Front Door Was Decorative
Last year I spent some time mapping how people I know actually got their last job. Not the official version — “I saw the posting and submitted my application” —…
The Most Tax-Efficient Account in America Is Sitting Unused in Your Benefits Portal
I looked at my HSA balance about two years into having one and felt genuinely embarrassed. I had been dutifully contributing, paying medical bills with the card, and congratulating myself…
Boring Businesses Are Changing Hands. Almost Nobody Is Paying Attention.
I started looking into this about a year ago after reading a statistic that I kept coming back to: Baby Boomers own approximately 41% of all small businesses in the…
The 60/40 Portfolio Had One Job. It Failed in 2022.
2022 is the year the argument against the traditional balanced portfolio stopped being theoretical. The S&P 500 fell roughly 18% that year. In a functioning 60/40 world, that should have…
Travel Hacking is Not a Loophole: The 2026 Strategy Guide
Travel hacking is not a loophole. It is not illegal. It is not something that requires a finance degree or a spreadsheet addiction. It is, at its simplest, the observation…
Building Your AI Chief of Staff
An AI chief of staff is not a chatbot with a fancier name. The distinction matters because most people who think they’re using AI as a productivity tool are actually…
The Renaissance Window: Why the AI Generalist is the High-Value Role of 2026
The AI generalist is, in a sense, a very old idea wearing a new name. The Renaissance polymath. The Victorian natural philosopher who studied botany on Monday and economics on…
