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…
The One Big Beautiful Bill: What Actually Happened to the 2026 Tax Brackets
For most of 2024 and early 2025, financial advisors were running the same playbook: execute Roth conversions now, accelerate income, act before the clock runs out on the Tax Cuts…
Private Credit Investing: Why Harvard’s Secret Strategy Just Went Retail
Private credit investing has been the quietly dominant strategy of endowments, family offices, and sovereign wealth funds for roughly two decades. While retail investors were cycling between stocks and bonds,…
