The 60/40 Portfolio Had One Job. It Failed in 2022.
I want to start with 2022 because it’s the year the argument against the traditional balanced portfolio stopped being theoretical. The S&P 500 fell roughly 18% that year. In a…
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,…
You’re Standing in Front of an Open Door: The Mega Backdoor Roth 2026
The mega backdoor Roth exists because the tax code has a gap in it, and the gap is large enough to drive a significant amount of money through. Most high…
You’ve Already Done the Hard Part. You’re Just Selling It Wrong.
I spent some time last year looking at the LinkedIn profiles of people who’d left VP and Director roles at companies like Salesforce, HubSpot, and various Series B startups —…
The Call That Sounds Like Your Mother
A researcher at a cybersecurity firm in London ran an experiment last year that I haven’t been able to stop thinking about. She took three seconds of audio from her…
The Solopreneur Dream Was Real. The Ceiling Was the Problem.
About two years ago I hit a wall that I suspect a lot of people running one-person operations recognize immediately when they hear it described. Revenue was growing. The work…
