
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…

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. It is not illegal. It is not something that requires a finance degree or a spreadsheet addiction. It is, at its simplest, the observation…

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 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…

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 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,…

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…

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 —…

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…

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…