Dividends, index funds, ETFs, REITs, bonds, and the tax-advantaged accounts that let you keep more of it. Long-horizon investing with the working shown.
Dividend investing has a beginner trap that the introductory articles tend to skip: the highest-yielding stocks are usually high-yielding for a reason, and that reason is rarely good. Here is the short version of how to read a yield without falling for the headline.
From 2018 to 2024 I held both a small REIT portfolio and a one-bedroom rental in a small US city. Here is the actual six-year P&L of both — fees, vacancies, repairs, taxes — and which one was genuinely passive.
A mutual fund tracking the S&P 500 and an ETF tracking the S&P 500 own the same companies. They behave differently in three small ways that, over a decade, add up to a non-trivial gap. Here is the short version.
I have held the same twelve dividend stocks for at least three years. Last year I logged every payment to the cent and ran the math against what the marketing of dividend investing promises. Five things were surprising.
For most of my adult life, US Treasury bonds yielded less than inflation. That stopped being true in 2022 and is still mostly true today. Here is what I actually do with the part of my portfolio that is not in stocks.
It was 2019. I had heard of the backdoor Roth. I had read three blog posts about it. I did the steps in the wrong order. The IRS was reasonable about it. It still cost me, by my accounting, $4,200 in compounding I will never get back.
Over twelve months in 2024 I wrote covered calls against three of my long-term equity positions. The income was real. The cost — in capped upside, in cognitive bandwidth, in one specific blow-up — was higher than the spreadsheet suggested.
Health Savings Accounts are sold as a medical-bills wrapper. The much more interesting use of one is as a triple-tax-advantaged retirement account that nobody seems to talk about. Here is the math, and the small list of conditions under which it works.
Eight years ago I split a small portfolio into two halves and let one of them run on autopilot. The autopilot half is now meaningfully ahead. The reasons are mundane and worth writing down.