Tax & Account Strategy
How tax-aware investing and the right account placement compound into thousands of dollars over decades, without changing what you own.
Most investors think the only thing that matters is what they own. The compounding evidence runs harder than that. WHERE you hold a position (taxable brokerage, traditional IRA, Roth IRA, HSA) and HOW you handle the tax consequences of trading inside that account changes the long-run dollar outcome by a margin that often dwarfs the difference between two reasonable stock picks.
This cluster covers the operating side of investing. Account types, tax treatment of dividends and gains, the asset-location decision, the role of tax-loss harvesting, and the math behind why a turnover-light strategy in a taxable account often outperforms a higher-return strategy that gets ground down by taxes. Educational only: we are not tax advisors and you should consult one for your specific situation.
Recommended reading order
5 articles, ordered for sequential learning. Skim by title if you already know the basics.
- 1Asset Location: Where to Hold Each Position for Maximum After-Tax Return
Why bonds belong in tax-deferred accounts, growth stocks belong in Roth, and dividend-heavy positions belong somewhere specific. The math compounds across decades.
Read → - 2Tax-Loss Harvesting: How a Loss Becomes Real Money
The mechanics of converting paper losses into tax savings without changing your underlying portfolio thesis. Wash-sale rules and how to stay clear of them.
Read → - 3IRA vs Roth vs Taxable: A Decision Framework, Not a Dogma
The right answer depends on your current tax bracket, your expected retirement bracket, and how soon you need access. A clear decision tree, not the usual hand-waving.
Read → - 4Qualified vs Ordinary Dividends: The Difference That Adds Up
Why one form of dividend gets taxed at long-term-capital-gains rates and the other gets taxed as income. What it means for which dividend stocks belong in which account.
Read → - 5How Portfolio Turnover Quietly Eats After-Tax Returns
Two strategies with identical pre-tax returns can land miles apart after taxes if their turnover differs by a factor of two. The math, plus what to look for on a fund fact sheet.
Read →
Core 20
The core 20 model portfolio applies the methodology this topic covers. 13.13% CAGR over the backtest, +3.81% alpha vs the S&P 500.
Explore Core 20→Other topics
The Market Normality Report
Where today’s S&P 500 sits in relation to market history since 1950. Twelve brand-designed pages. Print-ready. Free.
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