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 ReturnComing soon
Why bonds belong in tax-deferred accounts, growth stocks belong in Roth, and dividend-heavy positions belong somewhere specific. The math compounds across decades.
- 2Tax-Loss Harvesting: How a Loss Becomes Real MoneyComing soon
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.
- 3IRA vs Roth vs Taxable: A Decision Framework, Not a DogmaComing soon
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.
- 4Qualified vs Ordinary Dividends: The Difference That Adds UpComing soon
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.
- 5How Portfolio Turnover Quietly Eats After-Tax ReturnsComing soon
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.
Core 20
The core 20 model portfolio applies the methodology this topic covers. 14.7% CAGR over the backtest, +2.2% alpha vs the S&P 500.
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