Articles
Every read, by topic
25 short reads, about 89 minutes in all. Three to five minutes each. New to this? Follow the ladder walk first.
How much of my return does tax take, and what is worth doing about it?
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What a dollar of gain keeps after tax
Sell a winner at the top California bracket and 35 cents of every dollar of gain goes to tax. Sell it inside a year and 52 cents go. Where those two numbers come from.
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Eight tax levers, ranked by what they are worth
Never selling is worth the whole 35 cents, the one-year line 17, an ETF about 120 basis points a year. Loss harvesting, the lever with the marketing budget, 0 to 30 after year five. Each one, priced.
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The lever worth the most is never selling
A $100,000 position with a $40,000 gain costs $14,040 of tax to sell. Held to the estate it costs nothing; given to charity it earns a deduction. The quiet lever at the top of the ranking.
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The one-year line is worth 17 cents per dollar
Everyone knows the line. In 2015 individuals still realized $3.3 billion of stock gains within three months of it, at the short-term rate. Where a known rule gets crossed early, and what it costs.
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Loss harvesting, in one example
Sell a stock at a $10,000 loss, buy a similar one the same day, and the loss cuts this year's tax bill by up to $5,210. What actually happened, step by step, and the catch.
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Why the harvesting benefit fades after a few years
In AQR's simulation harvesting adds 155 basis points in year one and nothing by year five without new cash. Live accounts show the same curve. Why it fades, and the three things that keep it alive.
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The wash-sale rule in four facts
Buy back the same stock within 30 days of selling it at a loss and the loss is disallowed. That part is well known. The four facts that catch households are about spouses, IRAs, brokers, and ETFs.
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Two questions for any tax-savings pitch
Does the benefit last past year five? Does the long/short version make sense below $5 million? The published evidence says no to both as general claims. How to ask, and what a good answer sounds like.
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One rule holds up the ETF tax advantage, and Treasury is looking at it
As of September 2026 nothing pending changes the ranking of the levers. One live item: Treasury has said it is examining the in-kind mechanism behind every ETF's tax edge. A dated watchlist.
Which of my accounts should hold which piece of the portfolio?
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The rollover that never got invested
IRAs hold $19.2 trillion. Vanguard found that 28% of rollovers were still sitting in cash seven years later. The most under-managed retirement money is the money that never got invested at all.
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Four accounts, three tax treatments
Taxable, traditional IRA or 401(k), Roth, HSA. Each taxes the same dollar of return at a different time and a different rate. One table, then the one rule that follows from it.
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Turnover decides location, not asset class
Most households shelter index funds in the IRA and keep active holdings in taxable. A 3% return from monthly trading nets 1.4% in taxable and keeps its full value in an IRA. That setup is backwards.
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Fill the sheltered slots before adding taxable money
A dollar inside a shelter never meets the 52% short-term rate or the yearly dividend tax. The 2026 limits, the two back doors for high earners, and one Californian catch.
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What an IRA cannot do
It cannot borrow, so it cannot short. It destroys a loss harvested next door. And a long-only version of a long/short idea keeps about half the edge. Three limits of the best shelter most people have.
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California taxes the HSA every year
Federally an HSA is deductible going in, untaxed while it grows, and untaxed coming out for medical costs. California recognizes none of it. What that costs, and the bill that would change it.
Which fund wrapper keeps the most after tax, and who keeps the fees?
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Why ETFs pay less tax than mutual funds
The average stock mutual fund lost 1.9% a year to tax over the last decade; the average stock ETF lost 0.7%. The gap comes from one line in the tax code, not from smarter managers.
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Direct indexing, in one page
Own the 500 stocks instead of the fund that owns them. A $1.16 trillion business built on that idea. What you get, what you pay, and who it fits.
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Same harvesting, 9 basis points or 115
Retail direct indexing charges 9 basis points a year. Through an adviser and a platform the same logic costs about 115. Against a long-run benefit of 0 to 30, the price decides the sign.
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The dividend tax no wrapper removes
An index ETF defers its capital gains almost completely. It cannot defer its dividends. At a 1.3% yield and a 35% rate, that is 46 basis points a year, and it is most of the ETF's remaining tax drag.
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ETF share classes: the patent that expired
One firm held a patent on attaching an ETF share class to a mutual fund until May 2023. Since November 2025 the SEC has let others do it, and the funds that get one stop paying out gains.
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Section 351: moving a portfolio into an ETF without selling
Since December 2024, 113 ETFs have launched by taking in investors' stock portfolios for shares, no gain recognized, about $21 billion so far. The two tests, and why the IRS has not said yes.
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Exchange funds, for one big stock
Contribute one concentrated stock to a partnership, receive a slice of everyone's, pay no tax, wait seven years. The fee is 0.4% to 0.95% a year, and a fifth of the fund is real estate by law.
How much of the result does the mix of stocks, bonds and gold decide, before any other choice?
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The stock-bond mix alone swings twenty-year returns by up to three points a year
Since 1985, moving from an all-equity portfolio to 60/40 has changed trailing 20-year annualized returns by as much as 3.1 points a year, before any strategy or wrapper choice.
Which equity approach, and does the evidence support paying for it over the index?
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A value tilt has earned 0.5 points a year since 1985, and none of it since 2006
A 0.20 HML tilt run at roughly 2% tracking error beat the market by 0.5 points a year since 1985. Nearly all of that edge arrived before 2007, and it has not returned since.
What else, beyond stocks, bonds and gold, actually diversifies the portfolio?
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Trend following made money in all five of the worst US equity years since 1985
AQR's diversified trend strategy was positive in every one of the five worst US equity years since 1985, averaging +21.6% while stocks fell 6 to 39%.