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Colonial soldiers: a total return swap lets you invest in a fund without owning it; how is it taxed? Nobody knows.

Swap taxation: what is constructive ownership?

Jul 5, 2026
Paying taxes on fireworks

Paying taxes on fireworks

Jul 3, 2026
A little tax strategy in your fund's swap positions

A little tax strategy in your fund's swap positions

Jun 30, 2026
There is no cost basis in a notional principal contract

Swaps are in your funds. How are they taxed?

Jun 28, 2026
A wash sale is a wash sale no matter the wrapper

A wash sale is a wash sale no matter the wrapper

Jun 26, 2026
Managed futures "crisis alpha" is compelling, but...

Managed futures "crisis alpha" is compelling, but...

Jun 25, 2026
Charlie Chaplin in Pay Day (1922)

What do 100 years of trend data reveal about managed futures?

Jun 23, 2026
Après Tax is personalized, after-tax performance, and it's coming soon

Après Tax is personalized, after-tax performance, and it's coming soon

Jun 21, 2026
Why I left Substack

Why I left Substack

Jun 19, 2026
Long/short: Schwab adds "heightened maintenance standards" Tax-Aware Long-Short

Long/short: Schwab adds "heightened maintenance standards"

Jun 17, 2026
Chart showing managed futures returns uncorrelated with stocks and bonds Tax-Aware Long-Short

Managed futures are weirdly uncorrelated

Jun 16, 2026
Graphic on securities lending signals for a tax-aware long-short portfolio Tax-Aware Long-Short

Long/short: what can the securities lending market tell us about short risk?

Jun 14, 2026
Cartoon on the risk of betting big on a single pre-IPO stock like SpaceX Concentrated Stock

Is it okay to space out on SpaceX?

Jun 12, 2026
Map-style graphic sorting the 50 states into five capital-loss tax regimes for tax-loss harvesting State & Local Tax

Tax-loss harvesting in 50 states

Jun 11, 2026
Concept of a charitable stock donation being recast as a taxable sale once an M&A deal nears certainty Concentrated Stock

When a stock donation might be taxed like a sale

Jun 9, 2026
Cartoon of a stock position morphing into cash ahead of an announced all-cash acquisition closing Concentrated Stock

When an acquisition turns a stock into cash before the deal actually closes

Jun 7, 2026
Cartoon framing alpha as splitting into pre-tax and after-tax components, the theme of the Basis Northwest reading list Podcasts & Media

Some source articles from Basis Northwest 2026

Jun 5, 2026
Cartoon contrasting SPY and SPX call options to show their differing tax treatment under the 1256 rules Options

How options on SPY and SPX are taxed

Jun 4, 2026
Cartoon riffing on Washington State's unusual capital gains excise tax and its federal SALT deduction angle State & Local Tax

SALT in the Washington State Wound

Jun 2, 2026
Recap graphic from Basis Northwest 2026, the taxable wealth conference that drew 350 advisers to Seattle Basis Northwest

Basis Northwest 2026: self-selected

May 31, 2026
Flying money plushie marking the Day 1 recap of the Basis Northwest 2026 taxable wealth conference Basis Northwest

Basis Northwest 2026: Day 1 Notes

May 29, 2026
Cartoon showing long/short alpha flowing into a direct indexing portfolio like a cash infusion that refreshes basis Tax-Aware Long-Short

Long/short: alpha acts like a cash infusion

May 27, 2026
Cartoon contrasting a variable prepaid forward with a collar and margin loan as two routes to monetize concentrated stock Concentrated Stock

Variable Prepaid Forward vs. Collar/Margin Loan

May 24, 2026
Cartoon weighing investment risk against compensation, framing tax-aware bond strategy ahead of Basis Northwest Basis Northwest

Is the risk well compensated?

May 22, 2026
Cartoon on learning short-selling mechanics, the foundation behind tax-aware long/short investing Tax-Aware Long-Short

Where kids are learning how to short stocks

May 21, 2026
Graphic on Washington State capital gains tax, where only long-term losses carry harvesting value State & Local Tax

Tax-loss harvesting in wacky Washington State

May 19, 2026
Crowded tax-aware long/short strategies facing a simultaneous squeeze from coordinated deleveraging Tax-Aware Long-Short

Long/short: No one is talking about "coordinated deleveraging"

May 17, 2026
Cartoon meme riffing on taxable investing and coordinated deleveraging in long/short quant strategies Podcasts & Media

Taxable memes and "coordinated deleveraging"

May 15, 2026
Cartoon on writing a qualified covered call against an underlying position and the tax treatment it unlocks Options

The tax advantages of a qualified covered call

May 14, 2026
Cartoon illustrating the hidden cost of a concentrated single-stock position ahead of a Basis Northwest talk Basis Northwest

Erkko Etula on concentrated stock risk at Basis Northwest 2026

May 12, 2026
Cartoon comparing the Avis short squeeze to a famous 2008 squeeze and the risk to long/short portfolios Tax-Aware Long-Short

long/short: recent Avis squeeze looks like a famous 2008 squeeze (Pt. 2)

May 10, 2026
Graphic marking tax-aware long/short growth past $150 billion AUM alongside Schwab margin risk notes Tax-Aware Long-Short

Long/short: Schwab's margin risk addendum is worth reading

May 7, 2026
Basis Northwest 2026 reaching sold-out status with a waitlist for the taxable wealth conference Basis Northwest

Basis Northwest 2026 is sold out, but...

May 5, 2026
Cartoon illustrating the asymmetric, unbounded downside of a concentrated short position in a long/short strategy Tax-Aware Long-Short

Long/Short: The asymmetric risk in short positions

May 3, 2026
Cartoon depicting the rapid AUM growth of tax-aware long/short strategies past $150 billion Tax-Aware Long-Short

Tax-aware long/short grows to $150+ billion AUM

Apr 30, 2026
Cartoon previewing the Basis Northwest 2026 taxable wealth conference agenda and attendee lineup in Seattle Basis Northwest

Basis Northwest 2026: Agenda

Apr 28, 2026
Cartoon depicting an Avis short squeeze damaging a tax-aware long/short portfolio Tax-Aware Long-Short

Long/Short: Avis Short Squeeze (Pt. 1)

Apr 26, 2026
Graphic on Schwab reportedly limiting adviser access to tax-aware long/short strategies Tax-Aware Long-Short

Long/short: Schwab apparently limiting adviser access

Apr 23, 2026
Widget tracking the pipeline of ETFs seeding in-kind via Section 351 from weekly EDGAR filings Section 351 Exchanges

ETF in-kind pipeline

Apr 21, 2026
Cartoon of Schwab spotlighting tax-aware long/short as a low-capital activity across its 1Q26 earnings call Tax-Aware Long-Short

Schwab: long/short "not a balance sheet capital-intensive type of activity"

Apr 19, 2026
Tongue-in-cheek cartoon riffing on Tax Alpha Insider pivoting to AI infrastructure, spoofing Allbirds Basis Northwest

Tax Alpha Insider is pivoting to AI infrastructure

Apr 17, 2026
Cartoon showing 1256 futures gains degrading from capital to ordinary income once held inside a RIC wrapper ETF Taxation

Futures in RICs are kind of a bummer... for now.

Apr 16, 2026
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