Archive - Tax Alpha Insider

Tax memes and news - tax week edition

Tax memes were spicier this season. I curated some favorites and mixed in news.

Apr 18 •

Actual tax-aware long/short financing costs from the marketplace

Benchmarking leverage spreads

Apr 16 •

ETF return of capital distributions have a weird tax perk no one talks about

Return of capital grants investors access to portfolio basis. That's very rare.

Apr 13 •

AQR tax-aware long/short surges, plus a few memes

If Trump eliminates capital gains tax (or capital gains 🤨), I may have to re-brand as Tariff Alpha Insider.

Apr 11 •

I printed 50 copies of The Adviser's Guide To Seeding an ETF In-Kind

70 pages of full-color print. What the heck is Section 368 consolidation?

Apr 9 •

If tax-loss harvesting cushions downside, shouldn't investors take more risk?

Partners Capital (2019) argues more equity-like risk is appropriate for taxable investors

Apr 6 •

Tax-aware long/short market map

All the players on one page

Apr 4 •

Tax-aware long/short has a secret weapon

As long positions appreciate, portfolio equity grows and so does margin capacity, acting like a synthetic cash injection that sustains tax-loss…

Apr 2 •

March 2025

Is ETF return of capital a Ponzi Scheme?

Many ETF sponsors brag about the tax-efficiency of returning capital, but that's only part of the story.

Mar 30 •

Cliff Asness: "...lying long-only dinosaurs... desperate to stop the bleeding..."

Ignore tax-aware long/short at your peril

Mar 28 •

Is tax-aware long/short just a shiny object?

Serious doubt from several sizable investment managers

Mar 26 •

A checklist for ETF tax diligence

Explicit and implicit tax costs should be bundled with expense ratio to tell the "total cost" story of holding an ETF.

Mar 23 •

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