Archive - Tax Alpha Insider

Could tax-aware long/short power additional diversification?

How does portfolio design change if tax friction is solved?

Jul 11 •

OBBB (allegedly) increases $3,000 capital loss deduction; makes EBL limit permanent

ChatGPT "read" the OBBB and hallucinated. EBL limit is here to stay.

Jul 8 •

Would you rather pay $1 in tax this year or next?

Why isn't discounting common in investment tax analysis?

Jul 6 •

The taxable wealth revolution

Happy Fourth of July

Jul 4 •

Should you ever tax-loss harvest Nvidia?

Tax-loss harvesting with a tracking error mandate is a precise art

Jul 1 •

June 2025

The many failed attempts to update the $3,000 limitation on capital loss deductions

Also... Generative AI isn't ready to touch money.

Jun 29 •

Adventure capital returns to direct indexing

The next surge of acquisitions will be of the long/short variety

Jun 27 •

Is tax-aware long/short a capital gains escape hatch following an exit?

Possible, but depends on investor circumstances and the markets.

Jun 24 •

VPF + tax-aware long/short for diversifying concentrated stock

Plenty more content coming on this strategy...

Jun 20 •

How does direct indexing become an expensive index fund?

Folks new to direct indexing usually haven’t considered portfolio ossification.

Jun 17 •

0:53

The benefit of bonds without the drag

No-income bond ETFs could change everything about fixed-income investing, including the bonds

Jun 15 •

Spaceballs and the IRS data book are here

$5.1 trillion in predicted box office

Jun 13 •

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