Archive - Tax Alpha Insider

Bitcoin in-kind is "cheese on the beach"

SEC permits in-kind creation and redemption for crypto exchange-traded products

Aug 1 •

July 2025

Is tax-loss harvesting valuable after the first few years?

Dimensional shows factor rebalancing persists harvesting opportunities

Jul 29 •

Why seed an ETF in-kind only to sell a few months later?

Selling should undo the tax benefits of seeding in-kind... right?

Jul 27 •

Diversification vs. "lottery ticket"

DFA showed that diversification outperforms most of the time.

Jul 25 •

Tax-aware long/short and some bold ETFs could change everything

Tax Alpha Trends - July 2025

Jul 22 •

ETFs have a tax-loss harvesting rule nobody knows about

The 6-month rule is a tax landmine

Jul 20 •

and

Marketing tax-aware products

Here's what I'm reading…

Jul 18 •

Introducing Albatross, a sub-newsletter about concentrated wealth

Unique attention on a gnarly problem

Jul 15 •

Variable prepaid forwards for the rest of us

The basics of a common but complicated solution for hedging big stock positions

Jul 13 •

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 •

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