Archive - Tax Alpha Insider

The agony/ecstasy of concentrated stocks

Extreme winners are extremely rare

Sep 16 •

TIPS taxation: the other phantom menace

Taxation without realization

Sep 14 •

and

Taxes mess up the endowment model

Institutional managers are always surprised by the complexity of private wealth

Sep 12 •

Future Proof: Gen AI is the biggest thing since blockchain

WealthTech enters stache-mode

Sep 10 •

Managing short positions is "not a trivial exercise"

Why did so many 130/30 strategies fail during the global financial crisis?

Sep 7 •

"ploughing several billion dollars into [ARKK] even for a few days is pretty ballsy"

It wasn't a heartbeat trade

Sep 4 •

Tax-aware long/short doesn't lockup easily. Why?

Unlimited downside risk on the shorts is the key to understanding

Sep 2 •

August 2025

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