Topic

Concentrated Stock

58 posts

Graphic explaining variable prepaid forwards for hedging concentrated stock positions

Concentrated Stock

Variable prepaid forwards for the rest of us

Jul 13, 2025

Cartoon framing a taxable wealth revolution, tying revolutionary themes to modern tax-aware investing strategies

Concentrated Stock

The taxable wealth revolution

Jul 4, 2025

Cartoon testing whether tax-aware long/short losses can offset capital gains from a large concentrated exit

Tax-Aware Long-Short

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

Jun 24, 2025

Cartoon on combining a variable prepaid forward with tax-aware long/short to diversify concentrated stock

Concentrated Stock

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

Jun 20, 2025

Cartoon urging readers to skip the Trump-Musk feud and read a tax-aware investing roundup instead

Podcasts & Media

Trump/Musk cage match is boring. Read about taxes instead

Jun 6, 2025

An exchange fund unblocking billions by seeding an ETF in-kind under Section 351

Section 351 Exchanges

How an exchange fund unblocks billions by seeding an ETF in-kind

May 25, 2025

Cartoon on AQR's finding that direct indexing completion portfolios poorly hedge concentrated stock risk

Concentrated Stock

AQR's latest: direct indexing "largely ineffective" at culling single-stock risk

May 16, 2025

Cartoon charting how many Russell 1000 single stocks suffered catastrophic drawdowns and never recovered

Concentrated Stock

53% of the time, it worked every time

May 9, 2025

Cartoon on Cambria's ENDW ETF seeded in-kind via Section 351 conversion raising about $100 million

Section 351 Exchanges

Don't call it a comeback: Cambria's latest ETF seeded in-kind raises ~$100 million

Apr 22, 2025

Cartoon recapping a seven-expert panel on managing concentrated single-stock risk

Concentrated Stock

Single-stockapalooza: More talking heads than CNN election night

Mar 21, 2025

Graphic cataloging the reasons investors refuse to sell concentrated stock positions, from Baird and Reddit

Concentrated Stock

Absurd reasons investors don't sell concentrated positions: "I'm holding strong"

Mar 19, 2025

Moving past Enron scare tactics toward a calmer case for diversifying concentrated company stock

Concentrated Stock

"Diversify your company stock! Remember Enron!"

Mar 16, 2025

Cartoon comparing seeding an ETF in-kind with exchange funds, CRUTs, and tax-aware long/short alternatives

Section 351 Exchanges

Is seeding an ETF in-kind the right strategy?

Mar 11, 2025

Cartoon on de-risking concentrated stock by contributing up to 25% to a new ETF in-kind via Section 351

Section 351 Exchanges

De-risking concentrated stock by seeding an ETF in-kind

Dec 22, 2024

Section 351 diversification tests blocking a single large stock from tax-free ETF seeding

Section 351 Exchanges

Can I diversify a large single-stock holding tax-free by seeding an ETF in-kind?

Dec 17, 2024

Graphic lampooning a fortune-favors-the-brave ad while comparing exchange funds and Section 351 conversions

Concentrated Stock

Fortune Favors The Brave... Until it Doesn't

Nov 24, 2024