Sitemap - 2025 - Tax Alpha Insider

Jumbo portfolio manager adds tax-aware long/short private fund

Why "walking down" a concentrated position by seeding ETFs could be problematic

Tax-aware long/short: new entrants and innovation

Alpha Architect launches another low-distro equity ETF seeded in-kind: ~$470 million

Advisers report Fidelity pauses new tax-aware long/short accounts until mid-Jan 2026

"Significant undercount" in $1 trillion box borrowing possible AUM

Opportunity zone investing is real estate investing

Individual investors can seed ETFs in-kind thanks to an exception to an exception

Substance over form shenanigans

A new HOPES for derisking concentrated positions

Donate and deduct: AGI limit heatmap

"Just sell the damn stock"

Concentrated public stock solution Sankey diagram

Covered call ETFs to $650 billion?

Yes, really, $1 trillion in box-spread AUM

Donating appreciated stocks is NOT always better than donating cash

An exchange fund will seed an ETF in-kind... again

Tax-aware long/short AUM update "rampant growth"

Comprehensive wealth planning takes the cake

The exchange fund 7-year "lockup" is likely a myth

Direct indexing is a loss leader

"In tax-aware long/short, aren't my tax losses limited to contributed capital?"

Trader fund Excess Business Loss (EBL) limit gets worse in 2026

Emerging market ETFs have a spooky secret

88% surveyed plan to use tax-aware long/short

Trader fund losses can offset ordinary income, but must pass through a gauntlet

What is a trader fund?

How do you use tax-aware long/short, if at all?

The big bad list of concentrated stock solutions

Less rebalancing, less tax?

Add tax equalization to your mutual fund and ETF diligence checklist

Short-term capital gains distributed by mutual funds (and ETFs) are taxed as ordinary income

When is tax-aware long/short not the right choice?

Everyone is catching the long/short bug

$1 trillion box-spread AUM is up for grabs

The best conference for tax-aware investing?

Should tax-aware long/short investors care about black swan short sale bans?

Margin call me maybe

Cambria's GEW launched today with $155mm

Box spreads are "effectively free of credit risk"...I guess?

De-Risking Chonky Stock Positions with Tax-Loss Harvesting, Exchange Funds, CRUTs, and Section 351 Conversion

Better borrowing via box spread? Why it's worth grokking the box

2/3 of the time a concentrated stock would have underperformed the Russell 3000

The agony/ecstasy of concentrated stocks

TIPS taxation: the other phantom menace

Taxes mess up the endowment model

Future Proof: Gen AI is the biggest thing since blockchain

Managing short positions is "not a trivial exercise"

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

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

The (taxable wealth) times they are a-changin'

Give it away, give it away, give it away now (literally)

Tax-aware long/short reference papers going all the way back to Black-Scholes 1973

I built a tax-aware long/short simulator/dashboard

Climbing The Wealth Ladder With Nick Maggiulli

Surgeons use tax-aware long/short to offset royalty income

"The cost of tax mistakes increase tenfold with every new wealth level"

The end of fixed income with F/m's CEO

Holding Too Much Company Stock?

Ha... tax-aware long/short is growing faster than I thought

Avocado Orchard: RSUs, Vesting, and Too Much Company Stock

Is tax-aware long/short transforming taxable wealth? 181 people opined.

Worse than the wash sale rule? Betterment's head of investing weighs in.

Diversification "makes very little sense for anyone that knows what they’re doing" 🤨

Tax-aware long/short: "Not enough focus on the end game"... until now

How Bitcoin could become bone fide collateral

Bitcoin in-kind is "cheese on the beach"

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

Diversification vs. "lottery ticket"

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

ETFs have a tax-loss harvesting rule nobody knows about

Marketing tax-aware products

Introducing Albatross, a sub-newsletter about concentrated wealth

Variable prepaid forwards for the rest of us

Could tax-aware long/short power additional diversification?

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

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

The taxable wealth revolution

Should you ever tax-loss harvest Nvidia?

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

Adventure capital returns to direct indexing

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

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

How does direct indexing become an expensive index fund?

The benefit of bonds without the drag

Spaceballs and the IRS data book are here

Tax-aware long/short could cut Medicare costs

AQR addresses 5 critiques of tax-aware long/short

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

ETF share class “tax contagion” is, sadly, something we need to care about

Direct indexing FTSE Russell survey is interesting, but AI claims are 💩

14 use cases for tax-aware long/short strategies

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

Dividend chasers... YOU are the yield

Betterment acquired Rowboat Advisors for a quicker path to direct indexing and to "do it all"

What's behind the preposterous tax efficiency of buffer ETFs?

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

The One, Big, Beautiful Bill updates SALT, EBL, RQOF, but not LOL3K

The ETF share class proves the staying power of the mutual fund

53% of the time, it worked every time

What is asset location worth?

Five big questions from readers about tax-aware long/short strategies

Cerulli: Launching an ETF is expensive... but maybe worth it?

These 4 growth areas are driving taxable wealth

AQR on the record: Critics don't understand tax-aware long/short

More than one-quarter of advisors (26%) choose not to use direct indexing

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

Tax-aware long/short... what if the long is an ETF?

Tax memes and news - tax week edition

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

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

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

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

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

Tax-aware long/short market map

Tax-aware long/short has a secret weapon

Is ETF return of capital a Ponzi Scheme?

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

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

A checklist for ETF tax diligence

Single-stockapalooza: More talking heads than CNN election night

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

"Diversify your company stock! Remember Enron!"

I co-authored a blog for Kitces about seeding an ETF in-kind

Is seeding an ETF in-kind the right strategy?

Householding unlocks valuable tax and risk perks

A market maker leaked a list of 44 ETFs that were seeded in-kind

An ETF seeded with other ETFs launched with $440 million

How tax-loss harvesting works on a tax return

Where $50 billion AUM isn't a whale

"Direct indexing makes tax return prep harder"

Payment in lieu is taxing you

Tax-aware long/short AUM growth will accelerate if one problem is solved

Is direct indexing good but inconvenient?

Will the dad tax embitter the next generation?

Tax Alpha Trends - Q1 2025

Tax Alpha Trends

Parametric grows its support for active strategies - taxable wealth weekly

Are ETF fees really "tax-deductible?"

How Hill Investment Group gathered $500 million in-kind for its new ETF

Direct indexing market map - Jan 2025 edition

28 weeks later: What's stopping Cambria Tax Aware ETF from hitting its target allocation?

28 days later: Cambria Tax Aware ETF (ticker TAX) at launch and today

The adviser's memezine guide to seeding an ETF in-kind

Has your direct indexing portfolio become a high-cost index fund?

Can direct indexing + tax-gain harvesting beat the 529 plan?