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Box-spread strategy AUM estimated near one trillion dollars and possibly understated Box Spreads

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

Nov 20, 2025
Cartoon weighing a donation of appreciated stock against cash under differing AGI deduction limits Concentrated Stock

Donating appreciated stocks is NOT always better than donating cash

Nov 18, 2025
Cartoon showing an exchange fund seeding a new ETF in-kind, getting the band back together Section 351 Exchanges

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

Nov 16, 2025
Cartoon charting the rampant AUM growth of tax-aware long/short as it challenges direct indexing for SMA dominance Tax-Aware Long-Short

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

Nov 14, 2025
Cartoon on comprehensive wealth planning emerging as the theme from Nuveen's nPowered adviser conference Concentrated Stock

Comprehensive wealth planning takes the cake

Nov 12, 2025
Graphic challenging the exchange fund 7-year lockup myth and the liquidity investors actually have Concentrated Stock

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

Nov 9, 2025
Direct indexing crowded with vendors and fees falling into loss-leader territory Direct Indexing

Direct indexing is a loss leader

Nov 7, 2025
Cartoon showing how the wrapper and economic value at risk govern tax-aware long/short loss limits Tax-Aware Long-Short

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

Nov 5, 2025
Cartoon using a donut shop to explain the tightening Excess Business Loss limit on trader funds in 2026 Tax-Aware Long-Short

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

Nov 2, 2025
Cartoon revealing that emerging market ETFs cannot use in-kind redemption in many countries, raising tax costs ETF Taxation

Emerging market ETFs have a spooky secret

Oct 31, 2025
Cartoon on survey data showing 88% of respondents plan to use tax-aware long/short strategies Tax-Aware Long-Short

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

Oct 29, 2025
Graphic on trader fund losses offsetting ordinary income through the hedge fund wrapper Tax-Loss Harvesting

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

Oct 26, 2025
Trader fund classification generating ordinary business losses instead of capital losses Tax-Aware Long-Short

What is a trader fund?

Oct 24, 2025
Cartoon of advisers applying different tax-aware long/short hold patterns across client scenarios Tax-Aware Long-Short

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

Oct 22, 2025
Cartoon cataloging the full list of concentrated stock solutions: sell, wrap, hedge, cash, gift, swap, hold Concentrated Stock

The big bad list of concentrated stock solutions

Oct 19, 2025
Cartoon questioning whether less rebalancing means less tax and whether asset allocation truly matters Direct Indexing

Less rebalancing, less tax?

Oct 17, 2025
Cartoon on tax equalization protecting long-term mutual fund and ETF investors during redemptions ETF Taxation

Add tax equalization to your mutual fund and ETF diligence checklist

Oct 15, 2025
Graphic tracing short-term capital gain distributions from funds as ordinary income through IRS forms ETF Taxation

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

Oct 12, 2025
Weighing when tax-aware long/short and 130/30 are not the right fit for a client Tax-Aware Long-Short

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

Oct 10, 2025
Cartoon market map outgrowing its frame as more managers pile into tax-aware long/short Tax-Aware Long-Short

Everyone is catching the long/short bug

Oct 8, 2025
Cartoon on the box-spread options trade as a borrowing tool, framed as $1 trillion in AUM up for grabs Box Spreads

$1 trillion box-spread AUM is up for grabs

Oct 5, 2025
Cartoon introducing Basis Northwest, a Seattle conference dedicated to tax-aware investing and taxable wealth Basis Northwest

The best conference for tax-aware investing?

Oct 2, 2025
Cartoon on black swan short sale bans and the manager-dependent risk in tax-aware long/short Tax-Aware Long-Short

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

Sep 30, 2025
Graphic asking whether margin call risk threatens tax-efficient products built on long/short and box spreads Tax-Aware Long-Short

Margin call me maybe

Sep 28, 2025
Cambria GEW launching with $155 million as a test of mainstream in-kind ETF seeding Section 351 Exchanges

Cambria's GEW launched today with $155mm

Sep 25, 2025
Cartoon questioning whether box-spread borrowing is truly free of credit risk when the borrower is the weak link Box Spreads

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

Sep 23, 2025
Podcast cartoon walking through de-risking concentrated stock via harvesting, exchange funds, CRUTs, and Section 351 Podcasts & Media

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

Sep 21, 2025
Cartoon laying out five intuitive ways to understand the box spread as a low-cost borrowing tool Box Spreads

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

Sep 21, 2025
Cartoon visualizing that two-thirds of concentrated stocks underperformed the Russell 3000 from 1980 to 2020 Concentrated Stock

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

Sep 18, 2025
Graphic on the agony and ecstasy of concentrated stock positions and how rare the extreme winners are Concentrated Stock

The agony/ecstasy of concentrated stocks

Sep 16, 2025
TIPS inflation adjustments generating taxable phantom income without any cash flow ETF Taxation

TIPS taxation: the other phantom menace

Sep 14, 2025
Cartoon of the tax-free endowment model breaking down once taxes hit a private taxable portfolio Podcasts & Media

Taxes mess up the endowment model

Sep 12, 2025
Cartoon comparing the gen AI WealthTech hype to the earlier blockchain wave, WealthTech entering stache-mode Tax-Aware Long-Short

Future Proof: Gen AI is the biggest thing since blockchain

Sep 10, 2025
Cartoon showing the difficulty of managing short positions that sank many 130/30 strategies during the crisis Tax-Aware Long-Short

Managing short positions is "not a trivial exercise"

Sep 7, 2025
Cartoon on a multi-billion-dollar ARKK trade and the debate over whether it was a tax heartbeat trade ETF Taxation

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

Sep 4, 2025
Infographic explaining why short-side downside keeps tax-aware long/short from locking up like long-only Tax-Aware Long-Short

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

Sep 2, 2025
Eight product trends reshaping taxable wealth strategy, led by long/short and no-distribution ETFs Tax-Aware Long-Short

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

Aug 31, 2025
Cartoon urging donors to give now as OBBB charitable deduction limitations take effect in 2026 Concentrated Stock

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

Aug 29, 2025
Cartoon presenting a tax-aware long/short reading list tracing back to the 1973 Black-Scholes paper Tax-Aware Long-Short

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

Aug 26, 2025
Cartoon of a control panel simulating tax-aware long/short outcomes, balancing pretax alpha against costs and risks Tax-Aware Long-Short

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

Aug 24, 2025
Podcast cover for the Not Advice episode with Nick Maggiulli on The Wealth Ladder's six wealth stages Podcasts & Media

Climbing The Wealth Ladder With Nick Maggiulli

Aug 21, 2025
Graphic on surgeons using tax-aware long/short losses to offset patent royalty income under IRC 1235 Tax-Aware Long-Short

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

Aug 21, 2025
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