Brent Sullivan - Tax Alpha Insider (Page 3)

Fidelity hitting the brakes on new tax-aware long/short SMA business and the ripple to advisers

Tax-Aware Long-Short

Fidelity pumps the breaks on tax-aware long/short. Does this impact you?

Jan 9, 2026

Cartoon announcing a working group convening around tax-aware long/short strategies like the 130/30

Tax-Aware Long-Short

Announcing: Tax-aware long/short working group

Jan 8, 2026

Cartoon on the IRS questioning the economic substance of an immediate bitcoin repurchase after tax-loss harvesting

Tax-Loss Harvesting

Enrolled Agent: IRS is asking about substance of client's bitcoin tax-loss harvesting

Jan 6, 2026

Cartoon marking record-pace in-kind ETF seeding via SMA, tracking roughly $3 billion raised across 30 funds

Section 351 Exchanges

ETFs seeding in-kind raised ~$3bn in 2025

Jan 4, 2026

Cartoon on a large portfolio manager adding a tax-aware long/short private fund

Tax-Aware Long-Short

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

Dec 28, 2025

Graphic on the risks of walking down a concentrated stock position by seeding ETFs under Section 351

Section 351 Exchanges

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

Dec 21, 2025

New entrants raising the quality of play in the tax-aware long/short market

Tax-Aware Long-Short

Tax-aware long/short: new entrants and innovation

Dec 19, 2025

Cartoon of Alpha Architect seeding a $470 million low-distribution equity ETF in-kind via its two-step pitch

Section 351 Exchanges

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

Dec 17, 2025

Cartoon on Fidelity pausing new tax-aware long/short account onboarding into mid-January 2026

Tax-Aware Long-Short

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

Dec 14, 2025

Cartoon revealing the box-spread borrowing market is undercounted, closer to $2 trillion than $1 trillion

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

Dec 12, 2025

Cartoon arguing Opportunity Zone investing is really real estate investing, tax benefits aside

Concentrated Stock

Opportunity zone investing is real estate investing

Dec 10, 2025

Graphic on individual investors seeding ETFs in-kind and the RIC classification under the PARTNERSHIPS Act

Section 351 Exchanges

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

Dec 7, 2025

Tax Court reading of substance over form and step transaction doctrines in Smaldino v. Commissioner

Concentrated Stock

Substance over form shenanigans

Dec 5, 2025

Cartoon of the Morgan Stanley HOPES framework organizing strategies to derisk a concentrated equity position

Concentrated Stock

A new HOPES for derisking concentrated positions

Dec 2, 2025

Heatmap-style cartoon mapping charitable deduction AGI limits across gift types, updated for OBBBA

Concentrated Stock

Donate and deduct: AGI limit heatmap

Nov 30, 2025

Cartoon weighing simply selling a concentrated stock against more elegant derisking solutions for low-basis holders

Concentrated Stock

"Just sell the damn stock"

Nov 28, 2025

Sankey diagram organizing the range of solutions for concentrated public stock positions

Concentrated Stock

Concentrated public stock solution Sankey diagram

Nov 26, 2025

Graphic projecting covered call ETF growth toward $650 billion and questioning advertised distribution rates

Covered call ETFs to $650 billion?

Nov 23, 2025

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

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

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

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

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

$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