Tax Alpha Insider
New? Start here Subscribe Brent Sullivan About
Opening scene of the Quellos tax shelter fraud investigation tied to a billion-dollar stock sale Concentrated Stock

Introducing "Safe Harbor: The Quellos Fraud"

Feb 22, 2026
Cartoon of Fidelity halting new tax-aware long/short account openings as advisers shift business to Schwab Tax-Aware Long-Short

Fidelity indefinitely pausing new long/short account openings

Feb 19, 2026
Cartoon teasing Andrew Beer's new ETF innovation reveal at Basis Northwest, framed as not crypto or AI Basis Northwest

Andrew Beer is presenting something new at Basis Northwest

Feb 17, 2026
Cartoon showing phantom income appearing when the straddle rules apply to an option collar position Options

Option collar phantom income

Feb 15, 2026
Cartoon framing tax management as NPV netting benefits against complexity and brain-damage costs Basis Northwest

Tax management = NPV (complexity & brain damage costs)

Feb 13, 2026
Registration announcement graphic for Basis Northwest 2026, a taxable wealth conference in Seattle Basis Northwest

Basis Northwest 2026: registration is open

Feb 11, 2026
Dimensional Co-CIO Savina Rizova announced as a Basis Northwest 2026 conference speaker Basis Northwest

Savina Rizova (Co-CIO at Dimensional) will present at Basis Northwest

Feb 10, 2026
Cartoon visualizer showing how the straddle rules defer capital losses on a covered call position Options

Straddle rule basics with a covered call

Feb 8, 2026
Cartoon rounding up recent taxable-wealth news on in-kind ETFs and IRS priority guidance Podcasts & Media

In-Kind ETFs, IRS priorities, memes and more

Feb 6, 2026
Cartoon marking Canvas of Franklin Templeton as anchor sponsor of the Basis Northwest tax-aware conference Basis Northwest

Canvas (of Franklin Templeton) is the anchor sponsor of Basis Northwest

Feb 5, 2026
Cartoon announcing Dave Nadig at Basis Northwest alongside an ETF return of capital discussion Basis Northwest

Dave Nadig will present at Basis Northwest plus ETF Return of Capital jam session

Feb 3, 2026
Graphic for the SSRN paper on seeding an ETF in-kind with concentrated stock under Section 351 Concentrated Stock

Managing Concentrated Public Stock Positions by Seeding an Exchange-Traded Fund

Feb 1, 2026
Intake survey launching the tax-aware long/short practitioner working group Tax-Aware Long-Short

Tax-aware long/short working group intake

Jan 30, 2026
Cartoon tool showing the wide distribution of portfolio underperformance hidden behind a 1% tracking error figure Direct Indexing

What does 1% tracking error really mean?

Jan 29, 2026
Cartoon announcing taxable-wealth pioneer Rob Arnott as a Basis Northwest speaker in Seattle Basis Northwest

Rob Arnott is presenting at Basis Northwest

Jan 27, 2026
Cartoon comparing the step-up in basis at death to a free life insurance payout, drawn from a 1993 paper Direct Indexing

Is step-up in basis like free life insurance?

Jan 25, 2026
Cartoon on the economic substance doctrine and taxpayers successfully arguing IRS overreach Concentrated Stock

Economic substance really ties the room together

Jan 23, 2026
Jurassic Park-themed graphic revisiting the 1993 paper Is Your Alpha Big Enough to Cover Its Taxes Concentrated Stock

Is Your Alpha Big Enough to Cover its Taxes? (Jurassic Park edition)

Jan 22, 2026
Investors clinging to concentrated single-stock risk while markets sit at all-time highs Concentrated Stock

With stocks at all-time highs, reasons to diversify are apparently at all-time lows

Jan 20, 2026
Cartoon of volatility drag eroding a massively concentrated single-stock position over time Concentrated Stock

Concentration risk and volatility drag

Jan 18, 2026
Cartoon on staying home with the 1993 classic Is Your Alpha Big Enough To Cover Its Taxes Podcasts & Media

Staying home and reading "Is Your Alpha Big Enough To Cover Its Taxes?"

Jan 16, 2026
Cartoon framing concentrated single-stock wealth as a deliberate risk-seeking bet rather than a problem to fix Concentrated Stock

Concentrated risk = generational wealth?

Jan 15, 2026
Cartoon announcing Basis Northwest 2026 dates for the Seattle taxable wealth innovation conference Basis Northwest

Announcing: Basis Northwest event dates

Jan 13, 2026
Graphic on Fidelity pausing new tax-aware long/short accounts as advisers diversify custody Tax-Aware Long-Short

Advisers consider all options as Fidelity extends pause on new tax-aware long/short account openings

Jan 11, 2026
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 Box Spreads

"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 Options

Covered call ETFs to $650 billion?

Nov 23, 2025
← Newer Posts Page 3 of 7 Older Posts →

Get every issue in your inbox

Subscribe
Tax Alpha Insider
Start here About Single asset risk 351 explorer State tax rates
© 2026

Contact me

Questions, corrections, speaking, consulting. I read everything.