Brent Sullivan - Tax Alpha Insider (Page 2)

Section 351 in-kind ETF seeding moving from niche to mainstream as new launches multiply

Section 351 Exchanges

Two reasons seeding ETFs in-kind is going mainstream

Mar 29, 2026

Cartoon of Fidelity selectively raising financing costs on tax-aware long/short separately managed accounts

Tax-Aware Long-Short

Tax-aware long/short: Fidelity to selectively and substantially increase financing costs

Mar 26, 2026

Cartoon announcing 351.tax, a database and visuals of ETFs seeded in-kind under Section 351

Section 351 Exchanges

Announcing... 351.tax (database and visuals)

Mar 24, 2026

Cartoon dramatizing the Quellos POINT tax shelter case and its fabricated multibillion-dollar loss transactions

Podcasts & Media

Safe Harbor Ep 4: Uncompromising Integrity

Mar 22, 2026

Cartoon on Schwab courting RIAs for tax-aware long/short business as Fidelity pauses

Tax-Aware Long-Short

Long/short: While Fidelity pauses, Schwab CEO tells RIAs "We’d love to support you"

Mar 20, 2026

Speaker announcement graphic for Meb Faber at the Basis Northwest 2026 taxable wealth conference

Basis Northwest

Meb Faber is speaking at Basis Northwest

Mar 19, 2026

Long position cost basis depicted as a finite resource depleting across years of tax-loss harvesting

Tax-Aware Long-Short

Tax-aware long/short: integrated to overlay via Section 351

Mar 17, 2026

Cartoon depicting the Quellos tax shelter scheme unraveling for wealthy clients like the Zilkhas

Podcasts & Media

Safe Harbor Ep 3: How Quellos Got Caught

Mar 15, 2026

Cartoon on Washington State's wealth tax proposals driving high-net-worth clients to consider leaving

State & Local Tax

Washington State Wealth Taxstravaganza

Mar 13, 2026

Cartoon of an AI hallucinating at a conference playground, framing AI's limits in wealth and tax work

Podcasts & Media

Why I'm not worried about AI anymore

Mar 12, 2026

Cartoon announcing former Parametric CIO Paul Bouchey speaking at Basis Northwest, with an AI angle

Basis Northwest

Paul Bouchey (former Parametric CIO) is speaking at Basis Northwest

Mar 10, 2026

Safe Harbor episode graphic on the More Likely Than Not tax opinion standard behind the Jets sale

Podcasts & Media

Safe Harbor Ep 2: "More Likely Than Not"

Mar 8, 2026

Tax-aware long/short marketed as capital loss as a service, framed by a Twitter debate

Tax-Aware Long-Short

Capital loss as a service

Mar 6, 2026

Cartoon contrasting a variable prepaid forward against an option collar plus margin loan for concentrated stock

Concentrated Stock

Variable prepaid forward vs. option collar

Mar 5, 2026

Cartoon showing the ETF share class acting as a redemption pressure-release valve for a more tax-efficient mutual fund

How an ETF share class could make a mutual fund more tax efficient

Mar 3, 2026

Cartoon tying the Power Rangers franchise fortune to the origins of a high-stakes tax shelter story

Podcasts & Media

Safe Harbor Ep 1: Mighty Morphin Power Rangers

Mar 1, 2026

Cartoon announcing AQR's Joseph Liberman presenting research on VPFs and low-basis stock at Basis Northwest

Basis Northwest

AQR's Joseph Liberman is presenting at Basis Northwest

Feb 26, 2026

Speaker announcement graphic for Tax Foundation CEO Daniel Bunn presenting at Basis Northwest

Basis Northwest

Tax Foundation CEO, Daniel Bunn, will present at Basis Northwest

Feb 24, 2026

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

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

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