Tax Alpha Insider (Page 2)

Cartoon depicting the rapid AUM growth of tax-aware long/short strategies past $150 billion

Tax-Aware Long-Short

Tax-aware long/short grows to $150+ billion AUM

Apr 30, 2026

Cartoon previewing the Basis Northwest 2026 taxable wealth conference agenda and attendee lineup in Seattle

Basis Northwest

Basis Northwest 2026: Agenda

Apr 28, 2026

Cartoon depicting an Avis short squeeze damaging a tax-aware long/short portfolio

Tax-Aware Long-Short

Long/Short: Avis Short Squeeze (Pt. 1)

Apr 26, 2026

Graphic on Schwab reportedly limiting adviser access to tax-aware long/short strategies

Tax-Aware Long-Short

Long/short: Schwab apparently limiting adviser access

Apr 23, 2026

Widget tracking the pipeline of ETFs seeding in-kind via Section 351 from weekly EDGAR filings

Section 351 Exchanges

ETF in-kind pipeline

Apr 21, 2026

Cartoon of Schwab spotlighting tax-aware long/short as a low-capital activity across its 1Q26 earnings call

Tax-Aware Long-Short

Schwab: long/short "not a balance sheet capital-intensive type of activity"

Apr 19, 2026

Tongue-in-cheek cartoon riffing on Tax Alpha Insider pivoting to AI infrastructure, spoofing Allbirds

Basis Northwest

Tax Alpha Insider is pivoting to AI infrastructure

Apr 17, 2026

Cartoon showing 1256 futures gains degrading from capital to ordinary income once held inside a RIC wrapper

Futures in RICs are kind of a bummer... for now.

Apr 16, 2026

Cartoon announcing Shang Chou of Dishmi Capital co-hosting the Basis Northwest 2026 taxable wealth conference

Basis Northwest

Basis Northwest 2026 will be co-hosted by...

Apr 14, 2026

Graphic weighing whether borrow fees on tax-aware long/short short positions are tax deductible

Tax-Aware Long-Short

Tax-aware long/short: what is a borrow fee and is it deductible?

Apr 12, 2026

Small nondeductible expenses adding up as paper cuts while advisers learn tax-aware long/short reporting

Tax-Aware Long-Short

When you learn some minor expense is not deductible...

Apr 10, 2026

Cartoon on futures taxation and a Cayman blocker structure used to access managed futures as portfolio diversifiers

Futures taxation, the Cayman blocker... and who cares?

Apr 9, 2026

Cartoon marking F/m CEO Alexander Morris as a Basis Northwest speaker on the ETF mutual fund share class

Basis Northwest

F/m CEO Alexander Morris is Speaking at Basis Northwest

Apr 7, 2026

Cartoon explaining how dividends on long and short positions are taxed inside a tax-aware long/short strategy

Tax-Aware Long-Short

Tax-aware long/short: how short dividends work

Apr 5, 2026

Cartoon on the updated tax-aware long/short market map and choosing good investment managers

Tax-Aware Long-Short

Tax-aware long/short: updated market map and choosing gud investments

Apr 2, 2026

Graphic on tax alpha attracting assets and the economic substance line advisers should not cross

Tax-Aware Long-Short

Tax alpha and the (healthy) economic substance trend

Mar 31, 2026

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