Brent Sullivan - Tax Alpha Insider

Chart showing managed futures returns uncorrelated with stocks and bonds

Tax-Aware Long-Short

Managed futures are weirdly uncorrelated

Jun 16, 2026

Graphic on securities lending signals for a tax-aware long-short portfolio

Tax-Aware Long-Short

Long/short: what can the securities lending market tell us about short risk?

Jun 14, 2026

Cartoon on the risk of betting big on a single pre-IPO stock like SpaceX

Concentrated Stock

Is it okay to space out on SpaceX?

Jun 12, 2026

Map-style graphic sorting the 50 states into five capital-loss tax regimes for tax-loss harvesting

State & Local Tax

Tax-loss harvesting in 50 states

Jun 11, 2026

Concept of a charitable stock donation being recast as a taxable sale once an M&A deal nears certainty

Concentrated Stock

When a stock donation might be taxed like a sale

Jun 9, 2026

Cartoon of a stock position morphing into cash ahead of an announced all-cash acquisition closing

Concentrated Stock

When an acquisition turns a stock into cash before the deal actually closes

Jun 7, 2026

Cartoon framing alpha as splitting into pre-tax and after-tax components, the theme of the Basis Northwest reading list

Podcasts & Media

Some source articles from Basis Northwest 2026

Jun 5, 2026

Cartoon contrasting SPY and SPX call options to show their differing tax treatment under the 1256 rules

How options on SPY and SPX are taxed

Jun 4, 2026

Cartoon riffing on Washington State's unusual capital gains excise tax and its federal SALT deduction angle

State & Local Tax

SALT in the Washington State Wound

Jun 2, 2026

Recap graphic from Basis Northwest 2026, the taxable wealth conference that drew 350 advisers to Seattle

Basis Northwest

Basis Northwest 2026: self-selected

May 31, 2026

Flying money plushie marking the Day 1 recap of the Basis Northwest 2026 taxable wealth conference

Basis Northwest

Basis Northwest 2026: Day 1 Notes

May 29, 2026

Cartoon showing long/short alpha flowing into a direct indexing portfolio like a cash infusion that refreshes basis

Tax-Aware Long-Short

Long/short: alpha acts like a cash infusion

May 27, 2026

Cartoon contrasting a variable prepaid forward with a collar and margin loan as two routes to monetize concentrated stock

Concentrated Stock

Variable Prepaid Forward vs. Collar/Margin Loan

May 24, 2026

Cartoon weighing investment risk against compensation, framing tax-aware bond strategy ahead of Basis Northwest

Basis Northwest

Is the risk well compensated?

May 22, 2026

Cartoon on learning short-selling mechanics, the foundation behind tax-aware long/short investing

Tax-Aware Long-Short

Where kids are learning how to short stocks

May 21, 2026

Graphic on Washington State capital gains tax, where only long-term losses carry harvesting value

State & Local Tax

Tax-loss harvesting in wacky Washington State

May 19, 2026

Crowded tax-aware long/short strategies facing a simultaneous squeeze from coordinated deleveraging

Tax-Aware Long-Short

Long/short: No one is talking about "coordinated deleveraging"

May 17, 2026

Cartoon meme riffing on taxable investing and coordinated deleveraging in long/short quant strategies

Podcasts & Media

Taxable memes and "coordinated deleveraging"

May 15, 2026

Cartoon on writing a qualified covered call against an underlying position and the tax treatment it unlocks

The tax advantages of a qualified covered call

May 14, 2026

Cartoon illustrating the hidden cost of a concentrated single-stock position ahead of a Basis Northwest talk

Basis Northwest

Erkko Etula on concentrated stock risk at Basis Northwest 2026

May 12, 2026

Cartoon comparing the Avis short squeeze to a famous 2008 squeeze and the risk to long/short portfolios

Tax-Aware Long-Short

long/short: recent Avis squeeze looks like a famous 2008 squeeze (Pt. 2)

May 10, 2026

Graphic marking tax-aware long/short growth past $150 billion AUM alongside Schwab margin risk notes

Tax-Aware Long-Short

Long/short: Schwab's margin risk addendum is worth reading

May 7, 2026

Basis Northwest 2026 reaching sold-out status with a waitlist for the taxable wealth conference

Basis Northwest

Basis Northwest 2026 is sold out, but...

May 5, 2026

Cartoon illustrating the asymmetric, unbounded downside of a concentrated short position in a long/short strategy

Tax-Aware Long-Short

Long/Short: The asymmetric risk in short positions

May 3, 2026

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