Brent Sullivan - Tax Alpha Insider (Page 6)

Graphic cataloging the reasons investors refuse to sell concentrated stock positions, from Baird and Reddit

Concentrated Stock

Absurd reasons investors don't sell concentrated positions: "I'm holding strong"

Mar 19, 2025

Moving past Enron scare tactics toward a calmer case for diversifying concentrated company stock

Concentrated Stock

"Diversify your company stock! Remember Enron!"

Mar 16, 2025

Cartoon of a Section 351 exchange reallocating a portfolio of embedded-gain holdings into an ETF tax-free

Section 351 Exchanges

I co-authored a blog for Kitces about seeding an ETF in-kind

Mar 14, 2025

Cartoon comparing seeding an ETF in-kind with exchange funds, CRUTs, and tax-aware long/short alternatives

Section 351 Exchanges

Is seeding an ETF in-kind the right strategy?

Mar 11, 2025

Cartoon showing householding consolidating client accounts to unlock tax, risk, and rebalancing advantages

Direct Indexing

Householding unlocks valuable tax and risk perks

Mar 9, 2025

Cartoon on a leaked list of 44 ETFs seeded in-kind through Section 351 conversion

Section 351 Exchanges

A market maker leaked a list of 44 ETFs that were seeded in-kind

Mar 4, 2025

Graphic on the Longview Advantage ETF launching at $440 million, seeded 75% in-kind with other ETFs

Section 351 Exchanges

An ETF seeded with other ETFs launched with $440 million

Mar 2, 2025

Business-card infographic of how tax-loss harvesting flows through capital gains on a tax return

Tax-Loss Harvesting

How tax-loss harvesting works on a tax return

Feb 26, 2025

Cartoon of an RIA aggregator dwarfing wirehouses where $50 billion AUM no longer counts as a whale

Podcasts & Media

Where $50 billion AUM isn't a whale

Feb 23, 2025

Cartoon mapping the adviser camps split over direct indexing and its supposed tax-return complexity

Direct Indexing

"Direct indexing makes tax return prep harder"

Feb 16, 2025

Cartoon showing a payment in lieu replacing a qualified dividend with ordinary income through securities lending

Payment in lieu is taxing you

Feb 12, 2025

Cartoon on Schwab's lack of short rebate as the bottleneck for tax-aware long/short AUM growth

Tax-Aware Long-Short

Tax-aware long/short AUM growth will accelerate if one problem is solved

Feb 9, 2025

Graphic framing the direct indexing debate as Ethic crosses $6 billion AUM

Direct Indexing

Is direct indexing good but inconvenient?

Feb 7, 2025

Playful dad tax cartoon paired with the Cambria TAX ETF in-kind seeding post-mortem

Section 351 Exchanges

Will the dad tax embitter the next generation?

Feb 5, 2025

Cartoon of tax-savvy investors quietly harvesting losses while DeepSeek dominates the headlines

Tax-Loss Harvesting

Tax Alpha Trends - Q1 2025

Feb 2, 2025

Cartoon roundup of taxable-wealth news led by Parametric expanding its Custom Active SMA strategies

Direct Indexing

Parametric grows its support for active strategies - taxable wealth weekly

Jan 31, 2025

Cartoon contrasting ETF fees paid pre-tax against non-deductible post-tax separate account fees under the TCJA

Are ETF fees really "tax-deductible?"

Jan 28, 2025

Cartoon on Hill Investment Group seeding the $500 million Longview Advantage ETF in-kind

Section 351 Exchanges

How Hill Investment Group gathered $500 million in-kind for its new ETF

Jan 26, 2025

January 2025 direct indexing market map showing new entrants, partnerships, and Morningstar's exit

Direct Indexing

Direct indexing market map - Jan 2025 edition

Jan 24, 2025

Cambria TAX ETF still repositioning toward target allocation months after in-kind seeding

Section 351 Exchanges

28 weeks later: What's stopping Cambria Tax Aware ETF from hitting its target allocation?

Jan 22, 2025

Cartoon reviewing the Cambria Tax Aware ETF ticker TAX 28 days after its in-kind Section 351 launch

Section 351 Exchanges

28 days later: Cambria Tax Aware ETF (ticker TAX) at launch and today

Jan 19, 2025

Cartoon on a locked-up direct indexing portfolio drifting into a high-cost index fund and the fixes available

Direct Indexing

Has your direct indexing portfolio become a high-cost index fund?

Jan 12, 2025

Cartoon pitting direct indexing with tax-gain harvesting against a 529 plan using an unused kiddie tax benefit

Direct Indexing

Can direct indexing + tax-gain harvesting beat the 529 plan?

Jan 5, 2025

Cartoon on de-risking concentrated stock by contributing up to 25% to a new ETF in-kind via Section 351

Section 351 Exchanges

De-risking concentrated stock by seeding an ETF in-kind

Dec 22, 2024

Graphic showing Cambria Tax Aware ETF seeded in-kind with $27 million across ETFs and direct equities

Section 351 Exchanges

$27 million AUM contributed in-kind to Cambria Tax Aware ETF (TAX)

Dec 19, 2024

Section 351 diversification tests blocking a single large stock from tax-free ETF seeding

Section 351 Exchanges

Can I diversify a large single-stock holding tax-free by seeding an ETF in-kind?

Dec 17, 2024

Cartoon questioning whether seeding ETFs in-kind via Section 351 can scale beyond a local, niche move

Section 351 Exchanges

In-kind of a big deal: TAX launches soon

Dec 15, 2024

Cartoon on why mutual fund shares cannot practically seed an ETF in-kind under Section 351

Section 351 Exchanges

Can I seed an ETF in-kind using mutual fund shares?

Dec 11, 2024

Cartoon dissecting the BOXX box-spread ETF and how state income tax bites into its tax advantages on sale

What's in the BOXX? Part 1: State Rates

Dec 8, 2024

Cartoon questioning whether seeding ETFs in-kind via Section 351 will ever go mainstream

Section 351 Exchanges

Will seeding ETFs in-kind go mainstream? "I doubt it"

Dec 1, 2024

Graphic lampooning a fortune-favors-the-brave ad while comparing exchange funds and Section 351 conversions

Concentrated Stock

Fortune Favors The Brave... Until it Doesn't

Nov 24, 2024

ETF sponsors debating whether tax deferral drives the next wave of ETF asset growth

Tax Deferral Is The Hottest Thing In ETFs?

Nov 17, 2024

Cartoon splitting options-powered ETFs into democratizers and disruptors after the SEC's 6c-11 ETF Rule

Options-Powered ETFs: Democratizers & Disruptors

Nov 10, 2024

Cartoon on the love-hate view of Morningstar's Tax Cost Ratio for measuring ETF tax efficiency

Why I Love/Hate Morningstar's Tax Cost Ratio

Nov 3, 2024

Cartoon accompanying an FAQ on seeding an ETF in-kind featuring Meb Faber's Cambria Tax Aware ETF

Podcasts & Media

Seeding an ETF In-Kind: FAQs and Video with Meb Faber and Pat Cleary

Oct 27, 2024

Cartoon on Cambria's TAX ETF normalizing the Section 351 conversion for in-kind ETF seeding

Section 351 Exchanges

TAX distills a century of tax strategy into an ETF

Oct 20, 2024

Graphic on Section 351 conversions letting locked-up SMAs roll into ETFs in-kind without realizing gains

Section 351 Exchanges

ETFs Could Soon Bail SMAs Out of Lockup

Oct 13, 2024

Infographic series on covered call ETFs and the good, bad, and fugly of return of capital

Covered Call ETFs: The Good, the Bad and the Fugly

Sep 29, 2024

Cartoon pitting options-based covered call ETFs against bonds as the bigger tax-inefficient problem

Covered Call ETFs: The Flip Side of the Shitburger

Sep 22, 2024

Cartoon on a consolidated direct indexing vendor directory delivering tax efficiency on tap

Direct Indexing

The Direct Indexing Vendor Directory

Sep 15, 2024

Cartoon skewering covered call ETFs like JEPI for the heavy tax cost investors pay to chase current income

Covered Call ETFs: Shitburger With Extra Tax

Sep 8, 2024

Cartoon arguing direct indexing growth is overhyped while ETFs remain a strong alternative

Direct Indexing

Direct Indexing Is Not A Rocket Ship

Aug 25, 2024