Brent Sullivan
Independent Tax Analyst
Tax Alpha Insider is the only publication focused on taxable portfolio strategy. I ship new articles 3x per week.
I write about:
- ETF taxation
- Direct indexing
- Tax-aware long-short (e.g., 130/30)
- Single-stock concentration solutions
My audience
Mostly advisers and sub-advisers serving HNW families who want to:
- Keep up with the latest in taxable portfolio management
- Understand tax strategy through examples and illustrations
- Know the vendors delivering state-of-the-art tax products
Investment taxation nerd through and through
I just finished a 70-page visual guide to seeding an ETF in-kind. Dave Nadig wrote the foreword. Read more about it here, or buy my book.
Who am I?
I am Brent Sullivan, an independent tax analyst. Connect with me on LinkedIn or follow me on X.
- Studied financial engineering at Cornell
- Worked on PIMCO’s trading floor
- Worked as a software developer at Parametric
- Worked as a DevOps engineer at Zillow Group
- Raised money as a VC-backed founder
- Started my taxable product marketing and strategy consultancy, Tax Alpha, LLC in Dec 2023
- Live in Seattle, WA with my wife and two boys
Papers
-
Managing Concentrated Public Stock Positions by Seeding an Exchange-Traded Fund
When a Section 351 ETF seed is routine, and when “stuffing” or sequential seeding can trip Section 351(e) and force gain recognition.
-
Variable Prepaid Forward vs. Collar/Margin Loan
Two ways to hedge and monetize a concentrated low-basis position, compared on after-tax economics and where each one breaks.
Where the work has shown up
Print & online
- The Wall Street JournalStock Gains Without All the Taxes
- BloombergWall Street Helps Rich Investors Cut Tax Bills
- Barron’sThe 351 ETF Conversion
- MorningstarThe ETF Tax Loophole Wall Street Is Exploiting
- CIOTax Optimization Could Change the Endowment Model
- Financial Advisor MagazineAn ETF With Tax Benefits on Steroids
- Financial PlanningSection 351 Conversion ETFs Promote Tax Strategy
- KitcesSection 351 Exchanges: Tax-Efficient Reallocation
Guest spots · video
Talking Wealth · Michael Batnick
The Tax-Loss Machine: How Long-Short Took Over Wealth Management
How I Invest · David Weisburd
Why Tax Alpha Could Matter More Than Investment Returns
Wealth Actually · Frazer Rice
Tax Alpha: The Secret Investment Strategy You’ve Never Heard Of
Alpha Architect
How the 351 Exchange Is Revolutionizing Investing
Andrew Fallwell, CFA
Tax Alpha and the Next Frontier of Tax-Efficient Investing
Generation Capital Advisors
Tax Alpha Unpacked: Strategy, Risk, and Reality (Ep. 16)
Guest spots · audio
- The Investors First PodcastThe Tribology of Tax Alpha
- The Weighing Machine · OrionShould the Tax Tail Wag the Dog?
Confirmed appearances with links. Been on more? Send the show and URL and it goes up.
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