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
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.
Citations
Work that turned up in other people’s footnotes:
-
“Combining Charitable Remainder Unitrusts and Tax-Aware Strategies to Diversify Low-Basis Stock”
Cites the Kitces.com article on Section 351 exchanges, co-authored with Ben Henry-Moreland.
-
“Rebuffed: An Empirical Review of Buffer Funds”
Cited on the tax efficiency of buffer ETFs (FLEX options and in-kind redemptions); thanked in the acknowledgments.
Continuing education
-
Eaton Vance Tax Forward Investing Center
Presented as an independent analyst for several continuing education courses on taxable portfolio strategy, organized by Eaton Vance (part of Morgan Stanley Investment Management).
Where the work has shown up
Podcasts & video
The Meb Faber Show
The Tax Alpha Arms Race, with Wes Gray (Ep. 622)
Bloomberg TV
Bloomberg TV
351-Exchange ETFs: A Growing Tax Tool
Building Better Portfolios
Your Portfolio Has a Tax Problem. Here's How to Fix It
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)
Podcasts · audio only
- The Investors First PodcastThe Tribology of Tax Alpha
- The Weighing Machine · OrionShould the Tax Tail Wag the Dog?
Print & online
- The Wall Street JournalThe Tax Strategy for People Suffering From Stock-Market Success
- 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
- Financial PlanningBetween 2 Concentrated-Stock Strategies, a Clear Winner
- KitcesSection 351 Exchanges: Tax-Efficient Reallocation
- Portfolio Management ResearchWhat Basis Northwest Revealed
We use Microsoft Clarity for anonymized analytics (heatmaps and session replay) to see which parts of a post lose readers. Visitors in the EU, UK, and EEA are not tracked.