About
Brent Sullivan
Independent Tax Analyst
Tax Alpha Insider is the only publication focused on taxable portfolio strategy. I ship new articles 4x 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
Original research
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.
-
Listed Option Collars with Margin Loans Are Structurally Inferior to Variable Prepaid Forwards: Character Degradation and Phantom Income
Two ways to hedge and monetize a concentrated low-basis position, compared on after-tax economics and where each one breaks.
For the record
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.
Teaching
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).
In the press
Where the work has shown up
In the news
- U.S. Senate · Sen. Ron WydenLetter to Treasury and the IRS on tax-loss harvesting
- CIOThe Popularity of Tax Alpha Is Growing Among High-Net-Worth Investors
- Puget Sound Business JournalComplex tax code fuels growth at wealth management firms
- CNBCBoomers are buying into the promise of monthly income from options ETFs, but there’s a tax catch
- The Wall Street JournalA Popular Tax-Minimizing Trade Is Juicing Wall Street’s Borrowing Binge
- CNBCSchwab to create ‘tax-aware’ strategy that’s been attracting billions from wealthy investors
- BloombergGoldman’s $2.3 Billion Deal Puts Tax-Smart ETFs Under Scrutiny
- The EconomistAmerican investors’ trick to lower taxes: lose money
- CNBCTreasury Sec. Bessent, IRS crack down on ETF strategy the wealthy are using to avoid capital gains taxes
- CNBC · Inside WealthWealthy investors are pouring over $170 billion into a new kind of tax-savings strategy
- CNBC · Squawk BoxTake a look at the latest growing strategy among wealthy investors
- Pensions & InvestmentsTax-Aware Strategies: Treasury, IRS Scrutiny, 351 Exchanges
- Bloomberg · Money StuffThe SEC Pays a Texting Fine
- ETF.comBrent Sullivan: Why 351 Exchange ETFs Are Now Everywhere
- RIABizSchwab CEO ties his firm’s blowout RIA custody asset quarter to Fidelity’s long/short fund rethink
- RIABizSchwab and Fidelity beat Goldman Sachs to the punch on long/short fund sorcery for RIAs
- Financial PlanningWhen a long-short strategy is right for a client
- BloombergThe Latest Tax Dodge for the Ultra-Rich Is a Customized ETF
- The Wall Street Journal · PodcastHow This $150B+ Wall Street Strategy Could Lower Your Taxes
- The Wall Street JournalThe Tax Strategy for People Suffering From Stock-Market Success
Podcasts
Bloomberg · Trillions
351 Conversions: Smart Tax Alpha Strategy or Loophole in the Code?
Talking Wealth
Is Your “Tax Alpha” About to Become an Audit?
The Meb Faber Show
The Tax Alpha Arms Race, with Wes Gray (Ep. 622)
Bloomberg TV
Aggressive Tax Planning Draws US Treasury’s Attention
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)
The Investors First Podcast
The Tribology of Tax Alpha
The Weighing Machine · Orion
Should the Tax Tail Wag the Dog?
Print & online
- ModusTexas Family Office Settles Case Against Its Former CIO
- InvestmentNewsIRS Targets 351 ETF Conversions in New Guidance on Tax Strategies
- BloombergTreasury Takes Aim at Wall Street Tax Trades
- Financial TimesTax-Aware Strategies Under Treasury Scrutiny
- ETF.com351 Exchange Update: Sky Always Falling
- The Wall Street JournalStock Gains Without All the Taxes? How the Hottest Trade on Wall Street Works
- BloombergSlashing Tax Bills for Rich Investors Is a $1 Trillion Business
- Barron’sFinancial Advisors Are Turning Entire Client Portfolios Into ETFs. What’s Behind the Trend.
- MorningstarThe ETF Tax Loophole Wall Street Is Exploiting
- CIONeed for Tax Optimization, Liquidity Could Change ‘Endowment Model’
- Financial Advisor MagazineAn ETF With Tax Benefits on Steroids
- Financial PlanningNew ‘investor-friendly’ ETFs unlock tax deferral on appreciated assets
- Financial PlanningBetween 2 Concentrated-Stock Strategies, a Clear Winner
- KitcesUsing Section 351 Exchanges To Tax-Efficiently Reallocate Portfolios
- 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.