The Tax-Loss Machine: How Long-Short Took Over Wealth Management
On this episode of Talking Wealth, Michael Batnick is joined by Brent Sullivan to discuss the rise of tax-aware long-short investing and how it’s changing wealth management. They cover direct indexing, 130/30 and 250/150 strategies, why traditional tax-loss harvesting dries up in bull markets, the …
E375: Why Tax Alpha Could Matter More Than Investment Returns
What if the biggest source of alpha for taxable investors isn’t stock picking—but minimizing friction inside the portfolio itself?
In this episode, I sit down with Brent Sullivan, independent tax analyst and author of one of the leading research platforms on tax-aware investing, to discuss why tax…
Tax Alpha Unpacked: Strategy, Risk, and Reality with Brent Sullivan (Ep. 16)
What if chasing tax savings is actually costing you more than you think?
In this episode, Rex Berger and Sam Diarbakerly sit down with Brent Sullivan, founder of Tax Alpha Insider, to unpack what tax alpha really means and where investors often get it wrong. From direct indexing and long-short str…
Tax-Smart Investing, Why Bonds Are Back, and the Sentiment Paradox
Andy is recording from a hotel room in Seattle, attending the Basis Northwest Conference, a two-day deep dive into esoteric tax strategies run by Brent Sullivan of Tax Alpha Insider. The episode opens with a walkthrough of what tax-centric wealth management looks like in practice, including asset l…
Brent Sullivan - The Story Behind the 351 Exchange
We talked with Brent Sullivan, chief editor at Tax Alpha Insider, about the history, use cases and future of the 351 exchange. Brent is one of the most respected voices in the investing tax space.
How This $150B+ Wall Street Strategy Could Lower Your Taxes
In this week's episode of WSJ’s Take On the Week, co-hosts Miriam Gottfried and Telis Demos are joined by Brent Sullivan, founder of Tax Alpha Insider, to dive into a hot, over $150 billion investing strategy called “tax-aware long-short.” This strategy aims to help wealthy investors beat the marke…
Substance Over Shenanigans Still Matters in ETFs
Goldman Sachs' $2.3 billion acquisition of Neos kicks off this episode of ETF Zoo. Hosts Dave Nadig and Sumit Roy of ETF.com or joined this week by Brent Sullivan, Editor of Tax Alpha Insider, and Todd Sohn, Chief ETF Strategist at Baird Strategas.
The Zoo crew discusses if the acquisition is a s…
A Good Problem
The Albatross is about navigating concentrated wealth.
Markets are at all-time highs, and founders, executives, early employees, and investors have become rich... but highly concentrated. Many are unable or unwilling to diversify.
Solutions exist: selling, hedging, tax-loss harvesting, partnership…
Is Your "Tax Alpha" About to Become an Audit?
On this episode of Talking Wealth, Michael Batnick is joined by Brent Sullivan, author of Tax Alpha Insider, to discuss the growing scrutiny around tax-aware investing strategies. They break down new Treasury and IRS guidance targeting Section 351 ETF conversions, why regulators are taking a closer…
No CLARITY and New Treasury Tax Crackdowns
With the CLARITY Act dead, the SEC and CFTC are writing crypto rules on their own. Is that progress, or a pile of future lawsuits? ETF.com's Dave Nadig and Sumit Roy are joined by Nate Geraci (Novadius), Brent Sullivan (Tax Alpha Insider), and Mike Akins (ETF Action) to dig into Treasury's crackdow…
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