Uploaded July 2026 | Updated September 2026, 2 weeks ago
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 market while lowering their tax bill by using leverage and short selling to actively harvest losses. Sullivan breaks down how this compares to other forms of tax-loss harvesting and whether the strategy is worth the risk (and cost) for the average investor. He also explains other ways investors can implement tax-aware investing in their own portfolios.
Chapters:
02:00 - What is Tax-Aware Investing?
03:22 - Defining Tax-Aware Long-Short Investing
07:38 - Growth to $150+ Billion Assets Under Management
11:34 - Effects of the Bull Market
13:29 - Origins of Leverage: The Explosion of Margin Lending
14:40 - Costs of Tax-Aware Long-Short
16:37 - Is Tax-Aware Long-Short Worth It?
18:31 - Income vs. Wealth: Who Should Use These Strategies?
29:24 - Is this Strategy for Individual investors?
32:10 - Tax Strategies for Everyone
This is WSJ’s Take On the Week where co-hosts Telis Demos, writer for WSJ’s Heard on the Street, and Miriam Gottfried, WSJ’s investing and wealth management reporter, cut through the noise and dive into markets, the economy and finance—the big trades, key players and business news ahead.
Have an idea for a future guest or episode? How can we better help you take on the week? We’d love to hear from you. Email the show at takeontheweek@wsj.com.
🎧 Prefer just the audio version? Subscribe and listen on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts: on.wsj.com/3LBGo5Q?mod=WSJ_TOTWPOD
#WSJ #TaxAwareInvesting #TaxAlpha
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 market while lowering their tax bill by using leverage and short selling to actively harvest losses. Sullivan breaks down how this compares to other forms of tax-loss harvesting and whether the strategy is worth the risk (and cost) for the average investor. He also explains other ways investors can implement tax-aware investing in their own portfolios.
Chapters:
02:00 - What is Tax-Aware Investing?
03:22 - Defining Tax-Aware Long-Short Investing
07:38 - Growth to $150+ Billion Assets Under Management
11:34 - Effects of the Bull Market
13:29 - Origins of Leverage: The Explosion of Margin Lending
14:40 - Costs of Tax-Aware Long-Short
16:37 - Is Tax-Aware Long-Short Worth It?
18:31 - Income vs. Wealth: Who Should Use These Strategies?
29:24 - Is this Strategy for Individual investors?
32:10 - Tax Strategies for Everyone
This is WSJ’s Take On the Week where co-hosts Telis Demos, writer for WSJ’s Heard on the Street, and Miriam Gottfried, WSJ’s investing and wealth management reporter, cut through the noise and dive into markets, the economy and finance—the big trades, key players and business news ahead.
Have an idea for a future guest or episode? How can we better help you take on the week? We’d love to hear from you. Email the show at takeontheweek@wsj.com.
🎧 Prefer just the audio version? Subscribe and listen on Apple Podcasts, Spotify, Amazon Music, or wherever you get your podcasts: on.wsj.com/3LBGo5Q?mod=WSJ_TOTWPOD
#WSJ #TaxAwareInvesting #TaxAlpha
