March 5, 2026

Brent Sullivan, Tax Alpha Insider – Tribology of Tax Alpha

Brent Sullivan, Tax Alpha Insider – Tribology of Tax Alpha
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We are excited to welcome a friend of the show, Brent Sullivan of The Tax Alpha Insider. We discuss all things Tax Alpha as the investment puzzle is different when it comes to taxable investors. I have been fortunate to have known Brent since the very beginnings of his Tax Alpha Insider Newsletter, a highly successful, focused publication in the wealth management space. I often say that he could become the Michael Kitces of Tax Alpha. Brent is also behind the first Tax Alpha Conference, Basis Northwest, in Seattle on May 28th and 29th, which I will be attending.

Brent has an interesting career background, both corporate and entrepreneurial. As mentioned before, he is the Founder of The Tax Alpha Insider, as well as the Basis Northwest Conference. He was also a Software Engineer at Parametric, who is the godfather of direct indexing. Before that, he worked in Investment Banking and Asset Management. Brent holds a Masters of Engineering from Cornell University (Financial Engineering/Statistics), as well as a Bachelor of Science in Mathematics from the University of California, Riverside.

In this episode, we discuss all things Tax Alpha, as this is our first interview with Brent. We talk about the reasons he decided to launch this, why Tax Alpha is important now, and how this is one of the best times in history to be a taxable investor with all of the tools available. We discuss everything from householding/asset location, to direct indexing, to tax-aware long-short, buffer ETF’s, 351 exchanges, advisor launched ETF’s, assets that shouldn’t be used for taxable investors, collars/variable prepaid forward contracts, heartbeat trades/ETF share classes, box loans, tax alpha as a volatility buffer, trader funds, etc. We also discuss the impact of AI on advisors and taxable investing, as well as taking the other side, why not just pay the taxes and keep things simple.

Today's hosts are Steve Curley, CFA (Co-Managing Principal, 55 North Private Wealth) & co-host Chris Cannon, CFA (CIO/Principal, FirsTrust).
Please enjoy the episode. You can follow us on Twitter & LinkedIn or at investorsfirstpodcast.com

Learn more:
https://www.taxalphainsider.com/
https://www.basisconf.com/

Past guest include Cliff Asness, Jason Zweig, Annie Duke, Morgan Housel, Raphael Bostic, and many more.