On the latest episode of the Investors First Podcast, hosts Steve Curley, CFA (Founder, 55 North Private Wealth) and Chris Cannon, CFA (CIO/Principal, FirsTrust) welcomed Brent Sullivan, Founder of The Tax Alpha Insider and the Basis Northwest Conference.
The episode covers all things tax alpha — exploring why the investment puzzle looks fundamentally different for taxable investors, and why today's tools and strategies may make this one of the best times in history to be one.
Chris Cannon has followed Sullivan's work since the early days of The Tax Alpha Insider, describing it as "a highly successful, focused publication in the wealth management space." He has noted that Sullivan could become the Michael Kitces of Tax Alpha.
About Brent Sullivan
Sullivan is the Founder of The Tax Alpha Insider, a focused newsletter and media platform covering taxable portfolio strategy for wealth management professionals and sophisticated investors. He is also the creator of Basis Northwest, the first conference dedicated to taxable wealth innovation, taking place May 28–29, 2026 in Seattle, WA.
His career background spans both corporate and entrepreneurial roles. Sullivan was a Software Engineer at Parametric, widely regarded as the pioneer of direct indexing. Prior to that, he worked in investment banking and asset management. He holds a Master of Engineering in Financial Engineering and Statistics from Cornell University and a Bachelor of Science in Mathematics from the University of California, Riverside.
What Is Tax Alpha — and Why Does It Matter Now?
Tax alpha refers to the additional after-tax return that can be generated through deliberate, tax-aware portfolio management — strategies that go beyond simply picking good investments and focus on how taxes affect the net return that actually reaches the investor.
The episode addresses why this matters specifically for taxable investors, why tax alpha has become increasingly important in the current environment, and why Sullivan decided to launch The Tax Alpha Insider to cover this space. The conversation also explores the broad range of tools now available to taxable investors — tools that, in Sullivan's view as conveyed in the episode, make this one of the best times in history to manage a taxable portfolio.
For families and individuals working with a fee-only fiduciary advisor, the tax dimension of investment management is inseparable from the planning process. Every transaction, rebalance, and distribution decision carries potential tax consequences — and the gap between pre-tax and after-tax returns compounds significantly over time.
Topics Covered in the Episode
The conversation spans a wide range of strategies and concepts in the tax alpha space. The topics discussed include:
Foundational strategies
- Householding and asset location — coordinating across multiple accounts to place assets where their tax treatment is most favorable
- Direct indexing — owning individual securities rather than pooled funds, enabling tax-loss harvesting at the security level
Advanced portfolio construction
- Tax-aware long-short strategies — using long and short positions to generate additional tax efficiency
- Buffer ETFs — ETF structures designed to limit downside exposure while managing tax outcomes
- 351 exchanges — a mechanism that allows investors to contribute appreciated securities to an ETF in exchange for shares, with specific tax implications
- Advisor-launched ETFs — the growing trend of advisors creating their own ETF vehicles for client use
- Assets that should not be used in taxable accounts — a discussion of what to avoid, not just what to pursue
Specialized structures
- Collars and variable prepaid forward contracts — tools commonly used in concentrated position management
- Heartbeat trades and ETF share classes — structural mechanics that affect how ETFs manage embedded gains
- Box loans — a form of synthetic borrowing using options structures
- Trader funds — a specialized fund structure with distinct tax treatment
Broader themes
- Tax alpha as a volatility buffer — how tax-loss harvesting interacts with market volatility
- The impact of AI on advisors and taxable investing — how technology is changing the landscape
- The counterargument: why not just pay the taxes? — Sullivan and the hosts also take the other side, exploring the case for simplicity over optimization
The Case for and Against Tax Alpha
This episode is notable for addressing both sides of the debate. While the conversation covers a broad toolkit of tax alpha strategies, it also addresses the legitimate question of whether the complexity is always worth it — exploring when it may simply make more sense to pay the taxes and keep the portfolio straightforward.
This kind of balanced treatment reflects the fiduciary approach to financial planning: the right answer depends on the client's specific situation, tax profile, and the cost and complexity of implementation.
About the Investors First Podcast
The Investors First Podcast is a service of CFA Society Orlando, recognized with the CFA Institute's 2020 Impact and Innovation Award. Co-hosts Steve Curley and Chris Cannon are both former presidents of CFA Society Orlando and currently serve on the advisory council.
Past guests include Howard Marks, Annie Duke, Morgan Housel, Federal Reserve Bank President Raphael Bostic, Cliff Asness, Aswath Damodaran, Jason Zweig, Rick Rieder, Patrick O'Shaughnessy, Liz Ann Sonders, and Michael Mauboussin.
Listen to the Full Episode
Listen to the full interview with Brent Sullivan on the Investors First Podcast (https://www.investorsfirstpodcast.com). Also available on Apple Podcasts (https://podcasts.apple.com), Spotify (https://www.spotify.com), and other podcast platforms.
Follow Brent Sullivan's work at The Tax Alpha Insider (https://www.taxalphainsider.com) and learn more about the Basis Northwest Conference at basisconf.com (https://www.basisconf.com).