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 strategies to ETF innovation and concentrated stock solutions, the conversation goes beyond surface-level benefits and into the real trade-offs. Brent shares why tax strategies should never lead the conversation, how complexity can quietly introduce new risks, and what thoughtful, planning-first investing actually looks like for high-net-worth families. This episode is a grounded look at how to balance opportunity, risk, and long-term wealth stewardship.

What to expect:

• A clear breakdown of what tax alpha actually means in practice
• The most common strategies being used today, including direct indexing and long-short
• Why pre-tax investment rationale matters more than tax benefits
• The hidden risks, complexity, and misconceptions investors should understand
• How advisors think about implementing these strategies within a full financial plan
• And more!

Connect with Sam Diarbakerly:

• LinkedIn: Sam Diarbakerly
• LinkedIn: Generation Capital Advisors
• Generation Capital Advisors

Connect with Rex Berger:

• LinkedIn: Rex Berger
• LinkedIn: Generation Capital Advisors
• Generation Capital Advisors

Connect with Brent Sullivan:

• LinkedIn: Brent Sullivan
• LinkedIn: Tax Alpha Insider
• Tax Alpha Insider

About our Guest:

Brent Sullivan is the founder and editor of Tax Alpha Insider, where he focuses on tax-aware investing, portfolio construction, and the evolving strategies shaping high-net-worth wealth management. With experience spanning PIMCO’s trading floor, software development, and venture capital, Brent brings a unique perspective to integrating tax awareness into investment decisions while keeping planning at the center.