Tax Loss harvesting, Direct Indexing, Charitable Giving and MORE! | Ep. 25

Beyond The First Million · Oct 15, 2026 · 30m

For high earners, the most useful tax strategies are rarely the flashiest ones.

Many of them live inside one of the most underrated accounts in your financial life: the taxable brokerage account. It has no contribution limits, no waiting until 60 to use it, and it gives you access to the step-up in basis, a strategy most people have never heard of.

In Part 2 of our tax series, Gideon and Jordan pick up right where Part 1 left off. They start with how HSAs and 529 plans fit into the tax-free bucket. Then they walk through the strategies that make a taxable account so powerful for high earners…