How should you manage a large capital gain and minimize the taxes you pay?

In this episode, we break down how we think about direct indexing, tax-loss harvesting, concentrated stock, exchange funds, 351 exchanges, long/short strategies, and Qualified Opportunity Zones. We explain why long-only direct indexing can be compelling for high-tax investors—and why some sophisticated tax strategies may not be worth the added fees, illiquidity, complexity, and investment risk.

If you have significant capital gains or concentrated stock, this episode provides a framework for evaluating tax strategies based on what ultimately matters: long-term wealth creation after taxes and fees.

If you feel like you should be getting more value than the AUM fee you're currently paying at your brokerage firm, visit https://engagewithbirchwood.com

Holding a winning stock can build tremendous wealth, but when one company becomes too much of your portfolio, it can also create significant risk.

In this episode, we break down concentrated stock positions, why investors become emotionally attached to their biggest winners, and what the historical data says about the risks of owning too much of a single company.

We discuss diversification, behavioral biases, RSUs and inherited stock, and why even great companies don't stay great forever. If a single stock represents a meaningful portion of your wealth, this episode will help you think more clearly about the tradeoff between future upside and protecting what you've already built.

Next episode: How we actually manage concentrated stock positions and which popular strategies we typically avoid.

If you feel like you should be getting more value than the AUM fee you're currently paying at your brokerage firm, visit https://engagewithbirchwood.com

If you feel like you should be getting more value than the AUM fee you're currently paying at your brokerage firm, visit https://engagewithbirchwood.com

After interviewing both a successful entrepreneur and his adult son, we reflect on the biggest lessons they shared about raising grounded children, teaching financial responsibility, practicing generosity, and building a lasting family legacy. In this episode, we discuss the four biggest themes that emerged:

-- Why generosity may be the most important family wealth habit
-- When (and how) parents should financially help adult children
-- How to have meaningful conversations about money across generations
-- Why money alone will never bring lasting fulfillment

Whether you're building wealth, preparing your children for inheritance, or simply trying to create stronger family values, this conversation offers practical wisdom for parents and grandparents alike.