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.

If you've built significant wealth, one question probably keeps you up at night: Will my kids grow into capable, grateful adults?

In this episode, we hear from the adult son of a successful entrepreneur who grew up after his family experienced a major business sale. He shares what his parents did well, what shaped his character, what he wishes they'd talked about more, and the lessons he's now applying as a father himself.

We discuss parenting, money conversations, work ethic, generosity, faith, purpose, and how wealthy families can raise children who flourish—not despite wealth, but because they're intentional with it.

If you're a family with significant wealth looking to preserve both your assets and your family values, this conversation is for you.

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

What happens when a family experiences significant wealth—but the children still grow up grounded, generous, and motivated?

In this conversation, entrepreneur Steve R. shares how he and his wife navigated parenting through a successful business exit, taught their children about money, work, generosity, and faith, and avoided many of the pitfalls that often come with wealth.

You'll hear practical lessons on raising financially responsible kids, family values, inheritance expectations, generosity, and preparing the next generation for wealth.

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

What happens to great fortunes over generations—and why do so few billionaire families stay wealthy? In this episode, former Long-Term Capital Management co-founder Victor Haghani shares lessons from his book The Missing Billionaires, revealing why wealth preservation is harder than most people realize.

Learn about investing, risk management, diversification, intergenerational wealth planning, market crashes, tax-efficient investing, direct indexing, and why Victor invests his own family's money in low-cost index funds. If you're interested in family wealth, financial independence, investing, and preserving wealth across generations, this conversation is packed with practical insights.

Victor's firm: https://elmwealth.com/
Elm Wealth YouTube: https://www.youtube.com/@elmwealth

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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

Should inherited wealth stay separate in marriage?

In this video, we explore the difficult conversation many wealthy families face around prenups, inherited assets, and protecting family wealth. Rather than focusing only on financial risk, we discuss the relational and emotional impact prenups can have on agency, loyalty, unity, and equality within a marriage.

At Birchwood Capital, we believe wealth planning should consider both financial outcomes and family relationships. This episode examines how prenups, separate property trusts, and asset protection strategies can shape marriages long before any legal issue ever arises.

If you're part of a high-net-worth family, expecting an inheritance, or navigating marriage and wealth planning, this conversation offers a thoughtful perspective rarely discussed in traditional financial advice.

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

Think you can write off 100% of your income with charitable donations? Not so fast. In this video, we break down the IRS rules for charitable tax deductions, including the real limits on cash donations, appreciated stock, donor-advised funds, and private foundations.

Learn how high-income earners, business owners, and charitably inclined families can maximize tax savings, avoid costly mistakes, and use strategies like donating appreciated stock to reduce both income taxes and capital gains taxes. We also cover the new charitable deduction changes starting in 2026 and walk through real tax software examples to show how the rules actually work.