In this episode, I walk through a real scenario from Ann, a long-time Big Tech employee preparing for early retirement. She has a seven-figure concentrated stock position, a low cost basis, & a narrow tax window. Like many investors, she feels stuck.
We break down how to think through that tradeoff without guessing, panicking, or letting taxes make the decision for you.
You’ll learn:
• How capital gains taxes actually work once your income drops
• When the 0% capital gains bracket is real & when it isn’t
• Why waiting for the “perfect” tax year can increase risk
• How to unwind a concentrated stock position with a rules-based plan
• How to reinvest without creating new timing risk
• The single biggest threat to retirement income that most people miss
This isn’t about finding a loophole or avoiding taxes completely.
It’s about building a system that reduces regret, manages risk & protects your retirement when the stakes are highest.
If you’re approaching retirement, sitting on a large stock position, or trying to balance taxes against risk, this episode will help you think clearly and act deliberately.
Ready to build a retirement plan?
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The opinions expressed in this program are for general informational purposes only & are not intended to provide specific advice or recommendations for any individual or on any specific security. It is only intended to provide education about the financial industry. To determine which investments may be appropriate for you, consult your financial advisor prior to investing. Any past performance discussed during this program is no guarantee of future results. Any indices referenced for comparison are unmanaged and cannot be invested into directly. As always please remember investing involves risk and possible loss of principal capital; please seek advice from a licensed professional.
Ritholtz is a Registered Investment Adviser. Advisory services are only offered to clients or prospective clients where Ritholtz & its representatives are properly licensed or exempt from licensure. No advice may be rendered by Ritholtz unless a client service agreement is in place.
This commentary on this website reflects the personal opinions, viewpoints and analyses of the Ritholtz employees providing such comments, and should not be regarded as a description of advisory services provided by Ritholtz or performance returns of any Ritholtz Investments client. The views reflected in the commentary are subject to change at any time without notice. Nothing on this website constitutes investment advice, performance data or any recommendation that any particular security, portfolio of securities, transaction or investment strategy is suitable for any specific person. Any mention of a particular security and related performance data is not a recommendation to buy or sell that security. Ritholtz manages its clients’ accounts using a variety of investment techniques and strategies, which are not necessarily discussed in the commentary. Investments in securities involve the risk of loss. Past performance is no guarantee of future results.
Any particular strategy may not apply or benefit your particular stock concentration situation. There are no guarantees that investing in any stock or employing any of these strategies will be profitable, lead to positive outcomes, or not incur negative tax consequences. Investing in stock securities involves volatility risk, market risk, business risk, and industry risk. The prices of most stocks fluctuate. Volatility risk is the chance that the value of a stock will fall. Market risk is chance that the prices of all stocks will fall due to conditions in the economic environment. Business risk is the chance that a specific company’s stock will fall because of issues affecting it. Industry risk is the chance that a set of factors particular to an industry group will adversely affect stock prices within the industry.
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