307: How to Reduce Taxes on Company Stock (For Women in Tech)

If you’re a high-income woman in tech and your company stock has grown into a large portion of your net worth, you may be facing a difficult reality: Diversifying feels smart… but the tax bill feels overwhelming. In this episode, I walk through why this happens — and how tax-aware strategies can help you reduce taxes on company stock while creating more flexibility over time. You’ll learn: Why concentrated equity creates “gridlock” How capital gains taxes impact diversification decisions What tax-aware long/short investing is (in plain language) How tax loss harvesting can offset gains Why strategy matters more than timing For many high earners, the challenge isn’t knowing what to do — it’s managing the tax consequences of doing it. The goal isn’t to eliminate taxes. It’s to manage them intentionally so your wealth can grow with more flexibility and less risk. If you’re navigating RSUs, stock options, or concentrated company stock and wondering how to reduce taxes or diversify without triggering a massive tax bill, this conversation is for you. We’re a fee-only fiduciary team specializing in tax-aware wealth management for high-income earners and women with complex financial lives. Key Takeaways 0:00 Introduction 1:19 The “successful but stuck” problem 2:37 Strategy overview: tax-aware long/short 3:58 Why implementation matters 5:06 The risk of staying concentrated 5:42 Planning vs reacting to taxes 6:05 Final thoughts Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/reduce-taxes-company-stock-women-tech Follow Hilary on: LinkedIn Instagram YouTube Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.