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

Hilary Hendershott: If you’re a woman in tech and your company stock has become a large percentage of your net worth, I want you to stay with me for a few minutes because I know the position you’re in. You’ve worked incredibly hard. Your equity has grown, and now you’re staring at a tax bill that makes diversification feel almost impossible.

You’re successful, and you feel stuck. That tension is very real. I recently spoke with a female executive in Silicon Valley whose company stock had grown to more than half her net worth. She knew she needed to reduce risk, but every time she modeled selling shares, she calculated the capital gains tax and froze.

She said to me, “It feels like I’m being punished for doing well.” That is not a lack of insight or creativity. That’s the structural reality of concentrated equity combined with high tax brackets. Most investors experience markets in one direction. Markets rise, you gain. You sell, you pay tax. Markets fall, you lose.

That’s the basic framework most people operate within. But for high-income women with concentrated equity, that structure can definitely create gridlock because taxes aren’t a minor detail in your financial life. At this point, they’ve become one of the largest forces shaping it. There is a strategy designed specifically to address this issue.

It’s called tax-aware long-short investing. In plain language, it combines positions that participate in market growth, balanced with positions designed to generate tax losses. Those losses can be harvested and used to offset gains elsewhere, including gains from selling appreciated company stock. So, what’s the result?

No immediate tax hit and greater flexibility about when and how taxes are realized, and that flexibility can materially change your ability to diversify without being financially punished. When people hear long-short, they sometimes assume high-risk or hedge-fund-style speculation, but that’s not what I’m talking about.

When implemented properly, tax-aware long-short strategies are built on diversified, liquid, institutional-quality portfolios. The objective is not to chase outsized returns. The objective is to manage risk prudently while harvesting losses in a disciplined, rules-based way. Compared to much of what comes out of Wall Street, this approach is transparent, research-driven, and grounded in decades of institutional experience.

It is sophisticated, but it’s not reckless, and this is where expertise truly matters. Our firm is fortunate to have a chief investment officer whose education and experience place him alongside the professionals you’d typically find at large family offices, where strategies like the tax-aware methodology I’m sharing about today have been successfully implemented for years. Tax-aware long-short is relatively new at the RIA level.

Many advisory firms are just beginning to explore it. At the same time, most advisors are managing dozens, sometimes hundreds, of client relationships. That combination can create room for error. Strategies like this require deep technical knowledge, careful structuring, and continuous oversight. Most independent firms simply can’t afford to hire someone with that level of institutional investment experience, but we can, and our clients benefit from that depth.

This isn’t about access to a strategy. It’s about having the right professionals guiding it, and we don’t implement this casually. We don’t implement it for everyone. When we use it, it’s because it fits thoughtfully inside a comprehensive wealth plan. One of the most painful patterns I see is this: A woman builds meaningful wealth through equity compensation, but she delays diversifying because the capital gains consequences feel overwhelming.

Meanwhile, her financial future becomes increasingly tied to one company. This is great when it works and horribly painful when it does not. Tax-aware long-short strategies, when appropriate, can create room to diversify and reduce risk, not by eliminating taxes, but by managing them intentionally and strategically over time.

That shift from reacting to taxes to planning around them can be incredibly empowering. This isn’t financial magic. It’s disciplined strategy operating within the existing tax code. The tax code is complicated, but it is not random. And when you understand how it works, you can design around it instead of feeling trapped by it.

If you’re a high-earning woman in tech, and concentrated equity is starting to feel like both a blessing and a constraint, you’re not alone. The good news is there are credible lower-risk tools available to you now, but more importantly, there are experienced teams who know how to implement them responsibly.

If you’re thinking about your next financial chapter and want a partner who looks at the full picture, not just your investments, we’d love to connect. We’re a fee-only fiduciary team focused on after-tax outcomes and long-term planning, helping our clients keep more of what they earn so their money can support the life they’re building.

If that sounds like the kind of guidance you’re looking for, you can schedule a complimentary conversation with one of my lead advisors by visiting hendershottwealth.com/contact to see if our approach is the right fit for you