316: What High Earners Miss About Tax Strategy

If your income has grown and your investments have worked, are you actually keeping as much as you could?

For many high earners, this is where things start to slip. Your career takes off. Your income grows. You save, invest consistently, and make smart financial decisions. But over time, your financial life becomes more complex: more accounts, more moving pieces, more equity compensation, more taxable gains, and more at stake.

In this episode, Hilary Hendershott explains what high earners often miss about tax strategy, and why sophisticated strategies are not always something to fear.

Sometimes complexity is a warning sign. But in the right context, sophistication exists for a reason: to work within the rules of the system more effectively.

Hilary explains how tax-aware long-short investing can help certain investors manage taxes more intentionally, especially when they have significant gains, company stock, equity compensation, or meaningful taxable assets.

This is not about lowering your investment standards, taking on more risk, or chasing something speculative. It is about designing a portfolio with tax awareness from the beginning, so you can keep more of what you earn and reduce the tax cost of doing nothing.

Key Takeaways 

• 00:45 Are you keeping as much as you could?
• 01:22 The question many successful investors do not say out loud
• 02:08 What can be done without lowering investment standards
• 02:40 What tax-aware long-short investing is designed to do
• 03:01 Why this matters for company stock and equity compensation 
• 03:59 A simple way to think about tax-aware investing
• 04:35 Why implementation matters
• 04:58 Where to learn more about the mechanics
• 05:35 How to schedule a conversation 

 Show NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/high-earners-tax-strategy 

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.