Love, your Money - Wealth, Money, and Financial Advisor for Women

326 Episodes

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320: The Silicon Valley Tax Trap (And How High Earners Escape It)

2026-11-1007:58

You can earn $600,000 a year in Silicon Valley and still feel like you’re not getting ahead. That isn’t necessarily because you’re doing something wrong. It may be because the tax system, equity compensation, and concentrated stock risk are quietly working against you. In this episode, Hilary Hendershott explains the Silicon Valley tax trap many high earners face, especially those with RSUs, vested shares, or a large portion of their net worth tied to one company stock. When RSUs vest, they a...

319: Will the 2026 Midterm Elections Crash the Stock Market?

2026-11-0210:08

Will the 2026 midterm elections cause a stock market crash? And should you sell your investments before Election Day? Election years bring strong opinions, alarming headlines, and plenty of predictions about what will happen to the stock market. But history tells a more complicated story. In this episode, Hilary Hendershott, founder of Hendershott Wealth Management, examines historical market returns under Republican and Democratic administrations, what the data says about midterm election ye...

318: Is It Too Late To Catch Up On Retirement Savings

2026-10-2707:14

One of the most common conversations Hilary has with people in their 50s starts with the same concern: “I honestly have no idea whether I’m on track for retirement.” And often, that uncertainty is not coming from someone who failed to save. Many people asking this question have been saving consistently for decades and have accumulated meaningful wealth. The uncertainty comes from realizing they have never actually measured whether all that effort is going to produce the retirement they want. ...

317: The Tax Trap Most Business Owners Don’t See Coming

2026-10-2007:08

You can build a $10 million business and still wonder where the wealth went. For many business owners, the issue is not a lack of success. It is that taxes show up at multiple points across the financial life of the business, often without a coordinated strategy in place. In this episode, Hilary Hendershott explains the three tax challenges many business owners face: The success tax as income from a growing business flows through personallyThe exit tax when the business is soldThe enjoy it ta...

316: What High Earners Miss About Tax Strategy

2026-10-1308:06

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 oft...

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Love, your Money - Wealth, Money, and Financial Advisor for Women