# Hilary Hendershott
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304: 5 Questions Every Tax-Aware Investor Should Ask Before Hiring an Advisor
Choosing the right financial advisor isn’t just about performance — it’s about clarity, tax awareness, and long-term decision-making. Hilary Hendershott, CFP® and founder of Hendershott Wealth Management, walks through five thoughtful questions every tax-aware investor should ask before hiring or c…
305: How to Reduce Taxes on IPO Wealth (Before It’s Too Late)
If you’re holding startup equity and expecting a liquidity event, here’s what most people don’t realize:
The biggest tax decisions are made before your equity becomes liquid.
I walk through the most common tax mistakes I see with IPOs and startup equity — and what high-income professionals can do t…
306: Should You Pay Off Your Mortgage Early — Or Invest Instead?
Many homeowners locked in historically low mortgage rates over the last several years — often well below long-term expected market returns.So a common question comes up:Should you pay off your mortgage early, or invest that money instead?
Why low mortgage rates change the math
How long-term invest…
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…
308: Am I Financially Stable? Signs You’re Doing Ok (Even If It Doesn’t Feel Like It)
On paper, everything looks good.
You’re earning more. You’re saving. You’re investing.
So why doesn’t it feel settled?
In this episode, I walk through the subtle but powerful signs that your financial life is actually on track — even if it doesn’t feel that way yet.
Because at higher levels of inco…
309: Women in Tech: A Once-in-a-Decade Wealth Moment
If you’re a woman working in tech, your compensation may be changing faster than you expected.
Equity grants are larger.RSUs are vesting.Stock options are becoming real money.
And what’s coming in 2026 may not just be another wave of wealth — it could be a major liquidity event.
In this episode, I …
310: 7 Financial Mistakes to Avoid in Divorce (And How to Protect Your Wealth)
Divorce is one of the most financially complex transitions many people will ever navigate.
And the decisions you make during this process can affect your financial stability for decades.
In this episode, I'll walk you through 7 guiding principles to help you protect your finances during divorce and…
312: Why Paying More in Taxes Can Make You Wealthier
You could pay more in taxes and still end up with more money.
That sounds wrong at first, because most people assume the goal is always to pay as little tax as possible. But for high earners with appreciated assets, that instinct can actually cost millions over time.
Hilary Hendershott explains why…
313: Retirement Planning in Your 40s: Have You Saved Enough?
One of the most common questions people ask in their 40s is: Have I saved enough for retirement?And often, that question is not coming from someone who ignored saving or investing. It is coming from someone who has been working hard for years, building a career, raising a family, making smart decis…
314: The RMD Trap (Why Big IRAs Create Big Taxes)
A large IRA can feel like proof that you did everything right.
You saved, invested, deferred taxes, and built wealth over time. But once required minimum distributions begin, that same IRA can start forcing large taxable withdrawals whether you need the money or not.
Hilary Hendershott explains the…
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