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

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.

In this episode, Hilary Hendershott explains why retirement planning should not begin with the questi...

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 problem...

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.

Retiring at 55 can sound simple, especially if you’ve saved well and built meaningful wealth.

But early retirement is not just about having enough money. It is about whether your money can support your life for decades, through changing markets, taxes, healthcare costs, and unexpected life events.

Hilary Hendershott explains what really needs to be considered before retiring early, including why your retirement plan may be tested in the first few years after you stop working.

You’ll learn why retiring at 55 changes the financial picture, how the healthcare gap before Medicare can beco...

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 RMD trap and why large IRAs can create bigger tax problems in retirement.

Required minimum distributions can push you into higher tax brackets, increase the taxable portion of your Social Security, and even trigger higher Medicare premiums. That is why RMDs can feel like a...

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 decisions, and suddenly wondering, “How am I actually doing?”

Hilary Hendershott explains why retirement readiness is about more than looking at one account balance.

When her team evaluates whether someone is on track, they look at four key variables:

How...

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 the timing of taxes can matter just as much as the amount of taxes paid.

Imagine you have $4 million in company stock. If you sell it all at once to diversify, you may trigger a large tax bill immediately and reinvest...

If you’re a high-income earner — especially in tech leadership or business ownership — there’s something quietly shaping your financial future:

Taxes.

In this episode, I explain what’s known as tax drag — the slow, often invisible erosion of your wealth over time.

Because for many high earners, the biggest financial cost isn’t fees or investment performance…

It’s taxes.

You’ll learn:

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 avoid costly mistakes, including:

Divorce isn’t just the end...

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 explain:

Many women in tech freeze a...

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 income and wealth, progress doesn’t always feel obvious. It becomes quieter, more structural, and easier to miss.

You’ll learn:

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:

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?

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 to create more flexibility and control.

You’ll learn:

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 continuing with a financial advisor.

This conversation is especially relevant if your financial life is becoming more complex — whether you’re managing equity compensation, concentrated stock, business income, illiquid investments, or significant taxable assets. A single decision can meaningfully impact your after-tax outcomes for years to come.

You’ll learn:

If you have retirement savings spread across multiple 401(k)s, IRAs, or old employer plans, you’re not alone.

In fact, it often means you’ve had a successful and dynamic career.

But at some point, the question comes up:

Should you consolidate your retirement accounts?

I walk through when consolidating makes sense — and when it doesn’t — so you can make a more informed, strategic decision.

You’ll learn:

If you’re holding startup equity and expecting a liquidity event, there’s something most people don’t fully realize until it’s too late:

Your tax bill is largely determined before your equity becomes liquid.

In this episode, I walk through how pre-IPO employees, founders, and early team members can think about tax strategy before a liquidity event — and how tax-aware planning can dramatically change how much of your wealth you actually keep.

You’ll learn:

Women often build wealth differently — through career growth, equity compensation, business ownership, inheritance, or major life transitions like divorce.

But one of the biggest threats to long-term wealth for women is often overlooked:
Taxes.

In this episode, I explain why tax-aware investing matters — and why it can make an especially meaningful difference for women as their financial lives grow more complex.

We’ll cover:

If you’ve ever searched, “Are financial advisors worth it?” you’ve probably seen the same advice:

“You get market returns minus the fee.”

So why pay for help?

In this episode, I explain what often gets missed in that conversation — especially for high earners and people with more complex financial lives.

Key Takeaways

You can be objectively successful… and still feel financially unsafe.

Hilary Hendershott explores why so many high-earning women continue to experience financial anxiety — even while earning well, saving consistently, investing thoughtfully, and building significant wealth.

Key Takeaways

AI can answer almost any financial question now.

So naturally, more people are asking:

“Do I actually still need a financial advisor?”

Hilary Hendershott breaks down the difference between information and judgment — and why, for people with increasingly complex financial lives, thoughtful financial advice may matter more than ever in the age of AI.

Key Takeaways