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

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 Notes
To 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.

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 become a meaningful expense, why early market losses can have a lasting impact, and why your “number” is only part of the equation.

Hilary also introduces the Annual Spending Number, or ASN, a concept Hendershott Wealth Management uses with clients to clarify how much income your portfolio needs to produce each year, including taxes.

Because real retirement confidence does not come from seeing a large number on a statement. It comes from understanding how your income will show up, how your plan holds up in different environments, and how you will respond when things change.

 Key Takeaways 

•  00:45 What happens if the market drops after you retire?
•  01:27 Why retiring at 55 changes your financial picture
•  02:08 Taxes and account access before age 59½
•  02:38 Sequence of returns risk in early retirement
•  04:05 Why your retirement number is not enough
•  04:46 How your ASN connects your full retirement plan
•  05:04 Where real retirement confidence comes from
•  05:42 Download the retirement guide
•  06:30 What retiring at 55 really requires 

 Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/retiring-at-55 

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.

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 success penalty: the accounts you carefully built may eventually reduce your flexibility and control.

Hilary also explains why common defensive strategies, like qualified charitable distributions, may help in a given year but do not always solve the larger planning issue.

The real opportunity is to think about RMDs as part of a coordinated long-term strategy. Roth conversions, tax offsets, and tax-aware investment strategies can work together to reduce future RMD pressure without creating an unnecessarily large tax bill today.

At Hendershott Wealth Management, we call this Ultra Tax Efficient Wealth Management®. It is an ongoing process that coordinates tax-aware decisions across your full financial life.

If your IRA is starting to feel like a loss of control, that may be a signal that your strategy needs to evolve.

  Key Takeaways 

•  00:46 The RMD trap inside large IRAs
•  01:06 Why disciplined saving can create forced withdrawals
•  01:53 Why flexibility becomes limited once RMDs begin
•  02:43 A coordinated strategy for reducing future RMD pressure
•  03:17 Moving from reacting each year to designing the outcome
•  03:57 Ultra Tax Efficient Wealth Management®
•  04:12 When your IRA strategy needs to evolve 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/the-rmd-trap 

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.

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 much have you accumulated?
How much are you saving today?
How much do you expect to spend in retirement?
How many years do you still have to work with?

Those four variables tell a much clearer story than any one account balance alone.

Hilary also explains why your 40s can feel financially complicated. This is often the decade where multiple priorities collide: children, college planning, a mortgage, aging parents, travel, lifestyle goals, building wealth, and preparing for the future all at the same time.

But your 40s are also an incredibly powerful decade financially, especially for high earners. You may still have time to save more, invest more, make strategic adjustments, and get clarity about where you actually stand.

Retirement confidence does not come from optimism. It comes from clarity. And your 40s are not a decade for panic. They are a decade for measurement.

  Key Takeaways 

• 01:18 Have you saved enough for retirement? 
• 02:26 The four variables that determine retirement readiness 
• 03:05 Why your 40s can feel financially complicated 
• 03:55 Why your 40s are still a powerful decade financially 
• 04:32 Why coordination and oversight become more important 
• 05:55 Retirement planning is not a one-time calculation 
• 06:41 Your 40s are a decade for measurement 
• 07:10 Working with a fee-only fiduciary team 

 Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/retirement-planning-in-your-40s 

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.

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 a much smaller amount. That may feel responsible, but it also means your future growth is happening on a smaller base.

But with a tax-aware strategy, it may be possible to defer and manage gains over time, allowing more of your original capital to stay invested and continue compounding.

Hilary walks through an example where paying more taxes later can still result in more money kept overall, because compounding happened on a larger base for a longer period of time.

This is not about avoiding taxes or finding loopholes. It is about timing taxes, coordinating decisions, and keeping more capital productive for longer.

At Hendershott Wealth Management, we call this Ultra Tax Efficient Wealth Management®. It’s not a product. It’s a trademarked ongoing process that integrates tax strategy directly into how portfolios are built and managed.

If you have meaningful gains in company stock or another taxable asset and want to be more intentional about how those gains are managed over time, this is the kind of conversation worth having.

 Key Takeaways

• 01:19 Why paying more in taxes could still leave you with more money
• 01:58 A $4 million company stock example
• 02:40 Why higher taxes later may still mean more wealth
• 03:17 Who this strategy may be right for
• 03:46 Ultra Tax Efficient Wealth Management®
• 04:21 When to get help with your specific situation
• 04:53 How to schedule a conversation

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/paying-more-taxes-make-you-wealthier

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.

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:

• What tax drag actually is
• Why taxes are often your largest lifetime expense
• How taxes quietly reduce compounding
• What tax-aware investing means
• Why strategy and coordination matter more than tools

Tax-aware investing isn’t about avoiding taxes.
It’s about being intentional — structuring your financial strategy so that your wealth grows efficiently after taxes, not just before.

If taxes are starting to feel like one of the biggest forces shaping your financial life — or you’ve found yourself wondering whether you’re missing opportunities — that’s often a sign your financial life has reached a new level of complexity.

And that’s exactly where thoughtful, coordinated planning can make a meaningful difference over time.

We’re a fee-only fiduciary team focused on tax-aware wealth management for high-income earners, professionals, and women navigating complex financial lives.

 Key Takeaways

• 1:18 Why taxes grow faster than income
• 2:00 What is tax drag?
• 2:38 What tax-aware investing actually means
• 3:22 Why strategy matters more than tools
• 3:59 How planning supports long-term wealth 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/hidden-tax-cost

Follow Hilary on:

LinkedIn
Instagram
YouTube 

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.

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:

• Why you shouldn’t rush major financial decisions
• How assets are really divided under state law
• Why taxes can quietly create imbalance
• What documents you need to gather early
• How to avoid “crowdsourced” financial advice
• Why stability after divorce matters more than speed

Divorce isn’t just the end of a relationship — it’s the unwinding of a financial partnership. With thoughtful planning, it can also be the beginning of long-term clarity and independence.

If you’re navigating divorce or thinking about it, this conversation is for you.

 Key Takeaways 

• 1:20 Introduction
• 1:50 Principle #1 – Take It Slow
• 2:44 Principle #2 – The Details Matter
• 4:27 Principle #3 – Understand Before You Agree
• 5:40 Principle #4 – Taxes Change What’s Equal
• 6:36 Principle #5 – Gather Documents Early
• 7:39 Principle #6 – Get the Right Advice
• 8:43 Principle #7 – Focus on Stability
• 9:22 Final Thoughts

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/7-financial-mistakes-to-avoid-in-divorce/

Follow Hilary on:

LinkedIn
Instagram
YouTube 

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.

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:

• Why tech wealth cycles are compressing
• What happens when RSUs vest or options are exercised
• How concentrated stock creates risk
• Why taxes can quietly take 40–50% of your upside
• How to prepare before liquidity arrives

Many women in tech freeze at the moment of opportunity — not because they aren’t capable, but because no one taught them how to think about concentrated equity, timing, taxes, and long-term wealth together.

If you’re holding equity at companies like NVIDIA, Amazon, Google, OpenAI, SpaceX — or another high-growth firm — this conversation is for you.

The best time to prepare is before the wave hits.

 Key Takeaways 

• 1:20 A Once-in-a-Decade Wealth Moment 
• 1:45 The Tech Wealth Explosion 
• 3:03 Why 2026 Could Be Different 
• 3:56 The Tax Reality of Liquidity 
• 4:20 Why Smart Women Freeze 
• 5:32 How to Prepare Before It Hits 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/women-in-tech

Follow Hilary on:

LinkedIn
Instagram
YouTube 

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.

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:

• Why financial progress can feel unclear even when you’re doing well
• The key signals that your financial life is becoming more stable
• How coordinated decisions create long-term wealth
• What it means when your money starts working independently of your effort
• Why resilience and long-term thinking matter more than short-term wins

If you’ve ever found yourself wondering, “Am I actually doing okay?” — this is for you.

For many high-earning women and couples, the challenge isn’t building wealth.
It’s recognizing when it’s already working.

And sometimes, what you need isn’t more information — it’s perspective.

Key Takeaways 

• 1:20 “Am I actually doing okay?”
• 2:15  Sign #1: Your financial life is becoming coordinated
• 2:48 Sign #2: Your decision-making is evolving
• 3:18 Sign #3: Your money starts compounding
• 3:48 Sign #4: You’ve built resilience
• 4:11  Sign #5: You’re thinking long-term
• 4:28 How to assess if you’re on track
• 5:03 The emotional side of financial progress
• 6:08 Closing: “You’re okay. You can exhale.”

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/am-i-financially-stable-signs-youre-doing-ok/

Follow Hilary on:

LinkedIn
Instagram
YouTube 

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.

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:

• Why concentrated equity creates “gridlock”
• How capital gains taxes impact diversification decisions
• What tax-aware long/short investing is (in plain language)
• How tax loss harvesting can offset gains
• Why strategy matters more than timing

For many high earners, the challenge isn’t knowing what to do — it’s managing the tax consequences of doing it.

The goal isn’t to eliminate taxes.
It’s to manage them intentionally so your wealth can grow with more flexibility and less risk.

If you’re navigating RSUs, stock options, or concentrated company stock and wondering how to reduce taxes or diversify without triggering a massive tax bill, this conversation is for you.

We’re a fee-only fiduciary team specializing in tax-aware wealth management for high-income earners and women with complex financial lives.

Key Takeaways 

• 0:00 Introduction
• 1:19 The “successful but stuck” problem
• 2:37 Strategy overview: tax-aware long/short
• 3:58 Why implementation matters
• 5:06 The risk of staying concentrated
• 5:42 Planning vs reacting to taxes
• 6:05 Final thoughts 

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/reduce-taxes-company-stock-women-tech

Follow Hilary on:

LinkedIn
Instagram
YouTube 

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.