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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 loud02:08 What can be done without lowering investment standards02:40 What tax-aware long-short investing is designed to do03:01 Why this matters for company stock and equity compensation 03:59 A simple way to think about tax-aware investing04:35 Why implementation matters04:58 Where to learn more about the mechanics05:35 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 money01:58 A $4 million company stock example02:40 Why higher taxes later may still mean more wealth03:17 Who this strategy may be right for03:46 Ultra Tax Efficient Wealth Management®04:21 When to get help with your specific situation04:53 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 isWhy taxes are often your largest lifetime expenseHow taxes quietly reduce compoundingWhat tax-aware investing meansWhy strategy and coordination matter more than toolsTax-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 income2:00 What is tax drag?2:38 What tax-aware investing actually means3:22 Why strategy matters more than tools3:59 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 decisionsHow assets are really divided under state lawWhy taxes can quietly create imbalanceWhat documents you need to gather earlyHow to avoid “crowdsourced” financial adviceWhy stability after divorce matters more than speedDivorce 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 Introduction1:50 Principle #1 – Take It Slow2:44 Principle #2 – The Details Matter4:27 Principle #3 – Understand Before You Agree5:40 Principle #4 – Taxes Change What’s Equal6:36 Principle #5 – Gather Documents Early7:39 Principle #6 – Get the Right Advice8:43 Principle #7 – Focus on Stability9:22 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 compressingWhat happens when RSUs vest or options are exercisedHow concentrated stock creates riskWhy taxes can quietly take 40–50% of your upsideHow to prepare before liquidity arrivesMany 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 wellThe key signals that your financial life is becoming more stableHow coordinated decisions create long-term wealthWhat it means when your money starts working independently of your effortWhy resilience and long-term thinking matter more than short-term winsIf 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 coordinated2:48 Sign #2: Your decision-making is evolving3:18 Sign #3: Your money starts compounding3:48 Sign #4: You’ve built resilience4:11  Sign #5: You’re thinking long-term4:28 How to assess if you’re on track5:03 The emotional side of financial progress6:08 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 decisionsWhat tax-aware long/short investing is (in plain language)How tax loss harvesting can offset gainsWhy strategy matters more than timingFor 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 Introduction1:19 The “successful but stuck” problem2:37 Strategy overview: tax-aware long/short3:58 Why implementation matters5:06 The risk of staying concentrated5:42 Planning vs reacting to taxes6:05 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.

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 mathHow long-term investing and compounding factor into the decisionWhat financial professionals mean by arbitrageWhy paying off a mortgage early can reduce liquidity and flexibilityHow this choice should align with both short-term stability and long-term goalsThis isn’t about telling you what to do. It’s about understanding the trade-offs — and making decisions intentionally, based on your full financial picture.Whether you’re considering paying off your mortgage early or deciding how to deploy excess cash, this framework can help you evaluate the decision with more clarity and confidence.  Key Takeaways  00:00 Should You Pay Off Your Mortgage Early?02:21 The Real Benefits of Paying It Off03:16 The Trade-Offs Most People Miss04:41 The Non-Negotiable First Step (Emergency Reserves)05:20 The Right Way to Think About the Decision06:30 The Bottom Line Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/pay-off-mortgage-early-or-invest 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 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: Why IPOs and liquidity events can trigger massive tax billsThe risks of holding concentrated stock too longWhy borrowing against your equity doesn’t solve the problemThe limitations of opportunity zones and exchange structuresHow tax-aware investing can help manage capital gains more effectivelyKey Takeaways 0:00 Hook: Paying taxes on your terms1:26 IPOs creating massive wealth (and tax exposure)2:00 Common mistake: never selling3:01 Opportunity zones: pros and pitfalls3:45 Tax-aware long/short explained4:30 Why expertise mattersShow Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/how-to-reduce-taxes-on-ipo-wealth 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.

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: Why after-tax returns matter more than pre-tax performanceHow real advisor value shows up through coordination with your CPAWhat to ask about tax planning, fees, and fiduciary responsibilityHow great advisors help clients make confident, thoughtful decisions Key Takeaways 01:19 Why Choosing the Right Advisor Matters02:26 Question 1: After-Tax Returns02:54 Question 2: Working With Your CPA03:39 Question 3: Reducing Your Tax Bill04:37 Question 4: Fees and Value05:15 Question 5: How Advisors Help You Decide06:20 What These Questions Really Reveal Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/5-questions-before-hiring-a-financial-advisor 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 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: The real benefits of consolidating retirement accountsWhen keeping accounts separate may actually be betterHow fees, investment options, and flexibility impact your decisionWhat to consider before rolling over a 401(k) into an IRAWhy consolidation is about strategy — not just simplicityFor many high-income professionals, the goal isn’t just to simplify — it’s to create a coordinated investment strategy that aligns with your long-term plan. If you’re evaluating old 401(k)s, IRAs, or thinking about working with a financial advisor to organize your retirement strategy, this conversation will help you think more clearly about your options. Key Takeaways 1:19 The benefits of consolidating4:00 When NOT to consolidate5:52 What problem are you trying to solve? Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/should-you-consolidate-retirement-accounts 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 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: Why taxes become one of the biggest forces shaping your wealthThe costly mistake many startup employees make before an IPOWhy waiting until after a liquidity event limits your optionsHow tax-aware long/short strategies can help manage future tax exposureWhy planning early creates more flexibility, not more complexityFor many high-income professionals, the challenge isn’t just building wealth — it’s keeping it. If you’re navigating equity compensation, pre-IPO planning, or thinking about working with a financial advisor on tax strategy, this is one of the most important conversations to have early. We’re a fee-only fiduciary team focused on tax-aware wealth management for high-income earners, founders, and professionals with complex financial lives. Key Takeaways 1:19 IPO excitement vs costly mistakes3:29 Why taxes are easier to manage before liquidity5:17 How tax-aware long/short works (simple explanation)7:15 The risk of concentrated equity Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/pre-ipo-reduce-taxes-before-liquidity-event 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.