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

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 Takeaways01:19 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 conversationShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/paying-more-taxes-make-you-wealthierHendershott 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 Takeaways1:18 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 NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/hidden-tax-cost Follow Hilary on:LinkedInInstagramYouTube 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 NotesTo 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:LinkedInInstagramYouTube 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 NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/women-in-tech Follow Hilary on:LinkedInInstagramYouTube  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 NotesTo 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:LinkedInInstagramYouTube 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 NotesTo 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:LinkedInInstagramYouTube 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 NotesTo 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:LinkedInInstagramYouTube 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 Takeaways0:00 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 NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/how-to-reduce-taxes-on-ipo-wealthFollow Hilary on:LinkedInInstagramYouTube 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 decisionsKey Takeaways01:19 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 RevealShow NotesTo 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:LinkedInInstagramYouTube 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 Takeaways1:19 The benefits of consolidating4:00 When NOT to consolidate5:52 What problem are you trying to solve?Show NotesTo 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:LinkedInInstagramYouTube 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 Takeaways1:19 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 equityShow NotesTo 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:LinkedInInstagramYouTube 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.

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:What “tax drag” really meansWhy after-tax returns matter more than pre-tax performanceHow taxes quietly reduce flexibility and optionsWhy women may be more exposed to long-term tax riskHow thoughtful planning can preserve generational wealthTax-aware investing isn’t about avoiding taxes. It’s about being intentional about when and how much you pay — so your wealth supports your life, not the other way around.If you're building wealth and want to make smarter, more intentional decisions around taxes, this conversation is for you.Key Takeaways0:00 Introduction 1:20 Why Taxes Quietly Reduce Wealth 2:30 What Tax Drag Really Means4:07  Why It Matters More for Women4:46 How Tax-Aware Planning Changes the OutcomeShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/women-wealth-taxes-tax-aware-investing Follow Hilary on:LinkedInInstagramYouTube 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’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 Takeaways0:00 Introduction 1:19 Are financial advisors worth it?1:37 The common misconception about fees 2:17 The biggest costs are invisible2:48 Why advice matters more as wealth grows3:56 Where good advice creates real value4:58 The cost of one bad decision5:46 The emotional return of good advice5:57 Not all advice is the same6:44 Final thoughtsShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/high-quality-financial-advisorFollow Hilary on:LinkedInInstagramYouTube 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 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 Takeaways01:20 Why successful women still feel financial stress02:06 “You did all the right things…”02:00 The deeper fear beneath financial anxiety04:07 The “what if” fears many women carry04:41 The paradox: wealthier than ever, still anxious05:17 The real question: “Will I ever be truly safe?”05:27 Anxiety vs. instability06:06 The three forces affecting high-earning women07:17 Why your nervous system reacts before your balance sheet07:26 “Anxiety is not analysis.”08:05 Confidence vs. competence08:28 What changes the emotional experience of wealth08:51 The goal: clarity, steadiness, and intentional structureShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/financial-anxiety-high-earning-women Follow Hilary on:LinkedInInstagramYouTube Disclaimer:All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful. Advisory services provided by Hendershott Wealth Management, LLC (“HWM”), an investment advisor registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training.All content in this podcast episode is for information purposes only and does not constitute an offer, or solicitation of an offer, or any advice, or recommendation to purchase any securities or other financial instruments–and may not be construed as such. 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. Opinions expressed herein are solely those of Hilary Hendershott, CFP®, MBA, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another parties’ informational accuracy or completeness. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. HWM does not provide tax or legal advice.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.

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 Takeaways01:16 Do you still need a financial advisor?01:41 What AI does really well02:32 Why information was never the real problem02:58 When financial lives become interconnected03:24 The hidden problem: AI agrees with you04:16 Why good advice doesn’t always feel comfortable04:46 The accountability gap with AI05:18 Financial decisions happen during emotional moments07:04 Will AI replace financial advisors?07:21 The real value of advice07:40 Information vs. judgmentShow NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-part-2Follow Hilary on:LinkedIn InstagramYouTube Disclaimer:All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful. Advisory services provided by Hendershott Wealth Management, LLC (“HWM”), an investment advisor registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training.All content in this podcast episode is for information purposes only and does not constitute an offer, or solicitation of an offer, or any advice, or recommendation to purchase any securities or other financial instruments–and may not be construed as such. 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. Opinions expressed herein are solely those of Hilary Hendershott, CFP®, MBA, unless otherwise specifically cited. Material presented is believed to be from reliable sources and no representations are made by our firm as to another parties’ informational accuracy or completeness. All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation. HWM does not provide tax or legal advice.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.