Podcast
Love, your Money - Wealth, Money, and Financial Advisor for Women
Hosted by Hilary Hendershott, CFP · EN
If you are seeking your path to real financial success – this show is for you. Truly achieving financial freedom requires you master the “inner” world of money - your money mindset - and the “outer” world of money - consistently growing your net worth. One without the other is not enough. This show contains powerful systems and methodologies for women who run businesses and women who don’t. Love, your Money® with Hilary Hendershott tackles money beliefs and financial planning strategies like:
- What your family life growing up may say about your credit card debt
- What tax strategies make the most sense for business owners
- How to leverage compound investments to build truly passive income
- How the quality of your relationships rise and fall on your money habits
- Whether index funds are better to invest in than actively managed funds
- Taking charge of your income and cash flow so you have money for today and tomorrow
Hilary Hendershott is a CERTIFIED FINANCIAL PLANNER™ professional with more than two decades of experience as a wealth manager. She’s NBC’s “Investor’s Voice of Reason”, an Investopedia Top 100 Financial Advisor five years running, and a TEDx speaker with her own personal experience of making money mistakes before multi-million-dollar success. Love, your Money With Hilary Hendershott is an ongoing conversation for you to improve your relationship with money, deepen your understanding of how money works in every area of life, and gain the clarity you seek about strategic wealth building and investing decisions and questions.
Subscribe to Love, your Money® with Hilary Hendershott wherever you find your other favorite podcasts. And if you love what you hear, show some love with a five-star rating!
For more information, visit https://hendershottwealth.com
28episodes
Episodes
Newest firstAll episodes
305: How to Reduce Taxes on IPO Wealth (Before It’s Too Late)
2w ago00:07:15Tap to summarizeIf 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.
Transcribe →304: 5 Questions Every Tax-Aware Investor Should Ask Before Hiring an Advisor
3w ago00:08:20Tap to summarizeChoosing 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.
Transcribe →303: Should You Consolidate Retirement Accounts? (401k & IRA Explained)
4w ago00:08:47Tap to summarizeIf 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.
Transcribe →302: Pre-IPO? How to Reduce Taxes Before a Liquidity Event
Jul 700:10:21Tap to summarizeIf 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.
Transcribe →301: Women, Wealth & Taxes: Why Tax-Aware Investing Matters (Especially for Women Investors)
Jun 3000:07:36Tap to summarizeWomen 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.
Transcribe →300: Are Financial Advisors Worth It? The Real Value (After Fees)
Jun 2300:09:02Tap to summarizeIf 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.
Transcribe →299: Why Even High-Earning Women Deal With Financial Anxiety
Jun 1600:11:07Tap to summarizeYou 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.
Transcribe →298: Why Smart People Still Hire Financial Advisors in the Age of AI
Jun 900:09:32Tap to summarizeAI 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.
Transcribe →297: A Short Pause for Love, your Money®
Sep 3000:04:48Tap to summarizeIn this brief update, Hilary Hendershott shares that Love, your Money® is taking a short hiatus. Think of it as a quick intermission—not the end of the story. Hilary explains why this pause matters, what’s happening behind the scenes, and what you can look forward to when the show returns later this year.The heart of the podcast remains the same: transforming your relationship with money so it becomes a source of trust, freedom, confidence, and even love. During this pause, it’s the perfect time to revisit past episodes and stay connected with Hilary and the Hendershott Wealth Management team at hendershottwealth.com.Show NotesTo get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/short-pause-love-your-moneyFollow Hilary on:LinkedIn InstagramYouTube 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.
Transcribe →296: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 2 of 2)
Sep 2300:23:05Tap to summarizeIn our last episode, Hilary pulled back the curtain on tools many investors are taught to fear—like leverage, short selling, and active trading—and how, when used wisely, they can produce tax alpha: higher net returns that come from smart tax planning, not investment performance alone.If you left part one wondering, “Doesn’t this mean lots of trading and market timing? And hasn’t Hilary always said market timing underperforms index funds?”—this episode is for you.Because while active trading does often deserve its bad reputation, the “active” in tax-aware long-short is different; it isn’t about chasing headlines, jumping in and out of the market, or guessing what comes next.It’s a systematic, rules-based process designed to create a small excess return and generate consistent tax benefits—without changing your long-term investment plan.In this episode, Hilary explains what “active” really means in this context, breaks down how the tax-aware long-short strategy works from the ground up, and shows why, in many cases, it’s the single most powerful tool inside Ultra Tax Efficient Wealth Management℠.Because for many high-net-worth investors, taxes are your largest lifetime expense. And while taxes are inevitable, here’s what’s not: letting them control your life, your choices, or your financial future.Here’s what you’ll learn in this week’s episode of Love, your Money:02:45 Active trading to chase market returns versus its use as a disciplined, rules-based system to harvest tax losses and preserve your core investment plan05:36 The three building blocks of the tax-aware long-short strategy: the core portfolio, the long overlay, and the short overlay08:05 The due diligence we went through to vet AQR Capital Management, the custodians, and Flex SMA’s track record before making it available to suitable investors 10:52 The real impact of tax efficiency on your life, and financial scenarios or events that make someone a suitable investor for this approach13:23 The services we offer within our Ultra Tax Efficient Wealth ManagementSM suite–designed to proactively work to keep your wealth strong, flexible, and protected from unnecessary tax erosion15:59 The importance of acting now to preserve optionality, protect your wealth, and prevent unnecessary erosion of your financial freedom–and how to get in touch if you want to find out whether UTEWMSM and the tax-aware long-short strategy is right for youShow 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 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.
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