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

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.