295: Understanding Leverage, Short Selling, and Active Trading in Tax-Aware Long-Short Strategies (Part 1 of 2)

304: 5 Questions Every Tax-Aware Investor Should Ask Before Hiring an Advisor

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 performance * How real advisor value shows up through coordination with your CPA * What to ask about tax planning, fees, and fiduciary responsibility * How great advisors help clients make confident, thoughtful decisions Key Takeaways * 01:19 Why Choosing the Right Advisor Matters * 02:26 Question 1: After-Tax Returns * 02:54 Question 2: Working With Your CPA * 03:39 Question 3: Reducing Your Tax Bill * 04:37 Question 4: Fees and Value * 05:15 Question 5: How Advisors Help You Decide * 06:20 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 [https://hendershottwealth.com/podcast/5-questions-before-hiring-a-financial-advisor] Follow Hilary on: LinkedIn [https://www.linkedin.com/in/hilarytheCFP] Instagram [https://www.instagram.com/hendershottwealth] YouTube [https://www.youtube.com/c/HilaryHendershott/videos]  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.

303: Should You Consolidate Retirement Accounts? (401k & IRA Explained)

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 accounts * When keeping accounts separate may actually be better * How fees, investment options, and flexibility impact your decision * What to consider before rolling over a 401(k) into an IRA * Why consolidation is about strategy — not just simplicity For 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 consolidating * 4:00 When NOT to consolidate * 5:52 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 [https://hendershottwealth.com/podcast/should-you-consolidate-retirement-accounts] Follow Hilary on: LinkedIn [https://www.linkedin.com/in/hilarytheCFP] Instagram [https://www.instagram.com/hendershottwealth] YouTube [https://www.youtube.com/c/HilaryHendershott/videos]  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.

302: Pre-IPO? How to Reduce Taxes Before a Liquidity Event

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 wealth * The costly mistake many startup employees make before an IPO * Why waiting until after a liquidity event limits your options * How tax-aware long/short strategies can help manage future tax exposure * Why planning early creates more flexibility, not more complexity For 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 mistakes * 3:29 Why taxes are easier to manage before liquidity * 5:17 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 [https://hendershottwealth.com/podcast/pre-ipo-reduce-taxes-before-liquidity-event] Follow Hilary on: LinkedIn [https://www.linkedin.com/in/hilarytheCFP] Instagram [https://www.instagram.com/hendershottwealth] YouTube [https://www.youtube.com/c/HilaryHendershott/videos]  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.

301: Women, Wealth & Taxes: Why Tax-Aware Investing Matters (Especially for Women Investors)

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 means * Why after-tax returns matter more than pre-tax performance * How taxes quietly reduce flexibility and options * Why women may be more exposed to long-term tax risk * How thoughtful planning can preserve generational wealth Tax-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 Takeaways * 0:00 Introduction *  1:20 Why Taxes Quietly Reduce Wealth *  2:30 What Tax Drag Really Means * 4:07  Why It Matters More for Women * 4:46 How Tax-Aware Planning Changes the Outcome Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/women-wealth-taxes-tax-aware-investing [https://hendershottwealth.com/podcast/women-wealth-taxes-tax-aware-investing] Follow Hilary on: LinkedIn [https://www.linkedin.com/in/hilarytheCFP] Instagram [https://www.instagram.com/hendershottwealth] YouTube [https://www.youtube.com/c/HilaryHendershott/videos]  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.

300: Are Financial Advisors Worth It? The Real Value (After Fees)

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 Takeaways * 0:00 Introduction *  1:19 Are financial advisors worth it? * 1:37 The common misconception about fees *  2:17 The biggest costs are invisible * 2:48 Why advice matters more as wealth grows * 3:56 Where good advice creates real value * 4:58 The cost of one bad decision * 5:46 The emotional return of good advice * 5:57 Not all advice is the same * 6:44 Final thoughts Show Notes To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/high-quality-financial-advisor [https://hendershottwealth.com/podcast/high-quality-financial-advisor] Follow Hilary on: LinkedIn [https://www.linkedin.com/in/hilarytheCFP] Instagram [https://www.instagram.com/hendershottwealth] YouTube [https://www.youtube.com/c/HilaryHendershott/videos]  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.