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

Follow Hilary on:

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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 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

Follow Hilary on:

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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 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

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.

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

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’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

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.

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 Takeaways

• 01:20 Why successful women still feel financial stress
• 02:06 “You did all the right things…”
• 02:00 The deeper fear beneath financial anxiety
• 04:07 The “what if” fears many women carry
• 04:41 The paradox: wealthier than ever, still anxious
• 05:17 The real question: “Will I ever be truly safe?”
• 05:27 Anxiety vs. instability
• 06:06 The three forces affecting high-earning women
• 07:17 Why your nervous system reacts before your balance sheet
• 07:26 “Anxiety is not analysis.”
• 08:05 Confidence vs. competence
• 08:28 What changes the emotional experience of wealth
• 08:51 The goal: clarity, steadiness, and intentional structure

Show Notes
To 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:

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Instagram
YouTube 

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 Takeaways

• 01:16 Do you still need a financial advisor?
• 01:41 What AI does really well
• 02:32 Why information was never the real problem
• 02:58 When financial lives become interconnected
• 03:24 The hidden problem: AI agrees with you
• 04:16 Why good advice doesn’t always feel comfortable
• 04:46 The accountability gap with AI
• 05:18 Financial decisions happen during emotional moments
• 07:04 Will AI replace financial advisors?
• 07:21 The real value of advice
• 07:40 Information vs. judgment

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-part-2

Follow Hilary on:

LinkedIn
Instagram
YouTube 

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.

In 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 Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/short-pause-love-your-money

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.

In 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 plan
• 05:36 The three building blocks of the tax-aware long-short strategy: the core portfolio, the long overlay, and the short overlay
• 08:05 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 approach
• 13:23 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 erosion
• 15:59 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 you

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-part-2

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.

What if the financial tools you’ve been taught to fear—like leverage, short selling, and active trading—aren’t inherently dangerous?

What if the real risk isn’t the tool itself, but how it’s applied and who is using it? 

The truth is these tactics can create unnecessary risk if misused. But when they’re applied for a specific, evidence-based purpose–like generating consistent tax advantages–they can actually become powerful tools in a savvy investor’s toolkit.

In this episode of Love, your Money® (the first in a two-part series!) Hilary pulls back the curtain on a misunderstood strategy in modern wealth management: market-neutral leverage–and how it functions within a tax-aware long-short strategy.

You’ll learn:

• The difference between “long” and “short” overlays, and why it matters
• How leverage shows up in peoples’ financial lives–and what makes it high-risk vs low-risk
• How long-short overlays can reduce tax drag without adding market risk 
• How advanced strategies with a “bad reputation” can actually protect and grow wealth when used responsibly

If you’ve ever wondered whether strategies like leverage, short selling, and active trading are too risky to touch, this episode will show you why the answer isn’t so simple–and why dismissing them outright could mean missing out on meaningful, lasting tax benefits.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 02:44 What leverage is, the role it plays in building wealth, and low-risk versus high-risk
• 06:21 How leverage is used prudently in the tax-aware long-short strategy we execute within Ultra Tax Efficient Wealth Management℠ 
• 08:49 Introducing the market-neutral tax-aware long-short strategy we offer through Flex SMAs
• 11:03 Breaking down the long overlay, the short overlay, and the long-short overlay
• 14:57 How using the market-neutral, long-short overlay allows you to generate tax alpha whether the market is up or down
• 17:33 A few examples of real world outcomes that a tax-aware, long-short strategy can provide for investors
• 20:29 How farming can help us understand market-neutral leverage and tax-aware long-short strategies
• 24:03 How we implement long-short overlays and separately managed accounts in client portfolios
• 27:42 How to get in touch to learn more about Ultra Tax Efficient Wealth ManagementSM–and whether tax-aware long-short strategies are right for you

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/tax-aware-long-short-strategies-pt1

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.

Welcome to another episode of Ask Hilary, where we tackle money questions people are asking our advisors and the internet. Today, Hilary is exploring one big question:

What did you have to unlearn to do this work with integrity?

Her answer comes from the story of an experience early in her career–shortly after picking herself up from financial rock bottom–and the words from a mentor that made her rethink her work in the finance industry.

Listen in to hear what Hilary has learned–and get the lived experience perspective that ChatGPT and Google search results just can’t provide.

Here’s what you’ll learn in this week’s episode of Love, your Money:

• 01:42 Q - What’s one thing you had to unlearn about money in order to do this work with integrity?
• 02:20 The experience that taught Hilary how easy it is to compromise your integrity, and the words that changed her career trajectory
• 08:13 Why Hilary is okay turning away potential earnings from commission-based compensation, and some final thoughts on integrity, responsibility, and using your powers of influence for good

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/ask-hilary-doing-money-work-with-integrity

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.