Hilary Hendershott

10/30/2025

What does financial freedom look like for you?

✅ Living your ideal lifestyle—without compromise.
✅ Saying “yes” to opportunities that excite you.
✅ Feeling calm and confident knowing your wealth is working for you.

If you’re not quite there yet, let’s change that.

At Hendershott Wealth Management, we specialize in helping successful professionals and couples elevate their wealth strategy—so financial freedom isn’t a someday goal, it’s your new normal.

✨ No obligation. Just clarity.
🔗 Schedule your confidential call today: Hendershottwealth.com/contact

10/28/2025

Reaching out to a financial advisor can feel intimidating—especially when you’ve worked hard to build what you have.

That’s why at Hendershott Wealth Management, our first step is always listening.
No pressure. No jargon. Just a real conversation about your goals, values, and what financial freedom means to you.

Because clarity creates confidence—and confidence is the foundation of every smart money move.

📲 Start the conversation: Hendershottwealth.com/contact

10/27/2025

“You should’ve started sooner.”
Maybe you’ve heard it before — but wealth isn’t built in the past. It’s built in the present.

Whether you’ve been investing for years or only recently started taking your financial strategy seriously, what matters most is what you do next.

Because the most powerful decision you can make isn’t about timing—it’s about intention.

10/24/2025

Earlier this year, we started preparing content around a possible OpenAI tender offer.

Today, that rumor is reality — and thousands of employees are facing life-changing liquidity events and life-changing tax bills.

Here’s the thing: the strategy to minimize those taxes can’t be pulled together at the last minute.

At Hendershott Wealth Management, we help clients prepare for events like this—private tenders, IPOs, equity payouts—before the paperwork shows up. And we’re one of the few firms in the country offering a tax-aware long-short strategy through AQR’s Flex SMA.

If you're holding concentrated stock, this isn't just about cashing out. It’s about making your money work harder—so you can keep more of what you’ve built.
Let’s talk now, so you’re ready when it counts.

To learn more about the tax implications of tender offers and protecting your wealth after major liquidity events, check out this article: hendershottwealth.com/articles/openai-tender-tax-strategy
Disclaimer: All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful.
All written content in this post is for information purposes only. Opinions expressed herein are solely those of HWM, unless otherwise specifically cited.
All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation.""

Learn how OpenAI employees can reduce capital gains taxes on future tender offers using tax-aware investing strategies like tax-aware long-short.

10/23/2025

Trust isn’t about mahogany desks—it’s about consistency, communication, and care.

When most people think of financial advisors, they picture corner offices, leather chairs, and in-person meetings across polished desks. But real trust in money management doesn’t come from furniture or formality—it comes from the way you’re treated, heard, and supported over time.

Here’s the blueprint of what trust looks like with a virtual financial planner:

- Consistency – Showing up regularly to review your goals, progress, and life changes—without waiting months for an appointment.
- Communication – Staying connected through secure, easy-to-use tools that let you share documents, updates, and questions in real time.
- Care – Truly understanding your values, your fears, and your vision for the future—so your financial plan reflects your life, not just numbers.

The truth is: virtual advising often creates deeper relationships than traditional setups, because it meets you where you are—literally and financially.

Your wealth deserves more than a desk—it deserves a partner. 💜

Curious how a virtual advisor could support you? Check out our website at Hendershottwealth.com

10/22/2025

"Seeing this plan on paper provided us with all the confidence we needed to retire."

After working with our team for over 7 years, Jeff E. (current client) shared how having a personalized retirement plan—one that’s built around his goals and values and designed for the long term—gave him and his family true peace of mind. That’s the power of financial clarity.

If you’re ready to feel that same level of confidence about your retirement, book a call with us today → hendershottwealth.com/contact

10/17/2025

Trust isn’t a tagline—it’s the core of everything we do.
Too many people have worked with advisors who weren’t fully transparent about fees or incentives. We’re changing that.

At Hendershott Wealth Management, we operate as a fee-only fiduciary, meaning our only incentive is your success. No commissions. No conflicts. Just clear, honest guidance to help you build lasting wealth.

🔗 Read more about the difference between fee-only and fee-based advisors at the link in our bio.

Because trust shouldn’t have to be earned the hard way.

10/14/2025

Billions. Gone—because of timing.

OpenAI’s $6.6B tender offer just triggered one of the largest collective tax bills in history. And it didn’t have to.

By finalizing the tender in October, employees had almost no time to harvest losses before year-end—missing a massive opportunity to defer taxes through smart planning.

With more private companies using employee tenders for liquidity, this won’t be the last time poor timing costs millions.

In my latest article, I break down what went wrong and how tax-aware long-short strategies can help employees avoid that same mistake next time.

👉 Read it here: https://hendershottwealth.com/openai
Disclaimer: All investing involves risk, including the potential loss of principal. There is no guarantee that any investment plan or strategy will be successful.
All written content in this post is for information purposes only. Opinions expressed herein are solely those of HWM, unless otherwise specifically cited.
All information or ideas provided should be discussed in detail with an advisor, accountant or legal counsel prior to implementation."

10/09/2025

When I first started sharing my struggles with money, I worried about how it would be received. Would people roll their eyes? Think I was just another financial advisor preaching from an ivory tower?

But what I’ve realized through this journey is that vulnerability creates space. By opening up about my own challenges, I’ve been able to connect with ambitious women who are serious about taking control of their finances—many of whom I’ve never even met in person. It’s through the conversations on my podcast that we’ve built this connection.

If I were to write my story with money, it would be a transformation from nemesis to hero—because I’ve come to understand that the struggles we share don’t make us weak. They make us relatable, they build trust, and they allow us to grow together.

What’s been your journey with money? Let’s keep the conversation going.

10/08/2025

The financial advisory industry is evolving—and so are the firms leading it.

On Michael Kitces’ podcast, I shared how at Hendershott Wealth Management we’ve built a Blueprint for growth that empowers our clients to experience what we stand for: wealth as more than money, a life where every part of you thrives.

In this interview, Michael and I talked about:
🔹 How we’ve structured and nurtured growth while keeping impeccable client service at the core
🔹 How our Blueprint gives us a clear and unified direction, aligning our strategies and our voices so clients experience consistency, care, and abundance
🔹 How we’ve built a team environment where accountability, grace, and connection fuel both professional growth and personal thriving

This episode highlights why HWM is a place where both clients and team members thrive.
If you’re curious about the behind-the-scenes of building an advisory firm, or about what it’s like to be part of one—we’d love for you to give it a listen: Hendershottwealth.com/kitces

10/07/2025

Financial planning is more than just saving—it's about creating a strategy that ensures your future is secure and aligns with your life goals. 🏆

At Hendershott Wealth Management, we offer comprehensive financial planning services that integrate retirement planning, tax strategies, and investment management. But where should you start? Our retirement calculator is a great first step! It helps you estimate your retirement income and assess if you're on track to meet your financial goals.

Take control of your future today! hendershottwealth.com/retirement-calculator