283: What If Your Money Bought You More Freedom? The Real Life Impact of Smart Tax Planning

Over the past few episodes of Love, your Money®, we’ve taken you deep into the weeds of capital gains tax, alternative investments, and Ultra Tax Efficient Wealth Management℠ (UTEWM℠).

If you’ve been following along, you’ve heard terms like step-up in basis, long-short overlay, market-neutral strategy, and incremental returns. And if your eyes glazed over once or twice, you’re not alone.

But here’s the thing: these aren't just technical financial strategies. They’re tools. Tools that—when used correctly—give you more freedom, protect your peace of mind, and empower you to make the most of the wealth you’ve worked so hard to build.

Today’s episode zooms out from the technical to the transformational: we’re talking about what UTEWM℠ actually makes possible in your real life—not just on paper. You’ll learn why traditional financial planning around tax avoidance often falls short, and what makes this approach different. 

Hilary explains how to reduce your tax bill without being forced to sell at the wrong time, how long-term tax planning intersects with both healthcare and self-care, and why concentrating your wealth in a single stock or sector can quietly erode your quality of life. 

You’ll also hear how real people have the potential to turn multi-million dollar tax liabilities into powerful legacies, and get guidance on how to determine whether UTEWM℠ is the right fit for your financial future.

Because financial strategy isn't just about the numbers, it’s about how those numbers impact your future, your family, and your freedom.

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

• 01:45 The missing piece: What Ultra Tax Efficient Wealth Management℠ really means for your money, and your life 
• 05:12 Why choosing and holding onto investments just to avoid paying capital gains tax hasn’t worked, and the real impact of tax efficient solutions on your quality of life
• 08:02 Why the prospect of tax losses gave Hilary goosebumps at a financial conference, and the how the suite of tax efficient wealth management services HWM offers our clients has grown as a result
• 10:24 Why the fear of taxes (and refusal to sell) can quietly sabotage your financial success, and why long term tax planning is an important part of self care
• 13:54 How the Rule of 72 helps estimate how fast your money can grow—and the real cost of diversifying your stock positions without tax efficient planning
• 17:14 How our company Blueprint relates to Ultra Tax Efficient Wealth Management℠, and what we want to make possible for our clients
• 18:35 A tale of two investors–one with concentrated Apple stock and one with a robust real estate portfolio–and the (avoidable) mistakes made that can be unraveled with UTEWM℠
• 28:48 Case study: How UTEWM℠ could help a Silicon Valley Engineer diversify highly appreciated company stock and eliminate the potential $2.5 million capital gains tax hit
• 33:14 Leaving a powerful legacy: Building sustainable generational wealth, the magic of compound interest, and the power of giving
• 38:09 Case study: How UTEWM℠ can help a married couple who inherits $3 million in a taxable account and wants to retire early
• 41:53 Who UTEWM℠ is really for, how to know if it’s right for you, and what the client journey looks like if you decide to work with us

Show Notes
To

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.