Your Tax Strategy

Hey, Tom here.

Next month’s Wealth Workshop is coming up on April 9th at 11 AM CT — we’ll be talking cash flow management and answering your questions.

Reserve Your Spot

This week, we’re diving into something that’s top of mind for everyone: taxes, and how manage them and your portfolio.

Let’s get into it.

Retire with Confidence by Improving Your Cash Flow Now

Planning to retire in the next 10 years?

Join us on April 9th at 11 AM CT at our next Wealth Workshop where I will discuss how to optimize your cash flow before and after retirement. The goal is simple: preserve and grow your wealth, reduce risk, and ensure steady and consistent cash flow.

I look forward to seeing you there.

Reserve Your Spot Now

Death & Taxes

The only guarantees in life.

I don’t have a lot to say on death here on the newsletter, but taxes? Sure do.

Talking about taxes makes sense right now for two reasons:

1. You just filed (or are about to).

2. DOGE – the U.S. government is telling us exactly how our freshly paid tax dollars are being used, which has evoked many responses.

Interesting times.

Let’s start off with many people’s a “tax strategy”:

1. Collect documents

2. File

3. Pay

That’s about it.

Not a lot of thought goes into it.
And the outcome, as you can imagine, is something far from perfect.

Which is odd when you consider this:
Taxes are one of the, if not the, largest recurring bills in your financial life.

And the tax system itself is anything but simple—more than 75,000 pages of regulation and case law.

Filing taxes isn’t tax strategy, it’s just compliance. A byproduct of the financial decisions you made months ago.

What you need is strategy.

As investors, we have more options than we often realize.

And the choices you make shape your tax bill every year.

To illustrate, here’s a breakdown of some widely held ETFs and their average yields over the past five years:

If you had $1 million in each, here’s how much income they’d generate—along with the tax treatment:

• Municipal Bonds (MUB) – $30,700 – Federal and state (potentially) tax free

• T-Bills (BIL) – $48,500 – Federal taxable

• Tech Stocks (QQQ) – $6,100 – Qualified dividend

• Value Stocks (VONV) – $19,200 – Qualified dividend

• Real Estate (VNQ) – $37,900 – Federal and state, mainly

• High Yield Bonds (JNK) – $65,900 – Federal and state

That’s a $60,000 spread in income between those options—with very different tax consequences.

Now, let’s say you invested that million five years ago and spent the dividends each year.
Here’s what that outcome would’ve looked like:

No surprise: tech has dominated the past couple of years, fueled by AI.
Meanwhile, income-heavy assets—munis, high yield—are still recovering from 2022.

Cash is… still cash.

So what’s a person supposed to do?

If you’re within 10–15 years of retirement—or already there—you’re asking:

• Should I take the income path?

• Should I take the growth path?

• Which accounts should I even be investing in right now?

• Where will my retirement income come from?

• How do I integrate real estate or a business into this?

• How does all of this affect my taxes?

In short: How do you optimize what you’ve got?

Every investor I know is tempted by two things.

1. More income.

2. More growth.

Reading through that last section, maybe you thought:
"I should go all in on high yield—look at that income."
Then you saw the performance chart and thought:
"Wait… I'd rather have $2.6M from tech than $1M from income."

And there’s the tension.

It’s hard to have both growth and income at the same time.

For what it’s worth, and after sitting through many many meetings with families over the past decade, the only place I’ve seen large growth and large income is through ownership in successful operating companies.

The problem?
They’re hard to build, take decades to scale (usually), and they are littered with risk.

If you have one, I am happy for you, if you don’t, the show must go on.

So you work hard.
You invest.
And over decades, you build wealth.

And if you want to keep that wealth—you need to be thoughtful about taxes.

Let’s talk tax strategy.

If you tuned into the last Wealth Workshop on Tax Strategy, you saw the framework I personally use to manage the complexity of life, investing, and taxes.

Take a look:

I won’t go into detail here, but as you can see, there are a lot of things you need to iron out to make this work. Here’s the starting point of tax strategy:

Financial Planning

I’m not talking about the ad hoc planning that comes from a late-night conversation with your spouse around the kitchen table.

I’m talking about financial planning — and financial plans — built by professionals.
People who understand you, the tax landscape, investment strategy, and what it means to pay yourself.

You wouldn’t go to a gas station attendant to fix your broken foot. You’d go to a foot doctor.

In the same way, great financial plans are best built by seasoned pros.

Here’s why financial plans are essential — and why they’re the starting point for your tax strategy.

A financial plan is like a blueprint.

Blueprints are what contractors use to build houses.

They’re the result of working with architects and engineers — people who turn your needs, dreams, and constraints into a workable design. They factor in location, weather, city codes, and timelines.

Then the actual building starts.

You wouldn’t build a house without a blueprint.

You can build a financial life without a plan…

But it will almost certainly fall far short of what could be possible with the help of a professional. And one of the byproducts of not having a financial plan?
Missed tax-saving opportunities.

How do I know this?

I’ve seen the “before and after” for many families — the decisions they were making before working with us, and the smarter moves they started making after.

A financial plan helps you win – it’s that simple.

• It helps you win at investing.

• It helps you win with taxes.

• It helps you win at life.

They are an in-depth analysis at the intersection of your dreams, your needs, your income, your spending, and your balance sheet.

It’s a deep analysis of your income, your spending, your goals, and your balance sheet—
A blueprint for building your future.

To wrap this up:

• There are more funds than there are stocks.

• The tax code, with tax case law, is tens of thousands of pages.

• You can invest in whatever you want in the US.

The amount of access we have is unparalleled compared to an other timeframe in history.

And the consequences of how you invest, the plan you create, and the tax strategy you employ, or don’t employ, will have rippling effects on your wealth.

And the best place to start is to figure out what you have, where you want to go, and the best way to maximize your situation.

Two more ways I can help you:

• BluePrint — Not everyone wants/needs full-service wealth management, but we believe everyone needs a financial plan. That’s why we built BluePrint—a professional, customized financial planning service designed to give you clarity and direction. As I always say, fail to plan, plan to fail. If you don’t have a financial plan, now’s the time. Let’s start with a quick conversation.

• Bergen — Our team is actively working with clients to navigate market volatility, refine financial plans, and coordinate distributions for taxes. We’re in the trenches, solving their most pressing financial challenges, providing expert advice and perspective—so they can maximize their outcomes and sleep well at night. If you have $500,000+ in investable assets and want a new team of dedicated financial professionals in your corner, let’s talk.

Thanks for your time this week and best of luck filing if you haven’t already.

See you next week.

Tom