In today’s issue:

• Weekly Wisdom - From the poet/philosopher Chris Rock…

• Market Musings - Why isn’t the market taking with all the bad news?

• Financial Hack - How to buy real estate without triggering taxes…

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WISDOM

MARKET MUSINGS

With all the recent world events:

👎 Political unrest in the United States

👎 War between two nuclear powers: Israel and Iran

I was interested to see how the market opened this week.

Would it continue the crash that started on Friday, or stabilize.

On Sunday, as I’m writing this, the futures market just opened UP basically erasing the losses from Friday.

So, how can we contextualize this?

Shouldn’t bad news make the market crash?

I think this speaks to the concept of Multiple Timeframe Analysis where we can look to different timeframes to see what each shows us.

I’m updating the daily chart I shared with you a few weeks ago as a reminder of where we are at on that timeframe. Perhaps a bit sideways, but in an uptrend since the Trade War selloff earlier this year.

So not much information there.

What if we zoom out?

Let’s look at the weekly and monthly charts, ah, this is what everyone is missing…

Those charts are still signaling a secular bull market.

All of a sudden, the quick recoveries from the short-term news cycle pullbacks during the Trade War and tensions in the Middle East seem less impactful.

Against a backdrop of a steadily growing market with high rate of employment, enough inflation to keep prices rising, a large millennial generation entering their high spending years as economic tailwinds, it’s easier to make the case for being invested at the moment.

So, while short-term news cycle noise may make the daily charts look scary, be careful of overreacting while the long-term charts look so positive.

FINANCIAL PLANNING HACK

The Real Estate Strategy the IRS Hopes You Never Learn

A few weeks ago, Travis, a longtime reader, reached out.

He'd just watched a friend start earning six figures a year from a real estate portfolio.

No stock was sold. No capital gains tax. No mortgage headaches.

Only consistent income, while the stock portfolio stayed fully intact and growing.

His question was simple:

"How is this possible?"

A great question. And the answer shows how rich people think totally differently about money than the rest of us.

How Rich People Buy Stuff Without Selling Anything

When Mark Zuckerberg bought a $59 million home in Lake Tahoe, he didn’t sell his Meta shares to do it.

Instead, he did something much smarter. He went to the bank and said:

"Hey, I'll let you hold my Facebook stock as backup. Give me a loan for the house."

The bank said, "Sure!" and gave him the money at just 1% interest.

Think about it: He kept his stock (which kept growing).

He got his house. And he paid almost nothing in interest.

No taxes. No selling. Just pure genius.

And here's the thing: You don't need to be a billionaire to do this.

Turning Stocks into Real Estate

Let’s say you hold $300,000 in stocks that have appreciated over time. You don’t want to sell because of the tax hit, but you want to diversify into real estate.

You borrow $100,000 against the portfolio at 5% interest and invest in a property or syndication that yields 9% annually.

Now you’re earning money on two fronts:

• Your property is giving you steady rental income

• Your stock portfolio is still growing in the background

You’re collecting a 4% profit on money you never had to sell, while your original investment keeps working too.

Real estate also has a tax advantage called depreciation, which can lower your taxable income while keeping your cash flow untouched.

Over time, the property may appreciate and be refinanced, returning even more capital to you without triggering tax.

Why Most Investors Miss This Trick

This is how rich families have been doing it for decades. But most regular people never hear about it.

Why? Three reasons:

1. Your financial advisor won't tell you because they can't make money from real estate

2. Regular banks don't offer it because it’s too complicated

3. The government sure isn't going to teach you how to legally avoid taxes

That’s why Shrewd Investor exists. To fill in the gaps that no one else is talking about.

What to Watch Out For

This isn’t magic. Like any strategy, it comes with risk. But they’re manageable if you plan.

If your stock drops a lot in value, the bank might ask you to add more funds or reduce your loan. That’s why it’s best to avoid using risky or highly volatile stocks for this.

Interest rates can rise. If you’re planning to borrow long-term, it helps to look for fixed rates or set a cap on how high your rate can go.

And while rental income can be strong, managing a property isn’t completely hands-off. If you don’t want to deal with tenants or repairs, work with a property manager or invest through a company that handles the day-to-day.

Just remember: keep cash on hand, don’t over-borrow, and make sure the numbers work even if conditions change.

Smarter, Not Riskier

This isn’t about chasing higher returns. It’s about controlling your capital.

You’re borrowing without selling, creating income without giving up growth, and building wealth in a way that’s often more tax-efficient than the traditional route.

These are the quiet moves that separate investors who just work harder… from the ones who structure smarter.

And they may get even better when the new spending bills get through Congress…

It’s the same shift Travis began making after that conversation, moving from simply owning assets to using them with intention.

If this sparked something for you, stay tuned.

You don’t need to act right away. Just keep learning. That’s what being a Shrewd Investor is all about.

Until next time,

Josh

P.S. If you’d like us to break down your portfolio or ask a question, submit yours here: https://shrewdinvestor.com/roastme

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The content provided in this newsletter is for informational purposes only and should not be considered as specific advice for any specific individual. The information is prepared by knowledgeable individuals and is not written by certified tax professionals or investment advisors. For personalized advice tailored to your unique financial situation, consult with a qualified tax professional, financial advisor, or attorney.

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