End of August, and I’m ready. I love summer, but I like it when the world buckles up and gets to work.

Recently I built a custom financial model for a wealthy investor. Interesting thing is, the wealthier someone is, the more mistakes can be made. Too many assume money alone will protect them. It doesn’t—discipline and common sense does.

I’m proud of this one (screenshot below). If you want a sharper look at how your investing habits will impact your future, let me know.

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Personal Finance

Getting rich isn’t complicated. The formula is simple. And yet, most people will never follow it to riches. Why is that?

Below an exceptional discussion between comedian Hasan Minhaj and author JL Collins of the Simple Simple Path to Wealth. Highly recommend.

Outlook users can click this link if the image link below doesn’t work.

Thank you, Christina, for sending along 😇 

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Stock Markets

What does a 10% return look like? A picture tells a thousand words.

“Compounding comes in lumpy, unpredictable bursts. Most years are nowhere near the 10% average. Also worth noting: So far in the 2000s, 76% of the years show a positive return. That’s not far from the long-term 73% rate. But four of those years (2001, 2001, 2008 and 2022) showed double-digit losses. Success requires both enjoying good times and holding on through the storms.”

Thank you to Ben Cherniavsky for sharing.

Ben, by the way, apart from being my 2nd (maybe 3rd?) cousin, was also my boss at Raymond James, where he spent a 20+ year career as the number one ranked Analyst in Canada for many years running. His story is quite incredible, actually, and deserves a spotlight in a future newsletter, including a story when I almost (should have been?) got fired.

Real Estate

Over the last couple of weeks, we’ve discussed when it makes sense financially to rent instead of buy a home (see Issue #83 and Issue #84 ).

From a pure numbers standpoint renting can often come out ahead. Lower monthly costs, freed-up cash to invest in higher returning assets, and more flexibility. But money is only one side of the story.

Even though I love them, life is more than spreadsheets…

If owning a home gives you peace of mind, stability, and deep meaning—even if it costs more—that can be worth it. You can’t chart those things in Microsoft Excel.

Some of the qualitative factors people (including me) forget to weigh when comparing renting vs owning:

1. Stability: no landlord deciding to sell or raise rent. You control your future.

2. Freedom to customize: paint rooms, renovate, etc…you can do what you want.

3. Community: stay close to good schools, friends, family.

4. Inflation hedge: locking in a fixed mortgage today protects you against rent hikes tomorrow.

5. Psychological value: pride of saying, “this is mine.”

6. Legacy: a home can become part of your family story.

7. Forced Savings: getting a mortgage and paying principal forces you to build equity. Even though renting might be cheaper, most people will spend their extra cash flow instead of investing the surplus (except for all you Lions of course).

8. Principal Residence Tax Exemption (in Canada): home price appreciation is completely tax free when you sell. This is massive. Although it helps your beneficiaries more than you personally (when you die they get the house tax free), but you can’t spend your house along the way unfortunately.

That doesn’t mean you should ignore the math. But it does mean that numbers alone aren’t the whole picture.

So let me ask you this, if you had to choose today between:

1. Renting and investing the diff to potentially come out ahead financially, or

2. Owning and paying a premium for stability and security

Which one would you honestly pick, and why?

Let me know. Your answer might make it into a future issue.

1 Quote

“Keep your eyes on the stars and your feet on the ground”

Theodore Roosevelt

A Question

Many of the good things in life are downstream from being helpful and useful to others. What can you do today to be useful to someone else?

James Clear

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