Jerry Millionaire

08/27/2026

This week I was asked the classic question, "Should I pay down debt first, or invest first?".

Dave Ramsey has a good sequence for this:
1) Save a thousand dollars.
By saving a grand in a chequing account you demonstrate to yourself that you have a good enough handle on the basics of money management to not burn through all your cash before the next paycheque. It also ensures you don't incur nasty and unnecessary overdraft charges from your bank.

2) Set aside six months' living expenses as an emergency fund in a savings account.
This demonstrates that you can take the lessons in step #1 and expand them. It also demonstrates you can understand the difference between an emergency and a pseudo-emergency. An emergency is losing one's job or repairing your car so you can get back and forth to work. A pseudo-emergency is plane tickets to your friend's destination wedding, or the new racing slicks and tint job on your daily driver.

3) Pay down high-interest debt. Use either the Snowball or Avalanche method, whatever works for you. The Snowball method has a higher psychological chance of working, the Avalanche method saves you more money. If one method doesn't work, try the other.

4) Invest. Ramsey suggests 10% of your income. If you've been paying off debt, you've already been living on less than you earn and have gotten used to it. Take the money you were using to pay down debt and use it to invest. You'll never notice a difference in your lifestyle. If you can invest more, you can reach your retirement goals faster. MrMoneyMustache lived on a minuscule amount of his income and was able to save 75% of his take-home. He went from exiting University to retired in 9 years.

Where are you in your journey?

08/20/2026

How to Legally Hack the Canadian Tax Code

A recent Fraser Institute survey shows that Canadians are paying over 41% of their gross income to taxes. Income tax, sales tax, fuel tax, property tax, payroll and healthcare taxes, nickel-and-diming taxes, the whole lot.

In 1980, it was 40.8%. In 1961, it was about 33%. No wonder your parents were able build a retirement plan so easily!

So how do you get out from under the burden of the Canadian tax system?

Robert Kiyosaki says "Move from Employee to Business Owner.". This is how the rich think. This is how I did it:

I started a side gig. I picked something I'm good at, that people don't want to do themselves, and are willing to pay someone else to do.

I started as a Sole Proprietor. No need to register a business name if I use my own personal name. No need to set up an LLC in most cases either. I can register when I've made some money.

Do I need business insurance, business cards, a dedicated phone line, new clothes, new equipment, certifications?

Not at first. When I set up as a handyman I knew I couldn't do anything that required a certification or a permit. Instead I refer great contractors who can do the work better than I can. www.Duuo.com and www.PalCanada.com offer vendor insurance for pop-up markets at ridiculously cheap prices.

Staples has receipt books. I like the ones with the carbonless duplicates. Square.com offers credit and debit card processing at fees lower than any bank con offer.

I kept track of all my home expenses. Heat, hydro, water, sewer, maintenance, taxes, insurance, phone.

I set aside a room in my house as an office, and another as a workshop. I counted the number of rooms in my house, the number of rooms devoted to the side gig, and worked out what percentage of space is being used for business purposes.

That percentage is now a deduction. A percentage of all bills are no longer personal expenses, they are business deductions.

Same with my vehicle. I keep a mileage book, tracking which trips are for business and personal. At the end of the year I calculate what percentage of mileage is for business. That percentage of my vehicle loan interest, gas, oil, maintenance, parking fees and insurance are business deductions instead of personal expenses.

At tax time I get a copy of TurboTax Home and Small Business. I let the program lead me and fill in the numbers from all receipts, no need for an accountant. All those deductions are subtracted from my income before tax is calculated. As an added bonus, TurboTax itself is a business deduction.

The CRA allows you to lose money for your first 5 years, then they expect to see a profit. If no profit, they may audit you, thinking you're just doing it for the tax advantages.

How much money can I make before HST headaches kick in? The threshold is $30k gross.

Fun fact: You can claim expenses from Jan 1 in the year you start your business, not from the date you start your business. Bonus!

Welcome to Rich Thinking.

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08/13/2026

I just checked my LIF projected dividends for 2026. $14,203. My actual dividends for 2024 were $12,720. That's a 12% increase over 2 years, or 6% per year.

I converted it to a LIF from an RRSP in 2022, with a value of $212,177.01. I have added no capital to the account since 2022. I've been drawing $1k/month since April 2023 and using the leftover dividends to purchase more dividend-paying stocks.

My dividend income has gone up 6% per year over the past 2 years. When was the last time you got back-to-back 6% wage increases without asking?

Dividend investing as a retirement strategy works.

08/06/2026

I've just finished building an app that answers the question, "What Canadian Dividend Stock should I buy? It rank-orders almost 400 dividend stocks based on how much they will generate in dividends in 20 years if a thousand bucks is invested, dividends reinvested, and left alone.
Now I need your help.
Visit https://games.overskill.app/showcase and search for "THECHAINMAILGUY", my app will pop up. Click the Heart button.

Created with OverSkill - Turn your ideas into powerful apps with AI

07/23/2026

I want to take a moment to apologize.

For the past year, I have been sharing weekly notes about my 16-year journey from broke to retired. I'd HAD IT! with traditional financial advice at 40. I researched every get-rich-quick scheme and wealth strategy I could find, lost a lot of money sorting the winners from the losers, and ultimately found my way out of the Rat Race. It turns out, the exit wasn't locked.

Some individuals have perceived my stories as bragging. I sincerely apologize if I made you feel that way. My intention is not to boast, but to demonstrate that there is a way out, and it is not as difficult as it may seem.

If you can do grade 5 math and operate a web browser you can retire richer, faster. You may suspect that there is a better way than what you have been taught, but you might not know what it is or where to start. I understand that you may not have the time or resources to sift through winning strategies.

I apologize if I haven't made this clear; I have reached the top, and I am sending the elevator back down.

**First Floor:**
Go here:
https://drive.google.com/drive/u/1/folders/17UEQQeyLGYD1zSAaactQEHvLgEYmA7ao
Download for free:
+ my e-book "The Nine #1 Things You Need to Know to Retire Richer, Faster"
+ my Money Ed Super Secret Financial Summary Template
+ my Money Ed Super Secret Budget Calculator
This is a $30 value.

**Second Floor:**
Email me a copy of your completed Financial Summary Template and Budget Calculator, and I will provide a 1-hour consultation to help you map out your retirement plan. Email to [email protected]. This is a $100 value.

**Third Floor:**
If you find it challenging to navigate your finances, consider booking private one-on-one coaching with me. I will help you understand the Financial Summary Template and Budget Calculator, empowering you to chart your path to financial freedom. $400 gets you a 4-hour block of time with me, used at your discretion. If you feel confident handling this part on your own, that’s great too!

59% of Canadians believe they will NEVER be able to retire. If you are among that 59%, I aim to reduce that number, starting with you.

I hope this clears up any confusion about my intent.

07/09/2026

Even Med Techs need financial guidance.
This week I had some blood work done. The Med tech made small talk, asking me what my plans were for the rest of the day. I told her I was going to be printing books.

"Books? What are they about?" she asked.
I told her that I'd HAD IT! with traditional financial advice at age 40 and researched every get-rich-quick scheme and investment strategy I could find in order to retire comfortably in a reasonable amount of time.

As she worked I told her about the money that I had lost sorting the losing strategies from the winners, and how I was able to put together a plan that had me retired in 16 years. Once retired, I started telling people what I had done and the most common question I got was, "What's the number one thing I need to know to retire richer, faster?". I told her there wasn't one, there were nine. That's why I wrote the book.

She was definitely interested in exiting the working world early so she could enjoy her life. She asked me for a copy.

I said, "I'll do you one better. Here's my card. Visit this link:
https://www.jerrypenner.com/fire_educator.html
and check out my free resources.
Then go here:
https://www.jerrypenner.com/fire_educator.html

and send me an email requesting:
+ my e-book 'The Nine #1 Things You Need to Know to Retire Richer, Faster',
+ my Money Ed Super Secret Financial Summary Template,
+ and my Money Ed Super Secret Budget Calculator

and I'll get those to you for free, a $30 value.

Read the book, fill out the Financial Summary template and the Budget Calculator to the best of your ability and get that to me. Do that and I'll give you a one-hour consult to help you find direction in your retirement plan. This is a $100 value."

She was thrilled to have met a financial coach in such an unorthodox way. I look forward to hearing from her.

I extend the same offer to you. I look forward to hearing from you too.

07/05/2026

Today's task? Fixing my printer and industrial stapler so I can print books. Want a copy? www.jerrypenner.com/fire_educator.html and click on Books and Spreadsheets

07/04/2026

Vending at pop-up events not only satisfies my desire to bring useful and pretty things to people who didn't know they needed them, it also fits in with the Rich Dad philosophy. How does it do that?

Over the past 2 weeks I have been getting caught up on making stuff. I have a number of pop-up vendor events coming in the next few months and I want to make sure I have handmade items to fill my booth and delight old and new customers.
It's been awhile since I've spent much time in the shop and I miss it. Shop time brings a sense of peace to my soul when I turn a pile of disparate parts into something nobody has ever imagined before. Beautiful order from chaos. Treasure from trash, putting together things that aren't supposed to go together.

I'm not the kind of person who can spend a vacation holding down a beach towel. I have to be making *something*. Years ago when I went camping with my S.O. and there was nothing to do, I made a tool to tend the fire, and another tool to get cooking pots on and off the fire. I can't sit still.
Even in my vending booth I bring stuff to work on.

Robert Kiyosaki taught me that poor and middle class folks spend money on vacations. Rich people make money on vacations.

He talked about traveling to different states and countries to buy land, rental properties, gold mines, and oil wells. Traveling to actually see the assets he was considering and evaluating them in person as well as on paper. The asset pays for the trip.

I do the same thing with pop-up events. I get to enjoy music festivals, medieval festivals, camping festivals, and pagan festivals for less than nothing. If I bring the right products and services, the customers pay me to be there and have a good time.

One of my most favourite festivals is a 10 day camping event in a 200 acre evergreen forest with 500 like-minded folks from around the globe. I set my own vending hours, enjoy live music, drumming and dancing circles, any any number of varied workshops and discussion forums. If I want to attend a workshop or discussion, I put up a "Back in an Hour" sign and participate.

When I return from my vacation I come back with less stuff, more cash, and plenty of great memories. I can't imagine vacationing any other way.

06/25/2026

This week I was asked, "What stock should I buy and hold long-term for dividend investing?".

If you like stability, BMO.TO is tough to beat. It meets 5 of my 6 investment criteria.

BMO.TO has:
+ A 2.79% dividend yield. I prefer something with at least 4%. If your desire is to replace your income and you are making the average of $60,400 annually, you'll need $2.165 million bucks ($60,400 / 0.0279) working for you to do this. The good news is that if it continues to increase its dividend yield by 11.5% annually, the money you invest now will be working harder for you in the future.

+ Increased is dividend annually for the past 5 years by 11.5%, beating my requirement of 4% minimum.

+ A payout ratio of 50.69%, well under my limit of 80%. More than 80% is a danger signal. More than 100% and I start wondering what sort of stupid accounting games they are playing to fund the dividend. If the payout ratio drops below their historical average, that can signal a dividend increase.

+ A stock price that has risen in the past 5 years. As of this writing, it has almost doubled its stock price. A company whose stock price falls is just trading capital gains for dividends. I want to get paid while I watch the stock gain in value.

+ Hasn't missed a dividend payment in 140 years. This is superhero territory. I can't think of any other stock with a longer unbroken dividend history. That covers both world wars, the 1929 stock crash, and every financial crisis and conflict since 1886. That stability indicates they know what they are doing.

+ Is traded on the TSX, making taxation rules simpler than if it were traded on a foreign exchange.
If your plan is to buy and hold forever and live off the dividends, this should be in your portfolio.

That's only one. Want 6 more so you can diversify? Go here:
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06/18/2026

Who is right, Kiyosaki or Ramsey?

Kiyosaki describes the difference between good debt and bad debt. Good debt puts money in your pocket, bad debt takes it out. One feeds you, the other eats you.
Borrowing money to buy a rental property that returns more than all expenses combined? Good debt. Borrowing money to buy a house to live in? Bad debt.

Ramsey says all debt is bad debt. He likes quoting biblical scripture: "The Borrower is slave to the Lender.". He advocates getting out of debt as fast as you can, starting by selling things you don't need, things whose value are depreciating faster than the debt can be paid, and debts that won't go away even if you declare bankruptcy.

I can see the reasoning for both men's arguments. With the Ramsey method, there is a certain mental freedom that comes with not owing any money. People will sometimes throw a Mortgage Burning party when they have made their last payment.
When buying rental properties with borrowed money, there is always the possibility that Something Stupid will happen. Mortgage rates might spike, tenant may stop paying, major catastrophe that isn't fully covered by insurance may come up, or the place may sit vacant for reasons beyond control. Kiyosaki remedies this with the Law of Averages. Buy 10 houses that have positive cashflow on each at 100% financing. If 1 property experiences Something Stupid, the other nine will carry the tenth. For a small-time landlord with one rental property the risk of going bust becomes greater; one tenant not paying is 100% of property income not coming in.

Buying stocks on borrowed money rides the same double-edged sword. As long as the interest payments are less than the dividend income, all is well. If the bank boosts the interest rate, or the stock stops paying dividends and the share price tanks, or the bank suddenly calls in the loan, there is a problem. If the stock stops paying dividends and the share price tanks, selling the stock to pay off the loan is not going to completely fill the hole. If the bank boosts the interest rate or calls in the loan, selling the stock and zeroing the loan brings the ride safely to a halt. Arbitrage works great, until it doesn't.

What's my take?
Borrowing money to buy stocks is a dangerous game. I've paid the equivalent of 4 university degrees to learn that. I now remember to do my due diligence every time when analyzing a stock or rental property and ask myself, "What's the worst that could happen?", because it probably will.

When I started buying properties the plan was to buy 1 a year for 10 years, then spend 10 years paying them off. Then the federal government started mucking with the lending rules and made it difficult for me to do that. I had a squatter not paying for a year before I could get him out, then had a $20,000 mess to clean up before it could be made habitable again. I didn't have 9 other properties to pick up the slack and it hurt. Bad.

Thoughts?