Wes Hall explains the biggest money myth and the value of a well-tailored suit


Canadian entrepreneur and Dragons’ Den star Wes Hall talks about his investing lessons and the things he values the most.

Wes Hall explains the biggest money myth and the value of a well-tailored suit

Photo by CBC courtesy of Wes Hall.

Founder, philanthropist and Dragons’ Den star Wes Hall arrived in Canada from rural Jamaica as a teenager. On the night he landed, he says he promised himself that he was going to “kill it” here. Despite the obstacles he faced in a new country, Hall made good on that promise. 

In his memoir, No Bootstraps When You’re Barefoot (Penguin Random House, October 2022), Hall writes about wearing a suit on his first day as a mail clerk at a law firm. Although everyone else in the mailroom wore jeans and a T-shirt, he quickly learned that, in the corporate world, first impressions matter. In the elevator, junior lawyers would casually speak to him about mergers and acquisitions, thinking that he was “one of them.” Hall wanted to keep up, so he read after-hours at the firm’s library. He later launched his own consulting business.  

Unwavering and determined, Hall later opened his own private equity firm, WeShall Investments Inc., and an advisory firm, Kingsdale Advisors, and he now leads the board of directors at the BlackNorth Initiative, which aims to end systemic racism affecting Black people in Canada. Read about the life lessons and money management skills he learned along the way. 

Who are your financial heroes? 

American businessman Robert Smith. He has been extremely successful in backing entrepreneurs but also in giving back to uplift the Black community.

How do you like to spend your free time? 

With my family on vacation.

What was your earliest memory about money?

My earliest memory about money was my grandmother not having enough to feed her 10 grandkids and needing to stretch a dollar.

What’s the first thing you remember buying with your own money? 

I bought a car—a 1980 Dodge Omni.

What was your first job? 

Delivering The Toronto Star. I deposited my first paycheque in the bank, as I was always conscious of saving money. Most people in lower-income households are taught to save—not about how to invest. Saving helped me, though. When I moved out of my dad’s house at 18, I had money in the bank to cover the first few months of rent and a down payment.

What was the biggest money lesson you learned as an adult? 

Never get too emotionally involved in any investment.

What’s the best money advice you’ve ever received? 

Don’t be married to money. Money is like sand in the palm of your hand.

What’s the worst money advice you’ve ever received? 

If you make it, spend it!

Would you rather receive a large sum of money all at once or a smaller amount of money regularly for life? 

I’d rather get a large sum at once, so I can use it as I deem fit. I can manage my cash better than most.

What do you think is the most underrated financial advice, tip or strategy? 

Bet on the jockey, not the horse. With poor management, a business will never see its true potential.

What is the biggest misconception people have about growing money?

The biggest misconception people have about money is that you can just put it in the bank and you will get rich. Banks are successful because of this myth. They take in all these deposits and then loan money at high interest and make billions in profits. There are banks, however, that will work with you to optimize the value of your dollar.

Can you share a money regret? 

My biggest money regret is when I put too much money in a single investment or sector. Diversification will allow you to sleep at night. You may not get the home run, but you will not strike out.

What does the word “value” mean to you? 

I like tailored suits. They’re costly but made with good fabric and are customized for me. When I travel with my suits, I just hang them and wear them to a meeting the next day without ironing them. Some people prefer to buy suits off the rack and don’t pay much attention to the fabric, and then their suits have to be replaced after just months of wear. When they travel, they have to spend money on laundering, or they look like they slept in the suit. My suits last for a decade or more. That’s what value for money looks like to me.

What’s the first major purchase you made as an adult? 

My first house. I paid $112,000 for it and I couldn’t afford it, but I stretched my wallet to do it. Turned out it was the best purchase I’ve made. I sold that house five years later for twice the original purchase price, and after I used the equity built up in my house to start Kingsdale. Today that house is worth over $1.5 million.

What was your most recent splurge? 

A G-Wagon hot off the assembly line.

What is the last money-related book you read? 

Values by Mark Carney (Public Affairs Books, May 2021). I like the lessons on what to value. It was not just about financing but knowing the value of things like relationships. He quoted Oscar Wilde—Jay Z did in one of his raps as well. “Nowadays people know the price of everything, and the value of nothing.” And that describes our current attitude.

What is something you always have in your wallet? 

My Nexus card.

What is the best business asset? 

Smart people. I am in the “people business,” and the people I work with use their brain to make my company money. If those people don’t show up to work, I have no business. In other words: no assets. Smart people make me money and provide value to me. 

What’s your next money goal?

I no longer have one. It’s no longer about the money for me but what I can do with it to change society.

My MoneySense quick questions 

Rent or own? 

Own. You can build equity and leverage it to send your kids to college, invest in a great opportunity, build your credit or start your own business like I did. Renting fattens the bank account of owners.

Buy or lease? 

It depends. I mostly “buy” things because I have liquidity. If you don’t have liquidity, leasing is a great option, especially when interest rates are low. However, when rates are low, you could take advantage of investment opportunities, giving you a better return than what you would pay to lease.

Save or invest? 

Invest. Our collective savings builds up the banks to make billions on our money, and the interest on our investment makes little or no return. No one becomes a millionaire or billionaire by “saving” money. And if you know someone, point them out to me.

Budget or not? 

Budget. This gives you a sense of your spending habits. Every single business I know sets a yearly budget that not only curtails their spending but determines where the money will come from. Every government sets a budget. They are terrible at it mostly, but at least they have one.

Read more My MoneySense:

  • Shannon Lee Simmons defines “emotional return on investment” and her take on personal debt
  • “My first experience of buyer’s remorse has guided my spending ever since”, Kerry K. Taylor
  • Mixed Up Money’s Alyssa Davies on striving for CoastFIRE, the value of time, and more
  • Dragons’ Den tech titan Michele Romanow on taking risks, betting on yourself