Joe Canavan: How to Build Wealth That Lasts

Joe Canavan is a Canadian venture capitalist and the principal of Canavan Capital. Recently named Angel of the Year by the National Angel Capital Organization, he was an early investor in companies such as Wealthsimple, KOHO and Borrowell. Earlier in his career he helped grow Fidelity Investments Canada’s assets under management from roughly $60 million to $6 billion.

In this interview, Joe shares his views on money—how early experiences shaped his thinking, the habits he believes lead to long-term financial success, and the common misconceptions he sees about building wealth.

Who are your financial heroes?

People who stand out for me include John Fisher, Marc Andreessen and Vinod Khosla. I also admire Chamath Palihapitiya, Jason Calacanis, David Sacks and David Friedberg—voices I follow for their entrepreneurial perspective. What unites these figures is a belief in entrepreneurship: in the power of founders to create meaningful change, even when most startups fail. They back risk and innovation, and they accept that the path to big impact is paved with uncertainty.

How do you like to spend your free time?

I travel frequently. I enjoy experiencing new cities through food and wine, but travel also doubles as research: a way to see how technology and artificial intelligence are progressing in different hubs. When I visit San Francisco or Austin, I soak up the cultural energy while also meeting founders, investors and builders to understand shifting trends around taxation, innovation and startup strategies. Wherever I go, I try to get a sense of the local community and what’s being built there.

If money were no object, what would you be doing right now?

Fortunate as I am, I’m already doing it. My current work—investing in founders, building businesses and supporting community impact—aligns with what I would pursue if money weren’t a constraint.

What was your earliest memory about money?

I remember realizing, as a child, that despite my parents’ love and support we often didn’t have extra money. That awareness drove me to want to create something for myself. I was inspired by leadership and the idea of building something meaningful—work that could change the world. Later, when I launched startups and managed assets, my goal became creating prosperity for Canadian families, as well as for myself.

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

The first thing I bought with my own money was a used sports car—mostly to get off a risky motorcycle. I rode that bike because I couldn’t afford a car or insurance at the time; it was how I got around, even while playing semi-pro football and hauling gear on the back. By age 25 I also bought a cottage before I owned a house—somewhere to bring friends and family together, which reflects a philosophy I still value today.

What was your first job?

Delivering newspapers.

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

Pay yourself first. With every paycheck, especially when you’re young, direct as much as you reasonably can into investments. Automating savings transforms paychecks into the foundation of long-term growth.

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

“Pay yourself first” comes from David Chilton’s book The Wealthy Barber. The principle of turning income into automatic savings is one of the most impactful habits for maximizing long-term returns.

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

Buy gold and silver—advice I received when those assets were at a peak. Timing and speculation can be costly lessons.

What do you think is the most underrated financial advice?

Tithing, or regularly giving back. Whether it’s to your local community, broader society or people in need, forming a habit of generosity can bring meaningful personal and social benefits. The practice creates positive momentum and helps keep values aligned with wealth.

What is the biggest misconception people have about growing money?

Many people assume building wealth is either effortless or impossible. The truth is that real wealth requires discipline, vision, strategy and sustained execution. I often ask younger clients to create a ten-year vision and then work backwards: what must be achieved in years seven, five, three and one? Breaking a big vision into concrete milestones is how long-term growth becomes attainable.

What’s your take on debt?

Debt can become an anchor if unmanaged. But when your assets are in order, leverage can be a useful tool: borrowing to unlock idle assets for investment can amplify returns—particularly when interest is deductible and the investment generates higher returns than the cost of borrowing. The key is disciplined use of leverage, focused on maximizing long-term return on assets.

What is the last money-related book you read?

I recently read The Coming Wave by Mustafa Suleyman. While it’s not a finance book per se, it sharpens my view of where AI is headed. Reading about technology and business trends helps me identify where future value and investment opportunities might emerge.

What is something you always have in your wallet?

Goal cards. I write down objectives and milestones for three, five, seven and ten years and keep them where I’ll see them regularly. Those reminders help maintain focus. Today they live in a digital wallet, but the habit is the same.

What’s your next money goal?

Over the next decade or two I want to continue increasing my philanthropic impact and make that giving more profound. I make major decisions with my family—my wife and children are part of every big choice—and I aim to pass along the financial lessons I’ve learned so they can create impact in their own lives.

My MoneySense lightning round

Rent or own?

Renting is reasonable if the money saved is invested. Keep your capital working in appreciating assets, especially equities.

Buy or lease?

Buy. Leasing often hides costs and typically carries higher interest that isn’t deductible.

Save or invest?

Invest. Where possible, deploy savings into growth assets to compound over time.

Budget or not?

A budget provides protection on the spending side of your balance sheet. Tight spending controls build discipline and increase the likelihood of long-term success—especially against impulsive or short-term gratification.