Venture capitalist Joe Canavan discusses how wealth is built, why discipline matters more than luck, and what Canadians often misunderstand about long-term financial success.
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Joe Canavan is a Canadian venture capitalist and Principal of Canavan Capital, recently named Angel of the Year by the National Angel Capital Organization. He was an early backer in companies like Wealthsimple, KOHO, and Borrowell, and scaled Fidelity Investment Canada’s assets from $60 million to $6 billion.
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Joe sat down to share his perspective on money, from early lessons that shaped his thinking to the habits and misconceptions he believes most influence long-term financial success.
Who are your financial heroes?
John Fisher. Mark Andreessen. Vanad Khosla. I also admire Chamath Palihapitiya, Jason Calacanis, David Sacks, and David Friedberg from the All-In podcast.
The common thread with all these people is that they believe in entrepreneurship. They believe in innovation, creation, and making the world better and more successful. They believe in betting on founders even though there is an 80% chance of failure.
How do you like to spend your free time?
I travel a lot; I’m constantly jumping on planes, experiencing new places through wine and food, but also through investing. When I’m in San Francisco, I’m there to explore, but just as much to get a sense of what’s happening in technology and artificial intelligence (AI). When I was in Austin recently, it was as much about the music and energy as it was about understanding the evolving playbook around taxation, innovation, and how Canadian and American startups are building. Wherever I go, I’m always trying to get a deeper sense of local communities.
If money were no object, what would you be doing right now?
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What was your earliest memory about money?
Growing up and realizing that, despite the love and the support of my parents, we didn’t have any money. I wanted to make something of and for myself. Aspirationally, I thought of what could happen. I loved the idea of leadership and building something really cool that was going to change the world.
When I went on to build my startups and asset management companies, it was about creating wealth and prosperity for Canadian families. I felt empowered that I could do that, not just for others, but for myself, too.
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What’s the first thing you remember buying with your own money?
A used sports car to get myself off my dangerous motorcycle! I only had a motorcycle because I wouldn’t afford a car or insurance. I had to get around somehow. I was even playing semi-pro football at the time, and had to carry my equipment on the back of that bike!
I also bought a cottage at 25 years old, before I ever bought a house. I wanted a place that could bring people together—something to share with friends and family, which is still a philosophy I live by today.
What was your first job?
Delivering newspapers!
What was the biggest money lesson you learned as an adult?
Pay yourself first. With every single paycheck, young people should plow as much as they can tolerate into an investment account.
What’s the best money advice you’ve ever received?
“Pay yourself first” is actually a quote from David Chilton’s first book The Wealthy Barber. The idea of turning paychecks into automatic savings is so important to maximize growth.
What’s the worst money advice you’ve ever received?
Buy gold and silver, and I got this advice when it was at its peak!
What do you think is the most underrated financial advice?
Tithing. I think it’s really important to think about giving back, whether it’s to your community, to society, or to those less fortunate. I think it’s a habit that if you form it early, there’s so much positive karmic, energetic resonance that comes with that way of thinking.
What is the biggest misconception people have about growing money?
One common misconception is that building wealth is either easy or impossible. In reality, it takes discipline, vision, strategy, and long-term execution. Anything is possible, but most people aren’t willing to do the work required for real success.
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I spend a lot of my time working with people in their 20s and 30s, and sometimes even older Canadians. I ask them to create a vision board for perfection in 10 years. What would success look like? Then, what goals must you achieve working backwards from perfection to year seven, year five, year three, year one, and what milestones would you have to hit every step along the way?
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Debt can be an anchor unless you’ve got your assets under control and use leverage to unlock stale or idle assets for investment purposes. The benefit is that you are earning money on that loan, and the interest is tax-deductible. You are maximizing your return on assets, which is critical over the long run.
What is the last money-related book you read?
The Coming Wave by Mustafa Suleyman isn’t really about money, but it helps me think about where AI is headed. For me, reading about technology and business trends translates into understanding where future value and investment opportunities will come from.
What is something you always have in your wallet?
My goal cards. I set goals and milestones for myself for the next three, five, seven, and 10 years. I used to write them on the back of a business card and keep it in my wallet, so every time I opened it, I would see my goals and be reminded of my long-term plan. I still have those goal cards; they’re just in my digital wallet now.
What’s your next money goal?
When I think about the next 10 to 20 years, I want to continue making an impact through philanthropy and deepen that impact even further into something really profound. I’m also a family man—I go to my wife and kids with every big decision I make. I value their opinions immensely. I hope to pass on the money lessons I’ve learned so they feel empowered to create an impact of their own.
My MoneySense lightning round
Rent or own?
Renting is fine if you use the money you save to invest. Always keep your money working for you in appreciating assets, especially equities.
Buy or lease?
Buy. There are too many hidden costs with leasing, and the interest rates are quite high (and not deductible).
Save or invest?
Invest!
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Budget or not?
Having a budget keeps me safe on the spending/expense side of the ledger. The tighter you are with spending controls, the more disciplined and successful you are likely to be—especially if you spend on near-term gratification or frivolously.
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