Andrew D'Souza's entrepreneurial journey started when he was 10 years old and convinced his local newspaper, The Mississauga News, to start delivery in his neighbourhood – and put him in charge of the route. He then recruited some of the local kids to help him pack the papers. Mr. D'Souza later took on dog walking, lawn mowing, landscaping and babysitting as other ways to make money as a kid. He wasn't even a teenager when he opened his first investment account with his earnings, and began buying index and mutual funds.
After studying engineering at the University of Waterloo, Mr. D'Souza worked in a number of technology roles, including chief operating officer of educational software company Top Hat and as president of Nymi, a biometrics authentication software and technology company, before becoming the co-founder and chief executive of Clearbanc, a financial services startup for freelancers and entrepreneurs.
The Globe recently spoke with Mr. D'Souza, 31, about what's in his portfolio and the investment that forever changed his opinion about stock picking.
What's your investing style?
I never really wanted a lot of things. I always found that owning stuff feels like more of a burden to me than brings me joy. Even now, I rent furnished apartments; I don't own a car. It allows me to keep my lifestyle flexible and keep a lot of cash flow going through. That allows me to take most of my earnings, especially early in my career, and put them in index funds … and to invest in startups.
What's in your portfolio today?
About two-thirds of my investments are in low-cost ETFs [exchange-traded funds] through Wealthsimple and in my own trading account. I'm also a private investor in a handful of technology companies such as Wealthsimple, Tulip Retail, Top Hat, Street Contxt and of course my own company, Clearbanc. All of these private investments are high risk, but I know the businesses, I know the founders and the teams intimately and I know I can actually have an impact beyond just providing capital. I can actually help them grow the business and have some kind of impact on the outcomes of the investment. I keep about 5 per cent of my investments in cash for immediate opportunities or needs.
What's your investment strategy?
I have a broad public-market portfolio. I'm a big believer in the capital markets as a whole and want to have exposure to it as much as possible. I try to spend as little time and mental energy thinking about my portfolio allocation in the public markets. With my private investments, I invest in founders that I've gotten to know and trust and who have businesses that are compelling and solve a problem in the market. You have to have a big enough portfolio where, if any of them fail – which happens in startups – you have enough really big wins that you still have positive returns. I have a few companies that have grown 10 times in a couple of years. Those really buoy the returns.
What has been your best investment to date?
Wealthsimple has been my best investment to date in terms of a private company. My own startup, Clearbanc, has also been on a great trajectory and will end up being my best investment.
What has been the worst investment?
My investment in BlackBerry years ago. It was the first stock that I ever bought, around late 2008. It was a small investment in a company I thought I knew really well. That was the first and last individual stock I owned. That taught me that picking individual stocks wasn't going to be my strength as an investor. I'm glad that I Iearned that early in my investing life.
This interview has been edited and condensed. For this series, a high-net-worth investor has investable assets of more than $750,000.