At an age when most venture capitalists are settling into their careers, Mark Leonard walked away from his. He was 39, and by his own account the fund he had spent eleven years inside, Ventures West, had delivered mediocre returns.
The odd part is how he got there. A bio prepared for a speaking event at Ivey, where he did his MBA, reportedly lists gravedigger, bouncer, mason and dog handler among his early jobs. Profiles add draftsman and furniture mover, and a student stint as a stonemason. As an intern at Barclays, a senior colleague told him he would make a poor banker. A managing director gave him other advice: study the bank's clients. That nudge pointed him toward venture capital in Canada.
Buy these businesses, never sell them, and put the cash into the next one.
Then came the itch. Inside the portfolio, Leonard noticed something the industry ignored. The steady winners were not the glamorous bets. They were small software companies serving one narrow trade, too tiny to move a big fund's returns, so nobody wanted them.
What almost nobody knew was that the idea began with a modest name. He proposed a company he called "Software Co.", and in 1995 raised C$25 million, reportedly from OMERS, the Ontario municipal pension fund, and former colleagues at Ventures West. The rule was simple. Buy these businesses, never sell them, and put the cash into the next one.
It worked slowly, then enormously. The company listed on the TSX in 2006. In 2013 it bought Total Specific Solutions for US$360 million, which later became part of Topicus.com. Leonard wrote shareholder letters that investors treated like scripture. "Hurdle rates are magnetic in nature," he wrote in one. He avoided interviews so completely that the one he is known to have given was reportedly pulled offline.
The price was a certain opacity. In 2018 the company stopped holding quarterly earnings calls, which analysts called highly unusual. In 2016 the founder of Innoprise sued over a Harris unit's free software. Leonard himself stopped drawing a salary in 2016. In September 2025 he stepped down as president for health reasons, staying on the board, with Mark Miller taking over.
Revenue reached US$10.07 billion in 2024. He has said his biggest regret is not spending more time with his family.
For a first-time founder the takeaway is quiet. Leonard did not invent a product. He looked at a fund's weakest-looking holdings, realised the dull ones were the best, and spent the next thirty years refusing to be talked out of it.