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Dave Chan/The Globe and Mail

Mr. Wonderful, a tongue-in-cheek nickname the hard-nosed 1990s software entrepreneur uses himself, was one of five venture capitalists on CBC Television’s Dragons’ Den from 2006 to 2014, and has appeared on ABC’s Shark Tank in the United States since 2009. In April, O’Leary was the headline speaker at a “wealth-building” event in Toronto.

1. “Over 90% of my returns have come from companies run by women.”

O'Leary has invested in more than 50 companies through his TV work. Women tend to set modest goals for growth and achieve them, while men set “testosterone targets” and fall short.

2. “The customer acquisition cost was zero.”

Many businesses fail because they spend too much to acquire customers. O’Leary’s most successful Shark Tank investment was in Wicked Good Cupcakes—each packaged in a jar—run by a Massachusetts mom and her daughter. Knowing 10 million people would see the show, her husband borrowed enough computer server capacity at his office to handle a deluge of online orders.

3. “Social media also has a dark side.”

Social media can not only instantly create buzz but also scandals. Remember the viral video of a passenger dragged off a United Airlines flight? You have to respond immediately. “I carry two phones,” O’Leary says. “The blue one has social media alerts for every business I’m invested in.”

4. “The apprenticeship of Justin Trudeau must be ended in six months.”

Consider just the federal Liberals’ gaffes with China. Canada needs to sell to China and attract investment, O’Leary says. “Instead, we arrested the daughter of one of the most important members of the Chinese economy.”

5. “If you give me 20 bucks, I will give the local food bank $40.”

Before dropping out of the federal Conservative leadership race in 2017, O’Leary racked up more than $500,000 in debts. But candidates can’t give more than $25,000 to their own campaigns, so he’s still soliciting donations.