In 2006, O'Leary appeared as one of the five venture capitalists on the then-new show "Dragons' Den" on CBC, the Canadian instalment of the international "Dragons' Den" format. On the show, O'Leary developed a persona as a blunt, abrasive investor, who at one point told a contestant who started crying, "Money doesn't care. Your tears don't add any value." This television persona was encouraged by executive producer Stuart Coxe, who during the first two seasons occasionally asked O'Leary to be "more evil". "Dragons' Den" became one of the most-watched shows in CBC history, with around two million viewers per episode. Coxe attributed the show's success in large part to O'Leary's presence.