Take 5: Kevin O'Leary's Top Five Uniquely Toronto Innovations
Kevin O’Leary received an honours bachelor’s degree in environmental studies and psychology from the University of Waterloo and an MBA from the University of Western Ontario. After he graduated, he became a founding partner in Special Event Television. He co-founded SoftKey Software Products in Toronto, and in 1995 SoftKey acquired the first of six companies, making it the world leader in the development of educational, reference and home-productivity software with annual sales of over $800 million, 2,000 employees and subsidiaries in 15 countries. In 1996 SoftKey became The Learning Company, and three years later The Mattel Toy Company acquired The Learning Company for $4.2 billion. O’Leary is the chairman of O’Leary Funds and the manager of the publicly traded O’Leary Global Equity Income and O’Leary Global Infrastructure Fund. He is a frequent cohost on the Business News Network and one of the dragons on CBC’s venture capital reality TV program Dragon’s Den.
- Energy Savings Income Fund: Publicly traded income trust providing more than one million residential, small to mid-size commercial and small industrial customers with the peace of mind that comes from knowing that they are protected from energy-price volatility by offering access to fixed utility pricing.
- 407 ETR: First Canadian public/private endeavour for building out infrastructure. It’s the world’s first all-electronic open-access toll highway. With 530 million total trips under its belt since 1997, it’s one of the largest construction projects in Canadian history and remains one of the world’s most modern highway systems.
- Income trusts: An innovative way to raise funds for resource-based companies. These trusts that hold income-producing assets have allowed the investor to participate in the income and capital based on the cash flows of the underlying business. They have offered consistent monthly double-digit cash flow to the investor for over 15 years, which became especially attractive when cash yields on bonds were low.
- Toronto Maple Leafs: One of the most profitable and valuable sports entertainment franchises in the NHL, at $488 million in 2008, despite not having won the Stanley Cup in more than 40 years.
- Trattoria Sotto Sotto restaurant (Yorkville): Best place in Canada for a power dinner or to conduct a business deal. Always consistent in food quality, service and wine selection and packed every day of the week.


