Star of ABC’s Shark Tank, top business speaker, serial entrepreneur, venture capitalist and investor, featured in Harvard Business Review case study in 2023

Kevin O’Leary’s success story began in his native Canada, “with a big idea and zero cash.” In 1986, he founded SoftKey Software Products, later to be called The Learning Company, in his Toronto basement. Under O’Leary’s leadership, the company became a giant in its sector before it was acquired for $4.2 billion. Since then, O’Leary has founded or cofounded several ventures to great success.

Reflecting his commitment to “eco-preneurship,” O’Leary also co-hosted The Discovery Channel’s Project Earth series, which explored radical ideas to combat global warming.

A strong believer in financial education and fostering the next generation of entrepreneurs, O’Leary is the author of a bestselling series of books: Cold Hard Truth; Men, Women and Money; and Family, Kids and Money. He has spoken to future entrepreneurs at Harvard Business School, MIT Sloan, Notre Dame, Waterloo and McGill.

O’Leary received an honors bachelor’s degree in environmental studies and psychology from the University of Waterloo and an MBA in entrepreneurship from the Ivey Business School at the University of Western Ontario.

Founder & Chief of Content at Barstool Sports | One Bite Pizza Reviews

Dave Portnoy, widely known as "El Presidente," is the founder and face of Barstool Sports — a powerhouse media brand that has redefined what it means to connect with modern audiences. Under Dave's leadership, Barstool Sports has gone from a humble gambling newspaper in Boston to a national empire with a massive reach across all media.

Unfiltered and unapologetic, Dave speaks on brand building, the importance of authenticity in business and how to disrupt established industries. He brings insights into today’s digital landscape from his experience scaling Barstool from a small project to a cultural force.

Additionally, through Dave’s leadership, Barstool didn’t just grow — it soared. At a time when many traditional media companies were struggling to adapt, Dave relentlessly focused on what resonated with his audience and propelled Barstool into the digital media spotlight. His impact extends far beyond Barstool’s loyal fan base. For instance, his famous One Bite pizza reviews spawned the One Bite app, now the largest pizza review database in the U.S. The “One Bite Bump” has transformed local pizza businesses, drawing nationwide attention to the pizzerias he endorses.