Kevin O’Leary
Keynote Speaker | Toronto , Ontario
Entrepreneur & Investor
Shark Tank Star | Business Strategy & Finance Expert
Kevin O’Leary Expertise Business Growth, Innovation & Creativity, Brand Strategy & Storytelling, Sales, Strategic Thinking, Business Management, Entrepreneurship, Mergers & Acquisitions and Small Business Development.
About Kevin O’Leary
Kevin O’Leary is a Canadian entrepreneur, investor, author, and television personality recognized globally for his roles on Shark Tank, Dragons’ Den, and The Lang & O’Leary Exchange. He co-founded SoftKey Software Products, later known as The Learning Company, which became a leader in educational software and sold to Mattel for $3.7 billion. As founder of O’Leary Ventures and O’Shares Investments, he has built a diverse portfolio across finance, technology, and consumer products. Kevin O’Leary is also the bestselling author of the Cold Hard Truth book series and a regular business contributor to major media networks. He speaks on entrepreneurship, leadership, finance, and economic outlook.
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KEVIN O’LEARY BIOGRAPHY
Kevin O’Leary is a Canadian entrepreneur, investor, author, and television personality known internationally for his expertise in business, finance, and market strategy. He is recognized for his appearances on Shark Tank, Dragons’ Den, and The Lang & O’Leary Exchange.
Born in Montreal, Quebec, in 1954, Kevin O’Leary grew up in a multicultural family with Irish and Lebanese heritage. His mother, a skilled investor, taught him the value of saving, reinvestment, and portfolio balance—principles that became the foundation of his future success.
Kevin O’Leary earned an honours bachelor’s degree in Environmental Studies and Psychology from the University of Waterloo and an MBA in Entrepreneurship from the Ivey Business School at Western University. His early career began at Nabisco, where he developed expertise in brand management and marketing analytics.
He co-founded Special Event Television, producing sports programming before launching SoftKey Software Products in 1986. Under his leadership, SoftKey acquired multiple competitors, including The Learning Company, Mindscape, and Broderbund, creating a dominant global presence in educational software.
The 1999 sale of The Learning Company to Mattel for $3.7 billion established Kevin O’Leary as a leading figure in Canadian entrepreneurship. The deal remains one of the largest in the consumer software sector.
Following his exit from software, Kevin O’Leary became an active investor and fund manager. He founded O’Leary Ventures, a private venture capital firm, and O’Leary Funds, a mutual fund management company that grew to manage over $1 billion in assets.
Kevin O’Leary later launched O’Shares Investments, an exchange-traded fund company focused on rules-based investing. His disciplined, yield-oriented approach reflects his philosophy that every investment must generate measurable returns.
He has written multiple bestselling books, including Cold Hard Truth: On Business, Money & Life and Cold Hard Truth on Men, Women, and Money. His writing provides practical insights into finance, negotiation, and leadership, emphasizing accountability and value creation.
As an investor on Shark Tank, Kevin O’Leary evaluates new ventures with a focus on profitability, scalability, and founder integrity. He is known for his candid assessments and preference for structured deals that reward performance.
Beyond investing, Kevin O’Leary has appeared on Discovery Channel’s Project Earth, hosted Redemption Inc., and served as co-anchor of The Lang & O’Leary Exchange on CBC. His commentary on business and economics continues to influence policy and investment audiences worldwide.
Kevin O’Leary also ran for leadership of the Conservative Party of Canada in 2017, advocating for entrepreneurship, fiscal responsibility, and innovation within government.
An active philanthropist and patron of the arts, Kevin O’Leary supports charitable causes through proceeds from his photography and other creative ventures. He is also a member of the Confrérie des Chevaliers du Tastevin and a lifelong enthusiast of wine, watches, and fine art.
Kevin O’Leary continues to mentor founders, invest globally, and speak to organizations on the principles of disciplined investing, market leadership, and sustainable success.
His international profile spans media, academia, and finance, with a reputation built on transparency, measurable outcomes, and strategic execution.
Kevin O’Leary remains one of the most influential voices in global entrepreneurship and financial education, combining decades of business experience with a commitment to teaching others how to build, scale, and sustain success.
Kevin O’Leary Topic Presentations
Kevin O’Leary Toronto , Ontario, Canada delivers keynote presentations, workshops, fireside chats, moderated Q&A, and other presentation formats on a wide variety of topics. Each presentation is unique, customized and tailored for audiences, industries, conferences and event formats.
The Cold Hard Truth on Business Success
Investing with Discipline: Rules for Financial Independence
Leadership, Negotiation & Decision-making Under Pressure
The Future of the Economy: Markets, Innovation & Global Shifts
Building Wealth Through Entrepreneurship
Kevin O’Leary Books & Articles
Kevin O’Leary Speaking Testimonials
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Frequently Asked Questions
What is Kevin O’Leary known for and what is their expertise as a keynote speaker in Canada?
Kevin O’Leary is known for defined subject matter expertise based on professional experience and industry background. As a keynote speaker in Canada for conferences and conventions, their presentations align with organizational objectives and audience outcomes. Corporate keynote speakers in Canada are selected based on credibility, relevance, and practical application. Expertise alignment supports informed booking decisions. Read More
What topics does Kevin O’Leary speak on for conferences, conventions, corporate events, and annual general meetings in Canada?
Kevin O’Leary delivers keynote presentations on defined topic areas confirmed during booking. Canadian business speakers for corporate meetings in Canada align topic selection with event objectives and audience priorities. Conference speakers in Canada adapt messaging for conventions, trade shows, and summits. Topics are finalized prior to written confirmation. Read More
How do I know if Kevin O’Leary is the right fit for my audience, conference, convention, or AGM?
Kevin O’Leary is evaluated based on audience alignment, event objectives, and subject matter relevance. Event planners booking keynote speakers in Canada for corporate conferences review experience, delivery style, and industry context. Canadian business speakers for annual general meetings must align with program goals and audience expectations. Fit is clarified during the pre decision call. Read More
Where is Kevin O’Leary from and where do they speak across Canada?
Kevin O’Leary is from Toronto, Ontario and is available for events across Canada. Conference speakers in Canada frequently travel nationally with defined travel terms. Corporate keynote speakers coordinate scheduling through structured agreements. Availability is confirmed through formal inquiry. Read More
Is Kevin O’Leary available as a virtual keynote speaker for online conferences, webinars, or hybrid events in Canada?
Kevin O’Leary is available as a virtual keynote speaker for online conferences, corporate webinars, and hybrid events in Canada. Virtual keynote speakers in Canada deliver structured presentations adapted for remote audiences. Format, platform coordination, and timing are confirmed during booking. Virtual availability is documented through written agreement in Canada. Read More
Does Kevin O’Leary deliver keynote presentations, workshops, training sessions, breakout sessions, fireside chats, or panel discussions?
Kevin O’Leary may deliver keynote presentations as well as workshops and breakout sessions. Canadian business speakers for corporate training in Canada define session length and format during booking. Conference speakers may also participate in fireside chats or panel discussions depending on program design. Session formats are confirmed in writing. Read More
How do I contact Kevin O’Leary to check availability and begin the booking process in Canada?
Kevin O’Leary is contacted through Speakers Bureau of Canada to confirm availability and event details. Event planners and meeting planners typically schedule a pre decision call to clarify format, objectives, and scope. Booking begins once event requirements are defined. Written confirmation follows agreement execution. Read More
How do I book Kevin O’Leary for a conference, convention, trade show, summit, or corporate meeting in Canada?
Kevin O’Leary is booked through a structured agreement process confirming availability, fee structure, and logistics. Booking keynote speakers in Canada for conventions and trade shows includes written contracts and defined payment terms. Canadian business speakers for annual general meetings require scope confirmation before date holds convert to confirmed status. Booking is finalized upon agreement execution. Read More
How much does it cost to book Kevin O’Leary as a keynote speaker in Canada?
Kevin O’Leary keynote speaker fees depend on event type, audience size, format, and location. The cost to book a keynote speaker in Canada varies based on preparation scope and delivery structure. Corporate keynote speakers in Canada confirm fees through a booking agent and written agreement. Final pricing reflects defined scope and contract terms. Read More
Are there additional costs to hire Kevin O’Leary for a corporate event, convention, or trade show in Canada?
Additional costs to hire Kevin O’Leary may include travel expenses, extended sessions, workshops, meet and greets, emcee duties, or event host roles. Keynote speakers in Canada for business conventions often separate honorarium from travel and related logistics. Canadian business speakers confirm these components in writing before agreement execution. All additional costs are outlined contractually. Read More
How far in advance should I book Kevin O’Leary for a conference, convention, or business meeting in Canada?
Kevin O’Leary should be booked once event dates, location, and format are confirmed. Conference speakers in Canada often secure dates several months in advance. Corporate keynote speakers for annual general meetings may have limited availability during peak seasons. Early inquiry improves confirmation certainty. Read More
Is Kevin O’Leary represented by an agent in Canada and how is the agreement handled?
Kevin O’Leary is represented by Speakers Bureau of Canada for booking coordination and agreement management. Keynote speakers in Canada often work through an agency to formalize contracts and payment handling. Agent representation ensures structured communication between organizers and the speaker. Representation clarifies agreement terms before confirmation. Read More













