Kevin O'Leary
Kevin O’Leary is a Shark Tank star, serial entrepreneur and investor known for his sharp insights on business, finance and building scalable companies.
Why book Kevin O'Leary for your next event
- Delivers direct, no-nonsense insights on entrepreneurship, investing and leadership, shaped by decades of building and exiting global companies.
- Brings real-world experience from Shark Tank, venture capital and boardrooms, connecting strategy, execution and financial discipline.
- Inspires audiences with practical frameworks for growth, risk management and wealth creation that resonate across industries and markets.
Non-binding request for Kevin O'Leary
Shark Tank Star, Serial Entrepreneur, Investor and Global Business Speaker
Kevin O’Leary is one of the most recognized business voices in the world, known for his role on ABC’s Shark Tank and his career as a serial entrepreneur, venture capitalist and investor. From founding companies with limited resources to leading billion-dollar exits, O’Leary brings a rare mix of credibility, candor and clarity to the stage. His keynotes are fast-paced, opinionated and grounded in experience, offering audiences practical lessons on building businesses, managing risk and creating long-term value.
Kevin O’Leary: From Startup Founder to Global Business Figure
Kevin O’Leary’s entrepreneurial journey began in Canada with what he describes as “a big idea and zero cash.” In 1986, he founded SoftKey Software Products in the basement of his Toronto home. Under his leadership, the company grew rapidly, later becoming The Learning Company and a major force in educational software. The business was ultimately acquired for $4.2 billion, marking one of the most notable success stories in the sector. This early experience shaped O’Leary’s lifelong focus on discipline, scalability and profitability.
Following this milestone, Kevin O’Leary continued to build and invest in companies across industries. In 2000, he founded O’Leary Ventures, a generalist venture capital investment platform that has since invested in startups and early-stage companies in virtually every sector. His track record includes co-founding Storage Now, a leading developer of climate-controlled storage facilities that was later acquired for $110 million, and investing in Stream Global Services, which was acquired for $820 million.
Shark Tank, Media Impact and Cultural Reach
Kevin O’Leary became a household name in 2006 when he joined the Canadian cast of Dragon’s Den, the international business reality show that later inspired Shark Tank. His direct feedback, tough questioning and unapologetic honesty quickly made him a standout judge. In 2009, he joined the founding cast of ABC’s Shark Tank alongside Mark Cuban, Robert Herjavec, Lori Greiner, Daymond John and Barbara Corcoran.
Shark Tank has become one of the most successful television programs of its kind, earning multiple awards and nominations, including four Emmy Awards. Through the show, O’Leary has evaluated thousands of business ideas, invested in numerous companies and influenced how entrepreneurship is viewed by a global audience. In 2025, he expanded his media presence further with his acting debut in the film Marty Supreme, appearing alongside Gwyneth Paltrow and Timothée Chalamet.
Investing, Leadership and Modern Business Strategy
Beyond television, Kevin O’Leary serves as chairman and active leader for a portfolio of companies that reflect his core business principles. These include O’Leary Ventures, Beanstox, an automated internet-based investment advisory service, and O’Shares Investments, which provides ETFs designed for long-term wealth management. He is also the founder of O’Leary Financial Group and Chief Sommelier of the award-winning O’Leary Fine Wines.
Since 2021, O’Leary has been a strategic investor in WonderFi, now one of the largest regulated crypto asset trading platforms in the world. His investment approach emphasizes transparency, governance and sustainability, themes that frequently appear in his keynote presentations. His commitment to “eco-preneurship” has also been reflected in his role as co-host of the Discovery Channel’s Project Earth, which explored innovative solutions to combat global warming.
Kevin O’Leary as a Keynote Speaker
When you book Kevin O’Leary for your event, you gain access to decades of experience at the intersection of entrepreneurship, finance and leadership. His speaking topics often include building scalable businesses, making disciplined investment decisions, managing risk, understanding markets and developing financial literacy. O’Leary’s style is candid and engaging, blending storytelling with clear frameworks that audiences can apply immediately.
He has delivered keynote presentations to corporate audiences such as Ernst & Young, MassMutual, First Third Bank, Constant Contact, Comcast, Zendesk, Cisco Systems, the National Conference of State Legislatures and ExxonMobil. His ability to adapt his message to entrepreneurs, executives and institutional leaders makes him a highly versatile speaker for conferences, leadership summits and corporate events.
Education, Thought Leadership and Personal Drive
A strong believer in financial education and nurturing the next generation of entrepreneurs, Kevin O’Leary is the author of several bestselling books, including Cold Hard Truth, Men, Women and Money, and Family, Kids and Money. He has spoken to students and future founders at institutions such as Harvard Business School, MIT Sloan, Notre Dame, Waterloo and McGill. His influence in the financial world also includes serving on the investment committee of Boston’s 200-year-old Hamilton Trust.
Kevin O’Leary holds 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 the University of Western Ontario. Outside of business, he is an avid chef, wine enthusiast, world traveler, photographer, electric guitarist and guitar collector, as well as a devoted New England Patriots fan.
Book Kevin O’Leary for your event to deliver a powerful, unfiltered perspective on business, investing and leadership, grounded in experience, driven by results and designed to challenge how your audience thinks about success.
Keynotes
Keynote by speaker Kevin O'Leary:
Cold Hard Truth
Kevin O’Leary, one of North America’s most successful entrepreneurs, reveals the secrets that made him rich and shares his personal advice for those from every walk of life. Kevin describes his incredible journey, from his sometimes difficult childhood to the way he built his first company, managed personal pressures, and ultimately achieved remarkable success. His advice is engaging and practical – and will help audience members become the best entrepreneurs and business people that they can be. Topics cover business, money, and life, including how to find your calling and turn your talents into a profitable venture; building a dream team; transforming adversity into opportunity, and making and growing your business–and your money.
Keynote by speaker Kevin O'Leary:
Lessons From A Shark
Kevin O’Leary will take you on a behind-the-scenes look at his hit show
Shark Tank.
He’ll share entertaining and insightful outtakes from his TV shows – videos you can’t see anywhere else, along with a current economic overview and how it relates to your industry, and finally, he’ll be a ‘secret agent’ for your industry with insights into how your industry is performing, where the innovation is coming from and more. All based on a content review of your industry prior to the event.
Shark Tank.
He’ll share entertaining and insightful outtakes from his TV shows – videos you can’t see anywhere else, along with a current economic overview and how it relates to your industry, and finally, he’ll be a ‘secret agent’ for your industry with insights into how your industry is performing, where the innovation is coming from and more. All based on a content review of your industry prior to the event.
Keynote by speaker Kevin O'Leary:
Fireside chat with Kevin O'Leary: Understanding & Thriving in an Uncertain World
We are all facing a new and potentially challenging era at home and in our businesses: unusual presidential campaigns and high-pressure elections, high-interest rates, stock markets declining, and growing geopolitical tensions.
An industry titan and champion of small businesses who frequently appears on major networks including CNBC and Fox, Kevin O’Leary has an ear to the ground on all things business and economics. In this moderated fireside chat, he brings the host and audience up to speed on the economy, rising interest rates, elections, and how to better understand the intersections between politics and economics and how they influence our world. Questions can be custom-tailored to your company and audience.
Recommended topics include:
- Where is the US and international economy headed in 2024 and beyond?
- What is the outlook for US interest rates, consumer and business spending, inflation, and energy prices?
- What changes can we expect in supply chains, labor markets, and real estate?
- How do small business owners protect themselves in an increasingly chaotic market?
- How US – Chinese tensions are being managed and what are the implications?
- What is the likely end game in Russia’s invasion of Ukraine?
- Which geopolitical threats are likely to erupt next — and what can you do to protect your business from catastrophe?
- American Business 2.0
When the great Covid Pandemic of 2020 hit the world, it altered the American business landscape. While many businesses like restaurants, airlines, and shared workplaces (think WeWork) went out of business or were reduced drastically, online businesses like Zoom, Adobe, and Shopify flourished. Meanwhile, changes that were happening slowly in the workplace, such as remote work, flexible schedules, and online retailing, accelerated rapidly and became the norm. In this talk on the future of business, Kevin O’Leary will share other changes that are happening so you and your company can be prepared for American Business 2.0.
Kevin O'Leary Sizzle Reel
Watch Kevin O'Leary in action
