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Kevin O'Leary

Kevin O'Leary is a Canadian businessman, author, and television personality best known as 'Mr. Wonderful' on the reality TV show Shark Tank and its Canadian counterpart Dragons' Den. He co-founded SoftKey International, a software company he later sold to Mattel for $4.2 billion. He is also the chairman of O'Leary Financial Group and a prominent advocate for financial discipline and investing.

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Shark Tank investor Dragons' Den O'Leary Financial Group authoring 'Cold Hard Truth' book series blunt money advice and investment philosophy
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About Kevin O'Leary

Kevin O'Leary is a Canadian businessman, author, and television personality best known as 'Mr. Wonderful' on the reality TV show Shark Tank and its Canadian counterpart Dragons' Den. He co-founded SoftKey International, a software company he later sold to Mattel for $4.2 billion. He is also the chairman of O'Leary Financial Group and a prominent advocate for financial discipline and investing.

Money is a tool and should work for you — never be emotional about it. Financial freedom comes from strict discipline, smart investing, and treating every dollar as a soldier that goes out to bring back more.

Chat with Kevin when you're...

  • Working on shark tank investor or dragons' den
  • Making a hard decision and need a direct, honest perspective
  • Setting a bold long-term vision and pressure-testing whether it holds up
  • Figuring out what to cut and what to double down on
  • Preparing for a high-stakes pitch, presentation, or conversation

Try asking

Sample questions

  • "How would you think through whether this risk is worth taking?"
  • "What's your first move when money feels tight?"
  • "What would you tell me if I were about to give up on this?"
  • "What's a mistake you made early on that you'd want me to avoid?"