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Episode 113 — Kevin O’Leary — The Entrepreneurial Journey: Inside the Mind of Mr. Wonderful

"The whole idea of being an entrepreneur is to get to a place in your life where you do not have to pick up the phone when it rings. Only you have control over your destiny.” - Kevin O'Leary

  • What hard lessons and life philosophies shaped Kevin O'Leary into the man he is today?
  • What common denominator allows women to excel in business?
  • What happens the day after selling a business for $4 billion?
  • How did an emotionally charged interview with a reporter lead to Kevin's first role on Dragons’ Den?
  • When considering a new investment, what does Mr. Wonderful look for and what does he avoid?
  • How does Kevin deal with critics?
  • Can entitlement ruin your child's future?

Hold The Phone

To Kevin O'Leary, entrepreneurship is not a destination. It's a journey. The path is long and hard, and it's not for everyone. But those who decide to take on the challenge can win the ultimate prize: freedom, funded, beholden only to personal desire and only taking the meeting — or picking up the phone — when it is of interest. 

Love him or hate him, the wildly successful businessman best known as Mr. Wonderful is a straight shooter who has captured the eyes — and hearts — of millions. But it’s not the simple pursuit of cash that drives this multimillionaire. Passion. Freedom. Meaningful use of time. These are the underlying drivers of the success of the world-renowned entrepreneur, investor, four-time Emmy winner, and best-selling author.

Today Kevin reminisces on lessons he's learned over the years and how they paved the path to Shark Tank, reveals the investment strategy passed down from his mother, and outlines how to tell a solid investment from a bad one.

Drown Them Out

"If it's not relevant to my goals — to achieve success for my customers, my business, my investors, my objective — if you don't like it, I don't care." - Kevin O'Leary

Critics are just noise. With each tier of success comes a fresh batch of naysayers, adding to the growing cacophony of judgments. To push ahead, be effective, and change the game, develop a filter that blocks the sound. Protect your energy and vision. Don't let criticism stall your momentum and waste your time. 

Key takeaways:

  • Connect to your why. Passion drives success. Great entrepreneurs are motivated not by the greed of money, but by the passion of the project.
  • Worry less. Focus only on what is in your control. Learn from mistakes — from missed cases to investments — and let the rest go.
  • Leadership is an act of service, and the firm owner comes last. Kevin's hierarchy for a successful business: clients, staff, investors, and owners.

Links and Resources


Michael Mogill, Crisp, and Kevin O'Leary