Home / Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing) / Kevin O'Leary: The Game-Changing Habits That Set Top Entrepreneurs Apart | Entrepreneurship | YAPLive | E376

Kevin O'Leary: The Game-Changing Habits That Set Top Entrepreneurs Apart | Entrepreneurship | YAPLive | E376

Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing)

Dec 01, 2025

1h 16m

Description

Now on Spotify video! Starting a business is brutally hard, and Kevin O’Leary is a living example of that truth. Despite early failures, he went on to build and sell The Learning Company for $4.2 billion in one of the most competitive tech markets in history. As an investor in over 50 companies,...

Now on Spotify video!

Starting a business is brutally hard, and Kevin O’Leary is a living example of that truth. Despite early failures, he went on to build and sell The Learning Company for $4.2 billion in one of the most competitive tech markets in history. As an investor in over 50 companies, he can spot true entrepreneurs from a mile away and knows exactly what it takes to stay in the game. In this episode, Kevin exposes the harsh realities of entrepreneurship and shares the essential traits, skills, and strategies that separate successful founders from those who fail.

In this episode, Hala and Kevin will discuss:

(00:00) His Early Life and Path to Entrepreneurship

(06:04) Kevin’s Rules for Scaling Beyond $5M

(14:05) Lessons From a $4.2B Business Exit

(22:37) Transitioning From Operator to Investor

(27:42) Managing the Highs and Lows in Business

(32:32) What Makes a Successful Entrepreneur?

(36:51) Rating the Traits of True Entrepreneurs

(46:29) High-Performance Habits for Entrepreneurs

(01:01:16) The Power of Creator Entrepreneurship

Kevin O’Leary is a serial entrepreneur, venture capitalist, and television personality, best known as “Mr. Wonderful” on ABC’s Shark Tank. He co-founded and built The Learning Company, which was later sold for $4.2 billion, making it one of the largest tech exits of its time. Kevin is also the Chairman of O’Leary Ventures, as well as a bestselling author, global speaker, and advocate for entrepreneurship and financial literacy.

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