Kevin O’Leary Says ‘Salary Can Make It Very Easy to Forget About Your Dreams,’ Calls Fear of Failure an ‘Incredible Motivator’
Investor and entrepreneur Kevin O’Leary argued that the security of a steady paycheck can sometimes make people less willing to pursue entrepreneurial ambitions, saying the risk of failure can instead become a powerful motivator. O’Leary Says Fear of Failure Drives Entrepreneurs On Monday, in a post on X, O’Leary said "a salary can make it very easy to forget about your dreams," while stressing that being an employee is not inherently negative. "There’s nothing wrong with being an employee, great employees are essential to building successful businesses," he wrote. He added entrepreneurship requires "leaving that security behind and putting your own income at risk," adding that "that fear of failure becomes an incredible motivator." O’Leary also discussed the difficult periods entrepreneurs experience. "Every entrepreneur faces dark moments where they don’t know what comes next," he s...
Investor and entrepreneur Kevin O’Leary argued that the security of a steady paycheck can sometimes make people less willing to pursue entrepreneurial ambitions, saying the risk of failure can instead become a powerful motivator.
O’Leary Says Fear of Failure Drives Entrepreneurs On Monday, in a post on X, O’Leary said "a salary can make it very easy to forget about your dreams," while stressing that being an employee is not inherently negative. "There’s nothing wrong with being an employee, great employees are essential to building successful businesses," he wrote.
He added entrepreneurship requires "leaving that security behind and putting your own income at risk," adding that "that fear of failure becomes an incredible motivator." O’Leary also discussed the difficult periods entrepreneurs experience. "Every entrepreneur faces dark moments where they don’t know what comes next," he said, saying that overcoming those moments "builds the confidence and resilience that define the journey." A salary can make it very easy to forget about your dreams.
There’s nothing wrong with being an employee, great employees are essential to building successful businesses, but entrepreneurship means leaving that security behind and putting your own income at risk.
That fear of… pic.twitter.com/Vmz6e0R6ld — Kevin O'Leary aka Mr.
Wonderful (@kevinolearytv) August 17, 2026 Read Also: Kevin O'Leary Says You're Not Rich Until You Have '$5 Million Liquid,' Urges Entrepreneurs To Sell Businesses, Chase New Ventures Entrepreneurial Risk and Success Lessons Earlier, O’Leary said aspiring entrepreneurs should solve problems customers were willing to pay for, emphasizing execution, discipline and proven demand.
He also warned that entrepreneurship required risk-taking, long hours and the ability to handle uncertainty.
Billionaire entrepreneur Mark Cuban said starting a business could be ideal when someone had little to lose, based on his experience launching MicroSolutions after losing his job.
Cuban also advised entrepreneurs to save at least six months of living expenses and research their industries thoroughly.
Meanwhile, beverage entrepreneur Mike Repole, who sold Glaceau and BodyArmor to Coca-Cola Co. (NYSE: KO ) for billions of dollars, warned that entrepreneurship was far riskier than success stories often suggested.
He described the first five years as "survival years" and said entrepreneurs could face bankruptcy and repeated failures before succeeding.
Repole emphasized the need for a bold mindset, saying, "Crazy people change the world." Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published editors.
Read Also: Steve Jobs Once Said 'Everything's A Remix'—How Mark Cuban Used This Philosophy As The Cornerstone Of His Billion-Dollar Ventures Photo courtesy: Kathy Hutchins / Shutterstock.com