Speaking on “the Iced Coffee Hour” podcast in 2024, O’Leary said many people are better suited to careers where they provide expertise without carrying the full weight of running a company.
“Almost half the classes I teach become consultants because they don’t have the guts,” he said. “They don’t have the ability to make a decision.”
Getting Fired Changed Everything
O’Leary believes entrepreneurs are often shaped by defining moments rather than born with a business plan. For him, that moment came on the very first day of his first job.
“I got fired the first day I ever had a job,” he recalled. “I realized that that was just somebody else had power over me. I couldn’t even deal with that concept.”
Looking back, O’Leary said on the podcast that the experience taught him that working for someone else wasn’t for him. It pushed him toward building businesses instead of climbing a traditional career ladder.
He also pushed back against the idea that people should start businesses simply to become wealthy.
“If you’re hungry for money, I guarantee you’ll fail 100%,” he said. “If you start into entrepreneurship… and all you care about is getting rich, you will fail.”
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Even Family Isn’t Exempt
O’Leary also explained why he believes business leaders sometimes have to make uncomfortable decisions, even when family members are involved.
“When you start a business, you’re no longer number one,” he said. Customers come first, followed by employees, shareholders and lenders. The business owner, he argued, is ultimately responsible to everyone else.
That’s why he believes personal relationships can’t come before the company.
“If you use nepotism in your business and they don’t perform, that’s hurting all of the rest of the stack,” O’Leary said on the podcast. “So, if you have your mother and she can’t perform… you’ve got to take her out behind the barn, shoot her.”
He quickly clarified that the comment wasn’t about family itself, but about protecting the business. “It’s the business that matters the most,” he said. “If they’re not team members, they’re cancer. Surgery immediately. Gone.”
For O’Leary, difficult personnel decisions are part of leadership. Compassion has its place, he said, but a business ultimately has one objective. “You either make money or you lose money,” he said on the podcast. “The DNA of a business is actually to make money.”
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