This story appears in the November 2025 issue of Entrepreneur. Subscribe »
Robert Herjavec quit Shark Tank after its first year.
Technically speaking, he quit Dragons’ Den — which was the show’s name in Canada, where it appeared in 2006 before expanding to the U.S. in 2009. In the beginning, the show seemed destined to fail. The producers had low expectations. And the premise made no sense: Very serious investors were supposed to put real money into…random little products?
“I thought, What am I doing here?” Herjavec recalls. Before this, Herjavec’s entire career had been in enterprise sales. He’d founded a cybersecurity company, Herjavec Group, around 2003. Humble at first, it would go on to expand from a single employee to about 1,000 people globally, and has an enterprise value of about $1 billion today. He describes himself as “very, very technical.” His background is serious. “Then I do the show, and people are pitching me socks,” he says. “What do I know about socks?”
So Herjavec quit. Let someone else invest in socks, he figured.
Then Kevin O’Leary took him out for dinner. O’Leary was also on that inaugural season of Dragons’ Den, long before anyone called him Mr. Wonderful.
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“There are two things I’m gonna say to you,” O’Leary told Herjavec. “Let me start with saying you’re an idiot. This show is going to be huge. The second thing is: You have to let go of the subject matter. You have to focus on the execution of the dream.”
Here’s what O’Leary was saying: Shark Tank is not a show about investing in things like socks. It’s a show about aspiring entrepreneurs’ dreams. Therefore, the sharks (or dragons) aren’t there to be “serious investors” in a traditional sense. They’re there to help test people’s dreams against reality, and to show what it truly takes to execute those dreams.
“I thought about that,” Herjavec says. “I realized that, in starting a business, there are certain execution steps that you do. You have to have an idea, you have to sell, you have to market, you have to raise money. Like, none of those things are related necessarily to the subject matter.”
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