Robert Herjavec on AI, Cybersecurity and Dreaming Bigger
Robert Herjavec on AI, Cybersecurity and Dreaming Bigger
https://www.success.com/dream-bigger-robert-herjavec
Publish Date: 2026-06-03 11:02:00
Source Domain: www.success.com
Robert Herjavec was about to make a $100 million mistake. He’d built a successful cybersecurity company, found a buyer and was ready to sell. Then, a dinner with fellow Shark Tank star Mark Cuban changed everything.
“I walked away from that conversation thinking, ‘What am I doing?‘” Herjavec recalls. He decided not to sell at that time. A few years later, he sold for many times the original amount.
Cuban had asked him three simple questions: Is the business dying? Do you not want to do it anymore? Will the money fundamentally change your life? When the answer to all three was no, the path forward became clear. But the real lesson went deeper than mechanics.
“What I learned out of that was: I wish I would’ve approached every situation with an expectation to win,” Herjavec says. “I approached every situation not wanting to lose. Whereas somebody like Mark says, ‘Every time I get into something, I expect it’s going to be huge, and I’m going to win.’ I wanted to win, but I wanted a backstop in case I lost.”
That mindset shift—from playing defense to offense—took decades to develop. And it began in circumstances about as far from Silicon Valley as possible.
The Accidental Technologist
Herjavec was admittedly not destined for tech. Growing up in a household with a blue-collar father and a receptionist mother after immigrating to Canada from Croatia, technology wasn’t part of the conversation. “I never saw technology as a future for me until I was about 20,” he recalls.
The spark came unexpectedly. Living with a roommate who had a master’s degree in math and computer science, Herjavec thought the field was “super boring” and computer people were “super geeky.” He wanted nothing to do with it. Then his roommate interviewed for a sales job with a former IBM Canada executive who had recently launched a startup. He didn’t get it, but Herjavec, ever the opportunist, talked his way into an interview and landed the position instead.
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