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.
What happened next was nothing short of transformative. “I remember so clearly somebody explaining mainframe computing to me, and these images went off in my head and I could see it,” he says. “With no technology background, nothing, people are explaining this stuff to me, and I see these images in my head just connecting. I could see the mainframe. I could see the connector. It just spoke to me.”
That moment of clarity shaped everything that followed. But Herjavec’s lack of technical training became his greatest asset. “Because I didn’t have a technology background, my view on it was [that] I was never enamored with the technology. I was enamored with what the technology could do,” he explains. “A lot of people that I competed with in business were engineers, were technologists, so they would love the technology for its sake. I never cared enough about the technology unless it added value to the end user.”
Lessons from the Sales Trenches
Those early years selling computer equipment taught Herjavec the principles that still guide him today. The first: Obsolescence is guaranteed. “If you don’t eat your own, somebody will eat your lunch for you,” he says. “Technology by nature has obsolescence built in. If you’re not getting better, increasing value, lowering price, something, you’re going to go out of business.”
The second lesson was equally important: Great marketing beats good technology. “Technology doesn’t typically sell itself, and there’s a lot of bad technology that dominates markets because it has better marketing,” Herjavec notes. His go-to example is DOS, the first PC operating system. “It was not the best operating system. It was simply the most distributed and the best marketed system. So never underestimate the value of great marketing versus good technology.”
A chance encounter at a computer trade show proved pivotal to Herjavec’s career. Seated next to Ethernet inventor Robert Metcalfe, Herjavec listened as Metcalf explained how networking would allow computers to share printers through a hub rather than requiring a physical connection to each device.
“I’m like, ‘Oh my god, it’s an aha moment again. I’ve seen the future,'” he recalls. He flew home immediately, told his boss they should abandon their current business model and pursue networking. His boss refused. “He says, ‘Nope, it’s not what made us successful. We’re going to stick to our guns.'”
Herjavec left to start his own networking company. He built it up and sold it to AT&T. His former employer went out of business. “That was kind of driving home the point that obsolescence more or less is guaranteed in the computer business,” he says.
Building a Cybersecurity Empire
Before founding Herjavec Group in 2003, Herjavec had already built and sold BRAK Systems, an early company selling VPN and multisite firewalls, to AT&T for more than $30 million in 1999. He could see that the internet was exploding and that businesses would eventually need protection.
“My vision was, ‘You’re going to be connected to every single house in the world, but nobody is locking their door,'” he explains. “And so I thought there must be a great business in helping companies secure it.”
His only regret was not thinking big enough. He recalls having dinner with Gil Shwed, the founder of cybersecurity firm Check Point, who predicted that every business in the world would have a firewall one day. “I remember thinking, ‘He’s nuts. There’s no way every business will have one,'” he says. “But it turns out, we were both wrong. I was wrong that every business wouldn’t have one, and he was wrong that every business would have only one. We had clients at Herjavec Group that had 500; 3,000; 5,000 firewalls. I saw the trend. But I didn’t dream big enough as to how big it could have been.”
The AI Revolution
Having witnessed the rise of the internet, mobile computing and cloud technology, Herjavec sees artificial intelligence as the next seismic shift—and perhaps the most consequential. “I think every company is an AI company,” he says frankly.
He draws the parallel to how we think about the internet today. “In the ‘90s and early 2000s, we were all talking about, ‘Is every company an internet company?' Now nobody thinks of themselves as an internet company. It just is. The internet has become electricity. I don’t notice it until it’s not working,” he explains. “That’s what AI is going to become. AI will become electricity.”
From a cybersecurity perspective, AI presents both unprecedented threats and powerful new defenses. What keeps Herjavec up at night, though, is the automation of hacking that AI allows. “AI has given you an element of speed and scale to a hack that wasn’t possible before,” he says. “I can initiate an attack with an AI, and AI can tell me on its own which part’s working, which part is not. There’s an automation to it that scares me.”
His concerns extend beyond corporate breaches to critical infrastructure. “I don’t worry about a bank threat or hack. I mean, that’s inconvenient, but I worry about an electrical grid. I worry about a subway system. I worry about air traffic control.”
Yet Herjavec remains optimistic. “AI allows you to do the same things with the defenses,” he says. “My ability to defend my environment with AI is way better than it used to be.”
For business owners feeling overwhelmed, his advice is straightforward: Educate yourself. “Fear is caused by uncertainty, and fear is caused by doubt. And the only way to overcome that fear is to get rid of the doubt,” he says. “We have the greatest possible university in the world that’s free and accessible to everybody, and it’s called YouTube.”
AI is fundamentally changing what it means to build a technology company. In the past, proprietary software was the barrier to entry. Today, anyone can create applications without programming knowledge.
“No longer is the software or the program your barrier to entry. It’s ‘What does the business actually provide?'” Herjavec explains. “Is it the relationship? Is it the value? Is it solving a problem that requires a high level of touch?”
This represents a profound shift. “I couldn’t start a software company five years ago because I don’t have a programming background,” he says. “Today, I could start a software program as well as anybody else.”
Evolution of a Leader
After 18 years on Shark Tank and decades of building companies, Herjavec has learned that ideas are cheap, but execution is everything. When evaluating entrepreneurs, whether on TV or in his own investments, he looks for adaptability above all else.
“Every idea has to eventually pivot. There’s no such thing as a business plan that stays true to its course over changing environments,” he says. “Survivability is based on adaptation, not on size or skill set.”
His own leadership style has evolved dramatically. Early in his career, Herjavec was plagued by panic and a desperate fear of losing everything—a holdover from his immigrant upbringing. Growing up poor in a small Croatian village with dirt floors and an outhouse didn’t feel like poverty until his family arrived in Canada. “I didn’t know we were poor until we came to Canada,” he says. “Poverty is a learned response, and I learned we were poor.”
That fear of returning to poverty shaped his early approach to business. “I remember when I was 12 years old, I just didn’t want to be poor,” he says. “It took me a long time to be able to not feel that element of panic and fear.”
The biggest shift has been learning to build leaders rather than trying to do everything himself. “If you want to build a $10 million company, you can be the best sales guy, the best accounting guy, the best everything,” he says. “You want to build a billion-dollar company? Your No. 1 skill has to be the ability to create other leaders. If you’re the best sales guy in the company, you’re always limiting the size you’re going to be.”
Rules for the AI Era
Robert Herjavec’s advice for business owners navigating technological disruption:
1. Develop native knowledge. You don’t have to become a technology expert, but you have to have some element of native knowledge. Fear is caused by uncertainty—the only way to overcome it is to get rid of the doubt.
2. Automate the repetitive. Anything in your business that has a repetitive task—administration, accounting, finance, customer service—should be evaluated for AI automation.
3. Focus on human value. Software is no longer your barrier to entry. Focus on what makes your business different in front of the customer.
4. Act on 80%. It’s better to have 80% of the answer and act on it than wait for 100% of it in a fast-changing technology environment.
5. Expect to win. Don’t approach situations not wanting to lose. Approach every situation with an expectation to win.
Beyond the Bucket List
Despite his wealth and accomplishments, Herjavec doesn’t dwell on legacy—at least not the kind most people imagine. “I think we’re all sands in time, and I don’t care what people think of me,” he says. “I just want my kids to remember me as full of joy and happiness.”
What still drives him isn’t checking items off a list. “Everything I’ve wanted to do, I’ve played at or done. I wanted to race cars. I’ve raced cars. I wanted to scuba dive. I’ve scuba dived,” he says. “What I think about now is where do I have the opportunity to really create scale and lasting value? I’m really into disruption on a larger scale than necessarily just building something.”
And for anyone building something today, Herjavec’s advice echoes that hard-won wisdom from his dinner with Mark Cuban: “Dream bigger.”
Photography by Lindy Lin.
This article was first published in the July/August 2026 issue of SUCCESS Magazine. Get your copy here.
