{"id":225241,"date":"2026-06-03T11:02:00","date_gmt":"2026-06-03T15:02:00","guid":{"rendered":"https:\/\/testing.news-you-need.com\/index.php\/2026\/06\/03\/robert-herjavec-on-ai-cybersecurity-and-dreaming-bigger\/"},"modified":"2026-06-03T11:10:09","modified_gmt":"2026-06-03T15:10:09","slug":"robert-herjavec-on-ai-cybersecurity-and-dreaming-bigger","status":"publish","type":"post","link":"https:\/\/testing.news-you-need.com\/index.php\/2026\/06\/03\/robert-herjavec-on-ai-cybersecurity-and-dreaming-bigger\/","title":{"rendered":"Robert Herjavec on AI, Cybersecurity and Dreaming Bigger"},"content":{"rendered":"

Robert Herjavec on AI, Cybersecurity and Dreaming Bigger<\/a><\/p>\n

https:\/\/www.success.com\/dream-bigger-robert-herjavec<\/a><\/p>\n

Publish Date: 2026-06-03 11:02:00<\/a><\/p>\n

Source Domain: www.success.com<\/a><\/p>\n

Author: <\/a><\/p>\n

Using an unordered list, summarize the following article with between 4 and 8 key points. Robert Herjavec was about to make a $100 million mistake. He\u2019d 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.\u201cI walked away from that conversation thinking, ‘What am I doing?\u2018\u201d 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.\u201cWhat I learned out of that was: I wish I would\u2019ve approached every situation with an expectation to win,\u201d Herjavec says. \u201cI approached every situation not wanting to lose. Whereas somebody like Mark says, \u2018Every time I get into something, I expect it\u2019s going to be huge, and I\u2019m going to win.’ I wanted to win, but I wanted a backstop in case I lost.\u201dThat mindset shift\u2014from playing defense to offense\u2014took decades to develop. And it began in circumstances about as far from Silicon Valley as possible.The Accidental TechnologistHerjavec 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\u2019t part of the conversation. \u201cI never saw technology as a future for me until I was about 20,\u201d he recalls.The spark came unexpectedly. Living with a roommate who had a master\u2019s degree in math and computer science, Herjavec thought the field was \u201csuper boring\u201d and computer people were \u201csuper geeky.\u201d 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\u2019t 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. \u201cI remember so clearly somebody explaining mainframe computing to me, and these images went off in my head and I could see it,\u201d he says. \u201cWith 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.\u201dThat moment of clarity shaped everything that followed. But Herjavec\u2019s lack of technical training became his greatest asset. \u201cBecause I didn\u2019t 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,\u201d he explains. \u201cA 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.\u201dLessons from the Sales TrenchesThose early years selling computer equipment taught Herjavec the principles that still guide him today. The first: Obsolescence is guaranteed. \u201cIf you don\u2019t eat your own, somebody will eat your lunch for you,\u201d he says. \u201cTechnology by nature has obsolescence built in. If you\u2019re not getting better, increasing value, lowering price, something, you\u2019re going to go out of business.\u201dThe second lesson was equally important: Great marketing beats good technology. \u201cTechnology doesn\u2019t typically sell itself, and there\u2019s a lot of bad technology that dominates markets because it has better marketing,\u201d Herjavec notes. His go-to example is DOS, the first PC operating system. \u201cIt 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.\u201dA chance encounter at a computer trade show proved pivotal to Herjavec\u2019s 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.\u201cI\u2019m like, \u2018Oh my god, it\u2019s an aha moment again. I\u2019ve seen the future,’\u201d he recalls. He flew home immediately, told his boss they should abandon their current business model and pursue networking. His boss refused. \u201cHe says, \u2018Nope, it\u2019s not what made us successful. We\u2019re going to stick to our guns.’\u201dHerjavec left to start his own networking company. He built it up and sold it to AT&T. His former employer went out of business. \u201cThat was kind of driving home the point that obsolescence more or less is guaranteed in the computer business,\u201d he says.Building a Cybersecurity EmpireBefore 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.\u201cMy vision was, \u2018You\u2019re going to be connected to every single house in the world, but nobody is locking their door,’\u201d he explains. \u201cAnd so I thought there must be a great business in helping companies secure it.\u201dHis 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. \u201cI remember thinking, \u2018He\u2019s nuts. There\u2019s no way every business will have one,’\u201d he says. \u201cBut it turns out, we were both wrong. I was wrong that every business wouldn\u2019t 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\u2019t dream big enough as to how big it could have been.\u201dThe AI RevolutionHaving witnessed the rise of the internet, mobile computing and cloud technology, Herjavec sees artificial intelligence as the next seismic shift\u2014and perhaps the most consequential. \u201cI think every company is an AI company,\u201d he says frankly.He draws the parallel to how we think about the internet today. \u201cIn the \u201890s and early 2000s, we were all talking about, \u2018Is every company an internet company?’ Now nobody thinks of themselves as an internet company. It just is. The internet has become electricity. I don\u2019t notice it until it\u2019s not working,\u201d he explains. \u201cThat\u2019s what AI is going to become. AI will become electricity.\u201dFrom 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. \u201cAI has given you an element of speed and scale to a hack that wasn\u2019t possible before,\u201d he says. \u201cI can initiate an attack with an AI, and AI can tell me on its own which part\u2019s working, which part is not. There\u2019s an automation to it that scares me.\u201dHis concerns extend beyond corporate breaches to critical infrastructure. \u201cI don\u2019t worry about a bank threat or hack. I mean, that\u2019s inconvenient, but I worry about an electrical grid. I worry about a subway system. I worry about air traffic control.\u201dYet Herjavec remains optimistic. \u201cAI allows you to do the same things with the defenses,\u201d he says. \u201cMy ability to defend my environment with AI is way better than it used to be.\u201dFor business owners feeling overwhelmed, his advice is straightforward: Educate yourself. \u201cFear 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,\u201d he says. \u201cWe have the greatest possible university in the world that\u2019s free and accessible to everybody, and it\u2019s called YouTube.\u201dAI 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.\u201cNo longer is the software or the program your barrier to entry. It\u2019s \u2018What does the business actually provide?’\u201d Herjavec explains. \u201cIs it the relationship? Is it the value? Is it solving a problem that requires a high level of touch?\u201dThis represents a profound shift. \u201cI couldn\u2019t start a software company five years ago because I don\u2019t have a programming background,\u201d he says. \u201cToday, I could start a software program as well as anybody else.\u201dEvolution of a LeaderAfter 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.\u201cEvery idea has to eventually pivot. There\u2019s no such thing as a business plan that stays true to its course over changing environments,\u201d he says. \u201cSurvivability is based on adaptation, not on size or skill set.\u201dHis own leadership style has evolved dramatically. Early in his career, Herjavec was plagued by panic and a desperate fear of losing everything\u2014a holdover from his immigrant upbringing. Growing up poor in a small Croatian village with dirt floors and an outhouse didn\u2019t feel like poverty until his family arrived in Canada. \u201cI didn\u2019t know we were poor until we came to Canada,\u201d he says. \u201cPoverty is a learned response, and I learned we were poor.\u201dThat fear of returning to poverty shaped his early approach to business. \u201cI remember when I was 12 years old, I just didn\u2019t want to be poor,\u201d he says. \u201cIt took me a long time to be able to not feel that element of panic and fear.\u201dThe biggest shift has been learning to build leaders rather than trying to do everything himself. \u201cIf you want to build a $10 million company, you can be the best sales guy, the best accounting guy, the best everything,\u201d he says. \u201cYou want to build a billion-dollar company? Your No. 1 skill has to be the ability to create other leaders. If you\u2019re the best sales guy in the company, you\u2019re always limiting the size you\u2019re going to be.\u201dRules for the AI EraRobert Herjavec\u2019s advice for business owners navigating technological disruption:1. Develop native knowledge. You don\u2019t have to become a technology expert, but you have to have some element of native knowledge. Fear is caused by uncertainty\u2014the 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\u2014administration, accounting, finance, customer service\u2014should 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\u2019s 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\u2019t approach situations not wanting to lose. Approach every situation with an expectation to win.Beyond the Bucket ListDespite his wealth and accomplishments, Herjavec doesn\u2019t dwell on legacy\u2014at least not the kind most people imagine. \u201cI think we\u2019re all sands in time, and I don\u2019t care what people think of me,\u201d he says. \u201cI just want my kids to remember me as full of joy and happiness.\u201dWhat still drives him isn\u2019t checking items off a list. \u201cEverything I\u2019ve wanted to do, I\u2019ve played at or done. I wanted to race cars. I\u2019ve raced cars. I wanted to scuba dive. I\u2019ve scuba dived,\u201d he says. \u201cWhat I think about now is where do I have the opportunity to really create scale and lasting value? I\u2019m really into disruption on a larger scale than necessarily just building something.\u201dAnd for anyone building something today, Herjavec\u2019s advice echoes that hard-won wisdom from his dinner with Mark Cuban: \u201cDream bigger.\u201dPhotography by Lindy Lin.This article was first published in the July\/August 2026 issue of SUCCESS Magazine. Get your copy here.
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