Robert Herjavec: The Shark Tank investor on how to stay ahead of the current

Robert Herjavec has a confession to make.

"I don’t think I’ve built the great company of my potential," he tells The CEO Magazine.

Coming from someone who’s spent more than three decades building and selling technology businesses, it’s a surprising admission to say the least.

Herjavec remains deeply involved in cybersecurity. He’s invested across emerging areas of technology and after roughly 23 years on television, he’s become one of the world’s most recognizable investors.

By largely every measure, Herjavec has already made it. He’s just not entirely convinced he’s finished.

"In the back of my mind, like most entrepreneurs, I always think I probably sold my company too soon," Herjavec says.

"I mean, I’m not complaining – it was a great exit. But I always think, what more could I do? How could I change the landscape that I’m in?"

Something worth building

The questions seem to be driving much of what comes next. At this point, it’s clear that Herjavec isn’t looking for another business for the sake of having one. Now, the opportunity has to be big enough – and interesting enough – to pull him back in.

Right now, there’s plenty vying for his attention. AI is transforming what and how quickly companies can build and realistically, who can compete. Cybersecurity is changing alongside it. And technology that would have once required a huge amount of capital and specialist expertise is suddenly available to much smaller players.

Herjavec loves the dynamism.

"I’m super bullish," he says with a grin. "There is so much opportunity in so many areas right now."

On that note, he says he’s already itching to get back into the game himself. And his next idea is coming from a world he knows extremely well – cybersecurity.

Herjavec still owns a significant part of the cybersecurity company he founded in 2003 and remains on its board. But after years working at the enterprise end of the market, he’s been thinking about who isn’t getting the same level of protection.

"We just did a lot of research and are about to launch a company in the consumer space," he reveals.

Consumers are dealing with identity theft, hacking and malware. Now AI has added deepfakes and other convincing ways to deceive people. Herjavec knows the technology to fight those threats exists; the problem is the average person doesn’t necessarily have access to it.

"We used to protect some of the largest governments and enterprises in the world," he says. "Why can't the power of that kind of technology be brought down at a cost-effective rate to the average consumer?"

There’s an obvious catch though, he says. People want to be secure, but they can’t necessarily pay enterprise prices to make it happen.

"Consumers care about security, but only to a point of how much they’re willing to pay for it," he acknowledges.

Herjavec isn’t giving away much more than that yet. But the market is there and the problem is only worsening, so there’s room to do something differently.

"What motivates me now is doing big things, changing the landscape and really building a sustainable company," he says.

"Every entrepreneur and founder feels a certain sense of pride in their business; that they built it and the team brought it to this next level. It’s such an incredible feeling, and I want to do it again."

Moving at speed

It’s also not lost on Herjavec that what businesses need to succeed in today’s landscape is vastly different from what was required even a few years ago.

"During the COVID-19 pandemic, I used to say that business moves at COVID speed, but now businesses are moving at AI speed," he says.

The problem is, many of today’s businesses aren’t designed for that pace.

CEOs have been trained to plan. There are annual budgets, three-year strategies, approval processes and boards to answer to. Big decisions are supposed to be considered from every angle before anyone makes a move.

AI doesn’t play well with that kind of caution.

"Traditional business is the general standing on a hill with a great plan," Herjavec says. "AI is hand-to-hand combat in an apartment building in some city, and you have no idea where you are, but you just have to react very quickly."

Indeed, leaders must get comfortable making decisions while the ground is still shifting as there’s no shortage of companies spending on AI. In fact, Herjavec says it’s increasingly taking budget away from traditional software and infrastructure.

But in the rush to keep up, he warns there’s something leaders are missing.

"Business leaders aren’t watching the pace of change closely enough," Herjavec says.

"It’s not enough to spend money on AI. You have to start seeing tangible results in three-to-six months. And if you’re not, then don’t be afraid to pivot."

Of course, that’s easier said than done when a company has decades of legacy systems and data sitting behind it.

Herjavec saw that problem up close through his involvement with the AI and data company Lovelytics, where he served on the board before its sale to CDW.

"The interesting thing is something like 70 percent of AI projects after two years are still not completed because it's really complicated and people find it hard," he points out.

"Part of the challenge is so many enterprises have data in such disparate areas, they really don't know what to do with it.

"And most AI projects are really big data projects. So getting all that data together from all those different systems is really hard.

"At the same time, a lot of large enterprises have legacy data. Some of our banking customers are using applications that were written 30 years ago. So how do you integrate that data with new AI?"

Meanwhile, AI keeps getting better.

"As the projects get more complex, they’re also getting simplified. Then new data sources are being brought in," he says.

"So it’s this continuous cycle."

The great equalizer

For all of the headaches AI is creating for established businesses, Herjavec sees a massive upside.

"I’ve always believed that technology is one of the greatest democratic forces of equalization in the world," he says.

It’s one of the few places, Herjavec argues, where a person can enter without legacy relationships or infrastructure and still have a genuine shot.

AI is pushing that further. Herjavec shares how he recently found himself opening a trust account for one of his children and trying to calculate what an investment index fund might be worth after 18 years.

He started working it out when it struck him – why was he even bothering?

"I was like, ‘What am I doing?’ And I just asked Claude, who did it for me," he says.

It’s a small example of what is happening everywhere these days. People suddenly have access to capabilities they either didn’t have before or would have needed someone else to provide.

Herjavec jokes that the skills he once prided himself on have lost some of their shine.

"I don’t think I’ll ever do a PowerPoint presentation again," he muses. "I was great at PowerPoint. I was great at Excel. Now, nobody cares."

But if everyone has access to the same tools, simply using them isn’t going to set anyone apart. Something better must be done with them.

So if a small company were to take on a giant, Herjavec believes it’s entirely possible and one advantage matters more than almost anything else.

"Move faster," he advises. "The smaller you are, the faster you need to move and the less options you need to explore."

A large organization has good reasons to move carefully. There are boards, shareholders, layers of leadership and risks to manage. A startup has another risk entirely.

"Your biggest risk as a small player is survival," Herjavec stresses. "So you have to pick and execute better and faster – fortune favors the bold."

Betting on obsession

After decades of looking at businesses, Herjavec still believes he’s good at spotting what might be coming two or three years down the road.

Part of that comes from understanding technology. Part comes from talking to customers. And part, he says, comes from being scrappy.

"I’ve built multiple companies with no money," he says. "I think most founders take on too much equity or too much money too early. They give up way too much equity for a big valuation."

Having less forces entrepreneurs to work things out, Herjavec explains. They have to know whether customers actually want what they’re selling because there isn’t an endless stream of money to keep going if they don’t.

"The challenge when you have no money is that you have limited opportunity, and you have to make it work," he adds.

"When you have more money or more capital, you tend to have more opportunity – you start to drown in opportunity."

Now in the latter category himself, Herjavec says the difference is in how he assesses those opportunities.

"I still believe it's all about the execution, so I’m more focused now, in terms of risk, on the entrepreneur," he says.

"How disciplined are they? How important is this business to them? Because I think a great entrepreneur can take a crappy business and they can pivot. A bad entrepreneur can ruin a good business."

And there’s one word that signals ‘red flag’ more than any other, and that’s passion.

"We don’t care about your passion. We care about your obsession," Herjavec stresses.

"Everybody is passionate. Everybody’s passionate about something for a little while, a day or two, a couple of weeks, a couple of months. But when it gets hard, how obsessed are you with it and how committed are you to it?"

Reading the tank

Herjavec has now spent around two decades watching entrepreneurs make that case on television. He first stepped into the investor’s chair on Canada’s Dragons’ Den, alongside Kevin O’Leary, before joining Shark Tank in the United States.

At the time, Herjavec was still very much a cybersecurity executive, competing against tech giants like IBM. Competitors, as he recalls, had a field day when they saw him on the show.

"They’d say, ‘Oh Robert’s company is great. He’s super smart at cyber, but he’s gone Hollywood,’" he says, admitting it got under his skin more than he would’ve liked.

"I was a serious business guy and was actually going to quit after the first season."

Herjavec was on his way to see the network president and tell him that television just wasn’t for him when O’Leary intervened and took him to dinner.

"Kevin said to me, ‘What are you doing? You have no idea how big this show is going to be. It’s going to be huge, and it’ll help your business. You’ll help a lot of people. It’ll change your life.’

"He was so convinced. I didn’t necessarily believe him, but I believed in his conviction. So I gave it another season and after that, the show just blew up. He was right."

Years later, Herjavec, now the show’s Emmy Award-winning executive producer and lead ‘Shark’ sees its impact as much bigger than a hit TV show. Shark Tank has helped make business feel accessible.

"I never met anybody who owned a business until I was like 27 or 28," he says. "My dad’s a blue-collar guy. My mom’s a receptionist. We weren’t hanging in those circles."

Now people who grow up without entrepreneurs around the dinner table can watch them negotiate deals from their couch.

"Every Wednesday, you get five self-made business people speaking business in your living room," he says. "It’s so powerful."

It’s given Herjavec a front-row seat to how entrepreneurship itself keeps changing.

"Shark Tank is a mirror of what’s happening in America," he points out.

The show began around the global financial crisis, when founders were struggling to get bank loans. Then came the crowdfunding years and now, the game-changer is AI.

"It doesn’t really matter to me how big your business is today," Herjavec says. "It matters to me what industry you are in, how you can disrupt it and how you’re using AI in some kind of proprietary way."

Again, simply using AI is not enough.

"What people don’t realize is the disadvantage of AI is that it’s accessible to everybody," he says. "While you may be good at it, the person next to you can be just as good at it very quickly.

"So we look for people that are using some element of proprietary systems or going to legacy systems and applying technology to them. And, of course, the power of Shark Tank is consumer brands – if you can hit it off with consumers, the product can really take off."

From fear to freedom

What makes Herjavec’s next act different isn’t solely related to technology and the current business landscape or even his fame or fortune. Rather it’s the absence of something that powered much of everything that has come before this point – fear.

"When I started out, I wasn’t running toward something; I was running away from poverty," he says. "It’s similar, but it’s different. Today, I run toward opportunity."

He’s also at a place where he can see value in his early desperation. It generated an urgency that forced action. It also made failure feel utterly unacceptable.

"Desperation is great when you’re starting out," Herjavec says. "But it needs to be balanced because desperate people can do stupid things. To run a great business, you have to balance desperation, aggression, execution, planning, all of it.

"I’m much more balanced today than I used to be."

Herjavec says much of that balance has come from gratitude.

"I’ve been so fortunate to achieve a level of success I couldn’t have imagined," he says.

The sale of his first company BRAK Systems for US$30 million in 2000, in particular, gave him a level of financial success he had never imagined possible. Each achievement since has only added to something that’s been a bit slower to arrive for Herjavec: confidence.

Ironically, it’s something he remembers discussing recently with fellow ‘Shark’ Mark Cuban.

"He is utterly confident – from the moment he was born," he says with a laugh. "It took me a long time to develop that. But success is the greatest booster of confidence you can have."

With eight-year-old twins, Herjavec shares that his days look different than they once did. Instead of rushing to another boardroom to close a deal after our interview, he’s heading to a school event.

"Being there for them is my number one priority in life, and I’m grateful to get to do it," he says. "That’s what money buys you – freedom to do the things that are really important to you. That is the dream."

Maybe that’s why the great company of Herjavec’s potential can remain, in his mind at least, somewhere ahead of him. Success has given him the luxury of no longer needing to build it.

But confidence has given him a more compelling reason to try.

"You realize that everything is possible," he concludes. "Somebody else is doing it. Why not you?"