Mark Cuban's Tips on Selling Businesses Helped Robert Herjavec Make a Fortune on His Cybersecurity Deal

With an estimated net worth of £221.85 million ($300 million), Shark Tank star Robert Herjavec is among the top entrepreneurs and cybersecurity experts in the US.

Herjavec built his fortune by founding top cybersecurity companies and selling them to leading technology corporations and private equity firms. His first breakthrough came in 2000 when he sold Brak Systems, an internet security software integrator, to AT&T Canada for over £22.18 million ($30 million).

His strong business acumen helped him build and sell more companies to tech giants, including Nokia. He also frequently advises governments and leading enterprises on enhancing cybersecurity strategies. In March, Herjavec was named the executive director of global strategy for Zetaris, an AI company aggressively expanding in the US and global markets.

'Zetaris is an absolute game changer set to revolutionise the way the world leverages real-time data for AI,' Herjavec said in a press release. 'I see a lot of companies with great ideas, but Zetaris is set to become a household name and challenge billion-dollar companies,' he said, adding that he has 'personally invested' in the company, whose leading technologies facilitate rapid success in AI projects.

In his 35-year entrepreneurial journey, Herjavec actively invested in diverse businesses, evidenced by his £11.83 million ($16 million) investments across 57 Shark Tank deals. He is also an accomplished author with three published books. Herjavec's journey includes many hard lessons and setbacks, which he overcame with invaluable advice he picked up from fellow investors and entrepreneurs like billionaire Mark Cuban.

Cuban Helped Herjavec Sell His Firm For an 'Extraordinary Amount of Money'

In 2021, Herjavec was mulling the sale of his cybersecurity company for almost £73.95 million ($100 million). At the time, he had shared his plans with Cuban over lunch, who advised that an entrepreneur should consider selling his business only if three of the following reasons pop up:

Cuban told Herjavec that business owners should sell their businesses if they can't run them anymore or don't want to. Secondly, it could be a good decision to divest if the business owner doesn't see a clear path to scale and growth, which could imply the business has already peaked. Lastly, selling a business could make sense only if the money from the sale is going to 'fundamentally' change your life.

After discussing the 'amazing offer' for his cybersecurity firm with Cuban, Herjavec understood that selling his firm would bring massive amounts of money. However, he was already a 'happy guy,' and the sales wouldn't fundamentally change that.

Herjavec was also confident he had it in him to keep running the company and scaling it to new heights. These factors led him to change his mind and decide not to sell the company at that time, which proved to be a financially wise decision.

'I didn't sell, and then four years later, I sold for an extraordinary amount of money,' Herjavec said about selling and the current exit landscape for Inc.'s Shark Tank series for Small Business Week.

He explained that the original $100 million offer was 'considerably less' than the final sale price.

'To this day, Mark always says, "I never got a commission check,"' Herjavec jokingly said.