Robert Herjavec says 1 part-time job helped turn him into a billionaire — he learned how to spot wealthy men and ‘sell to them.’ Here’s the business legend that taught him ‘everything’

However, he also learned about another perk available to employees: A chance to learn from the company’s founder.

“The guy who owns the place called Harry Rosen … used to teach on Saturdays if you showed up an hour before the store opened,” Herjavec told Howes, adding that he jumped at the opportunity because of Rosen’s reputation. “The guy's a legend! Even then, it was like the biggest shop in Canada.”

These weekly mentorship sessions ultimately taught Herjavec everything he needed to know about running a business and selling to wealthy clients.

Spotting wealth

Harry Rosen, a high school dropout, transformed his humble men's fashion store into a business empire that generated revenues approaching $350 million in 2023. Key to his success was his focus on training employees, such as Herjavec, on how to develop and sustain a good relationship with customers.

Besides learning how to dress and inspect suit fabric, Herjavec says his mentorship sessions with Rosen taught him “how to spot someone with money” and sell to them. These lessons were so valuable that Herjavec couldn’t believe he was learning while also getting paid.

“I would have paid him to teach me,” he said. “It was great, he taught me everything.”

Herjavec used some of these skills to sell his cybersecurity company BRAK Systems to AT&T Canada for $30.2 million in 2000, as well as a majority stake in his other cybersecurity startup, Herjavec Group, which was sold to private equity firm Apax Partners in 2021.

“I'm probably one of a handful of the top cyber people in the world,” Herjavec explains to Howes. “But I'm not wealthy because of my knowledge of a task, I'm wealthy because of my knowledge of sales.”

Here’s how the art of persuasion can help your career and business, too.

The art of selling

Like Herjavec, learning to spot high-value customers — or a receptive audience for your pitch — could be your key to career success.

Whether you’re looking for a job or trying to find new clients for your business, take the time to research your market and find companies and consumers that are most likely to say yes to what you’re offering.

The ability to build and sustain a strong relationship with your clients or colleagues is also a key career skill. According to a study by LinkedIn, communication and customer service were the top two most sought-after “soft skills” by employers in 2024. Do yourself a favour and take the time to develop and hone these competencies to unlock better prospects for your career.

Finally, consider finding a mentor who can help you develop these skills. Herjavec says he was fortunate to work not only with Harry Rosen, but also Warren Avis, who started the Avis Car Rental company.