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’

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.

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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.

“I always think if somebody would've taken me under their wing and they were, like, a con man, I would have been a con man, right?” he told Howes. “I was just very lucky. I've just been really fortunate to have great role models who are good human beings.”

You don't need to find a billionaire celebrity to be your mentor, just someone who has achieved what you aspire to and has the time to share some insights.

Check LinkedIn, alumni groups, industry events, professional associations or even within your current workplace to find people you admire and ask them for help.

Sources

1. YouTube: Shark Tank Host: My Parents & I Escaped Communism With $20! THIS Unlocked Wealth for Me! (Feb 5, 2025)

2. The Globe and Mail: Harry Rosen launching $50-million overhaul of its retail stores over five years, by Susan Krashinsky Robertson (Mar 14, 2024)

3. CNBC: ‘Shark Tank’ star Robert Herjavec’s first big splurge cost $6 million — and it wasn’t a house, by Sarah Berger (Feb 14, 2019)

4. LinkedIn: ‘LinkedIn 2024 Most In-Demand Skills: Learn the Skills Companies Need Most, by Sonya Bessalel (Feb 8, 2024)