Herjavec founded BRAK Systems, a Canadian integrator of Internet security software, and sold it to AT&T Canada (now Allstream Inc.) in 2000 for $30.2 million.

[3][4][5] In 2003, he founded The Herjavec Group, now one of the largest information technology and computer security companies in Canada, with over $200 million in annual revenue.

[7] Herjavec was born in 1962 in Varaždin, SFR Yugoslavia (present-day Croatia),[8] and spent his early childhood in Zbjeg.

Herjavec has told a seminal memory of his, when he came home one day to complain to his mother that his classmates were making fun of him.

[5] Another influential episode in his youth came when a traveling salesman persuaded Herjavec's mother to buy a vacuum cleaner for $500, which was seven weeks' salary.

[5] To make a living and help support his family, Herjavec took on various minimum wage jobs in the 1980s, such as waiting tables, delivering newspapers,[10] retail sales, and debt collection.

[5] In the mid-1980s, Herjavec worked in several productions as a third assistant director, including Cain and Abel and The Return of Billy Jack.

[3] In 1990, after being fired from Logiquest,[17] he founded BRAK Systems, a Canadian integrator of Internet security software, from the basement of his home.

[21][5] In October 2017, Herjavec was phished by "email prankster" James Linton as the company CEO, inviting him to a toga party.

... Chris's appointment as CEO ensures that Cyderes will continue to innovate and lead in the cybersecurity space.” [26] Herjavec has appeared as a regular on the Canadian CBC Television series Dragons' Den (seasons 1-6, 17-18) and in the United States on ABC's version of the series, Shark Tank, where business pitches from aspiring entrepreneurs are presented to a panel of potential investors.

[citation needed] On February 24, 2015, Herjavec was announced as one of the contestants for season 20 of the American edition of Dancing with the Stars.

[32][33] "The Will to Win" is also the name of public presentations that Herjavec has given, which feature his advice to business people based on his life experiences.

[38][39][40] In June 2019, a judge ruled that Herjavec must pay his ex-wife additional sums that would bring the total she received from the marriage to $25 million.

[49] Herjavec is a major donor to the Union Gospel Mission homeless shelter in Seattle, Washington, after being turned on to the organization by his pastor, whom he consulted to deal with his depression after his marriage fell apart.

[51] Herjavec paid $7.5 million for the mansion,[4] featured on MTV Cribs, Joan Rivers's TV show How'd You Get So Rich?, and a Rolling Stones tour video.

[52] In December 2023, Herjavec was returning from his Newport Beach, California home when his private jet was met by the Canadian news media at Toronto Pearson International Airport.

[56] Herjavec competed as #007 for The Herjavec Group Racing team in the North American Ferrari Challenge Series, where he won the Rookie of the Year title in 2011, after winning both races at the season-opener in St. Petersburg, Florida and following up with wins in Laguna Seca Raceway and Lime Rock, Connecticut.