Diane Plese was running her own optometry practice in Toronto when Robert Herjavec walked into her clinic as a patient in 1988. She had trained through the 1970s, qualified as a licensed optometrist in the early 1980s, and built her own patient base on her own terms. He had arrived from Yugoslavia as a child with next to nothing and was still years away from the technology deals that would make him one of Canada’s wealthiest entrepreneurs. By 2014, when she announced their separation after 24 years of marriage, Robert was a fixture on both Dragons’ Den and Shark Tank. She had spent those same years almost entirely out of public view.
The divorce changed that. A Canadian judge later confirmed, in her own written ruling, that Herjavec had been involved in an extramarital affair during the marriage’s final year. A letter from his former girlfriend alleged he had arranged for his company to be valued at roughly half its actual worth to limit what Diane would receive in the settlement. The court ordered a total of $25 million from an estate worth many times that figure. Diane Plese accepted the terms, moved back to Toronto, and has not spoken to the press since.
| Full Name | Diane Plese |
| Born | 1959, Parkdale, Toronto, Canada |
| Nationality | Canadian |
| Heritage | Croatian descent |
| Profession | Optometrist |
| Former Husband | Robert Herjavec |
| Married | 1990 |
| Divorced | 2016 |
| Children | Brendan, Skye, Caprice Herjavec |
| Net Worth | Approx. $25 million (court ordered, 2019) |
Table of Contents
A Career She Built Before the Marriage
Diane Plese was born in 1959 in Parkdale, a working Toronto neighbourhood historically shaped by immigrant families. Her parents had come from Croatia and raised her with a straightforward set of values: study, work, and keep your private life private. She did all three. She studied through the 1970s, earned her optometry qualification in the early 1980s, and opened her own practice in Toronto.
That practice is where she met Robert Herjavec in 1988. He was not yet a name anyone recognised. He was still moving through the Canadian technology industry, years before BRAK Systems, years before The Herjavec Group. They shared Croatian roots and that, by her own account, mattered. She later described him to the National Post in simple terms: “He’s so excited about life. How can you not want to be with someone who is so happy and motivated?”
They married in 1990 at a Croatian church in Ontario.
The Marriage and the Life Behind It
After Robert sold BRAK Systems to AT&T Canada in 2000 for $30.2 million, the financial picture shifted completely. Diane stepped away from her optometry practice to raise their children full time. The family moved into the Bridle Path area of Toronto, one of Canada’s most expensive postcodes, in a 50,000 square foot French style chateau built by developer Shane Baghai. The property featured on MTV Cribs and hosted guests including Michael Bublรฉ and John Travolta.
Robert founded The Herjavec Group in 2003, which grew into a major Canadian cybersecurity company with over $200 million in annual revenue. His television career followed. Diane stayed out of it.
In October 2013, the couple gave an interview together about their home and their life. Nine months later, she announced the marriage was over.
Diane Plese’s Three Children: Where They Are Today
Robert and Diane raised three children together. All three attended Havergal College in Toronto before going on to build their own careers.
Brendan Herjavec, the eldest, born in the early 1990s, studied business and marketing at Wilfrid Laurier University and continued his education at Yale. He works in strategy and revenue operations and serves as a client manager for Inkblot Therapy, a mental health services company. He announced his engagement to Jessica Herjavec in April 2022.
Skye Herjavec, born in 1996, studied business administration at the University of Southern California. She interned at JPMorgan Chase, Walter Baker, and Badgley Mischka, later worked as an associate in JPMorgan’s Leveraged Finance Group, and joined Stone Point Capital in 2024.
Caprice Herjavec, the youngest, born in 1998, was named Mayor for a Day in Toronto at age 14. She studied at Barnard College at Columbia University, where she coxed for the women’s rowing team and wrote for the Columbia Daily Spectator. She has worked as a consultant at executive compensation firm Frederic W. Cook and Co. since July 2020.
The Separation and What the Court Papers Actually Said
Diane announced the separation on July 24, 2014. Her statement to the National Post was short and gave nothing away: “Robert is a caring husband and a responsible person towards his family, but I cannot live with him anymore and the reasons behind our separation will not be disclosed among the public.”
Robert told People magazine at the time: “It’s been a terribly difficult year. We were great parents and a great team, but over time we drifted apart.”
Diane filed for divorce in March 2015. It was finalised in June 2016.
What surfaced during proceedings went further than either of those statements. The judge confirmed in her written ruling that Herjavec had been “involved in an extramarital affair” in 2014. His former girlfriend, actress Danielle Vasinova, had dated him from January 2014 to early 2015. In 2017, she wrote directly to Diane claiming that Herjavec had allegedly arranged for his company to be appraised at roughly half its actual value during the divorce to reduce what his ex-wife would receive. An affidavit confirmed Vasinova was prepared to testify. Herjavec denied the allegations. Both related lawsuits were dismissed in 2018.
Diane Plese’s Net Worth and the Divorce Settlement
The financial terms were finalised in June 2019 following a second round of court proceedings. According to the Toronto Sun, the court ordered the following:
| Settlement Component | Amount |
|---|---|
| Monthly spousal and child support | $125,000 per month |
| Total marital assets awarded | $25 million |
| Equalization payment (2019 ruling) | $2.6 million |
| Proceeds from property sales | $2.8 million |
| Properties | Caledon ski chalet and Florida property |
Robert Herjavec’s net worth at the time of proceedings sat between $200 and $300 million, with The Herjavec Group generating over $200 million in annual revenue.
Diane Plese’s net worth is estimated at approximately $25 million, reflecting the court ordered settlement. Figures of $100 million cited on various websites carry no court documentation and should be read with that in mind.
Where Is Diane Plese Now?
As of 2026, Diane Plese lives in Toronto. She has no social media presence. She has not remarried and has not given a public interview since her separation statement in July 2014.
Robert Herjavec married Kym Johnson, his Dancing with the Stars Season 20 partner, on July 31, 2016, at the Four Seasons in Beverly Hills. Their twins, Hudson Robert and Haven Mae, were born on April 23, 2018, via IVF. In September 2024, Robert stepped down as CEO of Cyderes, the cybersecurity company that grew out of The Herjavec Group.
Diane has not commented on any of it.
Every profile written about Diane Plese describes her silence as a form of strength. Dignified. Restrained. A woman who chose not to perform her own grief in public. That reading is not wrong. It is also worth being clear about what that silence came after.
She walked into the marriage as a working medical professional with her own practice and her own professional identity. She gave that up and spent the years that followed raising three children inside a household built entirely around someone else’s career. The court that was eventually asked to put a number on that arrangement came up with $25 million. She took it and went back to Toronto, to the city where she had been before any of this started.
Her name now appears almost exclusively in articles about her former husband. The optometrist who existed before the marriage is harder to find. She has not seemed particularly interested in being found.
