Capital Wealth
FRI CLOSE · SEP 25   S&P 500 7,743.41 ▲0.51%  ·  DJIA 51,828.62 ▲0.93%  ·  NASDAQ 27,068.72 ▲0.48%  ·  10-YR 5.17%  ·  2-YR 4.81%  ·  WTI $92.44 ▼2.3%  ·  GOLD $4,320.50 ▲0.5%  ·  VIX 14.87 ▼5.1%
Mansion · House Call · Behavioral

Robert Herjavec Arrived With $50, Worked Six Months for Free, Then Handed His Father the Keys to a Cadillac

His father was jailed 22 times in Yugoslavia, and the family reached Halifax with $50 and no English. At 23 he worked six months for free; later he turned his father’s someday into today.

By Sean Anees Saifi · Capital Wealth · Published Friday, September 25, 2026 · Source: The Wall Street Journal, Friday, September 25, 2026 edition, whose market figures are the Thursday, September 24 close (Mansion)
Key Points
$50
the family’s cash on arrival in Halifax in 1970
22
times his father was jailed in Yugoslavia
6 months
of unpaid work he offered LogiQuest at 23
$30M
what his basement startup, BRAK Systems, sold for in 2000
A city skyline at dusk, its towers reflected in still water.
His latest home splurge is a soft-serve ice-cream machine in L.A. He says it gets used in moderation.
In one line: Herjavec’s story turns on two well-timed investments — six unpaid months in his own career, and a Cadillac for his father while his father could still enjoy it — and it’s the second kind families tend to put off.

Robert Herjavec’s first big deal looked terrible on paper. He was 23, had no experience, and wanted a job selling mainframe boards at a company called LogiQuest — so he offered to work six months for free. The boss agreed. Three years later, Herjavec was general manager. The Shark Tank investor, now 64, tells the story in the Journal’s House Call column, and it starts, as the best ones do, with almost nothing: $50.

He was 5 when Yugoslav authorities arrested his father, Vladimir, a singer who’d refused to join the Communist Party and been overheard criticizing the government; from then on, his father was jailed 22 times. In 1970, when Robert was 8, the three of them drove into Italy late one night. U.S. customs turned his father down, and he was told to try Canada instead. They landed in Halifax — Canada’s Ellis Island, as Herjavec puts it — with $50, their suitcases and no English, and moved into a family friend’s basement in Toronto, where his father pumped gas.

The climb was steep. Within nine months his mother, Katica, had learned English and found work as a receptionist; when he was 14, his parents bought a brown two-bedroom house. They paid part of his $5,000 University of Toronto tuition, and he worked for the rest. When he failed advanced algebra and came home to quit, his father, back from one of his two factory shifts, sent him straight back in blunt, broken English. He switched to English literature, went into TV — the Global TV Network sent him to the 1984 Winter Olympics in Sarajevo because he spoke Croatian — then got fired from a film job. Then came LogiQuest.

One day, dated

After sitting next to Ethernet co-inventor Bob Metcalfe on a flight, he told his boss Ethernet was the future. The boss disagreed, so Herjavec quit and started BRAK Systems, an internet-security and firewall company, in his basement. He sold it for $30 million in 2000. Soon after, he took his father to a Cadillac dealer. The old man sat in a pearl-white DeVille and sighed that he’d have one someday; his son handed him the keys and told him the day had come. A framed photo of their ship docking in 1970 now sits in Herjavec’s L.A. office, a reminder on bad days, he says, that “as a kid, my worst day was still a dream.”

Our read

Two planning lessons hide in here. The first is human capital: at 23, Herjavec’s most valuable asset wasn’t money but his future earning power, and six unpaid months got him in the door; within three years he was general manager. Early in a working life, that asset usually dwarfs anything in a brokerage account.

The second is the Cadillac, a behavioral lesson with an estate-planning edge. One day is how a lot of families schedule the spending that matters most — a trip with a parent, help with a first home, the thank-you gift — and one day has a way of arriving after the person it was meant for. His father got the car and, by our count, about six more years. If there’s a someday on your list, give it a date and a dollar figure, and decide which gifts belong in the will and which are worth more given with a warm hand.

What It Means For Your Portfolio

Hold — put a date on the someday gift

No portfolio action — the lesson is about timing a gift, not a trade: a someday gift given while the person can still enjoy it can deliver more than the same dollars left for later.

General planning principles, not advice for anyone in particular. List the one-day items — the trip with a parent, help toward a child’s first home, a grandchild’s tuition — and give each a date, a dollar figure and a funding source. Some belong in the estate plan; others are worth more given now.

Before any large lifetime gift, check your own retirement cash flow first, then gift-tax reporting and fairness among heirs. Herjavec bought the Cadillac soon after a $30 million sale; most families will need a smaller car and a spreadsheet.

Book a 15-Minute Review → Back to Edition No. 176 →