Every Watch Has a Story: Robert Herjavec’s Unforgettable Rise

Robert Herjavec didn’t grow up with money. In fact, he didn’t even grow up with privacy. After fleeing communist Yugoslavia in the 1970s, his family arrived in Canada with nothing but a suitcase and each other. They slept in a friend’s basement, spoke no English, and scraped by while his father—once a respected manager back home—took a job in a factory. To the outside world, they were just another immigrant family. To Robert, they were invisible.

But invisibility didn’t last.

Herjavec went on to become a multimillionaire tech entrepreneur, best-selling author, and household name thanks to his seat on Shark Tank. But behind the polished suits is a man who once delivered newspapers at dawn and bussed tables at night—who pressed his face to storefront windows and promised himself he’d one day afford the life inside.

For Robert, one of the most powerful symbols of that life? Watches.

Unlike celebrities who collect timepieces for flash, Herjavec buys them to mark turning points. In 2000, after selling his first company, BRAK Systems, to AT&T Canada for $32 million, he rewarded himself with a Rolex. In a November 2024 Instagram post, he wrote, “I’ve always been a Rolex guy,” revealing a collection of more than 75. Yet even a seasoned collector can be caught off guard—when Australian retail mogul Davie Fogarty gifted him a Patek Philippe Calatrava, Herjavec let out an audible gasp. “In business, it’s not just about the deals we make, but the bonds we form,” he posted. “This gesture speaks volumes about the power of gratitude and mutual respect.”

Long before the boardrooms and the lights of television, Robert took what he thought would be a simple part-time retail job at Harry Rosen, Canada’s premier luxury menswear store. He expected a discount on suits—but instead, he found a mentor. Harry Rosen himself showed up early on Saturdays to teach a teenaged Robert how to dress, how to spot quality, and—most importantly—how to sell to wealthy clients. Herjavec later said, “I would have paid him to teach me… he taught me everything. It was an open offer to the entire store—‘Show up a little early on a Saturday, and I’ll teach you’—and while no one else grabbed the opportunity, I took advantage of it. It was just me and Harry.” Those lessons in clothesmanship and persuasion became foundational—and would later prove invaluable in boardrooms and pitches.

He’s called watches “small pieces of art and engineering,” saying he chooses them not to show off, but to commemorate. They’re reminders of how far he’s come—symbols of arrival. Proof that the immigrant kid from Croatia didn’t just dream. He built.

But maybe the most powerful part of Herjavec’s story isn’t what he wears. It’s how he thinks.

“There’s a difference between being poor and being broke,” he once said. “Being broke is a temporary economic state. Being poor is a disabling frame of mind.”

It’s a belief that’s guided him for decades: that a poverty mindset keeps you stuck, while an abundance mindset lets you grow. Herjavec didn’t wait for permission to succeed. He outworked, outlearned, and outlasted the limits placed on him—turning self-doubt into strategy.

There’s something poetic about a man who once couldn’t afford a watch now owning some of the finest in the world. But he doesn’t wear them to impress. He wears them to remember: this is what it looks like when hard work meets vision.

His watches aren’t trophies. They’re timestamps. Quiet reminders of each chapter closed—and every mountain climbed.