“‘Someday’ isn’t a real day like Monday or Tuesday; it’s just another word for ‘never.’”
If you watch Shark Tank or Dragons’ Den, you already know Robert Herjavec as the friendly shark — the one who actually seems to care about the entrepreneurs standing in front of him. But what you might not know is the story behind the smile. This dude didn’t grow up with connections or family money. He arrived in Canada as an immigrant kid from Croatia with literally nothing, got bullied for being different, and had to claw his way into the business world from the absolute bottom.
That backstory alone makes The Will to Win worth picking up. But is the book itself a home run? Let’s get into it.
The Immigrant Hustle
The strongest thread running through the entire book is Robert’s origin story. His family arrived with nothing from authoritarian Croatia, and Robert was able to create something grand in the world. That’s not just a feel-good line — he genuinely started from zero. No network, no trust fund, no safety net.
What resonated with me is that Robert doesn’t glamorize the struggle. He’s honest about how painful it was to feel like an outsider in his own country. The bullying, the alienation, the constant feeling that he had to prove himself just to be treated as an equal — it’s raw, and it’s real.
I think anyone who has ever moved to a new country or started over in a new environment will feel this chapter in their bones. You don’t forget what it’s like to have nothing. And sometimes, that memory is the best fuel you’ve got.
Dragons’ Den and Celebrity Life
We learn a bit about Robert’s exodus from Dragons’ Den (I never knew he left), and the perks he gains and the pitfalls of becoming a celebrity. This section is surprisingly candid. Celebrity isn’t all champagne and red carpets — there’s a real cost to being recognized everywhere you go, and Robert doesn’t sugarcoat it.
What I found interesting is how he navigates the tension between being a serious businessperson and being a TV personality. Those two worlds don’t always mix well. People start treating you differently. Some want to pitch you in the grocery store. Others assume you’re just a showman with no real substance.
Robert is a bit more homely and humble than Kevin, yet his advice is just as relevant. From starting a business to pursuing your hobbies, to dealing with employees, and enjoying the celebrity lifestyle. He covers a LOT of ground, and most of it feels genuine rather than rehearsed.
Managing People and Growing a Business
Robert details some things he’s overcome while managing employees and growing a multimillion-dollar business. This is where the book becomes genuinely useful for anyone running a company or leading a team.
His approach to management is straightforward — treat people well, set clear expectations, and don’t be afraid to make tough calls. Nothing revolutionary on paper, but the way he frames it through personal experience makes it stick. He talks about hiring mistakes, the pain of firing someone you like, and the loneliness of being the person at the top who has to make the final decision.
One thing I appreciated is that Robert doesn’t pretend he had it all figured out. He admits to screwing up, losing money on bad deals, and trusting the wrong people. That kind of honesty is rare in books by successful CEOs. Most of them rewrite history to make themselves look like geniuses from day one.
Racing and Investing
He uncovers some deep game-changers for succeeding within his Ferrari racing hobbies, and how it transitions into life and his Shark Tank investments. This was actually one of my favorite sections. The parallels between racing and business are surprisingly tight — calculated risk, split-second decisions, knowing when to push and when to hold back.
Robert’s passion for racing is contagious. You can tell this isn’t just a rich-guy hobby for him — it’s a genuine obsession that teaches him something every time he gets behind the wheel. And the way he connects those lessons back to evaluating investments on Shark Tank is clever. In racing, you learn to read conditions instantly. In business, you need to read people and markets with that same speed.
The Chip on the Shoulder
Nonetheless, it seems Robert holds some resentment — a chip on the shoulder — towards those who bullied him and exiled him for not being Canadian. Apparently, this drives Robert to some extent.
And honestly? I get it. That chip on the shoulder is a POWERFUL motivator. I’ve seen it in so many entrepreneurs — the ones who succeed the most are often the ones who were told they couldn’t. They carry that rejection with them like a battery that never dies.
The question is whether that kind of fuel is sustainable. Robert seems to have found a balance between using the resentment to push forward and not letting it poison his relationships. But you can tell it’s always there, simmering under the surface. It’s what makes him relatable. He’s not some enlightened guru who’s transcended his past — he’s a guy who remembers EVERY slight and channels it into action.
Final Thoughts
The Will to Win is a great book with some sound advice and maybe a little celebrity gossip-like content mixed in. It’s not a 100% purposeful book, but the philosophies are great to own and reinforce into your reality.
If I’m being honest, the book jumps around a bit. Some sections feel like polished life lessons, while others read more like behind-the-scenes anecdotes from a reality TV star. But that mix is part of its charm. You get the business wisdom AND the human being behind it.
Robert Herjavec isn’t trying to be the smartest person in the room. He’s trying to be the most determined. And in a world full of people waiting for “someday,” that determination is worth more than any MBA.
3.5/5 — solid read for fans of Shark Tank and anyone who needs a reminder that starting from nothing is not a disadvantage, it’s a SUPERPOWER.
Thanks for reading.
— Leonidas
