Robert Herjavec Reveals How Mark Cuban Changed His Life for Good
Robert Herjavec thought he knew success—until Mark Cuban’s bold mindset changed everything. Here’s how Cuban’s advice made him millions.
Success in business often comes down to learning from the right people. For Robert Herjavec, his greatest mentor has been fellow Shark Tank investor Mark Cuban. Over 16 years of working together, Cuban has fundamentally reshaped the way Herjavec thinks about business, competition, and personal success.
In a recent video on his YouTube Channel, Robert shared the most important lessons he learned from famous billionaire, Mark Cuban—lessons that have helped him become a better entrepreneur, investor, and leader. These insights go beyond just business; they provide a blueprint for winning in any competitive environment.
1. Expect to Win—Always
One of the most profound lessons Cuban taught Herjavec was about mindset. Cuban doesn’t hope to win—he expects to win. This difference might seem subtle, but it completely changed how Herjavec approaches business.
“I asked Mark, ‘When you go into a meeting, do you expect to win?’ He said, ‘Yes, 100% of the time.“
Before meeting Cuban, Herjavec admits he would cautiously approach business deals, hoping for success but also preparing for failure. But Cuban’s unwavering confidence made him realize something crucial:
If you don’t fully believe you will win, you’ve already lost.
Cuban operates with the mindset that everything will work out—because he will make it work. This approach transformed Herjavec’s decision-making. Instead of focusing on minimizing losses, he started focusing on maximizing wins.
“This shift in thinking has probably made me worth hundreds of millions of dollars more than I would have been otherwise.”
When you walk into a business deal, a pitch, or even a negotiation, expect to win. That belief will shape your actions, decisions, and ultimately, your success.
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2. Time Kills All Deals—Speed is Power
Herjavec has been in business long enough to know that hesitation can cost you everything. But Cuban took this lesson to a whole new level.
When Cuban joined Shark Tank, he introduced a game-changing tactic—the 24-second shot clock.
“We were all competing for a deal, and out of nowhere, Mark told the entrepreneur, ‘I’ll do the deal, but you have 24 seconds to decide.’”
The entrepreneur hesitated, unsure of what to do. Cuban immediately pulled his offer.
That’s when it hit Herjavec: Speed forces honesty.
When people are given too much time, they second-guess themselves. They rationalize, they hesitate, and in many cases, they overthink to the point of inaction. Cuban’s approach forces decisive action—something that can make or break a deal.
Since learning this lesson, Herjavec has applied it to his own deals. He has learned that in business, if you wait too long, opportunities slip away.
3. The Bigger You Get, the Bigger the Target on Your Back
Cuban once told Herjavec that business is the most competitive sport in the world. It’s not basketball, football, or baseball—because those games have time limits and seasons. Business, on the other hand, never stops.
“Mark always says, ‘The bigger you get, the bigger the bullseye on your back.’”
When you start small, you’re just another entrepreneur fighting to survive. But once you become successful, you become a target. Competitors try to take your market share. New startups try to disrupt your industry. Investors scrutinize your every move.
Herjavec admitted that he once thought success would make things easier. But Cuban taught him the opposite:
Success makes things harder—because now you have something worth taking.
This lesson shifted Herjavec’s perspective. Instead of relaxing after a big win, he learned to push even harder. Every successful entrepreneur must work as if someone is trying to steal their success—because someone always is.
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4. Life Isn’t About Competing With Others—It’s About Purpose
At one point, Herjavec found himself falling into the trap of competing with Cuban over material things. He once joked in an interview that he wanted to buy a jet bigger than Cuban’s. Cuban’s response stunned him:
“Which one?”
That’s when it hit Herjavec—Cuban had multiple jets, and here he was obsessing over one.
“I realized I had lost my compass. I wasn’t competing for the right reasons anymore.”
Herjavec had started his business for freedom and purpose. But at some point, he had gotten caught up in comparing himself to others. Cuban’s casual remark forced him to reevaluate why he was working so hard.
He took a step back and realized: Success isn’t about beating someone else. It’s about staying true to your purpose.
Since then, Herjavec has focused less on competition and more on personal fulfillment. He no longer chases material success just for the sake of it. Instead, he builds businesses that inspire him and add real value to the world.
5. There Are Only Three Reasons to Sell Your Business
At one point, Herjavec was offered $100 million to sell his company. It was an all-cash offer, and he wasn’t sure whether to take it. So he turned to Cuban for advice.
Cuban’s response was simple but life-changing:
*“There are only three reasons to sell your business:
- You don’t want to do it anymore.
- You believe you’ve maxed out the opportunity.
- The money will fundamentally change your life.”*
Herjavec thought hard about those points. Did he still love his business? Yes. Had he maxed out its growth potential? No. Would $100 million change his life? It would make him richer, but it wouldn’t fundamentally change who he was.
So he turned down the offer. Years later, he sold a majority stake in his company for far more than $100 million—and still retained ownership.
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6. You Only Need to Be Right Once
Cuban once told Herjavec something that completely changed his perspective on failure:
“I have failed more times than I can count. But I was right once—and that was all that mattered.”
People assume Cuban has always been successful. But the truth is, he’s had countless failed ideas, investments, and businesses. The reason he’s a billionaire today is because he succeeded once—big time.
This taught Herjavec one of the most valuable lessons of his career:
Failure doesn’t matter. Success erases everything.
Since then, Herjavec has learned to take bigger risks and embrace failure. He now understands that every mistake, every setback, and every loss is just a stepping stone to the one big win that will change everything.
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Conclusion
Mark Cuban’s influence on Robert Herjavec goes beyond business—it’s about mindset, resilience, and purpose. These six lessons have shaped Herjavec’s career and made him a stronger, more fearless entrepreneur.
As Herjavec put it:
“These lessons have made me wealthier, wiser, and more fearless in business.”
Cuban’s legacy isn’t just about being a billionaire—it’s about empowering others to think and act like one.
