For billionaires, private jets represent the ultimate luxury – no security queues, no booking months in advance, and seamless comfort at 40,000 feet. Yet even among the ultra-wealthy, the desire to own more can become a trap. Shark Tank star and Emmy-winning entrepreneur Robert Herjavec learned this lesson not in a boardroom, but during a casual conversation with fellow Shark Mark Cuban.
How Mark Cuban’s sharp reply got Herjavec thinking
At a workshop, in front of high-schoolers, Herjavec was once questioned – Why do you still work so hard? A question that hit home for billionaires sitting on that panel, Herjavec jokingly added, without realising the consequence it would have on him, “So I can have a jet bigger than Mark Cuban.”
Introspecting and reflecting on these words, Cuban realised that it may have bothered him that a close associate was a bigger tycoon than him.
Herjavec, in a recent YouTube video, recalled this moment where he found himself comparing private planes with fellow Shark Mark Cuban. He was mid-brag when Cuban stopped him cold — not with an argument, not with numbers, but with two words: “Which one?”
One question. That’s all it took.
It’s a mindset Herjavec has carried since: one plane is better than two — not because it’s modest, but because if two feels like something to show off, you haven’t yet grasped what the next level actually looks like.
The philosophy behind ‘One plane is better than two’
It was then that Herjavec realised that Cuban had not two, but three private jets. However, the question was no longer about private planes, luxuries, or opulent lifestyles. It had sent Herjavec into a spiral and made him question his entire purpose of earning money.
“It really humbled me,” he recalled as he reflected on his words of boasting about a bigger plane. His words bothered him, and he realised that it was perhaps the wrong thing to flaunt or even compete with a friend.
“I had lost my compass as to why I was working so hard,” remarked the billionaire.
In a world where everyone pits one against the other, Herjavec realised that he had forgotten why he became a billionaire. “When I started my company, I didn’t do it for a bigger paycheck, I simply did it to pay my mortgage,” revealed the Shark Tank USA judge. He added, “My entire goal in life was to make $1000 for my age,” explaining how he wanted to make $50,000 at the age of 50, along with buying a Corvette and paying off his debts.
His comparison of the jets only made him question, “What is wrong with me?” However, he reflected on this and realised that he had lost his purpose and compass, explaining how he made peace with having one jet over three.
“Life is not about competing with someone else. It is about finding your own compass. There is no greatness without great purpose,” Herjavec shared. The simple comparison between jets and Cuban’s ‘which one?’ made him recall why he went into business at all and recalibrate his focus to doing what he set out to do. It reminded him of his roots and where it all began.
What is Mark Cuban’s key to success?
Mark Cuban’s life is often led by intense hard work and goal-driven entrepreneurship. Shark Tank judge and venture capitalist in several firms, once broke down his rule of life that he follows in business. In 2024, speaking to People magazine, Cuban also clarified that the key to success isn’t just hustle—it’s weird snacks, digital independence, and asking better questions.
In fact, this one statement points out the former NBA team owner’s philosophy towards growing, learning, and life. Acting like a team player at home, Cuban showed interest in Gen Z not to shame them, but actually to learn about a new target audience.
Moreover, he realised early that success and wins come from intention. “Life is half random,” he said and recalled his $5.7 billion sale of broadcast.com. And being unafraid of failure stayed strong beside him.