"Expect to win always" — Shark Tank mentor Robert Herjavec reflects on lessons learned from Mark Cuban

In a YouTube video posted on October 20, 2024, Robert Herjavec shared valuable lessons from his 16 years working alongside Mark Cuban on Shark Tank. The video is part of his new series, Things I Learned from a Billionaire to Become a Billionaire, where Robert explores key insights gained from successful entrepreneurs.

Mark Cuban, known for his business strategies, was a major influence on Robert’s journey.

One of the lessons Robert shared was Mark’s advice to "expect to win always."

On the Shark Tank set, Mark shared his philosophy of approaching every opportunity with full confidence in success. Inspired by this, Robert adopted a more decisive mindset, which he credited with helping him make bold decisions and grow his business.

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Shark Tank mentor Mark Cuban's influence on Robert's life

One of the first lessons Robert learned from Mark Cuban was to approach every opportunity with full confidence. During a pivotal moment on Shark Tank, Robert shared his doubts about a critical business deal with Mark, asking,

“When you go into a meeting, do you expect to win?” Mark responded immediately: “Yes, 100% of the time.”

This answer pushed Robert to rethink his approach to challenges. Mark explained his belief in fully committing to success: “It’s going to work out.” He emphasized that hoping for an outcome wasn’t enough, saying,

“Don’t protect your downside and don’t hope for an outcome—expect it.” This mindset, Mark said, was a key to his success, transforming doubt into decisive action.

Mark compared this confidence to the idea of “burning the boats,” where retreat isn’t an option, forcing you to move forward. Reflecting on this, Robert admitted,

“Before meeting Mark, I hoped things would work out. But he showed me the difference between hope and expectation.”

This approach led Robert to take risks he might have avoided before. He explained, “Mark’s level of confidence shook me. It made me realize that my hesitation was holding me back.” Robert credited this mindset with significantly increasing the value of his businesses, saying,

“This one shift probably made me worth hundreds of millions of dollars more than I was before.”

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Mark's lesson about business being a continuous competition

Another important lesson Robert learned from Mark Cuban was his view of business as a constant competition. Mark frequently emphasized that business never pauses, unlike sports, which have defined seasons or time limits. He often said,

“The bigger you get, the bigger the bullseye on your back,” highlighting how success attracts more competition.

This mindset came to life during a Shark Tank pitch, where Mark introduced his now-famous "24-second shot clock" strategy. As the Sharks debated their offers, Mark stunned everyone by giving the entrepreneur just 24 seconds to accept his deal.

“If you don’t take it now, I’m out,” Mark told the entrepreneur, who immediately accepted.

Inspired by basketball’s 24-second rule, the tactic showed how quick, decisive actions could shift power in a negotiation. Robert recalled,

“The rest of us were caught off guard. It was a masterclass in speed and decisiveness.”

Mark’s approach taught Robert the value of staying ahead in a competitive environment. “Mark always said, ‘Time kills all deals,’” Robert shared, underscoring the importance of acting promptly.

Mark often reminded Robert, “Nobody remembers your failures; they only remember your wins.”

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Watch both the mentors on Shark Tank season 16, airing every Friday at 8 pm ET on ABC.