Shark Tank investor Kevin O'Leary shares steps to balance business and pleasure while handling contentious deals

Kevin O'Leary, a prominent investor on Shark Tank and entrepreneur, has been known for his strategic approach to business, combining negotiation tactics with personal dynamics. In a recent Instagram video posted on April 12, 2025, O'Leary discussed how he balances business and pleasure while managing contentious deals.

He describes how combining both aspects can alter the nature of negotiations to eventually result in more successful trades. By bringing adversarial business conversations to an environment that encourages respect and understanding, O'Leary shows how relaxation and strategy can blend.

"It shifts the dynamic, builds respect, and makes closing the deal that much easier," he wrote in the caption.

In the video, the Shark Tank investor is seen aboard a yacht with family and friends, turning an otherwise formal business conversation into a more relaxed and productive discussion.

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Balancing business and pleasure: Shark Tank Kevin O'Leary's strategy for handling controversial deals

1) Mixing business with leisure

Kevin O'Leary emphasized that one can mix business and pleasure. In the video, he says that taking an opponent to a relaxed environment is not all about enjoying oneself, but it has a strategic advantage.

"Bringing an adversary into a setting like this isn’t just about having a good time— it’s strategy," he says.

As O'Leary explained, a casual setting can break the formal barriers of tension that characterize tense business deals. He points out that it is a signal of peace, even if the deal is not yet sealed, to invite a business partner into such an environment.

"If he sees that kind of respect, I know when we finally get off in the corner somewhere sometime this afternoon, we’re going at it a different way," O'Leary shared.

The Shark Tank investor underlined that his strategy is to encourage respect and cooperation, enabling the two sides to interact more candidly as they strive toward an agreement.

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2) Managing negotiations in informal settings

When discussing how to handle difficult negotiations, O'Leary emphasized the importance of creating an environment conducive to open communication. The Shark Tank investor mentioned that being in a relaxed setting, like a yacht, allows for more candid discussions and helps move negotiations forward.

“We’re stuck on the deal. We’re stuck. I needosomething from him, he needs something from me," he explains.

O'Leary stressed that this kind of setting enables both parties to engage without the pressure of formal office spaces, which can often escalate tensions. He underlined that the casual environment can lead to more productive conversations. Underscoring that a less tense atmosphere can help resolve business disagreements more effectively.

"This is how you can mix business with pleasure and still get results," O' Leary stated.

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3) Using casual settings to finalize deals

Kevin O'Leary's approach also includes using an informal setting to finalize agreements. After fostering a more cooperative environment, he stressed the importance of clear and direct negotiation.

"We’re 15% apart. Why don’t we just meet in the middle? I give you seven and a half. I take seven and a half. We got a deal done,” O'Leary mentions.

The Shark Tank investor underscored the value of maintaining the balance between business and leisure by wrapping up the negotiation in a more enjoyable way.

"We’re going to lay anchor right now. We’re going to bring out these soft shell crabs and have a great time," O'Leary says.

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