"They have never worked in an office" - Shark Tank's Kevin O'Leary shares that he negotiates office timings with his employees in their 20s

Shark Tank investor Kevin O’Leary uploaded a video on Instagram on April 30, 2025, in which he discussed how the working environment was no longer appealing to younger talents.

In a FOX Business interview, Kevin O'Leary said many people in their 20s have never worked in a traditional office. They prefer flexible work over cubicles and bright lights. To bring them into the office, he negotiates with them. He believes the gig economy has changed work expectations, and companies must adapt to attract top talent.

"I realized, particularly around engineering and in another area that's so important, social media talent for customer acquisition and return on ad spend, those people are in their 20s. They've never worked in an office in a real job," he shared.

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Shark Tank investor Kevin O’Leary explains the work environment expectations in the gig-based economy

The latest clip that he shared showed Shark Tank investor Kevin O'Leary during an interview with FOX Business.

One of the hosts shared with Kevin that he heard the bussineman demands his employees to be in the office five, if not six, days a week. In response, the Shark Tank star noted that he used to do that, but seeing how the demand for the working environment had changed, he doesn't do that anymore.

Kevin said that in today’s gig-based economy, skilled workers know they can work from home and don’t need an office. He believes they want flexibility, so instead of strict rules, he focuses on their performance and negotiates office hours with them.

"I don't even talk about that anymore. The good people have figured out they don't need to work in an office. You want the top talent. I go for performance and executional excellence. We negotiate how often they come into the office," he said.

When the host chimed in, noting that he thought the businessman had laid out the work law for his employees, Kevin responded that he didn't.

He then went on to share that most younger people, especially in fields like engineering and social media, have never worked in an office before. He believes that their expectations of the working environment are different, and they don't want to be forced into working in the confines of a cubicle.

"So I said 'Here's your cubicle. What do you think of this cubicle?' They said 'What is this prison? I'm not coming here'. I mean, it's so obvious to me that the new gig economy is never gonna work in an office. So I admire these CEO's that are giving this job boaning, but if they want the top talent, it's never gonna work that was," he concluded.

Further in the same interview, the host pointed out Amazon owner Jeff Bezos, launching satellites, trying to compete against Elon Musk's Starlink in the race to provide good internet services.

When asked if he had ever used Starlink, the Shark Tank star shared that some planes he flies in have the facility, and he finds it very amazing. However, he pointed out that such service isn't cheap, so he is open to the idea of Bezos entering with competition.

"Some airplanes I fly on have it, and it's unbelievable. It is phenomenal. It's better than ground-based Internet when you're in that plane. You can stream anything and have phone conversations with anybody around the world. Starlink is amazing. But I love competition because it ain't cheap. So if Bezos wants to compete, bring it on, and I'll try this tip," Kevin said.

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Shark Tank season 16 episodes air every Friday on ABC.